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Sigma-Aldrich

1-Methylimidazole

Synonym(s):

1-Methylimidazole, N-Methylimidazole, dna

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About This Item

Linear Formula:
CH3-NCH=NCH=CH-
CAS Number:
616-47-7
MDL number:
MFCD00005292
UNSPSC Code:
12352100
EC Index Number:
210-484-7

vapor pressure

0.4 hPa ( 20 °C)

Quality Level

200

form

liquid

pH

9.5-10.5 (20 °C, 50 g/L in H2O)

bp

198 °C/1013 hPa

mp

-2 °C

transition temp

flash point 92 °C

shipped in

ambient

storage temp.

room temp

InChI

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

InChI key

MCTWTZJPVLRJOU-UHFFFAOYSA-N

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Application

1-Methylimidazole can be used as an organocatalyst to synthesize:
  • 4-amino-3,5-dicyano-6-arylphthalates via one-pot, a three-component reaction between arylidenemalononitriles, dialkyl ­acetylenedicarboxylates, and malononitrile.
  • Aromatic and aliphatic carbamates from hydroxamic acids via the Lossen rearrangement.
  • Tetrahydrobenzo[b]pyrans via three-component cyclocondensation reaction between aromatic aldehydes, malononitrile, and dimedone.

It can also be used as:
  • A co-catalyst in copper-catalyzed, greener oxidation of alcohols to carbonyl compounds under aerobic conditions.
  • A solvent/complexing agent in the preparation of CuInS2 n-type semiconductive particles.
  • A co-additive in the synthesis of acid-sensitive epoxides by methyltrioxorhenium-catalyzed epoxidation of alkenes with H2O2.

Analysis Note

Assay (GC)99.0% minDensity at 20°C1.03-1.04g/mLFormClear, liquidWater (H2O)150ppm max

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Danger

Hazard Classifications

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

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 2

flash_point_f

197.6 °F - closed cup

flash_point_c

92 °C - closed cup

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Synthesis of n-type CuInS2 particles using N-methylimidazole, characterization and growth mechanism
Courtel FM, et al.
Chemistry of Materials, 22(12), 3752-3761 (2010)
1-Methylimidazole-catalyzed regioselective synthesis of highly substituted benzenes
Adib Mehdi, et al.
Synlett, 2007(16), 2497-2500 (2007)
A green synthesis of tetrahydrobenzo [b] pyran derivatives through three-component condensation using N-methylimidazole as organocatalyst
Lian Xi-Zhong, et al.
Monatshefte fur Chemie / Chemical Monthly, 139(2), 129-131 (2008)
Shigekazu Yamazaki
Organic & biomolecular chemistry, 8(10), 2377-2385 (2010-05-08)
An effective method for suppression of ring opening and rearrangement of acid-sensitive epoxides during methyltrioxorhenium(MTO)-catalyzed epoxidation of alkenes with H(2)O(2) by using 1-methylimidazole as a co-additive has been found. The combined use of 3-methylpyrazole and 1-methylimidazole as the additives has
Janelle E Steves et al.
Journal of the American Chemical Society, 135(42), 15742-15745 (2013-10-17)
Cu/TEMPO catalyst systems promote efficient aerobic oxidation of sterically unhindered primary alcohols and electronically activated substrates, but they show reduced reactivity with aliphatic and secondary alcohols. Here, we report a catalyst system, consisting of ((MeO)bpy)Cu(I)(OTf) and ABNO ((MeO)bpy = 4,4'-dimethoxy-2,2'-bipyridine;
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