Basic information
- CAS
5813-48-9- Standard SMILES
CSCl- InChIKey
DDCYYCUMAFYDDU-UHFFFAOYSA-N- Molecular formula
- CH3ClS
- Average molar mass
- 82.55 g/mol
- Monoisotopic mass
- 81.96439878
Names & identifiers
- Preferred name
- Methanesulfenylchloride
- IUPAC
- methyl thiohypochlorite
- English name
- Methanesulfenic acid chloride
- Molecular formula
- CH3ClS
- Molecular weight
- 82.55
Names & synonyms
MethanesulfenylchlorideMethanesulfenyl chloride5813-48-9methylsulfenyl chloridemethyl thiohypochlorite(chlorosulfanyl)methanemethylsulfonium chloridemethyl sulfenyl chloridemethyl sulphenyl chlorideSCHEMBL159813SCHEMBL8672472SCHEMBL9328851
Show more names
Methylthio chlorideMethylsulfur monochlorideMethanesulfenic acid chlorideMethanesulfenyl chloride (6CI,7CI,8CI,9CI)
DTXSID80206846DDCYYCUMAFYDDU-UHFFFAOYSA-N
Database identifiers
- CAS
5813-48-9- PubChem CID
- 138595
- DTXSID
DTXSID80206846- Nikkaji
- J8.070E
Properties
Computed structural properties
- XLogP
- 1.3
- Topological polar surface area
- 25.3 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 0
- Heavy atoms
- 3
- Formal charge
- 0
- Complexity
- 4.8
Experimental & physicochemical properties
SpringerMaterials PropertiesSchoenflies notation
Physicochemical properties
- Boiling point
- 27 · 27-28 °C(Press: 53-60 Torr)
- Density
- 1.172 · 1.172±0.06 g/cm3(Predicted)
- solubility
- sol ether, THF, dichloromethane, chloroform, carbon tetrachloride, dimethoxyethane
Chemistry & industry
Applications
UsesMethanesulfenic acid chloride reacts as a pseudohalogen; reacts with carbanions and enolates to add the thiomethyl group α to the carbonyl; adds across the double bonds of alkenes and allenes; adds across triple bond of alkynes.
Preparation methods
PreparationTo a flask containing 23.6 gm (0.25 mole) of dimethyl disulfide at - 1 5 ° to -20°C is slowly added dropwise 34 gm (0.25 mole) of freshly distilled sulfuryl chloride while keeping the temperature at -15° to -20°C. The reaction mixture is stirred for 1 hr, and then distilled to afford 37.1 gm (90%), b.p. 27-28°C (53-60 mm Hg); NMR, 2.91 ppm (singlet). The crude product can also be used without distillation since most of the material is product.
Upstream & downstream products
Downstream products
Suppliers1 total
Shaanxi Didu New Materials Co. Ltd+86-86-17392712779 +86-13289823923 · [email protected]
Related reactions
16 records
Compound notes
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