2-Dimethylaminoethylazide

Names
Preferred IUPAC name 2-Azido-N,N-dimethylethan-1-amine
Other names Dimethyl(2-azidoethyl)amine
Identifiers
CAS Number	86147-04-8
3D model ( JSmol)	Interactive image
ChemSpider	11308317
PubChem CID	22280928
CompTox Dashboard ( EPA)	DTXSID40624284
InChI InChI=1S/C4H10N4/c1-8(2)4-3-6-7-5/h3-4H2,1-2H3 Key: XIXCIVDAWWCJJR-UHFFFAOYSA-N InChI=1/C4H10N4/c1-8(2)4-3-6-7-5/h3-4H2,1-2H3 Key: XIXCIVDAWWCJJR-UHFFFAOYAI
SMILES CN(C)CCN=[N+]=[N-]
Properties
Chemical formula	(CH3)2NCH2CH2N3
Molar mass	114.152 g·mol−1
Appearance	Colorless liquid
Density	0.9930 g/cm3
Melting point	−68.9 °C (−92.0 °F; 204.2 K)
Boiling point	135 °C (275 °F; 408 K)
Solubility	Acetone, ethers, alcohols, hydrocarbons, THF
Thermochemistry
Std enthalpy of formation (ΔfH⦵298)	+586 cal/g
Hazards
Flash point	29.4 °C (84.9 °F; 302.5 K)
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

2-Dimethylaminoethylazide (DMAZ) is a liquid rocket fuel being investigated for use as a spacecraft propellent to replace the toxic, carcinogenic monomethylhydrazine. ^[1] It is a member of the competitive impulse non-carcinogenic hypergol (CINCH) family which were assessed as a replacement for hydrazine-derived propellants. ^{[2] [3]} DMAZ was also found to be sensitive to impact, direct flame, shock wave, heat in confined space, and electrostatic discharge. ^[4]

Formation and reactions

This section needs expansion. You can help by adding to it. (February 2022)

DMAZ is an organic azide, which is prepared by reacting the chloride of the corresponding alkyl-amine (in this case ethylamine) with sodium azide: ^[1]

NaN₃ + NH₂CH₂CH₂−Cl → NaCl + NH₂CH₂CH₂−N₃

Ideally, the complete combustion of DMAZ produces carbon dioxide, water, and nitrogen:

2 (CH₃)₂NCH₂CH₂N₃ + 13 O₂ → 8 CO₂ + 10 H₂O + 4 N₂

Ignition delays

During their inquiry into finding alternative hypergolic fuel, a joint effort by the Aviation and Missile Research, Development, and Engineering Center (AMRDEC), the U.S. Army Research Laboratory (ARL), and the National Aeronautics and Space Administration (NASA) determined that DMAZ could perform competitively with Aerozine-50 and is less toxic than hydrazine-based fuels. ^{[4] [5]} However, DMAZ- inhibited red fuming nitric acid (IRFNA) systems have demonstrated longer ignition delays than monomethylhydrazine-IRFNA systems. In an effort to address this issue, researchers synthesized the related compounds 2-azidoethanamines – 2-azido-N-methylethanamine (MMAZ) and 2-azido-N-cyclopropylethanamine (CPAZ) in hopes of enhancing the reactivity of DMAZ's amine nitrogen to reduce ignition delays. MMAZ is not hypergolic, while CPAZ is hypergolic. ^[6]

According to research conducted by Army Research Laboratory, the azido group in DMAZ's lowest energy structure will prevent the transfer of protons from nitric acid to the amine lone pair acid, a chemical reaction that may be associated with a rate-limiting step in DMAZ-IRFNA ignition. ^[6]

However, according to a 2014 ARL report, a correlation between compound basicities and ignition delays was not observed, which indicates that the proton transfer from nitric acid to DMAZ's amine may not be a rate-controlling step in the ignition process of DMAZ-IRFNA systems. ^[7]

References