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Sigma-Aldrich

1,2-Dimethylimidazole

97%

Synonym(s):

1,2-Dimethyl-1H-imidazole, 1,2DMZ

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About This Item

Empirical Formula (Hill Notation):
C5H8N2
CAS Number:
1739-84-0
Molecular Weight:
96.13
EC Number:
217-101-2
MDL number:
MFCD00005294
UNSPSC Code:
12352005
PubChem Substance ID:
24848259
NACRES:
NA.22

vapor pressure

1 mmHg ( 20 °C)

Assay

97%

form

solid

autoignition temp.

896 °F

bp

204 °C (lit.)

mp

37-39 °C (lit.)

density

1.084 g/mL at 25 °C (lit.)

SMILES string

Cc1nccn1C

InChI

1S/C5H8N2/c1-5-6-3-4-7(5)2/h3-4H,1-2H3

InChI key

GIWQSPITLQVMSG-UHFFFAOYSA-N

General description

1,2-Dimethylimidazole reacts with copper(II) tetraacetate to yield cis-bis(acetato)bis(1,2-dimethylimidazole) copper(II) complex. It undergoes Menschutkin reaction with benzyl bromide to yield 3-benzyl-1,2-dimethylimidazolium bromide and kinetics of reaction was studied in various ionic liquids and molecular organic solvents.

Application

1,2-Dimethylimidazole was used in the synthesis of 1,2-dimethyl-3-n-butylimidazoliumchloride and 1,2-dimethyl-3-n-propylimidazolium chloride. It was also used in the synthesis of 1-(2-methoxyethyl)-2,3-dimethylimidazolium chloride and hexafluorophosphate salts.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302,H315,H318

Precautionary Statements

P280 - P305 + P351 + P338

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

197.6 °F - closed cup

Flash Point(C)

92 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Wesley A Henderson et al.
Chemical communications (Cambridge, England), (35)(35), 3708-3710 (2006-10-19)
The crystal structures and thermal behavior of the 1-(2-methoxyethyl)-2,3-dimethylimidazolium chloride and hexa-fluorophosphate salts are compared with the analogous 1-butyl-2,3-dimethylimidazolium salts to examine the influence of the ether oxygen on salt thermal properties for a typical constituent cation used in the
The coordination environment of mitochondrial cytochromes b.
K R Carter et al.
FEBS letters, 132(2), 243-246 (1981-09-28)
Physical properties of substituted imidazolium based ionic liquids gel electrolytes.
Sutto TE, et al.
Zeitschrift fur Naturforschung, A, 57(11), 839-846 (2002)
M M Fitzgerald et al.
Protein science : a publication of the Protein Society, 4(9), 1844-1850 (1995-09-01)
The activated state of cytochrome c peroxidase, compound ES, contains a cation radical on the Trp-191 side chain. We recently reported that replacing this tryptophan with glycine creates a buried cavity at the active site that contains ordered solvent and
Alain Lesimple et al.
Journal of mass spectrometry : JMS, 43(1), 35-41 (2007-07-10)
A number of 1,2-dimethylimidazole ionic liquids substituted on N(II) with alkyl chains of varying lengths terminated with sulfur-containing groups were investigated by electrospray high-resolution tandem Fourier-transform mass spectrometry. Fragmentation pathways are strongly dependent on the oxidation state of the sulfur
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