14337-31-6

Basic information

• Product Name: BenzeneMethanol, 4-Methoxy-.alpha.-(trichloroMethyl)-
• Synonyms: BenzeneMethanol, 4-Methoxy-.alpha.-(trichloroMethyl)-;2,2,2-Trichloro-1-(4-methoxyphenyl)ethanol
• CAS NO: 14337-31-6
• Molecular Formula: C₉H₉Cl₃O₂
• Molecular Weight: 255.52556
• Mol File: 14337-31-6.mol
• Article Data: 21

Chemical Properties

• Appearance: /
• CAS DataBase Reference: BenzeneMethanol, 4-Methoxy-.alpha.-(trichloroMethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: BenzeneMethanol, 4-Methoxy-.alpha.-(trichloroMethyl)-(14337-31-6)
• EPA Substance Registry System: BenzeneMethanol, 4-Methoxy-.alpha.-(trichloroMethyl)-(14337-31-6)

Safety Data

• Hazardous Substances Data: 14337-31-6(Hazardous Substances Data)

Usage

Uses

2,2,2-Trichloro-1-(4-methoxyphenyl)ethanol is an intermediate in the synthesis of Methoxy-DDT (M260800), a metabolite of 4,4''-Dichlorodiphenyltrichloroethane (D434195), a synthetic organochlorine insecticide that functions by opening sodium ion channels in the insects’ neurons, causing them to fire spontaneously which in turn leads to death.

Upstream product

• 56-23-5 tetrachloromethane 
• 123-11-5 4-methoxy-benzaldehyde 
• 67-66-3 chloroform 
• 14202-31-4 4-methoxybenzaldehyde-1,1-diacetate 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 75-87-6 chloral 
• 100-66-3 methoxybenzene 
• 302-17-0 chloral hydrate 
• 7294-51-1 2,4,6-tris(4-methoxyphenyl)boroxine 
• 105-13-5 4-Methoxybenzyl alcohol 
• 650-51-1 sodium trichloroacetate 
• 77-78-1 dimethyl sulfate 
• 76-03-9 trichloroacetic acid 

Downstream Products

• 34197-08-5 2-(4-ethoxy-phenyl)-1,1,1-trichloro-2-(4-methoxy-phenyl)-ethane 
• 28463-03-8 [14C]-Mono-Hydroxy-Methoxychlor 
• 41448-64-0 1-(2,2-dichlorovinyl)-4-methoxybenzene 
• 58622-56-3 α-(dichloromethyl)-4-methoxybenzenemethanol 
• 81928-73-6 1-(2,2-Dichloro-1-isopropoxy-ethyl)-4-methoxy-benzene 
• 36458-91-0 2,2,2-trichloro-1-(4-methoxyphenyl)ethan-1-one 
• 108540-67-6 2,2,2-trichloro-1-(4-methoxy-3-nitro-phenyl)-ethanol 
• 67-66-3 chloroform 
• 123-11-5 4-methoxy-benzaldehyde 
• 100-09-4 4-methoxybenzoic acid 
• 78401-33-9 1-(1-Allyloxy-2,2,2-trichloro-ethyl)-4-methoxy-benzene 
• 104-01-8 4-Methoxyphenylacetic acid 
• 29003-60-9 2,2-dichloro-4'-methoxyacetophenone 
• 79881-24-6 1,4-bis(4-methoxyphenyl)-2,2,3,3-tetrachloro-1,4-butanedione 

Relevant articles and documents

General and Efficient Synthesis of 1,1,1-Trichloro-2-alkanols

1,1,1-Trichloroalkanols were readily obtained in good yields by reaction of trichloroacetic acid with aldehydes in hexamethylphosphoric triamide. 1,3-Dimethyl-2-imidazolidinone was found to be useful as an alternate solvent giving, however, lower yields.

Pd-catalyzed synthesis of 1-(hetero)aryl-2,2,2-trichloroethanols using chloral hydrate and (hetero)arylboroxines

1-(Hetero)aryl-2,2,2-trichloroethanols are useful key intermediates for the synthesis of various bioactive compounds. Herein, we describe N-heterocyclic carbene (NHC)-coordinated cyclometallated palladium complex (CYP)-catalyzed (hetero)aryl addition of chloral hydrate using (hetero)arylboroxines, providing a new approach to 1-(hetero)aryl-2,2,2-trichloroethanols. Notably, PhS-IPent-CYP which coordinated the bulky yet flexible 2,6-di(pentan-3-yl)aniline (IPent)-based NHC showed good catalytic activities and promoted the transformation in 24-97% yields.

One-Carbon Homologation of Primary Alcohols and the Reductive Homologation of Aldehydes Involving a Jocic-Type Reaction

(Trichloromethyl)carbinols, which are formed in one operation from either alcohols or aldehydes, can be converted into primary alcohols in a Jocic-type reaction involving LiBH4. The net result is a convenient two-step, one-carbon homologation of primary alcohols or a reductive one-carbon homologation of aldehydes featuring a broad substrate scope. The method is step-economical, and it nicely complements established one-carbon homologation strategies. (Trichloromethyl)carbinols, which are formed in one operation from either alcohols or aldehydes, can be converted into primary alcohols in a Jocic-type reaction involving LiBH4. The net result is a convenient two-step, one-carbon homologation of primary alcohols or a reductive one-carbon homologation of aldehydes featuring a broad substrate scope.