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Sigma-Aldrich

Allyl 1H-imidazole-1-carboxylate

95%

Synonym(s):

Heller-Sarpong Reagent, Allyl imidazolecarbamate, AllylImC, Imidazole-1-carboxylic acid 2-propen-1-yl ester, Sarpong reagent

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About This Item

Empirical Formula (Hill Notation):
C7H8N2O2
CAS Number:
83395-39-5
Molecular Weight:
152.15
MDL number:
MFCD18835431
UNSPSC Code:
12352005
PubChem Substance ID:
329765935
NACRES:
NA.22

Assay

95%

form

liquid

refractive index

n20/D 1.494

density

1.146 g/mL at 25 °C

shipped in

wet ice

storage temp.

2-8°C

SMILES string

C=CCOC(=O)n1ccnc1

InChI

1S/C7H8N2O2/c1-2-5-11-7(10)9-4-3-8-6-9/h2-4,6H,1,5H2

InChI key

NEFLGCHXJFBCQP-UHFFFAOYSA-N

General description

Allyl 1H-imidazole-1-carboxylate is an organic reagent used to introduce carboxyallyl groups to nucleophilic nitrogen, oxygen, and carbon centers. It is used in the acylation reactions of enolates and nitrogen compounds. Further, it can also be used in the synthesis of carbonates and allyl esters.

Application

Allyl 1H-imidazole-1-carboxylate can be used:
  • To prepare allyl enol carbonate derivatives by reacting with ketone enolates and boron trifluoride etherate.
  • In the acylation of a mixture of primary and secondary alcohols.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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A New Simple One-Pot Regioselective Preparation of Mixed Diesters of Carbonic Acid
Bertolini G, et al.
The Journal of Organic Chemistry, 63(17), 6031-6034 (1998)
Allyl 1H-imidazole-1-carboxylate
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2015)
Barry M Trost et al.
The Journal of organic chemistry, 72(24), 9372-9375 (2007-10-30)
A convenient access to substituted allyl enol carbonates was established through the reaction of ketone enolates with the complex of allyl 1H-imidazole-1-carboxylates and boron trifluoride etherate.

Related Content

Heller Group – Professor Product Portal

Professor Heller and coworkers are engaged in the development of mild and chemoselective acylation reactions using carbonylazole-derived reagents. To that end, they have developed a suite of carbonylimidazole derivatives for facile and chemoselective esterification (MImC, etc.) and amidation (WImC) of carboxylic acids, in collaboration with Professor Richmond Sarpong.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

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