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336092

Sigma-Aldrich

1-Methylimidazole

≥99%, purified by redistillation

Synonym(s):

N-Methylimidazole

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About This Item

Empirical Formula (Hill Notation):
C4H6N2
CAS Number:
616-47-7
Molecular Weight:
82.10
Beilstein:
105197
EC Number:
210-484-7
MDL number:
MFCD00005292
UNSPSC Code:
12352100
PubChem Substance ID:
57648790
NACRES:
NA.21

vapor pressure

0.4 mmHg ( 20 °C)

Quality Level

300

Assay

≥99%

form

liquid

autoignition temp.

977 °F

purified by

redistillation

expl. lim.

15.7 %

impurities

≤19 ppm Triazine
<0.005% water

refractive index

n20/D 1.495 (lit.)

bp

198 °C (lit.)

mp

−6 °C (lit.)

density

1.03 g/mL at 25 °C (lit.)
1.034-1.036 g/mL

SMILES string

Cn1ccnc1

InChI

1S/C4H6N2/c1-6-3-2-5-4-6/h2-4H,1H3

InChI key

MCTWTZJPVLRJOU-UHFFFAOYSA-N

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General description

1-Methylimidazole is an N-donor ligand generally used in the preparation of coordinate complexes.

Application

1-Methylimidazole may be used as a starting material to synthesize:
  • 1-(2-hydroxypropyl)-3-methylimidazolium salts used as ionic liquids
  • 1,3-dimethylimidazoyl-2-ylidene borane, a stable and easy to handle N-heterocyclic carbene borane
  • It can act both as a catalyst and a solvent in the synthesis of aldononitrile acetates from aldoses.

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Signal Word

Danger

Hazard Statements

H302,H311,H314,H361d

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 4 Oral - Eye Dam. 1 - Repr. 2 - Skin Corr. 1B

WGK

WGK 2

Flash Point(F)

197.6 °F

Flash Point(C)

92 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Nickel (II)-, cobalt (II)-, copper (II)-, and zinc (II)-phthalate and 1-methylimidazole coordination compounds: synthesis, crystal structures and magnetic properties.
Baca SG, et al.
Inorgorganica Chimica Acta, 357(12), 3419-3429 (2004)
The use of 1-methylimidazole as a solvent and catalyst for the preparation of aldononitrile acetates of aldoses.
Chen CC & McGinnis GD
Carbohydrate Research, 90(1), 127-130 (1981)
New ionic liquids containing an appended hydroxyl functionality from the atom-efficient, one-pot reaction of 1-methylimidazole and acid with propylene oxide.
Holbrey JD, et al.
Green Chemistry, 5(6), 731-736 (2003)
1,3-Dimethylimidazoyl-2-ylidene borane
Gardner S, et al.
Organic Syntheses, 92, 342-342 (2015)
Fumitoshi Shibahara et al.
The Journal of organic chemistry, 77(19), 8815-8820 (2012-09-15)
Synthetic methods for triarylated azoles containing three different aryl groups via one-pot sequential multiple C-H bond arylations are described. The one-pot sequential diarylation of C5-monoarylated azoles was achieved by the simple sequential addition of two different aryl iodides with a
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