683-72-7

Basic information

• Product Name: Dichloroacetamide
• Synonyms: DICHLOROACETAMIDE;2,2'-DICHLOROACETAMIDE;2,2-DICHLOROACETAMIDE;,-Dichloracetamide;2,2-dichloro-acetamid;Acetamide, dichloro-;dichloro-acetamid;Acetamide, 2,2-dichloro-
• CAS NO: 683-72-7
• Molecular Formula: C₂H₃Cl₂NO
• Molecular Weight: 127.96
• EINECS: 211-674-2
• Product Categories: Amides;Carbonyl Compounds;Organic Building Blocks
• Mol File: 683-72-7.mol
• Article Data: 14

Chemical Properties

• Melting Point: 98-100 °C(lit.)
• Boiling Point: 233-234 °C745 mm Hg(lit.)
• Flash Point: 233-234°C
• Appearance: white powder or crystals
• Density: 1.0875 (rough estimate)
• Refractive Index: 1.5680 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: 71g/l
• PKA: 13.29±0.50(Predicted)
• Water Solubility: soluble
• BRN: 1743236
• CAS DataBase Reference: Dichloroacetamide(CAS DataBase Reference)
• NIST Chemistry Reference: Dichloroacetamide(683-72-7)
• EPA Substance Registry System: Dichloroacetamide(683-72-7)

Safety Data

• Hazard Codes: Xi,T
• Statements: 36/37/38-43-24/25
• Safety Statements: 26-37/39-45-36-22
• WGK Germany: 3
• RTECS: AB6475000
• TSCA: Yes
• Hazardous Substances Data: 683-72-7(Hazardous Substances Data)

Usage

Chemical Properties

white powder or crystals

Uses

2,2-Dichloroacetamide was an aliphatic halogenated DBP precursor identified in drinking water treatment; a pollutant.

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 3, p. 260, 1955The Journal of Organic Chemistry, 26, p. 2270, 1961 DOI: 10.1021/jo01351a030

InChI:InChI=1/C2H3Cl2NO/c3-1(4)2(5)6/h1H,(H2,5,6)

Upstream product

• 302-17-0 chloral hydrate 
• 507-47-1 1-amino-2,2,2-trichloro-ethanol 
• 151-50-8 potassium cyanide 
• 29653-30-3 dimethyl 2,2-dichloromalonate 
• 35077-09-9 N-chloro-2,2-dichloroacetamide 
• 7664-41-7 ammonia 
• 16535-70-9 dichloro-acetic acid-(2,2,2-trichloro-1-hydroxy-ethylamide) 
• 79-04-9 chloroacetyl chloride 
• 37764-25-3 N-diallyldichloroacetamide 
• 10335-73-6 2,2-dichloro-acetohydroxamic acid 
• 20165-81-5 diethyl dichloromalonate 
• 7732-18-5 water 
• 64-17-5 ethanol 
• 3130-87-8 ASPARAGINE 

Downstream Products

• 10403-82-4 S,S-Diethyl-N-dichloracetyl-sulfilimin 
• 359-38-6 2,2-difluoroacetamide 
• 22031-63-6 (E)-3-cyclohexylacrylamide 
• 1224737-64-7 2-chloro-3-cyclohexyl-3-hydroxypropanamide 
• 1224737-65-8 2-chloro-3-hydroxy-5-phenylpentanamide 
• 35077-10-2 N-chloro-trichloroacetamide 
• 35077-09-9 N-chloro-2,2-dichloroacetamide 
• 116-54-1 dichloroacetic acid methyl ester 
• 621-79-4 cinnamamide 
• 25679-91-8 1-Butyl-3-(2-chloro-acetyl)-urea 
• 39089-35-5 bis(dichloroacetylamino)phenylmethane 
• 96793-31-6 Dichloressigsaeure-<(chlor-diphenyl-phosphoranyliden)-amid> 
• 15167-44-9 2.2-Bis-phenylmercapto-acetamid 
• 56224-95-4 N-(5-Amino-2,4-dinitro-phenyl)-2,2-dichloro-acetamide 

Relevant articles and documents

Thiazolyl-phosphine hydrochloride salts: Effective auxiliary ligands for ruthenium-catalyzed nitrile hydration reactions and related amide bond forming processes in water

A series of water-soluble N-protonated thiazolyl-phosphine hydrochloride salts have been synthesized and coordinated to the ruthenium(ii) fragment [RuCl2(η6-p-cymene)]. The resulting complexes were evaluated as potential catalysts for the selective hydration of nitriles to primary amides in environmentally friendly aqueous medium. The best results in terms of activity were achieved when tris(5-(2-aminothiazolyl))phosphine trihydrochloride was used as ligand. Using the Ru(ii) complex 9 derived from this salt (3 mol%), the catalytic reactions proceeded cleanly in pure water at 100 °C without the assistance of any additive, affording the desired amides in high yields (>78%) after short reaction periods (0.5-7 h). The process was operative with both aromatic, heteroaromatic, α,β-unsaturated and aliphatic nitriles, and tolerated several functional groups. The utility of 9 in promoting the formation of primary amides in water by catalytic rearrangement of aldoximes and direct coupling of aldehydes with NH2OH·HCl has also been demonstrated.

Efficient tandem process for the catalytic deprotection of N-allyl amides and lactams in aqueous media: A novel application of the bis(allyl)- ruthenium(IV) catalysts [Ru(η3:η2: η3-C12H18)Cl2] and [Ru(η3:η3-C10H16)-(μ-Cl) Cl}2]

An operationally simple and highly efficient methodology for the removal of the allyl protecting group in amides and lactams has been developed by using the commercially available bis(allyl)-ruthenium(IV) catalysts [Ru(η3:η2:η3-C12H 18)Cl2] (C12H18 = dodeca-2,6,10-triene-1,12-diyl) and [(Ru(η3:η3- C10H16)(μ-Cl)Cl}2] (C10H 16 = 2,7-dimethylocta-2,6-diene-1,8-diyl). The tandem process, which takes place in aqueous media and proceeds in a one-pot manner, involves the initial isomerization of the C=C bond of the allyl unit and subsequent oxidative cleavage of the resulting enamide.