2,2,2-Trichloroacetamide

Base Information

• Chemical Name: 2,2,2-Trichloroacetamide
• CAS No.: 594-65-0
• Molecular Formula: C2H2Cl3NO
• Molecular Weight: 162.403
• Hs Code.: 29241900
• European Community (EC) Number: 209-849-3,693-672-5
• NSC Number: 16599
• UNII: I8BL3305RO
• DSSTox Substance ID: DTXSID5021671
• Nikkaji Number: J55.332H
• Wikidata: Q27280571
• ChEMBL ID: CHEMBL331157
• Mol file: 594-65-0.mol

Synonyms:trichloroacetamide;trichloroacetimidate

Chemical Property of 2,2,2-Trichloroacetamide

Chemical Property:

• Appearance/Colour: white solid
• Vapor Pressure: 0.0411mmHg at 25°C
• Melting Point: 139-141 °C(lit.)
• Refractive Index: 1.52
• Boiling Point: 239 °C at 760 mmHg
• PKA: 12.75±0.50(Predicted)
• Flash Point: 88.5 °C
• PSA: 43.09000
• Density: 1.682 g/cm³
• LogP: 1.54220
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: methanol: 0.1 g/mL, clear
• Water Solubility.: 13 g/L (20 ºC)
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 160.920197
• Heavy Atom Count: 7
• Complexity: 85.4

Purity/Quality:

99% ^*data from raw suppliers

2,2,2-Trichloroacetamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,Xi,Xn
• Hazard Codes: T,Xn,Xi
• Statements: 23/24/25-36/37/38-22-36
• Safety Statements: 36/37-45-37/39-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Nitrogen Compounds
• Canonical SMILES: C(=O)(C(Cl)(Cl)Cl)N
• Uses: 2,2,2-Trichloroacetamide was an aliphatic halogenated DBP precursor identified in drinking water treatment; a pollutant.

Technology Process of 2,2,2-Trichloroacetamide

There total 73 articles about 2,2,2-Trichloroacetamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

trichloroacetonitrile (545-06-2) → trichloroacetamide (594-65-0)

Guidance literature:

With sulfuric acid; In nitrobenzene; chlorobenzene; at 60 ℃; Rate constant; Thermodynamic data; Mechanism; various temperatures, ΔG (excit.), ΔH (excit.), ΔS (excit.);

Reference yield: 96.0%

(2S)-3-(3-pivaloyloxyphenyl)-2-hydroxypropionic acid methyl (913722-82-4) + isopropyl 2,2,2-trichloroacetimidate (99418-52-7) → (2S)-3-(3-pivaloyloxyphenyl)-2-isopropoxypropionic acid methyl (913722-83-5) + trichloroacetamide (594-65-0)

Guidance literature:

With trifluorormethanesulfonic acid; In 1,2-dimethoxyethane; n-heptane; at 7 - 25 ℃; for 19.5h;

Reference yield: 88.0%

(2,6-dichloro-4-methoxyphenyl)-(2,4-dichlorophenyl)methyl trichloroacetimidate (1205121-89-6) + benzyl-N-acetylmuramyl-L-alanine phenylsulfonylethyl ester (1205121-99-8) → trichloroacetamide (594-65-0) + C43H46Cl4N2O12S (1205122-21-9)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 2h; Reagent/catalyst; Temperature;

DOI:10.1002/chem.201400307

upstream raw materials:

1,1,1,3,3,3-hexachloro-propan-2-one

Ethyl trichloroacetate

octachloro-pentane-2,4-dione

1-phenylethyl 2,2,2-trichloroacetimidate

Downstream raw materials:

S,S-Tetramethylen-N-trichloracetyl-sulfilimin

N-(4-methoxybenzyl)-2,2,2-trichloroacetamide

benzyl 2,2,2-trichloroacetamide

Methyl trichloroacetate

Refernces

• 1、 Nielsen, John,Tung, Truong Thanh. "Amide bond formation in aqueous solution: Direct coupling of metal carboxylate salts with ammonium salts at room temperature". supporting information. p. 10073 - 10080. Retrieved 2021/12/10.
• 2、 Tomás-Mendivil, Eder,Francos, Javier,González-Fernández, Rebeca,González-Liste, Pedro J.,Borge, Javier,Cadierno, Victorio. "Bis(allyl)-ruthenium(IV) complexes with phosphinous acid ligands as catalysts for nitrile hydration reactions". . p. 13590 - 13603. Retrieved 2016/09/04.