748811
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:
Molecular Weight:
152.15
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352005
MDL number:
Assay:
95%
Form:
liquid
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.
signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
10 - Combustible liquids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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Related Content
Professor Heller's research focuses on mild acylation reactions using carbonylimidazole-derived reagents.
Allyl 1H-imidazole-1-carboxylate
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2015)
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)
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.
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 748811-5G | 04061833358900 |
| 748811-25G | 04061833555712 |
| 748811-1G | 04061824605617 |