Basic information Safety Supplier Related
ChemicalBook >  Product Catalog >  Organic Chemistry >  Hydrocarbons and derivatives >  Hydrocarbon halides >  1-Chloro-N,N,2-trimethylpropenylamine

1-Chloro-N,N,2-trimethylpropenylamine

Basic information Safety Supplier Related

1-Chloro-N,N,2-trimethylpropenylamine Basic information

Product Name:
1-Chloro-N,N,2-trimethylpropenylamine
Synonyms:
  • TETRAMETHYL-ALPHA-CHLORENAMINE
  • 1-CHLORO-N,N,2-TRIMETHYL-1-PROPENYLAMINE
  • 1-CHLORO-N,N,2-TRIMETHYLPROPENYLAMINE
  • (1-CHLORO-2-METHYLPROPENYL)DIMETHYLAMINE
  • 1-Chloro-N,N,2-trimethylpropenylamine, 98.5+%
  • 1-Chloro-N,N,2-trimethylpropenylamine ,98%
  • Ghosez′s reagent
  • 1-Chloro-N,N,2-triMethylpropenylaMine, 98.5+% 5ML
CAS:
26189-59-3
MF:
C6H12ClN
MW:
133.62
Product Categories:
  • Alkenyl
  • Halogenated Hydrocarbons
  • Organic Building Blocks
Mol File:
26189-59-3.mol
More
Less

1-Chloro-N,N,2-trimethylpropenylamine Chemical Properties

Boiling point:
129-130 °C(lit.)
Density 
1.01 g/mL at 25 °C(lit.)
refractive index 
n20/D 1.453(lit.)
Flash point:
80 °F
storage temp. 
2-8°C
solubility 
Chloroform (Sparingly), Methanol (Slightly)
form 
Liquid
pka
4.27±0.70(Predicted)
color 
Colorless to yellow
Stability:
Hygroscopic, Moisture Sensitive, Unstable in Solution
More
Less

Safety Information

Hazard Codes 
C
Risk Statements 
10-34
Safety Statements 
16-26-36/37/39-45
RIDADR 
UN 2734 8/PG 1
WGK Germany 
3
HS Code 
29211990

MSDS

More
Less

1-Chloro-N,N,2-trimethylpropenylamine Usage And Synthesis

Chemical Properties

Colorless to yellow liquid

Uses

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.

Preparation

1-chloro-N,N,2-trimethylpropenylamine is conveniently prepared by the reaction of N,N,2- trimethylpropanamide with Phosgene followed by dehydrochlorination of the intermediate α-chloroiminium chloride (eq 1).[1,2] Recent unpublished results of our laboratory have shown that Phosphorus Oxychloride or dior triphosgene can also be used for the preparation of TMCE.

Application

1-Chloro-N,N,2-trimethylpropenylamine (TMCE) is used to mild halogenation of alcohols and acids under neutral conditions; conversion of N-protected amino acids into peptides without racemization; coupling of acids and allylic alcohols with organometallics; [2 + 2] cycloaddition synthons, more reactive than dimethylketene.

Synthesis Reference(s)

Journal of the American Chemical Society, 94, p. 2869, 1972 DOI: 10.1021/ja00763a061
Organic Syntheses, Coll. Vol. 6, p. 282, 1988
Tetrahedron Letters, 25, p. 5043, 1984 DOI: 10.1016/S0040-4039(01)91114-1

storage

1-chloro-N,N,2-propenylamines are thermally stable. It must be transferred in the absence of moisture and stored under nitrogen in sealed tubes. In spite of these precautions, light precipitates sometimes may form. 1-Iodo-N,N,2-trimethylpropenylamine is less stable and should be used when freshly prepared.

References

1. Ghosez, L.; Marchand-Brynaert, J. In Advances in Organic Chemistry; Raphael, R. A.; Taylor, E. C.; Wynberg, H., Eds.; Interscience: New York, 1976; Part 1, pp 421-523.
2. (a) Haveaux, B.; Dekoker, A.; Rens, M.; Sidani, A. R.; Toye, J.; Ghosez, L. OS 1979, 59, 26. (b) Ghosez, L.; Koch, I. Swiss Pat. 681 623A, 1993.

1-Chloro-N,N,2-trimethylpropenylamineSupplier

J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Email
jkinfo@jkchemical.com
Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
021-61259108 18621169109
Email
market03@meryer.com
Energy Chemical
Tel
021-021-58432009 400-005-6266
Email
sales8178@energy-chemical.com
Beijing Ouhe Technology Co., Ltd
Tel
010-82967028 13552068683
Email
2355560935@qq.com
JinYan Chemicals(ShangHai) Co.,Ltd.
Tel
13817811078
Email
sales@jingyan-chemical.com