2-Dimethylaminoethylazide

September 2026 changed 271672001 DMAZ.png 150px 2-Dimethylaminoethylazide Ball and Stick.png 150px 2-Dimethylaminoethylazide Space Fill.png 150px 2-Azido-N,N-dimethylethan-1-amine Dimethyl(2-azidoethyl)amine 86147-04-8 correct FDA 4RXN7MWX34 22280928 CN(C)CCN=[N+]=[N-] 11308317 1/C4H10N4/c1-8(2)4-3-6-7-5/h3-4H2,1-2H3 XIXCIVDAWWCJJR-UHFFFAOYAI 1S/C4H10N4/c1-8(2)4-3-6-7-5/h3-4H2,1-2H3 XIXCIVDAWWCJJR-UHFFFAOYSA-N (CH3)2NCH2CH2N3 4 10 4 Colorless liquid 0.9930 g/cm3 -68.9 135 Acetone, ethers, alcohols, hydrocarbons, THF +586 cal/g 29.4 2-Dimethylaminoethylazide (DMAZ) is a liquid rocket fuel being investigated for use as a spacecraft propellent to replace the toxic, carcinogenic monomethylhydrazine. A Preliminary Technical Review of DMAZ: A Low-Toxicity Hypergolic Fuel Mellor, B. Proceedings of the 2nd International Conference on Green Propellants for Space Propulsion 557 2004 2004ESASP.557E..22M 22 It is a member of the competitive impulse non-carcinogenic hypergol (CINCH) family which were assessed as a replacement for hydrazine-derived propellants.http://www.spacedaily.com/news/fuel-00c.html Army Develops New Fuel Spacedaily.com February 23, 2000 July 12, 2014The Structure of Secondary 2-Azidoethanamines: A Hypergolic Fuel vs. a Nonhypergolic Fuel Defense Technical Information Center https://apps.dtic.mil/sti/citations/ADA421464 April 2004 Michael J. McQuaid Army Research Laboratory DMAZ was also found to be sensitive to impact, direct flame, shock wave, heat in confined space, and electrostatic discharge.Xie Hui Mu Xiaogang Zhang Yue Wang Xuanjun May 8, 2017 Theory investigation progress of DMAZ AIP Conference Proceedings 1839 1 020016 10.1063/1.4982381 2017AIPC.1839b0016X free Formation and reactions February 2022 DMAZ is an organic azide, which is prepared by reacting the chloride of the corresponding alkyl-amine (in this case dimethyl ethylamine) with sodium azide: NaN3 + N(CH3)2CH2CH2\sCl → NaCl + N(CH3)2CH2CH2\sN3 Ideally, the complete combustion of DMAZ produces carbon dioxide, water, and nitrogen: 2 (CH3)2NCH2CH2N3 + 13 O2 → 8 CO2 + 10 H2O + 4 N2 DMAZ reacts readily with nitric acid.Zhang Peng Zhang Lidong Law Chung K. 2015-01-01 Density functional theory study of the reactions of 2-azido-N,N-dimethylethanamine with nitric acid and nitrogen dioxide https://www.sciencedirect.com/science/article/pii/S0010218014001941 Combustion and Flame 162 1 237–248 10.1016/j.combustflame.2014.06.016 0010-2180 subscription 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.McQuaid Michael December 2003 Computationally Based Measures of Amine Azide Basicity and Their Correlation With Hypergolic Ignition Delays Defense Technical Information Center https://apps.dtic.mil/sti/citations/ADA420016 Army Research Laboratory 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.McQuaid Michael September 2002 Computational Characterization of 2-Azidocycloalkanamines: Notional Variations on the Hypergol 2-Azido-N,N-Dimethylethanamine (DMAZ) Defense Technical Information Center https://apps.dtic.mil/sti/citations/ADA405699 Army Research Laboratory 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. 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.Chen Chiung-Chu McQuaid Michael January 2014 A Thermochemical Kinetic-Based Study of Ignition Delays for 2-Azidoethanamine-Red Fuming Nitric Acid Systems: 2 Azido-N-Methylethanamine (MMAZ) Vs. 2 Azido-N,N-Dimethylethanamine (DMAZ) Defense Technical Information Center https://apps.dtic.mil/sti/citations/ADA599206 Army Research Laboratory References Further reading Aliphatic Amines N,N-Dimethyl-2‑azidoethylamine (DMAZ) Encyclopedia of Liquid Fuels De Gruyter Schmidt Eckart W. 2022 156–172 10.1515/9783110750287-002 978-3-11-075028-7 Category:Rocket fuels Category:Organoazides Category:Dimethylamino compounds