tert-butyl(chloro)dimethylsilane

• ChemBase ID: 73799
• Molecular Formular: C6H15ClSi
• Molecular Mass: 150.7218
• Monoisotopic Mass: 150.06315469
• SMILES: [Si](C)(Cl)(C(C)(C)C)C
• Canonical SMILES: C[Si](C(C)(C)C)(Cl)C
• InChI: InChI=1S/C6H15ClSi/c1-6(2,3)8(4,5)7/h1-5H3
• InChIKey: BCNZYOJHNLTNEZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tert-butyl(chloro)dimethylsilane
• IUPAC Traditional name: t-butyldimethylchlorosilane
• Synonyms: tert-Butyldimethylchlorosilane; tert-Butyldimethylsilyl chloride; tert-Butylchlorodimethylsilane solution; TBDMSCl; tert-Butyl(chloro)dimethylsilane; tert-Butyldimethylsilyl chloride; Chloro(1,1-dimethylethyl)dimethyl-silane; Chloro-tert-butyldimethyl-silane; (1,1-Dimethylethyl)dimethylsilyl Chloride; Chlorodimethyl-tert-butylsilane; TBDMS; tert-Butyl(dimethyl)silane Chloride; TBS-Cl; (tert-Butyl)dimethylsilyl chloride; (tert-Butyl)(chloro)dimethylsilane, 50% solution in toluene; tert-butyl(chloro)dimethylsilane; tert-Butylchlorodimethylsilane solution; tert-Butyldimethylsilyl chloride; TBDMSCl solution; tert-Butyldimethylsilyl chloride solution; tert-Butyl(chloro)dimethylsilane; tert-Butylchlorodimethylsilane; tert-Butyldimethylchlorosilane; tert-ButylchlorodiMethylsilane; 叔丁基氯二甲基硅烷 溶液; 叔丁基(氯)二甲基硅烷; 叔丁基二甲基硅基氯; 叔丁基二甲基硅基氯 溶液; TBDMSCl 溶液; 叔丁基二甲基氯硅烷; 叔丁基二甲基硅基氯; 叔丁基氯二甲基硅烷 溶液; 叔丁基(氯)二甲基硅烷; 叔丁基二甲基氯硅烷

Database IDs

• CAS Number: 18162-48-6
• EC Number: 242-042-4
• MDL Number: MFCD00000501
• Beilstein Number: 505999
• PubChem SID: 162038718; 24851890; 24851442; 24863996; 24863185; 24851889; 24870907
• PubChem CID: 28928

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 2.741
• LogD (pH = 7.4): 2.741
• Log P: 2.741
• Molar Refractivity: 37.1988 cm^3
• Polarizability: 16.519724 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: White Low Melting Solid
• Melting Point: 86-89 °C(lit.); 86-89°C; 86-89°C; 86-90 °C
• Boiling Point: 113 °C; 113°C; 124-126°C; 124-126°C; 125 °C(lit.)
• Flash Point: 1.4 °F; 136.4 °F; -17 °C; 22 °C; 22°C(72°F); 44.6 °F; 58 °C; 7 °C; 7°C; 7°C(45°F); 71.6 °F
• Density: 0.81; 0.866; 0.866 g/mL at 25 °C; 0.87; 0.87 g/mL at 20 °C(lit.); 0.879 g/mL at 25 °C; 1.225 g/mL at 25 °C
• Refractive Index: n20/D 1.424; n20/D 1.459; n20/D 1.46

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere
• Storage Warning: Flammable/Corrosive/Moisture Sensitive; Highly Flammable/Corrosive/Harmful/Teratogenic/Moisture Sensitive/Store under Argon; Moisture Sensitive
• RTECS: VV2000000
• European Hazard Symbols: Corrosive (C); Flammable (F); X; Harmful (Xn)
• UN Number: 2920; 2924; 2925; UN2924; UN2925
• German water hazard class: 2; 3
• Hazard Class: 3; 4.1; 8
• Packing Group: 2; II
• Risk Statements: 10-34; 11-19-34-37; 11-34; 11-34-48/20-63-67; 34-40; 63-11-34-48/20-65-67; 63-11-36/37/38-48/20-65-67
• Safety Statements: 16-26-36/37/39-45; 16-26-36/37/39-45-62; 16-26-36/37-62; 26-36/37/39-45
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS05; GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H304-H314-H336-H361d-H373; H225-H304-H315-H319-H336-H361d-H373; H225-H314-H318-H361-H373-H336; H225-H314-H335; H226-H314-H351; H228-H314; H228-H314-H318
• GHS Precautionary statements: P210-P261-P280-P301 + P310-P305 + P351 + P338-P310; P210-P261-P280-P305 + P351 + P338-P310; P210-P261-P281-P301 + P310-P305 + P351 + P338-P331; P210-P280-P305 + P351 + P338-P310; P210-P280-P305+P351+P338-P309-P310; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter; Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2920 8/PG 2; UN 2924 3/PG 2; UN 2925 4.1/PG 2
• Supplemental Hazard Statements: May form explosive peroxides.

Product Information

• Purity: ≥95.0% (GC); 50% w/w in toluene; 97%
• Concentration: ~1 M in THF; ~50% in toluene (AT); 1.0 M in methylene chloride; 1.0 M in THF; 50 wt. % in toluene; 50% in methylene chloride
• Grade: purum; reagent grade
• Linear Formula: (CH3)3CSi(CH3)2Cl
• Empirical Formula (Hill Notation): C6H15ClSi

DETAILS

Sigma Aldrich - 19905

Other Notes
Useful derivatizing agent for preparative and analytical purposes1,2; Selective cleavage of TBDMS-ethers3,4
Packaging
5, 25, 100 g in glass bottle

Sigma Aldrich - 190500

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Packaging
1 kg in glass bottle
5, 25, 100, 500 g in glass bottle
Application
Versatile protecting reagent for amines, amides, and especially alcohols, among others.1 Can be selectively removed in the presence of a t-BuPh2Si-protected alcohol.2Used in a preparatrion of isoxazoline N-oxides from α-bromonitroalkanes.3

Sigma Aldrich - 473464

Packaging
50, 100 g in Sure/Seal™

Sigma Aldrich - 372951

Packaging
100 mL in Sure/Seal™

Sigma Aldrich - 384429

Packaging
100 mL in Sure/Seal™

Toronto Research Chemicals - B691080

Used to protect alcohols during organic synthesis.

REFERENCES

• Shen, H., et al.: J. Med. Chem., 53, 2666 (2010)
• Qiang, L., et al.: Bioorg. Med. Chem. Lett., 20, 836 (2010)
• Reagent for silylation of hydroxyl functions (see Appendix 4), giving silyl ethers more stable to aqueous hydrolysis e.g. during work-up, than TMS. Various conditions have been used for the introduction of the group:
• Imidazole in DMF: J. Am. Chem. Soc., 94, 6190 (1972); Et₃N - DMAP: Tetrahedron Lett., 99 (1979); Org. Synth. Coll., 9, 136 (1998); N-ethyldiisopropylamine: Tetrahedron Lett., 25, 227 (1984); 1,1,3,3-tetramethylguanidine: J. Org. Chem., 49, 4657 (1984); K₂CO₃ (phase-transfer): Synth. Commun., 11, 545 (1981); DBU - superior to imidazole for thiols, amines and carboxylic acids: Tetrahedron Lett., 26, 475 (1985).
• Cleavage is generally effected with fluoride ion e.g. TBAF in an aprotic system: J. Am. Chem. Soc., 94, 6190 (1972), or KF with a phase-transfer catalyst: J. Am. Chem. Soc., 90, 4462, 4464 (1968); 96, 2250 (1974); J. Chem. Soc., Chem. Commun., 514 (1979).
• Acidic ion-exchange resin: Tetrahedron Lett., 21, 137 (1980); NBS in DMSO: Synthesis, 234 (1980); BF₃ etherate: Synth. Commun., 9, 295 (1979); FeCl₃ or SnCl₂ in acetonitrile: Synth. Commun., 20, 757 (1990); K 10 clay in aqueous methanol: J. Org. Chem.61, 9026 (1996); DMSO-water at 90^o; many other groups unaffected: Tetrahedron Lett., 38, 495 (1997). See also Pyridinium p-toluenesulfonate, A15708, and Triethylamine trihydrofluoride, L14417.
• Many other reagents have been used, including: