Basic information
- CAS
2373-51-5- Standard SMILES
CSCCl- InChIKey
JWMLCCRPDOIBAV-UHFFFAOYSA-N- Molecular formula
- C2H5ClS
- Average molar mass
- 96.58 g/mol
- Monoisotopic mass
- 95.980049
Names & identifiers
- Preferred name
- Chloromethyl methyl sulfide
- IUPAC
- chloro(methylsulfanyl)methane
- English name
- Chloromethyl methyl sulfide
- Molecular formula
- C2H5ClS
- Molecular weight
- 96.58
Names & synonyms
Chloromethyl methyl sulfide2373-51-5Chlorodimethyl sulfideMethane, chloro(methylthio)-DTXSID10178406RefChem:125445DTXCID00100897219-148-4Chloro(methylsulfanyl)methaneMethylthiomethyl chlorideChloro(methylthio)methaneChloromethyl methyl thioether
Show more names
(chloroMethyl)(Methyl)sulfaneCH3SCH2ClMTMchloridechlorodimethylthioether
Chloromethyl methyl sulphideChlorodimethyl thioetherMonochlorodimethyl sulfideClorodimetilsolfurochloromethylmethylsulfideSULFIDE, CHLOROMETHYL METHYLClorodimetilsolfuro [Italian]NSC 63205
Database identifiers
- CAS
2373-51-5- PubChem CID
- 16916
- DTXSID
DTXSID10178406- EC Number
- 219-148-4
- Nikkaji
- J149.595J
Properties
Computed structural properties
- XLogP
- 1.6
- Topological polar surface area
- 25.3 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 1
- Heavy atoms
- 4
- Formal charge
- 0
- Complexity
- 10
Physicochemical properties
- Boiling point
- 105 °C · 105 °C (lit.)
- Density
- 1.153 g/mL · 1.153 g/mL at 25 °C (lit.)
- refractive index
- 20 · n20/D 1.498(lit.)
- Flash point
- 63 °F · 63 °F
- storage temp.
- 2 · 2-8°C
- form
- clear liquid
- color
- Colorless to Light orange to Yellow
- Water Solubility
- Soluble in acetonitrile, ether and dichloromethane. Insoluble in water.
- Sensitive
- Moisture Sensitive
- BRN
- 1730851 · 1730851
- InChI
- InChI=1S/C2H5ClS/c1-4-2-3/h2H2,1H3
- InChIKey
- JWMLCCRPDOIBAV-UHFFFAOYSA-N
- SMILES
- C(Cl)SC
- CAS DataBase Reference
- 2373 · 2373-51-5(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- UNSPSC Code
- 12352101 · 12352101
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 2 · GHS02
- Signal word
- Danger
- Hazard statements
- 225 · H225
- Precautionary statements
- 210 · P210-P233-P240-P241-P242-P243
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- Hazard Codes
- F,Xi
- Risk Statements
- 11 · 11-37
- Safety Statements
- 9 · 9-16-33
- RIDADR
- 1993 · UN 1993 3/PG 2
- WGK Germany
- 3 · 3
- RTECS
- 3700000 · WQ3700000
- F
- 13 · 13
- HazardClass
- 3 · 3
- PackingGroup
- II
- HS Code
- 2930909899 · 2930909899
- Storage Class
- 3 · 3 - Flammable liquids
- Hazard Classifications
- 2 · Flam. Liq. 2
- Limited Quantities
- 1 L · 1.0 L (0.3 gallon) (liquid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
Safety & regulation
Safety data
- F
- 13
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 3
- rtecs
- WQ3700000
- ridadr
- UN 1993 3/PG 2
- hs_code
- 2930909899
- risk_code
- 11-37
- Signal word
- Danger
- Symbol(GHS)
- GHS02
- hazard_code
- F,Xi
- safety_code
- 9-16-33
- hazard_class
- 3
- Storage Class
- 3 - Flammable liquids
- packing_group
- II
- Hazard statements
- H225
- Limited Quantities
- 1.0 L (0.3 gallon) (liquid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
- Hazard Classifications
- Flam. Liq. 2
- Precautionary statements
- P210-P233-P240-P241-P242-P243
Chemistry & industry
Applications
UsesChloromethyl methyl sulfide is used as a methylene transfer reagent for iron(II) mediated cyclopropanation and for carbonyl and aromatic compounds. It protects alcohols as their methylthiomethyl (MTM) ethers by reaction, e.g. with NaH/NaI in DME. It is also used for the preparation of MTM esters of carboxylic acids, e.g. by treatment of the K salt of the acid in the presence of NaI and 18-crown-6 and for reaction with cyclopentadienyl iron dicarbonyl dimer in the formation of an iron-containing methylene transfer agent.
UsesMethylthiomethylating reagent for carbonyl and aromatic compounds. Methylene transfer reagent for iron(II) mediated cyclopropanation.
Upstream & downstream products
Upstream raw materials
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Related reactions
131 records
Compound notes
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