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

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

Used in Pesticide Synthesis:
BenzeneMethanol, 4-Methoxy-α-(trichloroMethyl)is used as an intermediate in the synthesis of Methoxy-DDT (M260800), a metabolite of 4,4''-Dichlorodiphenyltrichloroethane (D434195). This synthetic organochlorine insecticide is effective in controlling insect populations due to its mode of action, which involves opening sodium ion channels in the insects' neurons. This causes the neurons to fire spontaneously, ultimately leading to the death of the insect.
In the Chemical Industry:
BenzeneMethanol, 4-Methoxy-α-(trichloroMethyl)is used as a key component in the production of various chemicals and pharmaceuticals. Its unique structure allows it to be a versatile building block for the synthesis of a wide range of compounds, making it valuable in the development of new products and applications within the chemical industry.

Upstream product

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

Downstream Products

• 123-11-5 4-methoxy-benzaldehyde 
• 62688-84-0 1-methoxy-4-(2,2,2-trichloro-1-methoxy-ethyl)-benzene 
• 20714-90-3 4-Methoxymandelic acid 
• 34197-08-5 2-(4-ethoxy-phenyl)-1,1,1-trichloro-2-(4-methoxy-phenyl)-ethane 
• 28463-03-8 [14C]-Mono-Hydroxy-Methoxychlor 
• 54034-89-8 [2,2,2-trichloro-1-(4-methoxyphenyl)ethoxy]trimethylsilane 
• 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 
• 100-09-4 4-methoxybenzoic acid 
• 78401-33-9 1-(1-Allyloxy-2,2,2-trichloro-ethyl)-4-methoxy-benzene 

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.

PESTICIDAL COMPOUNDS AND METHODS OF USE

Described herein are compounds, pesticidally acceptable salts thereof, and compositions thereof that are useful, for example, for pest management and for controlling pests. In certain embodiments provided are enantioenriched and/or enantiopure compounds and pesticidally acceptable salts thereof, and methods of making same. Methods of controlling pests with the compounds of the disclosure are also provided.

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.

A novel β-(oxy)alkyl radical during copper(I)-mediated stereoselective synthesis of (Z)-ene-1,4-diones in a reaction of 2,2,2-trichloro-1-phenylethanone

A novel β-(oxy)alkyl radical derived from trichloro methyl compound containing neither a suitably located C-C multiple bond nor a leaving group or a H-atom at the β-position of the radical in a reaction of 2,2,2-trichloro-1-phenyl-ethanone with 2 mol equiv each of CuCl and bpy in refluxing DCE under a N2 atm underwent intramolecular heterolysis (just like formation of intact radical cation-anion pair) during stereoselective radical dimerization to Z-ene-1,4-dione along with small amount of reductive dechlorination product. The stereochemistry was established by X-ray diffraction spectroscopy of various solid crystalline products.

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.

β-(Carbonatoxy)alkyl radicals: A new subset of β-(ester)alkyl radical fragmentation during copper(I)-mediated synthesis of 1,1-dichloro-1-alkenes

A new subset of β-(ester)alkyl radicals is presented. It is the first study on the chemistry of β-(alkoxycarbonyloxy)alkyl radicals that fill the gap in the spectrum of the migrating groups in β-(ester)alkyl radical reactions. The change from less nucleofugal (acetate) group to the more nucleofugal (carbonate) group in the spectrum of the migrating group changed the reaction path from rearrangement to fragmentation. This approach has been used for the synthesis of 1,1-dichloroalkenes in high yields. The formation of dichloroalkenes was accounted by the involvement of alkene radical cation and carbonate anion pair (a CIP) as a result of heterolysis of the CO bond of the carbonate at the β-position of the β-(alkoxycarbonyloxy)alkyl radical. The alkene radical cation was trapped by nucleophilic reaction with MeOH to form methyl ester.

Decarboxylative trichloromethylation of aromatic aldehydes and its applications in continuous flow

Two new protocols for the efficient synthesis of 2,2,2- trichloromethylcarbinols, starting from aromatic aldehydes, have been developed. A combination of sodium trichloroacetate in the presence of malonic acid proved efficient for the transformation of el

One-pot synthesis of trichloromethyl carbinols from primary alcohols

Versatile trichloromethyl carbinols can be prepared in one pot from primary alcohols by treatment with Dess-Martin periodinane (DMP) in CHCl3 followed by introduction of commercially available 1,5,7-triazabicyclo[4.4.0] dec-5-ene (TBD). A modification of the method was used to convert chiral primary alcohol (R)-(-)-2,2-dimethyl-1,3-dioxolane-4-methanol to the corresponding trichloromethyl carbinol with complete stereochemical fidelity, despite the reactant proceeding through a base-sensitive aldehyde intermediate.

Platinum on carbon-catalyzed precise reduction control of trichloromethyl to Geminal-dichloromethyl groups

Geminal-dichloromethyl derivatives could be efficiently synthesized by the highly chemoselective platinum on carbon-catalyzed mono-dechlorination of trichloromethyl substrates in dimethylacetamide (DMA) as a specific solvent at 25 °C under a hydrogen atmosphere. Copyright

Friedel-crafts hydroxyalkylation of anisole over oxalic acid modified Hβ zeolite

Oxalic acid modified Hβ (OA-Hβ) zeolite is found to have better catalytic performance than Hβ zeolite in the Friedel-Crafts hydroxyalkylation of anisole with chloral. This is attributed to the increase of weak and moderately-strong acid sites, caused by oxalic acid modification. Furthermore, it is believed that the carbonaceous deposits on the acid sites and the blockage of the pores, together with poisoning by chlorinated materials, are responsible for the deactivation of OA-Hβ zeolite, as indicated by NH3-TPD, BET, SEM, TG and XPS measurement results. Moreover, partial regeneration of OA-Hβ zeolite can be achieved via subsequent calcination.