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Sigma-Aldrich

1-Methylimidazole

Synonyme(s) :

1-Methylimidazole, N-Methylimidazole, dna

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About This Item

Formule linéaire :
CH3-NCH=NCH=CH-
Numéro CAS:
616-47-7
Numéro MDL:
MFCD00005292
Code UNSPSC :
12352100
Numéro de classement CE :
210-484-7

Pression de vapeur

0.4 hPa ( 20 °C)

Niveau de qualité

200

Forme

liquid

pH

9.5-10.5 (20 °C, 50 g/L in H2O)

Point d'ébullition

198 °C/1013 hPa

Pf

-2 °C

Température de transition

flash point 92 °C

Conditions d'expédition

ambient

Température de stockage

room temp

InChI

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

Clé InChI

MCTWTZJPVLRJOU-UHFFFAOYSA-N

Catégories apparentées

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.

Remarque sur l'analyse

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

Pictogrammes

Skull and crossbonesHealth hazardCorrosion
GHS06,GHS08,GHS05

Mention d'avertissement

Danger

Mentions de danger

H302,H311,H314,H361d

Classification des risques

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

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 2

Point d'éclair (°F)

197.6 °F - closed cup

Point d'éclair (°C)

92 °C - closed cup

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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)
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
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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