chloro(methylsulfanyl)methane

• ChemBase ID: 88105
• Molecular Formular: C2H5ClS
• Molecular Mass: 96.5791
• Monoisotopic Mass: 95.98004884
• SMILES: S(CCl)C
• Canonical SMILES: CSCCl
• InChI: InChI=1S/C2H5ClS/c1-4-2-3/h2H2,1H3
• InChIKey: JWMLCCRPDOIBAV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: chloro(methylsulfanyl)methane
• IUPAC Traditional name: chloromethyl methyl sulfide
• Synonyms: Methyl chloromethyl sulfide; Chlorodimethyl sulfide; Chloromethyl methyl sulfide; Chloro(methylsulphanyl)methane; Chloro(methylthio)methane; Chloromethyl methyl sulphide; 氯甲基甲基硫醚; 氯二甲基硫醚; 氯甲基甲硫醚

Database IDs

• CAS Number: 2373-51-5
• EC Number: 219-148-4
• MDL Number: MFCD00000923
• Beilstein Number: 1730851
• PubChem SID: 24892780; 162075144
• PubChem CID: 16916

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 1.5334265
• LogD (pH = 7.4): 1.5334265
• Log P: 1.5334265
• Molar Refractivity: 23.3789 cm^3
• Polarizability: 9.322174 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 104-105°C; 105 °C(lit.); 105-110°C
• Flash Point: 17 °C; 17°C; 17°C(62°F); 62.6 °F
• Density: 1.153; 1.153 g/mL at 25 °C(lit.); 1.160
• Refractive Index: 1.4980; n20/D 1.498; n20/D 1.498(lit.)

Safety Information

• Storage Warning: Highly Flammable/Stench/Irritant/Keep Cold; Moisture Sensitive
• RTECS: WQ3700000
• European Hazard Symbols: Flammable (F); Irritant (Xi)
• UN Number: 1993; UN1993
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 2; II
• Risk Statements: 11-36/37/38; 11-37
• Safety Statements: 9-16-26-33-37-60; 9-16-33
• TSCA Listed: 否
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H225; H225-H315-H319-H335
• GHS Precautionary statements: P210; P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1993 3/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥80% (GC); 95%
• Grade: technical
• Linear Formula: CH3SCH2Cl

DETAILS

Sigma Aldrich - C54007

Caution
May darken in storage.
Packaging
5, 25, 100 g in glass bottle
Application
Methylthiomethylating reagent for carbonyl1 and aromatic2 compounds. Methylene transfer reagent for iron(II) mediated cyclopropanation.3

Sigma Aldrich - 24390

Other Notes
Reagent for the introduction of the methylthiomethyl (MTM) protecting group into carboxylic acids. MTM esters are stable to mild reducing agents1

REFERENCES

• For reaction with cyclopentadienyl iron dicarbonyl dimer in the formation of an iron-containing methylene transfer agent, see: Org. Synth. Coll., 9, 372 (1998).
• Protects alcohols as their methylthiomethyl (MTM) ethers by reaction, e.g. with NaH/NaI in DME: Tetrahedron Lett., 3269 (1975), or with AgNO₃/Et₃N: Chem. Lett., 1277 (1979). MTM ethers are relatively stable to acid but can be cleaved selectively with HgCl₂ in aqueous acetonitrile or AgNO₃/2,6-lutidine: Tetrahedron Lett., 3269 (1975), by methylation (MeI) and hydrolysis: Austral. J. Chem., 31, 1031 (1978); Chem. Lett., 715 (1984), or with TMS chloride and Ac₂O: Chem. Ind. (London), 223 (1984). For protection of phenols, see: Tetrahedron Lett., 533 (1977); 24, 1189 (1984).
• Can also be 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: Tetrahedron Lett., 731 (1978) which also describes cleavage with HgCl₂. The ester can also be cleaved with TFA: J. Chem. Soc., Chem. Commun., 224 (1973); or by methylation-hydrolysis: Tetrahedron Lett., 689 (1979).