23213-96-9

Basic information

• Product Name: ETHYL 2,2,2-TRICHLOROACETIMIDATE
• Synonyms: ETHYL 2,2,2-TRICHLOROACETIMIDATE;Ethyl 2,2,2-trichloroacetimidate 98%
• CAS NO: 23213-96-9
• Molecular Formula: C₄H₆Cl₃NO
• Molecular Weight: 190.46
• Product Categories: Amidates/Imidates;Nitrogen Compounds;Organic Building Blocks;Building Blocks;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks
• Mol File: 23213-96-9.mol
• Article Data: 3

Chemical Properties

• Melting Point: −15 °C(lit.)
• Boiling Point: 74-75 °C39 mm Hg(lit.)
• Flash Point: 160 °F
• Appearance: /
• Density: 1.331 g/mL at 25 °C(lit.)
• Vapor Pressure: 2.86mmHg at 25°C
• Refractive Index: n20/D 1.469(lit.)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: ETHYL 2,2,2-TRICHLOROACETIMIDATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 2,2,2-TRICHLOROACETIMIDATE(23213-96-9)
• EPA Substance Registry System: ETHYL 2,2,2-TRICHLOROACETIMIDATE(23213-96-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 23213-96-9(Hazardous Substances Data)

Usage

Uses

Ethyl 2,2,2-trichloroacetimidate may be used in chemical synthesis studies.

InChI:InChI=1/C4H6Cl3NO/c1-2-9-3(8)4(5,6)7/h8H,2H2,1H3

Upstream product

• 64-17-5 ethanol 
• 545-06-2 trichloroacetonitrile 
• 67-64-1 acetone 
• 124-41-4 sodium methylate 

Downstream Products

• 14301-39-4 trichloro-acetic acid ethylamide 
• 18593-72-1 5-phenyl-2-trichloromethyl-3H-thieno[2,3-d]pyrimidin-4-one 
• 18593-64-1 6-phenyl-2-trichloromethyl-3H-thieno[2,3-d]pyrimidin-4-one 
• 2002-24-6 2-amino-ethanol hydrochloride 
• 3206-45-9 5-ethylsulfanyl-1-phenyl-1H-tetrazole 
• 134870-62-5 (3S)-3,6-dihydro-2,5-diethoxy-3-isopropylpyrazine 
• 78-09-1 orthocarbonic acid tetraethyl ester 

Relevant articles and documents

Radical-mediated intramolecular β-C(sp3)-H amidation of alkylimidates: Facile synthesis of 1,2-amino alcohols

A new radical-mediated intramolecular β-C(sp3)-H amidation reaction of O-alkyl trichloro- or arylimidates is reported. Various oxazolines were efficiently prepared from easily accessible alcohol starting materials. The trichloro-oxazoline products can be hydrolyzed under mild conditions to give valuable 1,2-amino alcohols. This amidation reaction exhibits a broad substrate scope and good functional group tolerance, and offers a powerful means for the C(sp3)-H functionalization of alcohols. Mechanistic studies suggest that a sequence of 1,5-HAT of an imidate radical, iodination and cyclization might be operative.

Orthoamides, XXXV. - Preparation of O,N-Functional Trisubstituted Acetonitriles

Trichloroacetonitrile (7) reacts with molar amounts of alcoholates in alcohols to give mixtures of orthocarbonates 10 and trichloroacetimidates 9.The action of 7 on 3 moles of sodium ethoxide in heptane affords triethoxyacetonitrile 3b among other products, such as 9b, 10b and the imidate 12.The nitrile 3a can be obtained from 7 and sodium methoxide in ether in moderate yields. - The orthocarbonic acid derivatives 10b, 20a and 21a are transformed by acyl cyanides into the nitriles 3b, 4a, and 5a, respectively.N,N,N',N',N'',N''-hexamethylguanidinium cyanide (23a) is f ormed in the reaction of 22 with acetyl cyanide. - The salts 30a-32a react with alkali cyanides to form the nitriles 3b, 4a, and 5a, respectively.The nitrile 2a transfers cyanide ions to the carbenium ions 30a and 31a to yield the nitriles 3b and 4a, respectively.