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748811 Sigma-Aldrich

Allyl 1H-imidazole-1-carboxylate

95%

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

  • CAS Number 83395-39-5

  • Empirical Formula (Hill Notation) C7H8N2O2

  • Molecular Weight 152.15

  •  MDL number MFCD18835431

  •  PubChem Substance ID 329765935

  •  NACRES NA.22

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Properties

Related Categories Alkyl Transfer, C-X Bond Formation (Non-Halogen), Chemical Synthesis, Heller-Sarpong Reagents, Protecting and Derivatizing Reagents,
Quality Level   200
assay   95%
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

Description

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.

Packaging

5, 25 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Target organs 
Respiratory system
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

Stephen Heller Group - Professor Product Portal

From our library of Articles, Sigma-Aldrich presents Stephen Heller Group - Professor Product Portal
Keywords: Acylations, Amidations, Catalysis, Esterifications

Peer-Reviewed Papers
15

References

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