What molecule am I?
1,1-Dimethylhydrazine, frequently called unsymmetrical dimethylhydrazine (UDMH), is the third member of the hydrazine family to appear in Molecule of the Week. The first two were the parent molecule hydrazine in 2010 and methylhydrazine earlier this year. All these highly toxic hydrazines are used in rocket fuels.
Australian chemist Henry H. Hatt reported a in the 1936 edition of Organic Syntheses. Hatt treated dimethylamine with nitric acid to produce the N-nitroso derivative, which was then reduced with zinc to form UDMH, isolated as the salt. Hatt later made UDMH by treating dimethylamine with chloramine; this is one of two current industrial production processes. In the other, acetylhydrazine is treated with formaldehyde and hydrogen to form a dimethyl derivative, which is then hydrolyzed to produce UDMH.
UDMH is a hypergolic rocket fuel, which means that it ignites when it is mixed with another component of the fuel. The second component is usually dinitrogen tetroxide. UDMH is generally preferred to hydrazine in rocket fuels because it autoignites at a higher temperature and is thus more stable in storage.
1. CAS Reg. No. 593-82-8.
1,1-Dimethylhydrazine hazard information*
| Hazard class** | GHS code and hazard statement | |
|---|---|---|
| Flammable liquids, category 2 | H225鈥擧ighly flammable liquid and vapor |  |
| Acute toxicity, oral, category 3 | H301鈥擳oxic if swallowed |  |
| Acute toxicity, dermal, category 3 | H311鈥擳oxic in contact with skin | |
| Skin corrosion/irritation, category 1B | H314鈥擟auses severe skin burns and eye damage |  |
| Serious eye damage/eye irritation, category 1 | H318鈥擟auses serious eye damage | |
| Acute toxicity, inhalation, category 2 | H331鈥擣atal if inhaled | |
| Germ cell mutagenicity, category 2 | H340鈥擲uspected of causing genetic defects |  |
| Carcinogenicity, category 1B | H350鈥擬ay cause cancer | |
| Specific target organ toxicity, single exposure, category 1 | H370鈥擟auses damage to respiratory system, nervous system | |
| Specific target organ toxicity, repeated exposure, category 1 | H372鈥擟auses damage through prolonged or repeated exposure to liver, blood system, respiratory system, nervous system | |
| Short-term (acute) aquatic hazard, category 2 | H401鈥擳oxic to aquatic life |  |
| Long-term (chronic) aquatic hazard, category 2 | H411鈥擳oxic to aquatic life with long-lasting effects | |
*Compilation of two safety data sheets.
**Globally Harmonized System (GHS) of Classification and Labeling of Chemicals.聽
Molecule of the Future
Darobactin A1 is a potential antibiotic that was discovered in 2019 by Kim Lewis at Northeastern University (Boston) and 14 collaborators there and at several other institutions in the United States and Germany. The authors isolated the molecule from species of Photorhabdus bacteria that live in the digestive systems of certain nematodes.
Lewis et al. found that darobactin A caused by Gram-negative bacteria in the Enterobacteriaceae family, including Escherichia coli. In 2022, two total syntheses of darobactin A were reported: Niki R. Patel, David A. Petrone, David Sarlah, and collaborators at Merck (Rahway, NJ) and the University of Illinois at Urbana鈥揅hampaign ; Phil S. Baran at Scripps Research (La Jolla, CA) to accomplish the feat.
1. CAS Reg. No. 2409072-20-2.
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1,1-Dimethylhydrazine
fast facts
| CAS Reg. No. | 57-14-7 |
| SciFinder nomenclature | Hydrazine, 1,1-dimethyl- |
| Empirical formula | C2H8N2 |
| Molar mass | 60.10 g/mol |
| Appearance | Colorless liquid |
| Boiling point | 64 掳C |
| Water solubility | Miscible |
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