2533-69-9

Basic information

• Product Name: METHYL 2,2,2-TRICHLOROACETIMIDATE
• Synonyms: Methyl 2,2,2-trichloroacetimidate, GC 98%;2,2,2-Trichloroethanimidic acid methyl ester;Trichloroacetimidic acid methyl ester;Methyl 2,2,2-trichloroacetimidate,98%;Methyl 2,2,2-Trichlorozcetimidate;Methyl 2,2,2-trichloroethanimidate;Methyl trichloroacetimidate;Methyl 2,2,2-trichloroethanecarboxiMidate
• CAS NO: 2533-69-9
• Molecular Formula: C₃H₄Cl₃NO
• Molecular Weight: 176.43
• EINECS: 219-796-8
• Product Categories: Amidates/Imidates;Nitrogen Compounds;Organic Building Blocks;Building Blocks;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks
• Mol File: 2533-69-9.mol
• Article Data: 4

Chemical Properties

• Melting Point: -30 °C
• Boiling Point: 148-149 °C(lit.)
• Flash Point: 165 °F
• Appearance: Clear colorless to pale yellow/Liquid
• Density: 1.425 g/mL at 25 °C(lit.)
• Vapor Pressure: 5.34mmHg at 25°C
• Refractive Index: n20/D 1.478(lit.)
• Storage Temp.: 0-6°C
• PKA: 2.22±0.70(Predicted)
• CAS DataBase Reference: METHYL 2,2,2-TRICHLOROACETIMIDATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 2,2,2-TRICHLOROACETIMIDATE(2533-69-9)
• EPA Substance Registry System: METHYL 2,2,2-TRICHLOROACETIMIDATE(2533-69-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 2533-69-9(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to pale yellow liquid

Uses

Methyl 2,2,2-trichloroacetimidate was used as starting material during the synthesis of novel bibenzimidazole oligomers and polymers. It was employed as reagent during the synthesis of 2,2′-bisbenzimidazole-5,5′-dicarboxylic acid.

InChI:InChI=1/C3H4Cl3NO/c1-8-2(7)3(4,5)6/h7H,1H3/b7-2-

Upstream product

• 545-06-2 trichloroacetonitrile 
• 124-41-4 sodium methylate 
• 67-56-1 methanol 

Downstream Products

• 2533-64-4 2,2,2-trichloro-N-phenylacetimidamide 
• 128203-16-7 (2R,5S)-5-benzyloxymethyl-5,6-dihydro-3-methoxy-2-methyl-2H-1,4-oxazin 
• 594-65-0 trichloroacetamide 
• 3584-66-5 5-chloro-2-(trichloromethyl)-1H-benzimidazole 
• 32174-46-2 methyl (R)-(-)-2-methoxy-2-phenylacetate 
• 3584-66-5 5-chloro-2-trichloromethyl-1H-benzoimidazole 
• 1622209-20-4 3-(4-chloro-3-fluorophenyl)-2-(trichloromethyl)-3H-imidazo[4,5-b]pyridine 
• 1455-92-1 5-methylsulfanyl-1-phenyl-1H-tetrazole 
• 673487-34-8 5-fluoro-2-(trichloromethyl)-1H-benzo[d]imidazole 
• 3584-65-4 2-trichloromethyl-1H-benzoimidazole 
• 6965-02-2 2,2'-bi-1H-benzimidazole 
• 148729-69-5 4,6-dichloro-2-trichloromethylbenzimidazole 
• 2533-68-8 trichloroacetamidine 
• 14468-56-5 5-chloro-7-phenyl-2-trichloromethyl-benzooxazole 

Relevant articles and documents

Regio- and stereoselective methods for the conversion of (2S,3R)-β-phenylglycidic acid esters to taxoids and other enantiopure (2R,3S)-phenylisoserine esters

A novel efficient method was proposed for the synthesis of enantiopure precursors of taxane-containing cytostatics, i.e., methyl esters of (2R,3S)- and (2S,3R)-N-benzoylphenylisoserine and similar taxoid esters. The method is based on the regio- and stereoselective hydrobromolysis of the corresponding trans-β-phenyl glycidate enatiomers, consecutive reactions of O-acylcarbamoylation of the obtained 3-bromohydrins, intramolecular cyclization to 4-phenyloxazolidin-2-one-5-carboxylic acid derivatives, and oxazolidinone ring opening.

Oligomerization of Trichloroacetonitrile (TCA) by Metal Salts

A CN bond was found to transform into a C=N bond under such a mild conditions as to mix trichloroacetonitrile, metal salts and methanol at 20 deg C.Ni(II) and Co(II) gave dimeric ring complexes and Mn(II) gave amidine, aminotriazine and brown powder.The aminotriazine was isolated as unstable liquid which spontaneously transformed into the crystal.A trimer structure was proposed for the liquid.In anhydrous systems, any oligomerization did not occur, so water was concluded to participate in the initiation.Keywords - trichloroacetonitrile; metal salt; methanol; nitrile; imino bond; dimeric ring complex; amidine; aminotriazine; trimer