26189-59-3

Basic information

• Product Name: 1-Chloro-N,N,2-trimethylpropenylamine
• Synonyms: 1-CHLORO-N,N,2-TRIMETHYL-1-PROPENYLAMINE;1-CHLORO-N,N,2-TRIMETHYLPROPENYLAMINE;(1-CHLORO-2-METHYLPROPENYL)DIMETHYLAMINE;TETRAMETHYL-ALPHA-CHLORENAMINE;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 NO: 26189-59-3
• Molecular Formula: C₆H₁₂ClN
• Molecular Weight: 133.62
• Product Categories: Alkenyl;Halogenated Hydrocarbons;Organic Building Blocks
• Mol File: 26189-59-3.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 129-130 °C(lit.)
• Flash Point: 80 °F
• Appearance: Colorless to yellow/Liquid
• Density: 1.01 g/mL at 25 °C(lit.)
• Vapor Pressure: 2.32mmHg at 25°C
• Refractive Index: n20/D 1.453(lit.)
• Storage Temp.: Freezer (-20°C)
• Solubility: Chloroform (Sparingly), Methanol (Slightly)
• PKA: 4.27±0.70(Predicted)
• Stability: Hygroscopic, Moisture Sensitive, Unstable in Solution
• CAS DataBase Reference: 1-Chloro-N,N,2-trimethylpropenylamine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Chloro-N,N,2-trimethylpropenylamine(26189-59-3)
• EPA Substance Registry System: 1-Chloro-N,N,2-trimethylpropenylamine(26189-59-3)

Safety Data

• Hazard Codes: C
• Statements: 10-34
• Safety Statements: 16-26-36/37/39-45
• RIDADR: UN 2734 8/PG 1
• WGK Germany: 3
• Hazardous Substances Data: 26189-59-3(Hazardous Substances Data)

Usage

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.

Synthesis Reference(s)

Journal of the American Chemical Society, 94, p. 2869, 1972 DOI: 10.1021/ja00763a061Organic Syntheses, Coll. Vol. 6, p. 282, 1988Tetrahedron Letters, 25, p. 5043, 1984 DOI: 10.1016/S0040-4039(01)91114-1

InChI:InChI=1/C6H12ClN/c1-5(2)6(7)8(3)4/h1-4H3

Upstream product

• 52851-35-1 1-chlor-N,N,2-trimethylpropaniminium-chlorid 
• 21678-37-5 N,N,2-trimethylpropionamide 
• 10596-50-6 1,1-bis(dimethylamino)-2,2-dimethylethylene 

Downstream Products

• 81391-08-4 2,2-dimethyl-3-phenylcyclobutanone 
• 689258-25-1 2,2-dimethyl-3-(p-methoxyphenyl)cyclobutanone 
• 1271911-39-7 2,2-dimethyl-3-(p-nitrophenyl)cyclobutanone 
• 1111-97-3 3-chloro-3-methylbut-1-yne 
• 78-80-8 2-methylbut-1-en-3-yne 
• 21678-37-5 N,N,2-trimethylpropionamide 
• 73630-93-0 1-bromo-N,N,2-trimethyl-1-propen-1-amine 
• 132409-92-8 FMOC-Tyr(t-Bu)-Cl 
• 7476-66-6 methyl 2-chloro-2-phenylethanoate 
• 4091-39-8 3-chloro-2-butanone 
• 447-31-4 Desyl chloride 
• 814-78-8 3-Methyl-3-buten-2-one 

Relevant articles and documents

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A mild method for the replacement of a hydroxyl group by halogen: 3. the dichotomous behavior of α-haloenamines towards allylic and propargylic alcohols

A study of the deoxyhalogenation of allylic and propargylic alcohols with tetramethyl-α-halo-enamines is reported. Primary allylic and primary and secondary propargylic alcohols gave the corresponding halides in high yields. Secondary allylic and propargylic alcohols yielded the corresponding secondary halides but the reaction also produced some rearranged primary halides (I > Br > Cl). The reactions with tertiary allylic and tertiary propargylic alcohols gave several products and was therefore of little synthetic value. However, the addition of triethylamine to the reaction mixture or the use of lithium alkoxide instead of alcohol brought about a major change of the course of the reaction which led to amides carrying an allyl or an allenyl group at C2. This was shown to result from a Claisen-Eschenmoser rearrangement of an intermediate α-allyloxy- or propargyloxy-enamine.

Alpha- haloenamine reagents

The present invention describes immobilized haloenamine reagents, immobilized tertiary amides, methods for their preparation, and methods of use.

A general and practical method of synthesis of 2-disubstituted-1- chloro- and 1-bromoenamines

Disubstituted-α-chloroenamines are useful synthetic intermediates which had earlier been prepared by the reaction of tertiary amides with phosgene. The toxicity of the latter led us to systematically investigate new synthetic routes towards α-chloro- and