75462-59-8

Basic information

• Product Name: 3,5-Bis(trifluoromethyl)benzyl chloride
• Synonyms: 1-CHLOROMETHYL-3,5-BIS(TRIFLUOROMETHYL)BENZENE;3,5-Bis(trifluoromethyl)benzyl chloride 99%;3,5-Bis(trifluoromethyl)benzylchloride99%;3,5-Bis(trifluoromethyl)-1-(chloromethyl)benzene;3,5-Bis(trifluoromethyl)benzyl choride;Benzene, 1-(chloromethyl)-3,5-bis(trifluoromethyl)-;3,5-DI(TRIFLUOROMETHYL)BENZYL CHLORIDE;3,5-BIS(TRIFLUOROMETHYL)BENZYL CHLORIDE
• CAS NO: 75462-59-8
• Molecular Formula: C₉H₅ClF₆
• Molecular Weight: 262.58
• EINECS: 278-216-1
• Product Categories: Fluorides;Miscellaneous;Fluorine series
• Mol File: 75462-59-8.mol
• Article Data: 3

Chemical Properties

• Melting Point: 29-32 °C(lit.)
• Boiling Point: 46°C 3mm
• Flash Point: 161 °F
• Appearance: /
• Density: 1.4425 (estimate)
• Vapor Pressure: 14.4mmHg at 25°C
• Refractive Index: 1.39
• Storage Temp.: 2-8°C
• Water Solubility: Slightly soluble in water.
• BRN: 656502
• CAS DataBase Reference: 3,5-Bis(trifluoromethyl)benzyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Bis(trifluoromethyl)benzyl chloride(75462-59-8)
• EPA Substance Registry System: 3,5-Bis(trifluoromethyl)benzyl chloride(75462-59-8)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 75462-59-8(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 75462-59-8 differently. You can refer to the following data:
1. 3,5-Bis(trifluoromethyl)benzyl chloride has been used in the preparation of 1-(azidomethyl)-3,5-bis-(trifluoromethyl)benzene. 1-(azidomethyl)-3,5-bis-(trifluoromethyl)benzene, in 94% yield by an efficient nucleophilic substitution reaction between 3,5-bis-(trifluoromethyl)benzyl chloride, 4, and sodium azide.
2. 3,5-Bis(trifluoromethyl)benzyl chloride has been used in the preparation of 1-(azidomethyl)-3,5-bis-(trifluoromethyl)benzene.

InChI:InChI=1/C9H6F6/c1-5-2-6(8(10,11)12)4-7(3-5)9(13,14)15/h2-4H,1H3

Upstream product

• 32707-89-4 3,5-bis(trifluoromethyl)benzenemethanol 
• 81577-14-2 1-Chloro-3-(1-chloro-2,2,2-trifluoro-ethyl)-benzene 

Downstream Products

• 380424-41-9 1-(3,5-bis-trifluoromethyl-benzyl)-piperidine-4-carboxylic acid amide 
• 346416-93-1 4-[2-(3,5-bis-trifluoromethyl-benzyloxy)-1-(3-chloro-phenyl)-ethyl]-piperazine-1-carboxylic acid ethyl ester 
• 346416-94-2 4-[2-(3,5-bis-trifluoromethyl-benzyloxy)-1-(4-fluoro-phenyl)-ethyl]-piperazine-1-carboxylic acid ethyl ester 
• 346416-92-0 4-[2-(3,5-bis-trifluoromethyl-benzyloxy)-1-(4-methoxy-phenyl)-ethyl]-piperazine-1-carboxylic acid ethyl ester 
• 346416-95-3 4-[2-(3,5-bis-trifluoromethyl-benzyloxy)-1-(3,4-dichloro-phenyl)-ethyl]-piperazine-1-carboxylic acid ethyl ester 
• 346416-96-4 4-[2-(3,5-bis-trifluoromethyl-benzyloxy)-1-(2,3-difluoro-phenyl)-ethyl]-piperazine-1-carboxylic acid ethyl ester 

Relevant articles and documents

PROCESS FOR THE PREPARATION OF 3,5-BIS (TRIFLUOROMETHYL)-N-METHYLBENZYLAMINE

The invention concerns a process for the preparation of 3,5-bis(trifluoromethyl)-N- methyl-benzylamine by means of an amino-dehalogenation reaction, more in particular starting from a 3,5-bis(trifluoromethyl)-benzyl halide, in particular starting from 3,5-bis(trifluoromethyl)-benzyl chloride and a new process for preparation of the latter.

Gas-phase substituent effects in highly electron-deficient systems. II. stabilities of 1-aryl-2,2,2-trifluoroethyl cations based on chloride-transfer equilibria

The relative stabilities of 1-aryl-2,2,2-trifluoroethyl cations were determined based on the chloride ion-transfer equilibria in the gas phase. An application of the Yukawa-Tsuno equation to this substituent effect on the equilibrium constants gave a remarkably larger r+ of 1.53 and a ρ of-10.6, supporting our previous conclusion that the highly electron-deficient benzylic carbocation systems are characterized by extremely high resonance demands. This r+ value, furthermore, conformed a linear relationship between the r+ value and the relative stability of the unsubstituted member of the respective benzylic carbocations, clearly demonstrating a continuous spectrum of varying resonance demands characteristic of the stabilities of carbocations. The π-delocalization of the positive charge into the aryl π-system increases with the destabilization of a carbocation by the α-substituent(s) linked to the central carbon. In addition, the r + value of 1.53 for 1-aryl-2,2,2-trifluoroethyl cations was found to be in complete agreement with that for the solvolysis of 1-aryl-2,2,2- trifluoroethyl tosylates in 80% aq acetone. This reveals that the r+ value observed for this solvolysis must be the intrinsic resonance demand of a highly electron-deficient cationic transition state in the SN 1 ionizing process. The identity of the r+ value was consistent with our previous observation for other benzylic carbocation systems, indicating that the degree of the π-delocalization of the positive charge is identical between the cationic transition state and an intermediate cation for all benzylic systems, which cover a wide range of reactivity and stability of the carbocation. This leads us to the conclusion that the geometry of the transition state in the ionizing process of the SN1 solvolysis, which is a highly endothermic reaction, closely resembles the high-energy product, an intermediate cation.