Aluminium hydride

Names
Preferred IUPAC name

Aluminium hydride

Systematic IUPAC name

Alumane

Other names

* Alane
* Aluminic hydride
* Aluminium(III) hydride
* Aluminium trihydride
* Trihydridoaluminium

Identifiers

CAS Number

* 7784-21-6 Y

3D model (JSmol)

* Interactive image

ChEBI |

* CHEBI:30136 Y

ChemSpider |

* 13833 Y
* 17625618 (3H3) Y

Gmelin Reference

| 245

PubChem CID

* 14488
* 14399066 (2H3)
* 16721258 (3H3)

UNII |

* KZJ3T010RQ Y

InChI

* InChI=1S/Al.3H Y

Key: AZDRQVAHHNSJOQ-UHFFFAOYSA-N Y

* InChI=1S/Al.3H

Key: AZDRQVAHHNSJOQ-UHFFFAOYSA-N

* InChI=1/Al.3H/rAlH3/h1H3

Key: AZDRQVAHHNSJOQ-FSBNLZEDAV

SMILES

* [AlH3]

Properties

Chemical formula

| AlH3
Molar mass | 30.006 g·mol−1
Appearance  | white crystalline solid, non-volatile, highly polymerized, needle-like crystals
Density | 1.477 g/cm3, solid
Melting point |  150 °C (302 °F; 423 K) starts decomposing at 105 °C (221 °F)

Solubility in water

| reacts
Solubility | soluble in ether
reacts in ethanol
Thermochemistry

Heat capacity (C)

| 40.2 J/(mol·K)

Std molar
entropy (S ~~o~~ 298)

| 30 J/(mol·K)

Std enthalpy of
formation (ΔfH⦵298)

| −11.4 kJ/mol

Gibbs free energy (ΔfG˚)

| 46.4 kJ/mol
Related compounds

Other cations

| Borane
Gallane
Indigane
Thallane

Related compounds

| Lithium aluminium hydride
Diborane
Digallane

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Y verify (what is YN ?)
Infobox references

Aluminium hydride (also known as alane[1] and alumane[1]) refers to a collection of inorganic compounds with the formula AlH
3. As a gas, alane is a planar molecule. When generated in ether solutions, it exists as an ether adduct. Solutions of alane polymerizes to a solid, which exists in several crystallographically distinguishable forms.[2]

## Contents

* 1 Structure
* 1.1 Gaseous alane
* 1.2 Solid alane
* 2 Handling
* 2.1 Reported accidents
* 3 Preparation
* 3.1 Electrochemical synthesis
* 3.2 High pressure hydrogenation of aluminium
* 4 Reactions
* 4.1 Formation of adducts with Lewis bases
* 4.2 Reduction of functional groups
* 4.3 Hydroalumination
* 4.4 Fuel
* 4.5 Deposition
* 5 References
* 6 Further reading
* 7 External links

## Structure

Alane can adopt 3-, 4-, or 6-coordination, depending on conditions.

### Gaseous alane

Monomeric AlH
3 has been isolated at low temperature in a solid noble gas matrix. It was shown to be planar.[3] The dimeric form, Al

6, has been isolated in solid hydrogen. It is isostructural with diborane (B

6) and digallane (Ga

6).[4][5][6]

### Solid alane

Solid alane, which is colorless and nonvolatile, precipitates from ethereal solutions over the course of hours at room temperature. Numerous polymorphs can be obtained, which have been labeled α-, α'-, β-, γ-, ε-, and ζ-alanes.[7] The best characterized solid alane is α-alane. According to X-ray crystallography, adopts a cubic or rhombohedral morphology. It features octahedral AlH6 centers interconnected by Al-H-Al bridges. The Al-H distances are all equivalent (172 pm) and the Al-H-Al angles are 141°.[8] α'-Alane forms needle-like crystals, and γ-alane forms bundles of fused needles.

Crystallographic Structure of α-AlH
3[9]

The α-AlH
3 unit cell | Aluminium coordination  | Hydrogen coordination
150px  | 125px  | 150px

## Handling

Alane is not spontaneously flammable.[10] Even so, it should be handled like Li[AlH
4] (the chemical reagent, lithium aluminium hydride) as its reactivity is comparable to this related reducing reagent.[2] For these reagents, both preparations in solutions and isolated solids are "highly flammable and must be stored in the absence of moisture".[11] Laboratory guides recommend alane use inside a fume hood.[2] Solids of this reagent type carry recommendations of handling "in a glove bag or dry box".[11] After use, solution containers are typically sealed tightly with concomitant flushing with inert gas to exclude the oxygen and moisture of ambient air.[11]

Passivation[clarification needed] greatly diminishes the decomposition rate associated with alane preparations. Passivated alane nevertheless retains a hazard classification of 4.3 (chemicals which in contact with water, emit flammable gases).[12]

### Reported accidents

Alane reductions are believed to proceed via an intermediate coordination complex, with aluminum attached to the partially reduced functional group, and liberated when the reaction undergoes protic quenching. If the substrate is also fluorinated, the intermediate may explode if exposed to a hot spot above 60 °C.[13]

In 1964, a lab explosion was reported during the reduction of perfluorosuccinimide using lithium aluminum hydride, which produces similar aluminum hydride complexes. Following the explosion, the lab tested various LAH complexes containing perfluorinated substrates, each of which were found to be explosive.[14]

In 2020, a lab reported an explosion when cold methanol was used to quench a solution containing alane complexed with a perfluorinated nitrile.[13]

## Preparation

Many different Synthesis processes of Aluminium hydride uses Li[AlH4] which can be synthesized by the following process under high pressure and temperature in step 1 and a salt metathesis reaction in step 2:

[Step 1] Na + Al + 2H
2 → Na[AlH

[Step 2] Na[AlH
4] + LiCl → Li[AlH
4] + NaCl

Aluminium hydrides and various complexes thereof have long been known.[15] Its first synthesis was published in 1947, and a patent for the synthesis was assigned in 1999.[16][17] Aluminium hydride is prepared by treating lithium aluminium hydride with aluminium trichloride.[18] The procedure is intricate: attention must be given to the removal of lithium chloride.

3 Li[AlH
4] + AlCl
3 → 4 AlH
3 \+ 3 LiCl

The ether solution of alane requires immediate use, because polymeric material rapidly precipitates as a solid. Aluminium hydride solutions are known to degrade after 3 days. Aluminium hydride is more reactive than Li[AlH
4].[19]

Several other methods exist for the preparation of aluminium hydride:

2 Li[AlH
4] + BeCl
2 → 2 AlH
3 \+ Li
2[BeH
2Cl

2 Li[AlH
4] + H
2SO
4 → 2 AlH
3 \+ Li
2SO
4 \+ 2 H

2 Li[AlH
4] + ZnCl
2 → 2 AlH
3 \+ 2 LiCl + ZnH

2 Li[AlH
4] + I
2 → 2 AlH
3 \+ 2 LiI + H

2 Li[AlH
4] + CH
3COOH → 2 AlH
3 \+ Li[CH
3CH
2O] + LiOH

### Electrochemical synthesis

Several groups have shown that alane can be produced electrochemically.[20][21][22][23][24] Different electrochemical alane production methods have been patented.[25][26] Electrochemically generating alane avoids chloride impurities. Two possible mechanisms are discussed for the formation of alane in Clasen's electrochemical cell containing THF as the solvent, sodium aluminium hydride as the electrolyte, an aluminium anode, and an iron (Fe) wire submerged in mercury (Hg) as the cathode. The sodium forms an amalgam with the Hg cathode preventing side reactions and the hydrogen produced in the first reaction could be captured and reacted back with the sodium mercury amalgam to produce sodium hydride. Clasen's system results in no loss of starting material. For insoluble anodes, reaction 1 occurs, while for soluble anodes, anodic dissolution is expected according to reaction 2:

1. [AlH
4]−
− e−
\+ n THF → AlH
3 * nTHF + 1/
2 H

2. 3 [AlH
4]−
\+ Al − 3 e−
\+ 4n THF → 4 AlH
3 * nTHF

In reaction 2, the aluminium anode is consumed, limiting the production of aluminium hydride for a given electrochemical cell.

The crystallization and recovery of aluminium hydride from electrochemically generated alane has been demonstrated.[23][24]

### High pressure hydrogenation of aluminium

α-AlH
3 can be produced by hydrogenation of aluminium at 10 GPa and 600 °C (1,112 °F). The reaction between the liquified hydrogen produces α-AlH
3 which could be recovered under ambient conditions.[27]

## Reactions

### Formation of adducts with Lewis bases

AlH
3 readily forms adducts with strong Lewis bases. For example, both 1:1 and 1:2 complexes form with trimethylamine. The 1:1 complex is tetrahedral in the gas phase,[28] but in the solid phase it is dimeric with bridging hydrogen centres, [(CH

3NAlH
2(μ-H)]
2.[29] The 1:2 complex adopts a trigonal bipyramidal structure.[28] Some adducts (e.g. dimethylethylamine alane, (CH
3CH
2)(CH

2N * AlH
3) thermally decompose to give aluminium and may have use in MOCVD applications.[30]

Its complex with diethyl ether forms according to the following stoichiometry:

AlH
3 \+ (CH
3CH

2O → (CH
3CH

2O * AlH

Similar adducts are assumed to form when alane is generated in THF from lithium aluminium hydride.

The reaction with lithium hydride in ether produces lithium aluminium hydride:

AlH
3 \+ LiH → Li[AlH

Various alanates have been characterized beyond lithium aluminium hydride. They tend to feature five- and six-coordinate Al centers: Na3AlH6, Ca(AlH4))2, SrAlH5).[31]

### Reduction of functional groups

Alane and its derivatives are reducing reagents in organic synthesis based around group 13 hydrides.[32] In solution—typically in ethereal solvents such tetrahydrofuran or diethyl ether—aluminium hydride forms complexes with Lewis bases, and reacts selectively with particular organic functional groups (e.g., with carboxylic acids and esters over organic halides and nitro groups), and although it is not a reagent of choice, it can react with carbon-carbon multiple bonds (i.e., through hydroalumination). Given its density, and with hydrogen content on the order of 10% by weight,[7] some forms of alane are, as of 2016,[33] active candidates for storing hydrogen and so for power generation in fuel cell applications, including electric vehicles.[not verified in body] As of 2006 it was noted that further research was required to identify an efficient, economical way to reverse the process, regenerating alane from spent aluminium product.

In organic chemistry, aluminium hydride is mainly used for the reduction of functional groups.[34] In many ways, the reactivity of aluminium hydride is similar to that of lithium aluminium hydride. Aluminium hydride will reduce aldehydes, ketones, carboxylic acids, anhydrides, acid chlorides, esters, and lactones to their corresponding alcohols. Amides, nitriles, and oximes are reduced to their corresponding amines.

In terms of functional group selectivity, alane differs from other hydride reagents. For example, in the following cyclohexanone reduction, lithium aluminium hydride gives a trans:cis ratio of 1.9 : 1, whereas aluminium hydride gives a trans:cis ratio of 7.3 : 1.[35]

Stereoselective reduction of a substituted cyclohexanone using aluminium hydride

Alane enables the hydroxymethylation of certain ketones (that is the replacement of C–H by C–CH
2OH at the alpha position).[36] The ketone itself is not reduced as it is "protected" as its enolate.

Functional Group Reduction using aluminium hydride

Organohalides are reduced slowly or not at all by aluminium hydride. Therefore, reactive functional groups such as carboxylic acids can be reduced in the presence of halides.[2]

Functional Group Reduction using aluminium hydride

Aluminium hydride reduces esters in the presence of nitro groups.[2]

Ester reduction using aluminium hydride

Aluminium hydride reduces acetals to half protected diols.[2]

Acetal reduction using aluminium hydride

Aluminium hydride reduces epoxides to their corresponding alcohols:[2]

Epoxide reduction using aluminium hydride

The allylic rearrangement reaction carried out using aluminium hydride is a SN2 reaction, and it is not sterically demanding:[2]

Phosphine reduction using aluminium hydride

4 AlH
3 \+ 3 CO
2 → 3 CH
4 \+ 2 Al

### Hydroalumination

Akin to hydroboration, aluminium hydride can, in the presence of titanium tetrachloride, add across multiple bonds.[37][38] When the multiple bond in question is a propargylic alcohols, the results are Alkenylaluminium compounds.[39]

Hydroalumination of 1-hexene

### Fuel

| Parts of this chemistry (those related to section) need to be updated. Please update this chemistry to reflect recent events or newly available information. (July 2022)

|

In its passivated form, alane is an active candidate for storing hydrogen, and can be used for efficient power generation via fuel cell applications, including fuel cell and electric vehicles and other lightweight power applications.[40] AlH
3 contains up 10.1% hydrogen by weight (at a density of 1.48 grams per milliliter),[7] or twice the hydrogen density of liquid H
2. As of 2006, AlH
3 was described as a candidate for which "further research w[ould] be required to develop an efficient and economical process to regenerate [it] from the spent Al powder".[7][needs update]

Alane is also a potential additive to solid rocket fuel and to explosive and pyrotechnic compositions due to its high hydrogen content and low dehydrogenation temperature.[40] In its unpassivated form, alane is also a promising rocket fuel additive, capable of delivering impulse efficiency gains of up to 10%.[41] However, AlH
3 can degrade when stored at room temperature, and some of its crystal forms have "poor compatibility" with some fuel components.[40]

### Deposition

Heated alane releases hydrogen gas and produces a very fine thin film of aluminum metal that can be deposited onto other materials.[42]

## References

1. ↑ 1.0 1.1 Favre, Henri A.; Powell, Warren H. (2014). Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. p. 375. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4. "The name ‘alane’ has been used, but must also be discarded because its systematically derived substituent group, H2Al–, would be named ‘alanyl’, the well entrenched name for the acyl group derived from the amino acid alanine. The name alumane has no negative connotation."
2. ↑ 2.0 2.1 2.2 2.3 2.4 2.5 2.6 2.7 Galatsis, P; Sintim, Herman O.; Wang J. (15 September 2008). "Aluminum Hydride". Encyclopedia of Reagents for Organic Synthesis (online ed.). New York, N.Y.: John Wiley & Sons. doi:10.1002/047084289X.ra082.pub2. ISBN 978-0-471-93623-7. https://onlinelibrary.wiley.com/doi/10.1002/047084289X.ra082.pub2. Retrieved 28 July 2022.
3. ↑ Kurth, F. A.; Eberlein, R. A.; Schnöckel, H.-G.; Downs, A. J.; Pulham, C. R. (1993). "Molecular Aluminium Trihydride, AlH3: Generation in a Solid Noble Gas Matrix and Characterisation by its Infrared Spectrum and ab initio Calculations". Journal of the Chemical Society, Chemical Communications 1993 (16): 1302–1304. doi:10.1039/C39930001302. (Abstract) Broad-band photolysis of a solid noble gas matrix containing Al atoms and H2 gives rise to the planar, monomeric AlH3 molecule.
4. ↑ Andrews, Lester; Wang Xuefeng (2003). "The Infrared Spectrum of Al2H6 in Solid Hydrogen". Science 299 (5615): 2049–2052. doi:10.1126/science.1082456. PMID 12663923. Bibcode: 2003Sci...299.2049A. See also emendations at doi:10.1126/science.300.5620.741a.
5. ↑ Pulham, C. R.; Downs, A. J.; Goode, M. J.; Rankin D. W. H.; Robertson, H. E. (1991). "Gallane: Synthesis, Physical and Chemical Properties, and Structure of the Gaseous Molecule Ga2H6 as Determined by Electron Diffraction". Journal of the American Chemical Society 113 (14): 5149–5162. doi:10.1021/ja00014a003. Bibcode: 1991JAChS.113.5149P.
6. ↑ Housecroft, Catherine (2018). Inorganic Chemistry (5th ed.). Pearson. p. 397. ISBN 978-1-292-13414-7.
7. ↑ 7.0 7.1 7.2 7.3 Graetz, J..; Reilly, J..; Sandrock, G..; Johnson, J..; Zhou, W.-M.; Wegrzyn, J. (2006). ﻿Aluminum Hydride, A1H3, As a Hydrogen Storage Compound﻿ (Report). Washington, D.C.: Office of Science and Technical Information [OSTI]. doi:10.2172/899889. https://www.osti.gov/biblio/899889-UGd8IT/. Retrieved 28 July 2022.
8. ↑ Turley & Rinn 1969. (Abstract) "The final Al⋯H distance of 1.72 Å, the participation of each Al in six bridges, and the equivalence of all Al⋯H distances suggest that 3c-2e bonding occurs." Angle is lasted as "Al(6)-H(5)-Al(4)" in Table IV.
9. ↑ Turley, J. W.; Rinn, H. W. (1969). "The Crystal Structure of Aluminum Hydride". Inorganic Chemistry 8 (1): 18–22. doi:10.1021/ic50071a005.
10. ↑ Galatsis, Sintim & Wang 2008, which describes the phenomenon using the synonym "inflammable".
11. ↑ 11.0 11.1 11.2 Paquette, L. A.; Ollevier, T.; Desyroy, V. (15 October 2004). "Lithium Aluminum Hydride". Encyclopedia of Reagents for Organic Synthesis (online ed.). New York, N.Y.: John Wiley & Sons. doi:10.1002/047084289X.rl036.pub2. ISBN 0-471-93623-5. https://onlinelibrary.wiley.com/doi/10.1002/047084289X.rl036.pub2. Retrieved 28 July 2022.
12. ↑ 2013 CFR Title 29 Volume 6 Section 1900.1200 Appendix B.12
13. ↑ 13.0 13.1 Taydakov, Ilya V. (2020-07-08). "Serious Explosion during Large-Scale Preparation of an Amine by Alane (AlH3) Reduction of a Nitrile Bearing a CF3 Group". ACS Chemical Health & Safety (American Chemical Society (ACS)) 27 (4): 235–239. doi:10.1021/acs.chas.0c00045. ISSN 1871-5532.
14. ↑ "SAFETY FORUM". Chemical & Engineering News Archive 29 (30): 3042. 1951-07-23. doi:10.1021/cen-v029n030.p3042. ISSN 0009-2347.
15. ↑ Brower, F. M.; Matzek, N. E.; Reigler, P. F.; Rinn, H. W.; Schmidt, D. L.; Snover, J. A.; Terada, K. (1976). "Preparation and Properties of Aluminum Hydride". Journal of the American Chemical Society 98 (9): 2450–2454. doi:10.1021/ja00425a011. Bibcode: 1976JAChS..98.2450B.
16. ↑ Finholt, A. E.; Bond, A. C. Jr.; Schlesinger, H. I. (1947). "Lithium Aluminum Hydride, Aluminum Hydride and Lithium Gallium Hydride, and Some of their Applications in Organic and Inorganic Chemistry". Journal of the American Chemical Society 69 (5): 1199–1203. doi:10.1021/ja01197a061. Bibcode: 1947JAChS..69.1199F.
17. ↑ Petrie, M. A.; Bottaro, J. C.; Schmitt, R. J.; Penwell, P. E.; Bomberger, D. C., "Preparation of Aluminum Hydride Polymorphs, Particularly Stabilized α-AlH3", US patent 6228338, issued 2001-05-08
18. ↑ Schmidt, D. L.; Roberts, C. B.; Reigler, P. F.; Lemanski, M. F. Jr.; Schram, E. P. (1973). "Aluminum Trihydride-diethyl etherate ( Etherated Alane )". Inorganic Syntheses. 14. pp. 47–52. doi:10.1002/9780470132456.ch10. ISBN 978-0-470-13245-6.
19. ↑ Lund, G. K.; Hanks, J. M.; Johnston, H. E., "Method for the Production of α-Alane.", US patent application 2007066839
20. ↑ Alpatova, N. M.; Dymova, T. N.; Kessler, Yu. M.; Osipov, O. R. (1968). "Physicochemical Properties and Structure of Complex Compounds of Aluminium Hydride". Russian Chemical Reviews 37 (2): 99–114. doi:10.1070/RC1968v037n02ABEH001617. Bibcode: 1968RuCRv..37...99A.
21. ↑ Semenenko, K. N.; Bulychev, B. M.; Shevlyagina, E. A. (1966). "Aluminium Hydride". Russian Chemical Reviews 35 (9): 649–658. doi:10.1070/RC1966v035n09ABEH001513. Bibcode: 1966RuCRv..35..649S.
22. ↑ Osipov, O. R.; Alpatova, N. M.; Kessler, Yu. M. (1966). "none". Elektrokhimiya 2: 984.
23. ↑ 23.0 23.1 Zidan, R.; Garcia-Diaz, B. L.; Fewox, C. S.; Stowe, A. C.; Gray, J. R.; Harter, A. G. (2009). "Aluminium hydride: a reversible material for hydrogen storage". Chemical Communications (25): 3717–3719. doi:10.1039/B901878F. PMID 19557259. https://zenodo.org/record/1229996.
24. ↑ 24.0 24.1 Martinez-Rodriguez, M. J.; Garcia-Diaz, B. L.; Teprovich, J. A.; Knight, D. A.; Zidan, R. (2012). "Advances in the electrochemical regeneration of aluminum hydride". Applied Physics A: Materials Science & Processing 106 (25): 545–550. doi:10.1007/s00339-011-6647-y. Bibcode: 2012ApPhA.106..545M.
25. ↑ Clasen, H., "Verfahren zur Herstellung von Aluminiumhydrid bzw. aluminiumwasserstoffreicher komplexer Hydride", DE patent 1141623, issued 1962-12-27, assigned to Metallgesellschaft
26. ↑ Zidan, R., "Electrochemical process and production of novel complex hydrides", US patent 8470156, issued 2013-06-25, assigned to Savannah River Nuclear Solutions, LLC
27. ↑ Saitoh, H; Sakurai, Y; Machida, A; Katayama, Y; Aoki, K (2010). "In situX-ray diffraction measurement of the hydrogenation and dehydrogenation of aluminum and characterization of the recovered AlH3". Journal of Physics: Conference Series 215 (1). doi:10.1088/1742-6596/215/1/012127. ISSN 1742-6596. Bibcode: 2010JPhCS.215a2127S.
28. ↑ 28.0 28.1 Greenwood, Norman N.; Earnshaw, Alan (1997). Chemistry of the Elements (2nd ed.). Butterworth-Heinemann. ISBN 978-0-08-037941-8.
29. ↑ Atwood, J. L.; Bennett, F. R.; Elms, F. M.; Jones, C.; Raston, C. L.; Robinson, K. D. (1991). "Tertiary Amine Stabilized Dialane". Journal of the American Chemical Society 113 (21): 8183–8185. doi:10.1021/ja00021a063. Bibcode: 1991JAChS.113.8183A.
30. ↑ Yun, J.-H.; Kim, B.-Y.; Rhee, S.-W. (1998). "Metal-Organic Chemical Vapor Deposition of Aluminum from Dimethylethylamine Alane". Thin Solid Films 312 (1–2): 259–263. doi:10.1016/S0040-6090(97)00333-7. Bibcode: 1998TSF...312..259Y.
31. ↑ Suárez-Alcántara, Karina; Tena-Garcia, Juan Rogelio; Guerrero-Ortiz, Ricardo (2019). "Alanates, a Comprehensive Review". Materials 12 (17): 2724. doi:10.3390/ma12172724. PMID 31450714. Bibcode: 2019Mate...12.2724S.
32. ↑ Brown, H. C.; Krishnamurthy, S. (1979). "Forty Years of Hydride Reductions". Tetrahedron 35 (5): 567–607. doi:10.1016/0040-4020(79)87003-9.
33. ↑ Lin-Lin Wang; Aditi Herwadkar; Jason M. Reich; Duane D. Johnson; Stephen D. House; Pamela Peña-Martin; Angus A. Rockett; Ian M. Robertson et al. (2016). "Towards Direct Synthesis of Alane: A Predicted Defect-Mediated Pathway Confirmed Experimentally". ChemSusChem 9 (17): 2358–2364. doi:10.1002/cssc.201600338. PMID 27535100. Bibcode: 2016ChSCh...9.2358W. https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/cssc.201600338.
34. ↑ Galatsis, P. (2001). Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rd245. ISBN 978-0-470-84289-8.
35. ↑ Ayres, D. C.; Sawdaye, R. (1967). "The Stereoselective Reduction of Ketones by Aluminium Hydride". Journal of the Chemical Society B 1967: 581–583. doi:10.1039/J29670000581.
36. ↑ Corey, E. J.; Cane, D. E. (1971). "Controlled Hydroxymethylation of Ketones". Journal of Organic Chemistry 36 (20): 3070. doi:10.1021/jo00819a047.
37. ↑ Sato, F.; Sato, S.; Kodama, H.; Sato, M. (1977). "Reactions of Lithium Aluminum Hydride or Alane with Olefins Catalyzed by Titanium Tetrachloride or Zirconium Tetrachloride. A Convenient Route to Alkanes, 1-Haloalkanes and Terminal Alcohols from Alkenes". Journal of Organometallic Chemistry 142 (1): 71–79. doi:10.1016/S0022-328X(00)91817-5.
38. ↑ Smith (2020), March's Advanced Organic Chemistry, rxn. 15-12.
39. ↑ Corey, E. J.; Katzenellenbogen, J. A.; Posner, G. H. (1967). "New Stereospecific Synthesis of Trisubstituted Olefins. Stereospecific Synthesis of Farnesol". Journal of the American Chemical Society 89 (16): 4245–4247. doi:10.1021/ja00992a065. Bibcode: 1967JAChS..89.4245C.
40. ↑ 40.0 40.1 40.2 Liu, Y.; Yang, F.; Zhang, Y.; Wu, Z.; Zhang, Z. (2024). "AlH3 as High-Energy Fuels for Solid Propellants: Synthesis, Thermodynamics, Kinetics, and Stabilization." (in English). Compounds 4 (2): 230–251. doi:10.3390/compounds4020012.
41. ↑ Calabro, M. (2011). "Overview of Hybrid Propulsion". Progress in Propulsion Physics 2: 353–374. doi:10.1051/eucass/201102353. ISBN 978-2-7598-0673-7. Bibcode: 2011EUCAS...2..353C.
42. ↑ Housecroft, C. E.; Sharpe, A. G. (2018). Inorganic Chemistry (5th ed.). Prentice-Hall. p. 401. ISBN 978-0-273-74275-3.

## Further reading

* Schmidt, Eckart W. (2022). "Metals of the 2nd and 3rd Row and their Hydrides". Encyclopedia of Liquid Fuels. De Gruyter. pp. 3799–3827. doi:10.1515/9783110750287-032. ISBN 978-3-11-075028-7.

## External links

* Aluminium Hydride on EnvironmentalChemistry.com Chemical Database
* Hydrogen Storage from Brookhaven National Laboratory
* Aluminum Trihydride on WebElements

* v
* t
* e

Aluminium compounds

Al(I)|

* AlBr
* AlCl
* AlF
* AlI
* Al2O

Al(II)|

* AlB2
* AlB12
* AlO

Al(III)|

* AlAs
* Al(BH4)3
* AlBr3
* AlCl3
* AlF3
* AlH3
* AlI3
* AlN
* Al(NO3)3
* Al2(CO3)3
* Al(OH)3
* Al(OH)2OAc
* Al(OH)(OAc)2
* Al(OAc)3
* Al2SO4(OAc)4
* AlP
* AlPO4
* AlSb
* Al(C5H7O2)3
* Al(MnO4)3
* Al2(MoO4)3
* Al2O3
* Al2S3
* Al2(SO4)3
* Al2Se3
* Al2Te3
* Al2SiO5
* Al4C3
* AlOHO
* Al(OH)2CO2C17H5
* NaAlH2(OC2H4OCH3)2
* LiAlH2(OC2H4OCH3)2

| Alums|

* (NH4)Al(SO4)2
* KAl(SO4)2
* NaAl(SO4)2

|

Organoaluminium(III) compounds|

* (Al(CH3)3)2
* (Al(C2H5)3)2
* Al(CH2CH(CH3)2)3
* Al(C2H5)2Cl
* Al(C2H5)2CN
* Al(CH2CH(CH3)2)2H
* Al(C2H5)2Cl2C2H5Cl
* Ti(C5H5)2CH2ClAl(CH3)2

* v
* t
* e

Binary compounds of hydrogen

Alkali metal (Group 1) hydrides|

* LiH
* NaH
* KH
* RbH
* CsH

Lithium hydride, LiH
ionic metal hydride

Beryllium hydride
Left (gas phase): BeH2
covalent metal hydride
Right: (BeH2)n (solid phase)
polymeric metal hydride

Borane and diborane
Left: BH3 (special conditions), covalent metalloid hydride
Right: B2H6 (standard conditions), dimeric metalloid hydride

Methane, CH4
covalent nonmetal hydride

Ammonia, NH3
covalent nonmetal hydride

Water, H2O
covalent nonmetal hydride

Hydrogen fluoride, HF
covalent nonmetal hydride

Alkaline (Group 2) earth hydrides|

| Monohydrides|

* BeH
* MgH
* CaH
* SrH
* BaH

|

Dihydrides|

* BeH2
* MgH2
* CaH2
* SrH2
* BaH2

|

Group 13 hydrides|

| Boranes|

* BH3
* B2H6
* B2H2
* B2H4
* B4H10
* B5H9
* B5H11
* B6H10
* B6H12
* B10H14
* B18H22

|

Alanes|

* AlH3
* Al2H6

|

Gallanes|

* GaH3
* Ga2H6

|

Indiganes|

* InH3
* In2H6

|

Thallanes|

* TlH3
* Tl2H6

|

Group 14 hydrides|

| Linear alkanes|

* CH4
* C2H6
* C3H8
* C4H10
* C5H12
* C6H14
* C7H16
* C8H18
* C9H20
* C10H22
* more...

|

Linear alkenes|

* C2H4
* C3H6
* C4H8
* C5H10
* C6H12
* C7H14
* C8H16
* C9H18
* C10H20
* more...

|

Linear alkynes|

* C2H2
* C3H4
* C4H6
* C5H8
* C6H10
* C7H12
* C8H14
* C9H16
* C10H18
* more...

|

Silanes|

* SiH4
* Si2H6
* Si3H8
* Si4H10
* Si5H12
* Si6H14
* Si7H16
* Si8H18
* Si9H20
* Si10H22
* more...

|

Silenes|

* Si2H4

|

Silynes|

* Si2H2
* SiH

|

Germanes|

* GeH4
* Ge2H6
* Ge3H8
* Ge4H10
* Ge5H12

|

Stannanes|

* SnH4
* Sn2H6

|

Plumbanes|

* PbH4

|

* CH
* CH2
* CH3
* C2H
* Cycloalkanes
* Cycloalkenes
* Annulenes
* Many more

Pnictogen (Group 15) hydrides|

| Azanes|

* NH3
* N2H4
* N3H5
* N4H6
* N5H7
* N6H8
* N7H9
* N8H10
* N9H11
* N10H12
* more...

|

Azenes|

* N2H2
* N3H3
* N4H4

|

Phosphanes|

* PH3
* P2H4
* P3H5
* P4H6
* P5H7
* P6H8
* P7H9
* P8H10
* P9H11
* P10H12
* more...

|

Phosphenes|

* P2H2
* P3H3
* P4H4

|

Arsanes|

* AsH3
* As2H4

|

Stibanes|

* SbH3

|

Bismuthanes|

* BiH3

|

* HN3
* NH
* radical

Hydrogen chalcogenides (Group 16 hydrides)|

| Polyoxidanes|

* H2O
* H2O2
* H2O3
* H2O4
* H2O5
* H2O6
* H2O7
* H2O8
* H2O9
* H2O10
* more...

|

Polysulfanes|

* H2S
* H2S2
* H2S3
* H2S4
* H2S5
* H2S6
* H2S7
* H2S8
* H2S9
* H2S10
* more...

|

Selanes|

* H2Se
* H2Se2

|

Tellanes|

* H2Te
* H2Te2

|

Polanes|

* PoH2

|

* HO
* HO2
* HO3
* H2O+–O–
* H2S=S
* (HS)2S+–S–
* HS
* HDO
* D2O
* T2O

Hydrogen halides (Group 17 hydrides)|

* HF
* HCl
* HBr
* HI
* HAt

Transition metal hydrides|

* ScH2
* YH2
* YH3
* TiH2
* ZrH2
* HfH2
* VH
* VH2
* NbH
* NbH2
* TaH
* CrH
* CrH2
* CrHx
* NiH
* PdHx (x < 1)
* FeH
* FeH2
* FeH5
* CuH
* ZnH2
* CdH2
* HgH2

Lanthanide hydrides|

* LaH2
* LaH3
* LaH10
* CeH2
* CeH3
* PrH2
* PrH3
* NdH2
* NdH3
* SmH2
* SmH3
* EuH2
* GdH2
* GdH3
* TbH2
* TbH3
* DyH2
* DyH3
* HoH2
* HoH3
* ErH2
* ErH3
* TmH2
* TmH3
* YbH2
* YbH2.5
* LuH2
* LuH3

Actinide hydrides|

* AcH2
* ThH2
* Th4H15
* PaH3
* UH3
* NpH2
* NpH3
* PuH2
* PuH3
* AmH2
* AmH3
* CmH2

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