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

Description

1-Chloro-N,N,2-trimethylpropenylamine is an organic compound characterized as a colorless to yellow liquid. It is an acid halogenation reagent developed by Ghosez, which is utilized for the conversion of carboxylic acids into their corresponding chlorides under strictly neutral conditions.

Uses

Used in Pharmaceutical Synthesis:
1-Chloro-N,N,2-trimethylpropenylamine is used as an acid halogenation reagent for the conversion of carboxylic acids into chlorides. This reagent is particularly useful in the total synthesis of various pharmaceutical compounds, including caloporoside, roseophilin, (-)-enniatin B, (±)-epimeloscine, and (±)-meloscine. Its application in these syntheses is due to its ability to facilitate the conversion process under neutral conditions, which helps to preserve the integrity of sensitive functional groups in the target molecules.
Used in Chemical Research:
In the field of chemical research, 1-Chloro-N,N,2-trimethylpropenylamine serves as a valuable tool for the synthesis of complex organic molecules. Its role as an acid halogenation reagent allows researchers to explore new synthetic pathways and develop innovative methods for creating a wide range of compounds with potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science.
Used in Organic Synthesis:
1-Chloro-N,N,2-trimethylpropenylamine is also employed in organic synthesis as a versatile reagent for the preparation of various organic compounds. Its ability to convert carboxylic acids into chlorides under neutral conditions makes it a preferred choice for chemists working on the synthesis of complex organic molecules, where the preservation of functional groups is crucial for achieving the desired product.

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

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

Downstream Products

• 73630-93-0 1-bromo-N,N,2-trimethyl-1-propen-1-amine 
• 4278-79-9 1-(4-(dimethylamino)phenyl)-2-methylpropan-1-one 
• 21678-37-5 N,N,2-trimethylpropionamide 
• 4451-35-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl chloride 
• 158867-55-1 (2R,4aS,5aS,8R,9aR,9bR)-1-perhydro-2,8-diphenyl-2H,5H,8H-bis<1,3>dioxino<5,4-b:4',5'-d>pyrrolidine 
• 158867-56-2 dimethyl (2S,5S)-1-pyrrolidine-2,5-dicarboxylate 
• 78685-51-5 2,2-dimethyl-3-oxo-cyclobutanecarboxylic acid methyl ester 
• 55991-37-2 4,4-dimethyl-2,3-diphenylcyclobut-2-enone 
• 951776-64-0 C₃₆H₃₀O₅ 
• 55985-95-0 C₁₄H₂₀N₂O₂S₂ 
• 55985-91-6 C₁₅H₂₂N₂O₂S₂ 
• 500903-64-0 (5-chlorocarbonyl-1-methyl-1H-pyrrol-3-yl)-carbamic acid tert-butyl ester 
• 201530-44-1 (4-(3,5-bis(2-hydroxyphenyl)-1H-1,2,4-triazol-1-yl)phenyl)(4-methylpiperazin-1-yl)methanone 
• 25320-59-6 tetra-O-benzyl glucopyranosyl chloride 

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