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498270 Sigma-Aldrich

1-Chloro-N,N,2-trimethyl-1-propenylamine

96%

Synonym: Ghosez′s reagent

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Properties

Related Categories Alkenyl, Building Blocks, Chemical Reagents, Chemical Synthesis, Development Quantities for Research,
InChI Key   GQIRIWDEZSKOCN-UHFFFAOYSA-N
assay   96%
refractive index   n20/D 1.453(lit.)
bp   129-130 °C(lit.)
density   1.01 g/mL at 25 °C(lit.)
storage temp.   2-8°C

Description

Packaging

5, 50, 250 mL in glass bottle

Application

1-Chloro-N,N,2-trimethyl-1-propenylamine is an acid halogenation reagent developed by Ghosez, that enables the conversion of carboxylic acids into the corresponding chlorides under strictly neutral conditions. This method was successfully used in the total synthesis of caloporoside, roseophilin, (-)-enniatin B, (±)-epimeloscine and (±)-meloscine.

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Precautionary statements 
RIDADR 
UN 2734PSN1 3(8) / PGI
WGK Germany 
3
Flash Point(F) 
78.8 °F
Flash Point(C) 
26 °C

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Protocols & Articles

Articles

Acid Halogenation Reagents

The generation of an acid chloride is an obvious way to activate the carboxy group for amide bond formation. However, practical application of acid chlorides in peptide synthesis is restricted, becau...
Matthias Junkers
ChemFiles 2007, 7.2, 3.
Keywords: Fluorinations, Halogenations, Peptide synthesis, Racemizations, Solid phase peptide synthesis

Azide Formation

Azide coupling procedures were introduced by Curtius as one of the first successful strategies for the synthesis of peptides. For a long time they were thought to be the only racemisation free method...
Matthias Junkers
Aldrich ChemFiles 2007, 7.2, 3.
Keywords: Azide formation, Cyclizations, Peptide synthesis

Peer-Reviewed Papers
15

References

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