874-87-3

Basic information

• Product Name: 4-(METHYLTHIO)BENZYL CHLORIDE
• Synonyms: P-(METHYLTHIO)BENZYL CHLORIDE;4-(METHYLTHIO)BENZYL CHLORIDE;4-(Chloromethyl)thioanisole;1-(chloromethyl)-4-(methylthio)benzene;P-(METHYLTHIO)BENZYL CHLORIDE (STABILIZED WITH CALCIUM CARBONATE);Einecs 212-870-0;4-(METHYLTHIO)BENZYL;4-Chloromethyl
• CAS NO: 874-87-3
• Molecular Formula: C₈H₉ClS
• Molecular Weight: 172.68
• EINECS: 212-870-0
• Product Categories: Organic Building Blocks;Sulfides/Disulfides;Sulfur Compounds
• Mol File: 874-87-3.mol
• Article Data: 22

Chemical Properties

• Boiling Point: 116°C 8mm
• Flash Point: >230 °F
• Appearance: /
• Density: 1.170 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0179mmHg at 25°C
• Refractive Index: n20/D 1.6020(lit.)
• Storage Temp.: 2-8°C
• Water Solubility: It hydrolyzes in water.
• Sensitive: Moisture Sensitive
• CAS DataBase Reference: 4-(METHYLTHIO)BENZYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(METHYLTHIO)BENZYL CHLORIDE(874-87-3)
• EPA Substance Registry System: 4-(METHYLTHIO)BENZYL CHLORIDE(874-87-3)

Safety Data

• Hazard Codes: C,Xi
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 1760 8/PG 2
• WGK Germany: 3
• HazardClass: IRRITANT, STENCH, CORROSIVE
• PackingGroup: II
• Hazardous Substances Data: 874-87-3(Hazardous Substances Data)

Usage

Uses

4-(Methylthio)benzyl chloride is used as pharmaceutical intermediate.

Synthesis Reference(s)

The Journal of Organic Chemistry, 40, p. 1920, 1975 DOI: 10.1021/jo00901a011

InChI:InChI=1/C8H9ClS/c1-10-8-4-2-7(6-9)3-5-8/h2-5H,6H2,1H3

Upstream product

• 100-68-5 methyl-phenyl-thioether 
• 107-30-2 chloromethyl methyl ether 
• 75-09-2 dichloromethane 
• 109-87-5 Dimethoxymethane 
• 107-06-2 1,2-dichloro-ethane 
• 3446-90-0 4-(methylthio)benzyl alcohol 
• 98-88-4 benzoyl chloride 
• 3795-79-7 methyl 4-(methylthio)benzoate 
• 13205-48-6 4-(methylthio)benzoic acid 

Downstream Products

• 38746-92-8 2-[4-(methylsulfanyl)phenyl]acetonitrile 
• 19927-29-8 4-methylsulfanyl-benzyl thiocyanate 
• 107419-13-6 acetylamino-(4-methylsulfanyl-benzyl)-malonic acid diethyl ester 
• 3446-89-7 4-(Methylthio)benzaldehyde 
• 99810-15-8 3-chloropropyl p-(methylthio)benzyl sulfide 
• 72138-31-9 2-(p-Thiomethoxyphenyl)-3,3-dimethylmethylenecyclopropane 
• 72138-43-3 2-(p-Thiomethoxyphenyl)isopropylidenecyclopropane 
• 3446-67-1 1-(4-methylthiobenzyl)-5-methoxy-2-methylindole-3-acetic acid 
• 144727-96-8 4-Fluoro-N¹-(4-methylsulfanyl-benzyl)-benzene-1,2-diamine 
• 144728-06-3 4-Chloro-N¹-(4-methylsulfanyl-benzyl)-benzene-1,2-diamine 
• 144727-54-8 4-<1-<<4-(methylthio)phenyl>methyl>-5-fluorobenzimidazol-2-yl>-3,3-dimethylbutanoic acid 
• 144727-65-1 4-[1-(4-methylthiobenzyl)-5-chlorobenzimidazol-2-yl]-3,3-dimethylbutanoic acid 
• 144727-53-7 4-[5-Fluoro-1-(4-methylsulfanyl-benzyl)-1H-benzoimidazol-2-yl]-3,3-dimethyl-butyric acid ethyl ester 
• 147643-81-0 4-[5-Chloro-1-(4-methylsulfanyl-benzyl)-1H-benzoimidazol-2-yl]-3,3-dimethyl-butyric acid ethyl ester 

Relevant articles and documents

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Systematic Evaluation of Sulfoxides as Catalysts in Nucleophilic Substitutions of Alcohols

Herein, a method for the nucleophilic substitution (SN) of benzyl alcohols yielding chloro alkanes is introduced that relies on aromatic sulfoxides as Lewis base catalysts (down to 1.5 mol-%) and benzoyl chloride (BzCl) as reagent. A systematic screening of various sulfoxides and other sulfinyl containing Lewis bases afforded (2-methoxyphenyl)methyl sulfoxide as optimal catalyst. In contrast to reported formamide catalysts, sulfoxides also enable the application of plain acetyl chloride (AcCl) as reagent. In addition, it was demonstrated that weakly electrophilic carboxylic acid chlorides like BzCl promote Pummerer rearrangement of sulfoxides already at room temperature. This side-reaction also provided the explanation, why sulfoxide catalyzed SN-reactions of alcohols do not allow the effective production of aliphatic and electron deficient chloro alkanes. Comparison experiments provided further insight into the reaction mechanism.

METHOD OF CONVERTING ALCOHOL TO HALIDE

The present invention relates to a method of converting an alcohol into a corresponding halide. This method comprises reacting the alcohol with an optionally substituted aromatic carboxylic acid halide in presence of an N-substituted formamide to replace a hydroxyl group of the alcohol by a halogen atom. The present invention also relates to a method of converting an alcohol into a corresponding substitution product. The second method comprises: (a) performing the method of the invention of converting an alcohol into the corresponding halide; and (b) reacting the corresponding halide with a nucleophile to convert the halide into the nucleophilic substitution product.