Diisopropylamine

Names
Preferred IUPAC name

N-(Propan-2-yl)propan-2-amine

Other names

Di(propan-2-yl)amine
N-Isopropylpropan-2-amine
(Diisopropyl)amine
(The name diisopropylamine is deprecated.)

Identifiers

CAS Number

* 108-18-9 Y

3D model (JSmol)

* Interactive image

Beilstein Reference

| 605284
ChemSpider |

* 7624 Y

EC Number |

* 203-558-5

PubChem CID

* 7912

RTECS number |

* IM4025000

UNII |

* BR9JLI40NO Y

UN number | 1158

InChI

* InChI=1S/C6H15N/c1-5(2)7-6(3)4/h5-7H,1-4H3 Y

Key: UAOMVDZJSHZZME-UHFFFAOYSA-N Y

SMILES

* CC(C)NC(C)C

Properties

Chemical formula

| C6H15N
Molar mass | 101.193 g·mol−1
Appearance  | Colorless liquid
Odor | Fishy, ammoniacal
Density | 0.722 g mL−1
Melting point |  −61.00 °C; −77.80 °F; 212.15 K
Boiling point |  83 to 85 °C; 181 to 185 °F; 356 to 358 K

Solubility in water

| miscible[1]
Vapor pressure | 9.3 kPa (at 20°C)[2]
Acidity (pKa)  | 11.07 (in water) (conjugate acid)
Basicity (pKb)  | 3.43[2]

Refractive index (nD)

| 1.392–1.393
Thermochemistry

Std enthalpy of
formation (ΔfH⦵298)

| −173.6 to −168.4 kJ mol−1

Std enthalpy of
combustion (ΔcH⦵298)

| −4.3363 to −4.3313 MJ mol−1
Hazards
GHS pictograms |
GHS Signal word | DANGER

GHS hazard statements

| H225, H302, H314, H332

GHS precautionary statements

| P210, P280, P305+351+338, P310
NFPA 704 (fire diamond)  |

Flash point |  −17 °C (1 °F; 256 K)

Autoignition
temperature

|  315 °C (599 °F; 588 K)
Explosive limits | 1.1–7.1%[1]
Lethal dose or concentration (LD, LC):

LD50 (median dose)

* 770 mg kg−1 (oral, rat)
* >10 g kg−1 (dermal, rabbit)

LC50 (median concentration)

| 1140 ppm (rat, 2 hr)
1000 ppm (mouse, 2 hr)[3]

LCLo (lowest published)

| 2207 ppm (rabbit, 2.5 hr)
2207 ppm (guinea pig, 80 min)
2207 ppm (cat, 72 min)[3]
NIOSH (US health exposure limits):

PEL (Permissible)

| TWA 5 ppm (20 mg/m3) [skin][1]

REL (Recommended)

| TWA 5 ppm (20 mg/m3) [skin][1]

IDLH (Immediate danger)

| 200 ppm[1]
Related compounds

Related amines

* Dimethylamine
* Diethylamine

Related compounds

* Triisopropylamine
* N,N-Diisopropylethylamine

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

N verify (what is YN ?)
Infobox references

Tracking categories (test):

* SizeSet

Diisopropylamine is a secondary amine with the chemical formula (Me2CH)2NH (Me = methyl). Diisopropylamine is a colorless liquid with an ammonia-like odor. Its lithium derivative, lithium diisopropylamide, known as LDA is a widely used reagent.

## Contents

* 1 Reactions and use
* 2 Preparation
* 3 Toxicity
* 4 References

## Reactions and use

Diisopropylamine is a common amine nucleophile in organic synthesis.[4] Because it is bulky, it is a more selective nucleophile than other similar amines, such as dimethylamine.[5]

It reacts with organolithium reagents to give lithium diisopropylamide (LDA). LDA is a strong, non-nucleophilic base[6]

The main commercial applications of diisopropylamine is as a precursor to the herbicide, diallate and triallate as well as certain sulfenamides used in the vulcanization of rubber.[7]

It is also used to prepare N,N-Diisopropylethylamine (Hünig's base) by alkylation with diethyl sulfate.[8]

The bromide salt of diisopropylamine, diisopropylammonium bromide, is a room-temperature organic ferroelectric material.[9]

## Preparation

Diisopropylamine, which is commercially available, may be prepared by the reductive amination of acetone with ammonia using a modified copper oxide, generally copper chromite, as a catalyst:[10][11]

3 \+ 2 (CH

2CO + 2 H
2 → C

15N + 2 H

Diisopropylamine can be dried by distillation from potassium hydroxide (KOH) or drying over sodium wire.[12](p186)

## Toxicity

Diisopropylamine causes burns by all exposure routes. Inhalation of high concentrations of its vapor may cause symptoms like headache, dizziness, tiredness, nausea and vomiting.

## References

1. ↑ 1.0 1.1 1.2 1.3 1.4 NIOSH Pocket Guide to Chemical Hazards. "#0217". National Institute for Occupational Safety and Health (NIOSH). https://www.cdc.gov/niosh/npg/npgd0217.html.
2. ↑ 2.0 2.1 Template:Pubchem
3. ↑ 3.0 3.1 "Diisopropylamine". Immediately Dangerous to Life and Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH). https://www.cdc.gov/niosh/idlh/108189.html.
4. ↑ John E. McMurry, Jack Melton (1977). "Conversion of Nitro to Carbonyl by Ozonolysis of Nitronates: 2,5-Heptanedione". Organic Syntheses 56: 36. doi:10.15227/orgsyn.056.0036.
5. ↑ Denmark, Scott; Ryabchuk, Pavel; Min Chi, Hyung; Matviitsuk, Anastassia (2019). "Preparation of a Diisopropylselenophosphoramide Catalyst and its Use in Enantioselective Sulfenoetherification". Organic Syntheses 96: 400–417. doi:10.15227/orgsyn.096.0400. PMID 34526731.
6. ↑ George M. Rubottom, John M. Gruber, Henrik D. Juve, Jr, , Dan A. Charleson (1986). "α-Hydroxy Ketones from the Oxidation of Enol Silyl Ethers with m-Chloroperbenzoic Acid: 6-Hydroxy- 3,5,5-trimethyl-2-cyclohexen-1-one". Organic Syntheses 64: 118. doi:10.15227/orgsyn.064.0118.
7. ↑ Eller, Karsten; Henkes, Erhard; Rossbacher, Roland; Höke, Hartmut (2000-06-15). "Amines, Aliphatic". Amines, Aliphatic. Wiley-VCH. doi:10.1002/14356007.a02_001. ISBN 978-3527303854.
8. ↑ Hünig, Siegfried; Kiessel, Max (1958-04-01). "Spezifische Protonenacceptoren als Hilfsbasen bei Alkylierungs- und Dehydrohalogenierungsreaktionen" (in de). Chemische Berichte (Wiley-VCH) 91 (2): 380-392. doi:10.1002/cber.19580910223. ISSN 0009-2940. OCLC 889715844.
9. ↑ Fu, Da-Wei; Cai, Hong-Ling; Liu, Yuanming; Ye, Qiong; Zhang, Wen et al. (2013-01-25). "Diisopropylammonium Bromide Is a High-Temperature Molecular Ferroelectric Crystal" (in en). Science 339 (6118): 425-428. doi:10.1126/science.1229675. ISSN 0036-8075. OCLC 1644869. PMID 23349285. Bibcode: 2013Sci...339..425F.
10. ↑ Löffler, Karl (1910-04-01). "Über eine neue Bildungsweise primärer und sekundärer Amine aus Ketonen" (in de). Berichte der Deutschen Chemischen Gesellschaft 43 (2): 2031–2035. doi:10.1002/cber.191004302145. ISSN 0365-9496. OCLC 219854722. https://zenodo.org/record/1426399.
11. ↑ Willard Bull, "One-step process for preparing diisopropylamine", US patent 2686811
12. ↑ Armarego, W. L. F.; Perrin, D. D. (1996-10-16). Purification of Laboratory Chemicals (4th ed.). Butterworth-Heinemann. ISBN 978-0750628396. OCLC 762966259.

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*[CID]: Compound ID
*[H225]: Highly flammable liquid and vapour
*[H302]: Harmful if swallowed
*[H314]: Causes severe skin burns and eye damage
*[H332]: Harmful if inhaled
*[P210]: Keep away from heat/sparks/open flames/hot surfaces – No smoking
*[P280]: Wear protective gloves/protective clothing/eye protection/face protection
*[P305+351+338]: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do – continue rinsing
*[P310]: Immediately call a POISON CENTER or doctor/physician