chloro(2,3-dimethylbutan-2-yl)dimethylsilane

• ChemBase ID: 149938
• Molecular Formular: C8H19ClSi
• Molecular Mass: 178.77496
• Monoisotopic Mass: 178.09445482
• SMILES: CC(C)C(C)(C)[Si](C)(C)Cl
• Canonical SMILES: CC(C([Si](Cl)(C)C)(C)C)C
• InChI: InChI=1S/C8H19ClSi/c1-7(2)8(3,4)10(5,6)9/h7H,1-6H3
• InChIKey: KIGALSBMRYYLFJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: chloro(2,3-dimethylbutan-2-yl)dimethylsilane
• IUPAC Traditional name: chloro(2,3-dimethylbutan-2-yl)dimethylsilane
• Synonyms: Chlorodimethylthexylsilane; Dimethyl(2,3-dimethylbutyl)chlorosilane; Dimethylthexylchlorosilane; Dimethylthexylsilyl chloride; TDSCl; Thexyldimethylsilyl chloride; Chlorodimethyl(1,1,2-trimethylpropyl)silane; Dimethyl-(2,3-dimethyl-2-butyl)chlorosilane; Dimethyl-thexylchlorosilane; Chloro(dimethyl)thexylsilane; 二甲基叔己基氯化硅; 二甲基-(2,3-二甲基-2-丁基)氯硅烷; 二甲基叔己基氯化硅; 氯二甲基(1,1,2-三甲基丙基)硅烷; 氯(二甲基)叔己基硅烷

Database IDs

• CAS Number: 67373-56-2
• MDL Number: MFCD00012175
• Beilstein Number: 3647960
• PubChem SID: 162244100; 24889083; 24889084; 24858253
• PubChem CID: 144239

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 3.6124
• LogD (pH = 7.4): 3.6124
• Log P: 3.6124
• Molar Refractivity: 46.1944 cm^3
• Polarizability: 20.200396 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 14-15°C
• Boiling Point: 55-56 °C/10 mmHg(lit.); 55-56°C/10mm
• Flash Point: 114.8 °F; 46 °C; 51°C(124°F)
• Density: 0.909 g/mL at 25 °C(lit.); 0.911
• Refractive Index: 1.4500; n20/D 1.449(lit.); n20/D 1.450

Safety Information

• Storage Warning: Moisture Sensitive
• European Hazard Symbols: Corrosive (C)
• UN Number: 2986; UN2986
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; II
• Risk Statements: 10-34; 10-34-37
• Safety Statements: 23-26-36/37/39-45; 26-36/37/39-45
• TSCA Listed: 否
• GHS Pictograms: GHS02; GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H226-H314; H314-H318-H226
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A; 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 2986 8/PG 2

Product Information

• Purity: ≥97.0% (GC); ≥99.0% (GC); 95%
• Grade: puriss.; purum
• Linear Formula: (CH3)2CHC(CH3)2Si(CH3)2Cl

DETAILS

Sigma Aldrich - 302449

Packaging
5, 25, 100 g in glass bottle
Application
Protecting reagent for alcohols and other functional groups.1,2 Employed in the synthesis of silicon naphthocyanine3 and cyclodextrin derivatives,4 which are useful as antitumor dyes and chiral stationary phases, respectively.

Sigma Aldrich - 88330

Other Notes
Protecting group reagent with some advantages compared to tert-butyldimethylchlorosilane (less expensive, liquid, slightly more stable)1,2,3

REFERENCES

• Reagent for the introduction, in the presence of a base such as triethylamine or imidazole in DMF, of the thexyldimethylsilyl (TDS) group for protection of hydroxyl functions. The greater steric hindrance of the TDS group compared with TBDMS confers greater (at least 2-3x) stability to acid or base hydrolysis. Cleavage with F^- is also about 2-3x slower than for TBDMS: Tetrahedron Lett., 26, 5511 (1985); 32, 2135 (1991). TDS is also an extremely useful protecting group for nitrogen functions, providing readily purifiable derivatives which survive a variety of chemical transformations, but are readily cleaved by F^-: Tetrahedron Lett., 26, 5515 (1985); J. Chem. Soc., Perkin 1, 423 (1998).