(chloromethyl)trimethylsilane

• ChemBase ID: 87753
• Molecular Formular: C4H11ClSi
• Molecular Mass: 122.66864
• Monoisotopic Mass: 122.03185456
• SMILES: [Si](C)(C)(CCl)C
• Canonical SMILES: ClC[Si](C)(C)C
• InChI: InChI=1S/C4H11ClSi/c1-6(2,3)4-5/h4H2,1-3H3
• InChIKey: OOCUOKHIVGWCTJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (chloromethyl)trimethylsilane
• IUPAC Traditional name: (chloromethyl)trimethylsilane
• Synonyms: CHLOROMETHYLTRIMETHYLSILANE; Silane CMM3; (Chloromethyl)trimethylsilane; (Trimethylsilyl)methyl chloride; (Chloromethyl)trimethylsilane; 三甲基氯甲基硅烷; (氯甲基)三甲基硅烷

Database IDs

• CAS Number: 2344-80-1
• EC Number: 219-058-5
• MDL Number: MFCD00000878
• Beilstein Number: 906705
• PubChem SID: 24850936; 162074793; 24852326; 24855086
• PubChem CID: 75361

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 3.057
• LogD (pH = 7.4): 3.057
• Log P: 3.057
• Molar Refractivity: 26.6836 cm^3
• Polarizability: 12.8536415 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 97-98°C; 98-99 °C(lit.); 98-99°C
• Flash Point: -2°C(28°F); 24.8 °F; -4 °C; -4°C
• Density: 0.879; 0.879 g/mL at 25 °C(lit.); 0.88 g/mL at 20 °C; 0.886
• Refractive Index: 1.4180; n20/D 1.418(lit.)
• Vapor Pressure: ~25 mmHg ( 20 °C)

Safety Information

• Storage Warning: Irritant/Highly Flammable/Keep Cold; Moisture Sensitive
• 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
• Safety Statements: 16-26-36; 9-16-23-26-33-37
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H224-H315-H319-H335; H225-H315-H319-H335
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A; P210-P261-P305 + P351 + P338
• 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

Product Information

• Purity: ≥98.0% (GC); 97%; 98%
• Grade: produced by Wacker; purum
• Linear Formula: (CH3)3SiCH2Cl

DETAILS

MP Biomedicals - 05205827

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 205354

Packaging
25, 4×25, 100 mL in Sure/Seal™

Sigma Aldrich - 18146

Other Notes
prices for bulk quantities on request
Packaging
1 kg in glass bottle
250 g in glass bottle

Sigma Aldrich - 25300

Other Notes
Reagent for the Peterson olefination and the homologation of ketones and aldehydes via α,β-epoxysilanes, reviews 1,2; For the synthesis of allylsilanes3

REFERENCES

• For a review of the chemistry of chloromethyltrimethylsilane, see: Synthesis, 717 (1985).
• Treatment with s-BuLi at -78^o gives ɑ-lithio-ɑ-chloromethyltrimethylsilane which reacts with aldehydes and ketones to give ɑ?-epoxy silanes, readily hydrolyzed to homologated aldehydes: Tetrahedron, 39, 867 (1983):
  
• Metallation gives useful precursors of various organosilicon compounds. For use of the Grignard in the olefination of ketones, see: J. Org. Chem., 39, 3264 (1974); 52, 281 (1987). For Ni-catalyzed reaction of the Grignard with allylic dithioacetals, see: J. Org. Chem., 53, 5582 (1988); Org. Synth. Coll., 9, 727 (1998); for an example with reaction scheme, see trans-Cinnamaldehyde, A14689.