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D161608

Sigma-Aldrich

N,N-Dimethylhydrazine

98%

Synonym(s):

1,1-Dimethylhydrazine, asym-Dimethylhydrazine

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About This Item

Linear Formula:
(CH3)2NNH2
CAS Number:
57-14-7
Molecular Weight:
60.10
Beilstein/REAXYS Number:
605261
EC Number:
200-316-0
MDL number:
MFCD00007628
UNSPSC Code:
12352100
PubChem Substance ID:
24893497
NACRES:
NA.22
form:
liquid
assay:
98%
Pricing and availability is not currently available.

vapor density

1.94 (vs air)

vapor pressure

103 mmHg ( 20 °C)

assay

98%

form

liquid

autoignition temp.

478 °F

expl. lim.

95 %

refractive index

n20/D 1.4075 (lit.)

bp

60-62 °C (lit.)

density

0.79 g/mL at 20 °C (lit.)

storage temp.

2-8°C

SMILES string

CN(C)N

InChI

1S/C2H8N2/c1-4(2)3/h3H2,1-2H3

InChI key

RHUYHJGZWVXEHW-UHFFFAOYSA-N

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Application

N,N-Dimethylhydrazine can react with:
  • β-Naphthol via radical amination to form 1-amino-2-naphthol.[1]
  • 2-Chloro- and 2,2-dichloro-(bromo)vinyl ketones via regioselective heterocyclization to form 3-substituted 1-methyl(5-halo)pyrazoles.[2]
  • Terminal alkynes in the presence of TpRuCl(PPh3)2 (Tp = tris(pyrazolyl)borate) to form nitriles.[3]


N,N-Dimethylhydrazine along with ferric chloride hexahydrate forms an effective reduction system for:
  • Synthesizing DNA binding pyrrolo[2,1-c][1,4]benzodiazepine (PBD) imines via reductive cyclization of the corresponding nitro aldehyde.[4]
  • Transforming a variety of nitroarenes and azido compounds into the corresponding anilines and amino compounds, respectively.[5][6]

Biochem/physiol Actions

Lung and colon tumor initiator in experimental animal model.[7][8]

signalword

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Aquatic Chronic 2 - Carc. 1B - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B - STOT SE 3

target_organs

Respiratory system

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

14.0 °F - closed cup

flash_point_c

-10 °C - closed cup

ppe

Faceshields, Gloves, Goggles

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Certificates of Analysis (COA)

Lot/Batch Number
BCCK3491
BCCC8136
BCCB5046
BCBW9907
BCBV8501

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B Toth
Cancer research, 35(12), 3693-3697 (1975-12-01)
The various synthetic substituted hydrazines, which cause tumors in animals, are briefly enumerated. To date, 19 of them have proved to be tumorigenic in animals. A number of these chemicals are found today in the environment, in industry, in agriculture
Takao Kaneko et al.
Biological & pharmaceutical bulletin, 30(11), 2052-2057 (2007-11-06)
The effects of esculetin (6,7-dihydroxycoumarin) and its 6-glycoside, esculin, on 8-oxo-2'-deoxyguanosine (8-oxodG) formation and carcinogenesis induced by a chemical carcinogen, 1,2-dimethylhydrazine (DMH), were examined in the colons of male Fischer 344 rats. Animals were given water containing esculetin or esculin
Dmitry S Kosyakov et al.
Chemosphere, 228, 335-344 (2019-05-01)
Existing methods for cleanup of wastewaters and soils polluted with the extremely toxic rocket fuel unsymmetrical dimethylhydrazine (UDMH) are mainly based on the treatment with various oxidative reagents. Until now, the assessment of their effectiveness was based on the residual
On the reaction of β-naphthol with N, N-dimethylhydrazine-a new radical amination process
Barton DHR, et al.
Tetrahedron Letters, 24(15), 1601-1604 (1983)
An efficient synthesis of pyrrolo [2, 1-c][1, 4] benzodiazepine antibiotics via reductive cyclization
Kamal A, et al.
Bioorganic & Medicinal Chemistry Letters, 7(14), 1825-1828 (1997)
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