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MX1123

Sigma-Aldrich

1-Methylimidazole

Sinónimos:

1-Methylimidazole, N-Methylimidazole, dna

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About This Item

Fórmula lineal:
CH3-NCH=NCH=CH-
Número de CAS:
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

Categorías relacionadas

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

signalword

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

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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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
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)
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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