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Merck
CN

D161608

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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24893497
EC Number:
200-316-0
Beilstein/REAXYS Number:
605261
MDL number:
MFCD00007628

Key Documents

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Product Name

N,N-Dimethylhydrazine, 98%

InChI key

RHUYHJGZWVXEHW-UHFFFAOYSA-N

InChI

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

SMILES string

CN(C)N

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

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Application

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


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.
  • Transforming a variety of nitroarenes and azido compounds into the corresponding anilines and amino compounds, respectively.

Biochem/physiol Actions

Lung and colon tumor initiator in experimental animal model.

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

WGK 3

flash_point_f

14.0 °F - closed cup

flash_point_c

-10 °C - closed cup

ppe

Faceshields, Gloves, Goggles

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
BCCK3491
BCCC8136
BCCB5046
BCBW9907
BCBV8501

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Masaki Honda et al.
Marine drugs, 17(2) (2019-02-06)
The red macroalga Agarophyton chilensis is a well-known producer of eicosanoids such as hydroxyeicosatetraenoic acids, but the alga produces almost no prostaglandins, unlike the closely related A. vermiculophyllum. This indicates that the related two algae would have different enzyme systems
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
Reaction of terminal alkynes with hydrazines to give nitriles, catalyzed by TpRuCl (PPh3)2: novel catalytic transformation involving a vinylidene ruthenium intermediate
Fukumoto Y, et al.
Organometallics, 21(19), 3845-3847 (2002)
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
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