ChemicalBook > CAS DataBase List > 1-Chloro-N,N,2-trimethylpropenylamine

1-Chloro-N,N,2-trimethylpropenylamine

Product Name
1-Chloro-N,N,2-trimethylpropenylamine
CAS No.
26189-59-3
Chemical Name
1-Chloro-N,N,2-trimethylpropenylamine
Synonyms
1-Chloro-N,N,2-trimethylprop-1-en-1-amine;1-CHLORO-N,N,2-TRIMETHYL-1-PROPENYLAMINE;Ghosez′s reagent;TETRAMETHYL-ALPHA-CHLORENAMINE;1-CHLORO-N,N,2-TRIMETHYLPROPENYLAMINE;(1-CHLORO-2-METHYLPROPENYL)DIMETHYLAMINE;1-chloro-N,N,2-trimethyl-1-Propen-1-amine;1-chloride-N, N, 2-trimethyl-1-acrylamine;1-Chloro-N,N,2-trimethylpropenylamine ,98%;1-Propen-1-amine, 1-chloro-N,N,2-trimethyl-
CBNumber
CB4484804
Molecular Formula
C6H12ClN
Formula Weight
133.62
MOL File
26189-59-3.mol
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1-Chloro-N,N,2-trimethylpropenylamine Property

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
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Safety

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
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H226Flammable liquid and vapour

H314Causes severe skin burns and eye damage

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P233Keep container tightly closed.

P240Ground/bond container and receiving equipment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
498270
Product name
1-Chloro-N,N,2-trimethyl-1-propenylamine
Purity
96%
Packaging
5ml
Price
$183
Updated
2024/03/01
Sigma-Aldrich
Product number
498270
Product name
1-Chloro-N,N,2-trimethyl-1-propenylamine
Purity
96%
Packaging
50ml
Price
$1270
Updated
2024/03/01
Sigma-Aldrich
Product number
498270
Product name
1-Chloro-N,N,2-trimethyl-1-propenylamine
Purity
96%
Packaging
250ml
Price
$6300
Updated
2024/03/01
TRC
Product number
C349260
Product name
1-Chloro-N,N-2-trimethylpropenylamine
Packaging
2.5g
Price
$155
Updated
2021/12/16
TRC
Product number
C349260
Product name
1-Chloro-N,N-2-trimethylpropenylamine
Packaging
500mg
Price
$55
Updated
2021/12/16
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1-Chloro-N,N,2-trimethylpropenylamine Chemical Properties,Usage,Production

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-trimethylpropenylamine Preparation Products And Raw materials

Raw materials

Preparation Products

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1-Chloro-N,N,2-trimethylpropenylamine Suppliers

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View Lastest Price from 1-Chloro-N,N,2-trimethylpropenylamine manufacturers

Henan Fengda Chemical Co., Ltd
Product
1-Chloro-N,N,2-trimethylpropenylamine 26189-59-3
Price
US $100.00-1.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
g-kg-tons, free sample is available
Release date
2023-12-26
Zhuozhou Wenxi import and Export Co., Ltd
Product
1-Chloro-N,N,2-trimethyl-1-propenylamine 26189-59-3
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-07-10
Zhuozhou Wenxi import and Export Co., Ltd
Product
1-Chloro-N,N,2-trimethyl-1-propenylamine 26189-59-3
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-07-08

26189-59-3, 1-Chloro-N,N,2-trimethylpropenylamineRelated Search:


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