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Sigma-Aldrich

N-Methyl-1,2-phenylenediamine

97%

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Synonym(s):
1-N-Methylbenzene-1,2-diamine, 2-(Methylamino)aniline, 2-Amino-N-methylaniline, 2-N-Methylbenzene-1,2-diamine, N-Methyl-1,2-benzenediamine, N-Methyl-1,2-diaminobenzene, N-Methyl-o-diaminobenzene, N-Methyl-o-phenylenediamine, N1-Methyl-1,2-benzenediamine
Linear Formula:
CH3NHC6H4NH2
CAS Number:
4760-34-3
Molecular Weight:
122.17
EC Number:
225-297-6
MDL number:
MFCD00192314
PubChem Substance ID:
24864778
NACRES:
NA.22

Assay

97%

form

liquid

refractive index

n20/D 1.612 (lit.)

bp

123-124 °C/10 mmHg (lit.)

mp

22 °C (lit.)

density

1.075 g/mL at 25 °C (lit.)

SMILES string

CNc1ccccc1N

InChI

1S/C7H10N2/c1-9-7-5-3-2-4-6(7)8/h2-5,9H,8H2,1H3

InChI key

RPKCLSMBVQLWIN-UHFFFAOYSA-N

Related Categories

General description

N-Methyl-1,2-phenylenediamine is an ortho-diamine. In situ generated diazonium cations of N-methyl-1,2-phenylenediamine were used for the electrochemical modification of glassy carbon electrode.

Application

N-Methyl-1,2-phenylenediamine may be used in the following studies:
  • One-pot synthesis of 1-methyl-2(hetero)arylbenzimidazoles.
  • Preparation of 1-methyl-1H-benzimidazole-2(3H)-thione.
  • Total synthesis of the angiotensin II receptor antagonist, telmisartan.
  • Preparation of benzimidazoles from ketene dithioacetals.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Hizbullah Khan et al.
Acta crystallographica. Section E, Structure reports online, 64(Pt 6), o1141-o1141 (2008-01-01)
The title compound, C(8)H(8)N(2)S, was prepared by the condensation of N-methyl-1,2-phenyl-enediamine and carbon disulfide. The crystal structure is stabilized by a C-H⋯π inter-action between a benzene H atom and the benzene ring of a neighbouring mol-ecule, and by inter-molecular N-H⋯S
Recent developments in use of heteropolyacids, their salts and polyoxometalates in organic synthesis.
Heravi MM and Sadjadi S.
Journal of the Iranian Chemical Society, 6(1), 1-54 (2009)
A Sanjeev Kumar et al.
Beilstein journal of organic chemistry, 6, 25-25 (2010-05-27)
An efficient synthesis of the angiotensin II receptor antagonist Telmisartan (1) is presented involving a cross coupling of 4-formylphenylboronic acid 10 with 2-(2-bromophenyl)-4,4-dimethyl-2-oxazoline (11) as the key step (90% yield). The benzimidazole moiety 15 was constructed regioselectively via a reductive
Synthesis, 1273-1273 (1992)
Rodrigo Quezada et al.
Nanomaterials (Basel, Switzerland), 10(6) (2020-06-12)
Type of metal and metal-oxide NPs added to modify Thin-Film Composites Reverse Osmosis Membranes (TFC-RO) can alter their anti-biofouling properties by changing the dissolution process. The development of a mathematical model can facilitate the selection of these NPs. This work
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