Benzyl Chloromethyl Sulfide
Basic information
- CAS
3970-13-6- Standard SMILES
ClCSCc1ccccc1- InChIKey
UMFDSFPDTLREFS-UHFFFAOYSA-N- Molecular formula
- C8H9ClS
- Average molar mass
- 172.68 g/mol
- Monoisotopic mass
- 172.01134897
Names & identifiers
- Preferred name
- Benzyl Chloromethyl Sulfide
- IUPAC
- chloromethylsulfanylmethylbenzene
- English name
- Benzyl chloromethyl sulfide
- Molecular formula
- C8H9ClS
- Molecular weight
- 172.68
Names & synonyms
Benzyl chloromethyl sulfideDTXSID90313035RefChem:566742DTXCID90264159678-049-83970-13-6Benzyl(chloromethyl)sulfanechloromethylsulfanylmethylbenzene{[(Chloromethyl)thio]methyl}benzene{[(CHLOROMETHYL)SULFANYL]METHYL}BENZENEMFCD02093436NSC266050
Show more names
(chloromethylthio)methylbenzeneBenzyl Chloromethyl Sulfide >ALPHA-(CHLOROMETHYLTHIO)TOLUENE(methylthio)chloranuidylmethylbenzeneBenzene, [[(chloromethyl)thio]methyl]-
benzyl chloromethyl thioetherchloro(phenylmethylthio)methaneSCHEMBL231574alpha-(Chloromethylthio)tolueneSBB055458AKOS025116850NSC 266050NSC-266050
Database identifiers
- CAS
3970-13-6- PubChem CID
- 319930
- DTXSID
DTXSID90313035- EC Number
- 678-049-8
Properties
Computed structural properties
- XLogP
- 3.1
- Topological polar surface area
- 25.3 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 3
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 79.3
Experimental & physicochemical properties
SpringerMaterials PropertiesNuclear quadrupole resonance spectroscopy
Physicochemical properties
- Boiling point
- 136 · 136-139 °C(Press: 25 Torr)
- Density
- 1.19 · 1.19
- refractive index
- 1.578 · 1.5780-1.5820
- storage temp.
- 2 · Keep in dark place,Sealed in dry,2-8°C
- solubility
- soluble in most organic solvents
- form
- clear liquid
- color
- Colorless to Light yellow
- Symbol(GHS)
- 5 · GHS05,GHS07
- Signal word
- Danger
- Hazard statements
- 302 · H302+H312+H332-H315-H318
- Precautionary statements
- 261 · P261-P264-P270-P271-P280-P301+P312+P330-P302+P352+P312+P362+P364-P304+P340+P312-P305+P351+P338+P310-P501
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P354+P338, P317, P321, P330, P332+P317, P362+P364, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- hs_code
- 2930.90.2900
- risk_code
- 36/37/38
- Signal word
- Danger
- Symbol(GHS)
- GHS05,GHS07
- safety_code
- 26-36/37/39
- Hazard statements
- H302+H312+H332-H315-H318
- Precautionary statements
- P261-P264-P270-P271-P280-P301+P312+P330-P302+P352+P312+P362+P364-P304+P340+P312-P305+P351+P338+P310-P501
Chemistry & industry
Applications
UsesBenzyl Chloromethyl Sulfide is used for protecting group in peptide synthesis, palladium complexes, biologically active iminium compounds, sulfones, and sulfoximes.
Preparation methods
PreparationBenzyl Chloromethyl Sulfide is obtained following the procedure of Fancher. Chloromethylation of phenylmethanethiol with paraformaldehyde in concentrated hydrochloric acid gives the desired benzyl chloromethyl sulfide. To paraformaldehyde (7.5 g) in 50 mL of benzene, 100 mL of concentrated HCl is added in 5 min with stirring. The mixture is kept at 40 °C for a while and phenylmethanethiol (33.75 g) in 50 mL of benzene is added slowly. The resulting mixture is maintained slightly above 40 °C for 2 h. After removing the solvent, the product is purified by distillation under reduced pressure. The unpleasant odor can be in large part suppressed by washing used apparatus immediately with alkaline permanganate. Other methods have been described elsewhere.
Related reactions
8 records
Compound notes
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