2,2,2-Trichloroethanol

Base Information

• Chemical Name: 2,2,2-Trichloroethanol
• CAS No.: 115-20-8
• Molecular Formula: C2H3Cl3O
• Molecular Weight: 149.404
• Hs Code.: 29055910
• European Community (EC) Number: 204-071-0
• NSC Number: 66407
• UNII: AW835AJ62N
• DSSTox Substance ID: DTXSID1021950
• Nikkaji Number: J2.895I
• Wikipedia: 2,2,2-Trichloroethanol
• Wikidata: Q4596742
• NCI Thesaurus Code: C83510
• Metabolomics Workbench ID: 49540
• ChEMBL ID: CHEMBL1171
• Mol file: 115-20-8.mol

Synonyms:2,2,2-trichloroethanol;trichloroethanol

Chemical Property of 2,2,2-Trichloroethanol

Chemical Property:

• Appearance/Colour: Clear colourless to light yellow liquid
• Vapor Pressure: 1 mm Hg ( 20 °C)
• Melting Point: 17.8 °C(lit.)
• Refractive Index: n20/D 1.49(lit.)
• Boiling Point: 152.066 °C at 760 mmHg
• PKA: 12.24(at 25℃)
• Flash Point: 45.768 °C
• PSA: 20.23000
• Density: 1.602 g/cm³
• LogP: 1.34890
• Storage Temp.: Store below +30°C.
• Sensitive.: Hygroscopic
• Solubility.: 83g/l
• Water Solubility.: Slightly soluble in water.
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 147.924948
• Heavy Atom Count: 6
• Complexity: 38.5

Purity/Quality:

99% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-41-67
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Halogenated Alcohols
• Canonical SMILES: C(C(Cl)(Cl)Cl)O
• Uses: Intermediate, anesthetic. 2,2,2-Trichloroethanol (TCE) is an active metabolite of Trichloroacetaldehyde monohydrate [chloral hydrate (CH)] (T774055), a sedative/hypnotic that increases cerebral blood flow (CBF). The 2,2,2-Trichloroethyl (TCE) moiety of 2,2,2-trichloroethanol is mainly used as a protecting group for acids, acetals and also phosphoryl groups of nucleotides. It can be easily cleaved by zinc reduction.Some of its other application include:Conversion of per-O-acetylated sugars to per-O-acetylated trichloroethyl derivatives.Preparation of TCE ester of chlorosulfuric acid.Preparation of 2,2,2-trichloroethyl acetimidate hydrochloride.

Technology Process of 2,2,2-Trichloroethanol

There total 75 articles about 2,2,2-Trichloroethanol 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: 70.0%

chloral (75-87-6) + cyclohexanol (108-93-0) → 1,1,1-trichloroethanol (115-20-8) + cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4)

Guidance literature:

With zirconium(IV) tert-butoxide; In toluene; at 0 ℃; for 9h; Product distribution; other primary and secondary alcohols; var. zirconium catalysts; var. reaction conditions;

DOI:10.1055/s-1996-4381

Reference yield:

2,2,2-trichloroethyl butyrate (57392-44-6) + hexan-1-ol (111-27-3) → 1,1,1-trichloroethanol (115-20-8) + hexyl butyrate (2639-63-6)

Guidance literature:

In diethyl ether; at 35 ℃; Candida cylindracea lipase;

Reference yield:

diethyl ether (60-29-7,927820-24-4) + chloral (75-87-6) + phenethyl magnesium (1+); bromide → styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + 1,1,1-trichloroethanol (115-20-8) + 1,4-diphenylbutane (1083-56-3)

Guidance literature:

DOI:10.1021/ja01293a042

upstream raw materials:

chloral hydrate

ethanol

Ethyl trichloroacetate

diethyl ether

Downstream raw materials:

2,2,2-Trichlorethyl-diethylphosphat

Bis-(2,2,2-Trichloraethyl)-d-tartrat

Trichlorethylphosphonsaeuredi-iso-butylester

Triphenyl-(2,2,2-trichloro-ethoxy)-silane

Refernces

• 1、 Jiang, Zhen,Taylor, Philip H.,Dellinger, Barry. "Laser Photolysis/Laser-Induced Fluorescence Studies of the Reaction of OH with 1,1,1-Trichloroethane over an Extended Temperature Range". . p. 8961 - 8964. Retrieved 1992.
• 2、 Jeong, Kyu-Man,Hsu, Kuang-Jung,Jeffries, J. B.,Kaufman, Frederick. "Kinetics of the Reactions of OH with C2H6, CH3CCl3, CH2ClCHCl2, CH2ClCClF2, and CH2FCF3". . p. 1222 - 1226. Retrieved 1984.
• 3、 Janczewski, ?ukasz,Walczak, Ma?gorzata,Fr?czyk, Justyna,Kamiński, Zbigniew J.,Kolesińska, Beata. "Microwave-assisted Cannizzaro reaction—Optimisation of reaction conditions". supporting information. p. 3290 - 3300. Retrieved 2019/11/05.
• 4、 Kornecki, Katherine P.,Berry, John F.. "Introducing a mixed-valent dirhodium(ii,iii) catalyst with increased stability in C-H amination". . p. 12097 - 12099. Retrieved 2013/01/16.