1,2,4-Butanetriol trinitrate

Names
Preferred IUPAC name

Butane-1,2,4-triyl trinitrate

Identifiers

CAS Number

* 6659-60-5 N

3D model (JSmol)

* Interactive image

ChemSpider |

* 455532 Y

EC Number |

* 229-697-1

PubChem CID

* 522216

UNII |

* ZV2U79W7V4 Y

InChI

* InChI=1S/C4H7N3O9/c8-5(9)14-2-1-4(16-7(12)13)3-15-6(10)11/h4H,1-3H2 Y

Key: RDLIBIDNLZPAQD-UHFFFAOYSA-N Y

* InChI=1/C4H7N3O9/c8-5(9)14-2-1-4(16-7(12)13)3-15-6(10)11/h4H,1-3H2

Key: RDLIBIDNLZPAQD-UHFFFAOYAH

SMILES

* O=[N+]([O-])OC(CCO[N+]([O-])=O)CO[N+](=O)[O-]

Properties

Chemical formula

| C4H7N3O9
Molar mass | 241.11 g/mol
Density | 1.52 g/cm3
Melting point | −27 °C
Boiling point | 230 °C (446 °F; 503 K) (explosion temperature)
Hazards
GHS pictograms |
GHS Signal word | Danger

GHS hazard statements

| HH200Script error: No such module "Preview warning".Category:GHS errors, HH300Script error: No such module "Preview warning".Category:GHS errors, HH310Script error: No such module "Preview warning".Category:GHS errors, HH330Script error: No such module "Preview warning".Category:GHS errors, HH373Script error: No such module "Preview warning".Category:GHS errors, HH411Script error: No such module "Preview warning".Category:GHS errors

GHS precautionary statements

| PP201Script error: No such module "Preview warning".Category:GHS errors, PP202Script error: No such module "Preview warning".Category:GHS errors, PP260Script error: No such module "Preview warning".Category:GHS errors, PP262Script error: No such module "Preview warning".Category:GHS errors, PP264Script error: No such module "Preview warning".Category:GHS errors, PP270Script error: No such module "Preview warning".Category:GHS errors, PP271Script error: No such module "Preview warning".Category:GHS errors, PP273Script error: No such module "Preview warning".Category:GHS errors, PP280Script error: No such module "Preview warning".Category:GHS errors, PP281Script error: No such module "Preview warning".Category:GHS errors, PP284Script error: No such module "Preview warning".Category:GHS errors, PP301+P316Script error: No such module "Preview warning".Category:GHS errors, PP302+P352Script error: No such module "Preview warning".Category:GHS errors, PP304+P340Script error: No such module "Preview warning".Category:GHS errors, PP316Script error: No such module "Preview warning".Category:GHS errors, PP319Script error: No such module "Preview warning".Category:GHS errors, PP320Script error: No such module "Preview warning".Category:GHS errors, PP321Script error: No such module "Preview warning".Category:GHS errors, PP330Script error: No such module "Preview warning".Category:GHS errors, PP361+P364Script error: No such module "Preview warning".Category:GHS errors, PP372Script error: No such module "Preview warning".Category:GHS errors, PP373Script error: No such module "Preview warning".Category:GHS errors, PP380Script error: No such module "Preview warning".Category:GHS errors, PP391Script error: No such module "Preview warning".Category:GHS errors, PP401Script error: No such module "Preview warning".Category:GHS errors

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

1,2,4-Butanetriol trinitrate (BTTN), also called butanetriol trinitrate, is an important military propellant. It is a colorless to brown explosive liquid.[2]

BTTN is used as a propellant in virtually all single-stage missiles used by the United States, including the Hellfire.[3] It is less volatile, less sensitive to shock, and more thermally stable than nitroglycerine,[4] for which it is a promising replacement.[5]

BTTN as a propellant is often used in a mixture with nitroglycerin.[4] The mixture can be made by co-nitration of butanetriol and glycerol.[6] BTTN is also used as a plasticizer in some nitrocellulose-based propellants.[7]

BTTN is manufactured by nitration of 1,2,4-butanetriol.[8] Biotechnological manufacture of butanetriol is under intensive research.[9]

## References

1. ↑ "1,2,4-Butanetriol, 1,2,4-trinitrate". https://pubchem.ncbi.nlm.nih.gov/compound/522216#section=Safety-and-Hazards.
2. ↑ Pisacane, Frank J. (1982). 1,2,4-Butanetriol: Analysis and Synthesis. PN. https://www.amazon.com/1-2-4-Butanetriol-Analysis-Synthesis/dp/B00BVD8Q06.
3. ↑ "Bacteria help make missile fuel". 2004-02-02. https://news.bbc.co.uk/2/hi/science/nature/3450853.stm.
4. ↑ 4.0 4.1 Varghese, T. L.; Krishnamurthy, V. N. (2017-01-03). The Chemistry and Technology of Solid Rocket Propellants (A Treatise on Solid Propellants). Allied Publishers. p. 187. ISBN 978-93-85926-33-4. https://books.google.com/books?id=_fmGDgAAQBAJ.
5. ↑ Bhowmik, D.; Sadavarte, V.S.; Pande, S.M.; Saraswat, B.S. (2015). "An Energetic Binder for the Formulation of Advanced Solid Rocket Propellants". Central European Journal of Energetic Materials 12 (1): 147. http://yadda.icm.edu.pl/baztech/element/bwmeta1.element.baztech-98bc795f-3fcd-4a08-9855-d57a0cdf95c3.
6. ↑ Farncomb, Robert E.; Carr, Walter A. (1987-07-06). "Patent application: Co-Nitration of 1,2,4-Butanetriol and Glycerin". http://www.dtic.mil/docs/citations/ADD013053.
7. ↑ Sutton, George P.; Biblarz, Oscar (2016-11-30). Rocket Propulsion Elements. John Wiley & Sons. ISBN 978-1-118-75391-0. https://books.google.com/books?id=uKihDQAAQBAJ.
8. ↑ Gouranlou, Farideh; Kohsary, Iraj (2010-06-01). "Synthesis and Characterization of 1,2,4-Butanetrioltrinitrate". Asian Journal of Chemistry 22: 4221–4228. https://www.researchgate.net/publication/287002330.
9. ↑ Cao, Yujin; Niu, Wei; Guo, Jiantao; Xian, Mo; Liu, Huizhou (2015-12-16). "Biotechnological production of 1,2,4-butanetriol: An efficient process to synthesize energetic material precursor from renewable biomass". Scientific Reports 5 (1). doi:10.1038/srep18149. ISSN 2045-2322. PMID 26670289. Bibcode: 2015NatSR...518149C.

## External links

* WebBook page for 1,2,4-Butanetriol, trinitrate

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*[CID]: Compound ID