Chloromethyl phenyl sulfide

Base Information

• Chemical Name: Chloromethyl phenyl sulfide
• CAS No.: 7205-91-6
• Molecular Formula: C7H7ClS
• Molecular Weight: 158.652
• Hs Code.: 29309099
• European Community (EC) Number: 230-579-7
• NSC Number: 203003
• UNII: SF6BSS54L2
• DSSTox Substance ID: DTXSID40222385
• Nikkaji Number: J208.224A
• Wikidata: Q72454631
• Mol file: 7205-91-6.mol

Synonyms:Chloromethyl phenyl sulfide;7205-91-6;Chloromethylthiobenzene;alpha-Chlorothioanisole;Chloromethyl phenyl sulphide;(chloromethyl)(phenyl)sulfane;chloromethylsulfanylbenzene;Phenyl chloromethyl sulfide;(Phenylthio)methyl chloride;Sulfide, chloromethyl phenyl;[(Chloromethyl)thio]benzene;Benzene, [(chloromethyl)thio]-;Benzene, ((chloromethyl)thio)-;AI3-26264;EINECS 230-579-7;NSC 203003;NSC-203003;chloromethylphenyl sulfide;[(Chloromethyl)sulfanyl]benzene;phenylthiomethyl chloride;chloromethyl phenylsulfide;phenyl(chloromethyl) sulfide;SF6BSS54L2;Sulphide, chloromethyl phenyl;Phenyl (chloromethyl) sulfide;SCHEMBL693421;Benzene,[(chloromethyl)thio]-;DTXSID40222385;Chloromethyl phenyl sulfide, 97%;[(Chloromethyl)sulfanyl]benzene #;MFCD00000921;NSC203003;AKOS006220525;AS-59129;CS-0326545;FT-0704708;D89325;W-104502

Chemical Property of Chloromethyl phenyl sulfide

Chemical Property:

• Vapor Pressure: 0.00847mmHg at 25°C
• Refractive Index: n20/D 1.594(lit.)
• Boiling Point: 275.6 °C at 760 mmHg
• Flash Point: 101.1 °C
• PSA: 25.30000
• Density: 1.2 g/cm³
• LogP: 2.97500
• Storage Temp.: Refrigerator
• Sensitive.: Stench
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 157.9956991
• Heavy Atom Count: 9
• Complexity: 69.3

Purity/Quality:

97% ^*data from raw suppliers

Chloromethyl phenyl sulfide ^*data from reagent suppliers

Safty Information:

• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)SCCl
• General Description: Chloromethyl phenyl sulfide is a reactive organosulfur compound that participates in cationic polar cycloaddition reactions, particularly [4+2] cycloadditions with alkenes and alkynes like styrene, trans-stilbene, and phenylacetylene in the presence of SnCl4, yielding thiochroman and thiochromen derivatives. It also facilitates intramolecular cycloadditions, as demonstrated with N-allyl-α-chloro-α-(phenylthio)acetamide, forming structurally defined products under mild conditions (0°C in CH2Cl2). These reactions highlight its utility as a versatile intermediate in synthesizing sulfur-containing heterocycles, with ongoing studies exploring its broader reactivity and stereochemical outcomes.

Technology Process of Chloromethyl phenyl sulfide

There total 32 articles about Chloromethyl phenyl sulfide 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: 99.0%

methyl-phenyl-thioether (100-68-5) → phenylthiomethyl chloride (7205-91-6)

Guidance literature:

With N-chloro-succinimide; In tetrachloromethane; for 11h; Ambient temperature;

DOI:10.1021/jo00289a059

Reference yield: 93.0%

racemic methyl phenyl sulfoxide (1193-82-4) → phenylthiomethyl chloride (7205-91-6) + methyl-phenyl-thioether (100-68-5)

Guidance literature:

With thionyl chloride; triphenylphosphine; In tetrahydrofuran; at 20 ℃; for 2h; Solvent; Inert atmosphere;

DOI:10.1021/jo4008157

Reference yield: 89.0%

S-Phenyl benzenethiosulfonate (1212-08-4) + Chloroiodomethane (593-71-5) → phenylthiomethyl chloride (7205-91-6)

Guidance literature:

With methyllithium lithium bromide; In tetrahydrofuran; diethyl ether; at -78 ℃; for 1h; Inert atmosphere;

DOI:10.1002/adsc.202000919

upstream raw materials:

methyl-phenyl-thioether

racemic methyl phenyl sulfoxide

hydroxymethyl phenyl sulfide

formaldehyd

Downstream raw materials:

benzyl-dimethyl-(phenylsulfanyl-methyl)-ammonium; chloride

chloromethyl phenyl sulfone

diethyl S-(phenylthio)methyl phosphorodithioate

phenylsulfanyl-methyl thiocyanate

Refernces

CATIONIC POLAR CYCLOADDITION WITH CHLOROMETHYL PHENYL SULFIDES

10.1016/S0040-4039(01)82017-7

The research investigates cationic polar cycloaddition reactions involving chloromethyl phenyl sulfides. These compounds undergo [4+2] type polar cycloadditions with styrene, trans-stilbene, and phenylacetylene in the presence of stannic chloride (SnCl4) to produce thiochroman and thiochromen derivatives. The study also explores intramolecular cycloaddition using N-allyl-α-chloro-α-(phenylthio)acetamide, yielding a specific cycloaddition product. The reactions are carried out in methylene chloride at 0°C, and the products are characterized by their yields and physical data, such as melting points and NMR spectra. The scope and stereochemistry of these cycloadditions are currently under further investigation.