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Hydrazine monohydrate is used as a reducing agent. It is also used in water treatment, especially effluents and industrial boilers, metal treatment and mine extraction process, and synthesis of active ingredients in the pharmaceutical industry like 3-amino-1,2,4-triazole cefazolin, rizatriptan, anastrozole, fluconazole, metazachlor metamitron pyrazole, metribuzin, paclobutrazol, diclobutrazole, propiconazole, and triadimefon. It is involved in the preparation of heterocycles like pyrazoles and pyridazines. It is actively involved in the Wolff-Kishner reduction, which converts the carbonyl group of a ketone into a methylene bridge through a hydrazone intermediate. Further, it is used to cleave N-alkylated phthalimide derivatives. In the Einhorn-Brunner reaction, it reacts with imides to get triazoles.
Forms stable, water-free solid complexes consisting of one hydrazine molecule associated with one molecule of hydroquinone or two molecules of 4-methoxyphenol. These have potential as replacements for the very hazardous anhydrous hydrazine, e.g. in the solid state reaction with esters to give pure hydrazides: J. Chem. Soc., Chem. Commun., 1531, (1995).
Diimide precursor: for generation of diimide by oxidation with O2, and use in selective reduction of a double bond in the presence of a cyclopropane ring, see: J. Chem. Soc., Chem. Commun., 525 (1973). Review of diimide reductions: Org. React., 40, 91 (1991). See also Hydroxylamine-O-sulfonic acid, A12560 .
In the Wolff-Kishner carbonyl to methylene reduction (heating with hydrazine and alkali hydroxide), diethylene glycol is now the usual solvent (the Huang Minlon modification): J. Am. Chem. Soc., 68, 2487 (1946); Org. Synth. Coll., 4, 510 (1963). The reduction has also been performed at ambient temperature by the use of KO-t-Bu in DMSO: J. Am. Chem. Soc., 84, 1734 (1962). See also Isatin, A12468 for an analogous reduction.
In the presence of Rh on carbon, nitrobenzene is selectively reduced to phenylhydroxylamine: Org. Synth. Coll., 8, 16 (1993).
For a brief feature on uses of the reagent in synthesis, see: Synlett, 2445 (2004).
Shiraishi, Y.; Hirakawa, H.; Hirai, T. Photocatalytic Hydrogenation of Nitroaromatics to Anilines on Silica-Supported Iron Oxides with Hydrazine Monohydrate as a Reductant. J. Chem. Eng. Jpn. 2015, 48 (2), 141-146.
Sun, J. K.; Xu, Q. Metal Nanoparticles Immobilized on Carbon Nanodots as Highly Active Catalysts for Hydrogen Generation from Hydrazine in Aqueous Solution. Chem. Cat. Chem. 2015, 7 (3), 526-531.
Hazard Statements: H227-H301-H311-H314-H317-H331-H335-H350
Combustible liquid. Toxic if swallowed. Toxic in contact with skin. Causes severe skin burns and eye damage. May cause an allergic skin reaction. Toxic if inhaled. May cause respiratory irritation. May cause cancer.
Precautionary Statements: P201-P202-P210-P235-P260-P264b-P270-P271-P272-P280g-P281-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P333+P313-P363-P370+P378q-P501c
Obtain special instructions before use. Do not handle until all safety precautions have been read and understood. Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep cool. Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Contaminated work clothing should not be allowed out of the workplace. Wear protective gloves. Use personal protective equipment as required. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. Rinse mouth. Do NOT induce vomiting. If skin irritation or rash occurs: Get medical advice/attention. Wash contaminated clothing before reuse. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant