chloro(methyl)diphenylsilane

• ChemBase ID: 150339
• Molecular Formular: C13H13ClSi
• Molecular Mass: 232.78082
• Monoisotopic Mass: 232.04750463
• SMILES: C[Si](c1ccccc1)(c1ccccc1)Cl
• Canonical SMILES: C[Si](c1ccccc1)(c1ccccc1)Cl
• InChI: InChI=1S/C13H13ClSi/c1-15(14,12-8-4-2-5-9-12)13-10-6-3-7-11-13/h2-11H,1H3
• InChIKey: OJZNZOXALZKPEA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: chloro(methyl)diphenylsilane
• IUPAC Traditional name: silane, chloromethyldiphenyl-
• Synonyms: DPMSCl; Methyldiphenylchlorosilane; Chloro-diphenyl-methylsilane; Diphenylmethylchlorosilane; Chloro(methyl)diphenylsilane; Chloro(methyl)diphenylsilane; Chlorodiphenylmethylsilane; 二苯基甲基氯硅烷; 氯-二苯基-甲基硅烷; 甲基二苯基氯硅烷; 二苯基甲基氯硅烷

Database IDs

• CAS Number: 144-79-6
• EC Number: 205-639-0
• MDL Number: MFCD00000498
• Beilstein Number: 2937445
• PubChem SID: 24846674; 162244500
• PubChem CID: 67349

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 5.165
• LogD (pH = 7.4): 5.165
• Log P: 5.165
• Molar Refractivity: 62.865 cm^3
• Polarizability: 26.51755 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Boiling Point: 294-295°C; 295 °C(lit.)
• Flash Point: 113 °C; 141°C(285°F); 235.4 °F
• Density: 1.104; 1.107 g/mL at 25 °C(lit.)
• Refractive Index: 1.5740; n20/D 1.574(lit.)
• Vapor Pressure: 3 mmHg ( 125 °C)

Safety Information

• Storage Warning: Moisture Sensitive
• European Hazard Symbols: Corrosive (C)
• UN Number: 2987; UN2987
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; II
• Risk Statements: 34; 34-37
• Safety Statements: 26-36/37/39-45
• TSCA Listed: 是
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H314; H314-H318
• GHS Precautionary statements: P280-P303+P361+P353-P305+P351+P338-P310; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2987 8/PG 2

Product Information

• Purity: ≥95.0% (GC); 95+%; 97%; 98%
• Grade: purum
• Linear Formula: CH3Si(C6H5)2Cl

DETAILS

Sigma Aldrich - 104760

Packaging
25, 100 g in glass bottle

Sigma Aldrich - 43120

Other Notes
Protecting group for alcohols1,2; The silyl ethers can be selectively cleaved with sodium azide in the presence of other silyl ethers (TBDMS, TBDPS)3; C-Silylation of ester enolates4

REFERENCES

• Silylating agent (see Appendix 4) for formation, in the presence of a base such as imidazole in DMF, of DPMS ethers, intermediate in hydrolytic stabilty between TMS and TBDMS. DPMS ethers are incompatible with acid, base, BuLi, Cr(VI) oxidants and LIAlH₄, but stable to silica chromatography: J. Org. Chem., 52, 165 (1987). They can be cleaved with mild acid or base, or F^-. Selective cleavage in high yield in the presence of TBDMS or TBDPS ethers with NaN₃ in DMF was reported: J. Chem. Soc., Chem. Commun., 381 (1989).
• In reactions with lithiated esters and lactones C-silylation predominates. The resulting ɑ-DPMS esters behave as vinyl dication equivalents: J. Am. Chem. Soc., 103, 2418 (1981); Pure Appl. Chem., 62, 2021 (1990), useful precursors of, e.g.: terminal alkenes: Synth. Commun., 13, 1163 (1983); 1,1-disubstituted alkenes: Tetrahedron Lett., 23, 271 (1982); Org. Synth. Coll., 8, 474 (1993); ?-keto silanes and ketones: J. Org. Chem., 50, 5260 (1985); 58, 2718 (1993):
  
• TBDMS esters react with aldehydes and ketones to give ?-hydroxy silanes, which undergo Peterson elimination to ɑ-substituted ɑ?-unsaturated esters: J. Org. Chem., 49, 3385 (1984).