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Basic Information
CAS No.: 57-14-7
Name: 1,1-Dimethylhydrazine
Article Data: 64
Molecular Structure:
Molecular Structure of 57-14-7 (1,1-Dimethylhydrazine)
Formula: C2H8N2
Molecular Weight: 60.0989
Synonyms: 1,1-Dimethylhydrazine;Dimazin;Dimazine;Heptyl;N,N-Dimethylhydrazine;NSC 60517;UDMH;Unsymmetrical dimethylhydrazine;as-Dimethylhydrazine;gem-Dimethylhydrazine;u-Dimethylhydrazine;unsym-Dimethylhydrazine;
EINECS: 200-316-0
Density: 0.829 g/cm3
Melting Point: -57.2 °C
Boiling Point: 63.9 °C at 760 mmHg
Flash Point: 1.1 °C
Solubility: miscible with water, ethanol, and kerosene
Appearance: clear colorless liquid with an ammonia-like odor
Hazard Symbols: FlammableF, ToxicT, DangerousN
Risk Codes: 45-11-23/25-34-51/53
Safety: 53-45-61
Transport Information: UN 1163
PSA: 29.26000
LogP: 0.12200
Synthetic route
127510-73-0

(5S,5aS,8aS)-5-(N',N'-Dimethyl-hydrazino)-1,3,7-trimethyl-5,5a,8a,9-tetrahydro-1H-pyrrolo[3,4-g]quinazoline-2,4,6,8-tetraone

A

127510-75-2

1,3,7-Trimethyl-8a,9-dihydro-1H-pyrrolo[3,4-g]quinazoline-2,4,6,8-tetraone

B

57-14-7

1,1-dimethylhydrazine

Conditions
ConditionsYield
With hydrogenchloride In ethanolA 92%
B n/a

(η5-C5Me4SiMe3)2Ti(Cl)(NHN(CH3)2)

57-14-7

1,1-dimethylhydrazine

Conditions
ConditionsYield
With (η5-C5Me5)Rh(2-pyridylphenyl)H; hydrogen In tetrahydrofuran at 23℃; under 3040.2 Torr; for 120h; Catalytic behavior; Reagent/catalyst; Inert atmosphere; Schlenk technique;87%
29817-35-4

1-acetyl-2-methylhydrazine

platinum-on-carbon

platinum-on-carbon

67-63-0

isopropyl alcohol

57-14-7

1,1-dimethylhydrazine

Conditions
ConditionsYield
With hydrogenchloride; formaldehyd; paraformaldehyde; platinum78%
62-75-9

N-Nitrosodimethylamine

57-14-7

1,1-dimethylhydrazine

Conditions
ConditionsYield
With titanium(III) chloride In water for 1h; Ambient temperature;70%
With lithium aluminium tetrahydride; diethyl ether
With sodium hydroxide; aluminium

(η5-C5Me4SiMe3)2Ti(NHN(CH3)2)

57-14-7

1,1-dimethylhydrazine

Conditions
ConditionsYield
With cyclopentadienylchromiumtricarbonyl hydride; hydrogen In tetrahydrofuran at 23℃; under 3040.2 Torr; for 120h; Catalytic behavior; Reagent/catalyst; Inert atmosphere; Schlenk technique;15%
56-23-5

tetrachloromethane

13750-17-9

N,N-dimethylcarbamoyl azide

57-14-7

1,1-dimethylhydrazine

1585-74-6

dimethylchloroamine

57-14-7

1,1-dimethylhydrazine

Conditions
ConditionsYield
With ammonia
With ammonia; dimethyl amine at 35℃; under 9000.72 Torr; for 0.833333h; Product distribution; Further Variations:; educt/reagent ratios;
With sodium amide In kerosene
With tri-n-propylamine
With ammonium hydroxide at 25℃; pH=13; Kinetics;
4164-28-7

N-nitrodimethylamine

57-14-7

1,1-dimethylhydrazine

Conditions
ConditionsYield
With acetic acid; zinc
With sulfuric acid durch elektrolytische Reduktion an einer verzinnten Kupferkathode;
13750-17-9

N,N-dimethylcarbamoyl azide

57-14-7

1,1-dimethylhydrazine

Conditions
ConditionsYield
With xylene und Erhitzen des in Xylol unloeslichen Anteils des Reaktionsprodukts mit konz. Salzsaeure im Autoklaven auf 150grad;

N-ethyl-N,N-dimethyl-hydrazinium; hydroxide

A

74-85-1

ethene

B

57-14-7

1,1-dimethylhydrazine

Conditions
ConditionsYield
at 170 - 250℃;
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Consensus Reports

NTP 10th Report on Carcinogens. IARC Cancer Review: Group 2B IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 ,1987,p. 56.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Sufficient Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 4 ,1974,p. 137.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . EPA Genetic Toxicology Program. Community Right-To-Know List. EPA Extremely Hazardous Substances List. Reported in EPA TSCA Inventory.

Standards and Recommendations

OSHA PEL: TWA 0.5 ppm (skin)
ACGIH TLV: TWA 0.01 ppm (skin), Confirmed Animal Carcinogen.
DFG MAK: Animal Carcinogen, Suspected Human Carcinogen
NIOSH REL: (Hydrazines) CL 0.15 mg/m3/2H
DOT Classification:  6.1; Label: Poison, Flammable Liquid, Corrosive

Specification

The IUPAC name of this chemical is 1,1-dimethylhydrazine. With the CAS registry number 57-14-7 and EINECS 200-316-0, it is also named as Dimethylhydrazine unsymmetrical. The classification codes are Mutation data; Reproductive Effect; Tumor data. It is clear colorless liquid with an ammonia-like odor which is miscible with water, ethanol, and kerosene. It turns yellowish on exposure to air and absorbs oxygen and carbon dioxide. Moreover, this chemical is a powerful reducing agent and can exhibit high acute toxicity as a result of exposure by all routes. When heated to decomposition it emits highly toxic fumes of NOx. In addition, 1,1-Dimethylhydrazine should be sealed in the container and stored in the cool and dry place which must be away from oxidant and acids.

The other characteristics of this product can be summarized as: (1)ACD/LogP: -1.28; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -3.85; (4)ACD/LogD (pH 7.4): -2.16; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 2; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 6.48 Å2; (13)Index of Refraction: 1.426; (14)Molar Refractivity: 18.57 cm3; (15)Molar Volume: 72.4 cm3; (16)Polarizability: 7.36×10-24 cm3; (17)Surface Tension: 27.8 dyne/cm; (18)Density: 0.829 g/cm3; (19)Flash Point: 1.1 °C; (20)Enthalpy of Vaporization: 30.6 kJ/mol; (21)Boiling Point: 63.9 °C at 760 mmHg; (22)Vapour Pressure: 168 mmHg at 25°C.

Preparation of 1,1-Dimethylhydrazine: It can be obtained by the reaction of ammonia, ammonium chloride and dimethylamine. First, we can get chloro amine by ammonia and sodium hypochlorite. Secondly, the reaction of chloro amine and dimethylamine aqueous solution can generate UDMH solution. Finally, after a series of treatment, we can get the product.
NH3+NaOCl→NH2Cl+NaOH
NH2Cl+HN(CH3)3+NaOH→(CH3)2NNH2+NaCl+H2O

Uses of 1,1-Dimethylhydrazine: It is often used in hypergolic rocket fuels as a bipropellant in combination with the oxidizer nitrogen tetroxide and less frequently with IRFNA (red fuming nitric acid) or liquid oxygen. It is also used in the production of plant growth regulator. What's more, this chemical is used as fuel additive and used in organic synthesis. In addition, it can react with pyridine-3-carbaldehyde to get pyridine-3-carbaldehyde-dimethylhydrazone. This reaction needs solvent ethanol by heating on a steam bath. The reaction time is 30 min. The yield is 77%.

1,1-Dimethylhydrazine can react with pyridine-3-carbaldehyde to get pyridine-3-carbaldehyde-dimethylhydrazone

When you are using this chemical, please be cautious about it as the following:
It is highly flammable and can cause burns and cancer. What's more, it is toxic by inhalation and if swallowed. And it is also toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) So it should avoid exposure - obtain special instructions before use and avoid release to the environment. Refer to special instructions / safety data sheets.

People can use the following data to convert to the molecule structure. 
1. SMILES:N(N)(C)C
2. InChI:InChI=1/C2H8N2/c1-4(2)3/h3H2,1-2H3
3. InChIKey:RHUYHJGZWVXEHW-UHFFFAOYAL

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo intraperitoneal 30mg/kg (30mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

VASCULAR: REGIONAL OR GENERAL ARTERIOLAR OR VENOUS DILATION

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
European Journal of Toxicology and Environmental Hygiene. Vol. 7, Pg. 238, 1974.
dog LC50 inhalation 3580ppm/15M (3580ppm) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: TREMOR

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
American Industrial Hygiene Association Journal. Vol. 24, Pg. 137, 1963.
dog LD50 intraperitoneal 60mg/kg (60mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

GASTROINTESTINAL: NAUSEA OR VOMITING
National Technical Information Service. Vol. AD292-689,
dog LD50 intravenous 60mg/kg (60mg/kg)   Medycyna Pracy. Industrial Medicine. Vol. 24, Pg. 71, 1973.
dog LDLo skin 301mg/kg (301mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Toxicology and Applied Pharmacology. Vol. 18, Pg. 649, 1971.
guinea pig LC50 inhalation 100mg/m3/4H (100mg/m3)   Toksikologicheskii Vestnik. Vol. (6), Pg. 39, 1999.
guinea pig LD50 skin 1329mg/kg (1329mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD U.S. Army Chemical Warfare Laboratories. Vol. CWL,
hamster LC50 inhalation 392ppm/4H (392ppm) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD AMA Archives of Industrial Health. Vol. 12, Pg. 609, 1955.
hamster LD50 subcutaneous 325mg/kg (325mg/kg)   Cancer Letters Vol. 35, Pg. 303, 1987.
human TDLo unreported 10mg/kg (10mg/kg) BEHAVIORAL: HEADACHE

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

LIVER: LIVER FUNCTION TESTS IMPAIRED
"Spravochnik po Toksikologii i Gigienicheskim Normativam Vol. -, Pg. 71, 1999.
monkey LD50 intraperitoneal 60mg/kg (60mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

GASTROINTESTINAL: NAUSEA OR VOMITING
National Technical Information Service. Vol. AD292-689,
mouse LC50 inhalation 172ppm/4H (172ppm) SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
AMA Archives of Industrial Health. Vol. 12, Pg. 609, 1955.
mouse LD50 intraperitoneal 113mg/kg (113mg/kg) SENSE ORGANS AND SPECIAL SENSES: MIOSIS (PUPILLARY CONSTRICTION): EYE

SKIN AND APPENDAGES (SKIN): HAIR: OTHER

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Proceedings of the Society for Experimental Biology and Medicine. Vol. 124, Pg. 172, 1967.
mouse LD50 intravenous 250mg/kg (250mg/kg)   Medycyna Pracy. Industrial Medicine. Vol. 24, Pg. 71, 1973.
mouse LD50 oral 155mg/kg (155mg/kg) BRAIN AND COVERINGS: RECORDINGS FROM SPECIFIC AREAS OF CNS

KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
"Spravochnik po Toksikologii i Gigienicheskim Normativam Vol. -, Pg. 71, 1999.
rabbit LD50 skin 1060mg/kg (1060mg/kg)   "Documentation of the Threshold Limit Values and Biological Exposure Indices," 5th ed., Cincinnati, OH, American Conference of Governmental Industrial Hygienists, Inc., 1986Vol. 5, Pg. 210.1(89), 1986.
rat LC50 inhalation 252ppm/4H (252ppm) SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
AMA Archives of Industrial Health. Vol. 12, Pg. 609, 1955.
rat LD50 intraperitoneal 102mg/kg (102mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Toxicology and Applied Pharmacology. Vol. 6, Pg. 371, 1964.
rat LD50 intravenous 119mg/kg (119mg/kg)   Medycyna Pracy. Industrial Medicine. Vol. 24, Pg. 71, 1973.
rat LD50 oral 122mg/kg (122mg/kg)   Medycyna Pracy. Industrial Medicine. Vol. 24, Pg. 71, 1973.
rat LD50 skin 770mg/kg (770mg/kg) BRAIN AND COVERINGS: RECORDINGS FROM SPECIFIC AREAS OF CNS

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE
"Spravochnik po Toksikologii i Gigienicheskim Normativam Vol. -, Pg. 71, 1999.
rat LDLo intracrebral 27mg/kg (27mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Biochemical Pharmacology. Vol. 14, Pg. 1901, 1965.