tert-butyl(chloro)diphenylsilane

• ChemBase ID: 90053
• Molecular Formular: C16H19ClSi
• Molecular Mass: 274.86056
• Monoisotopic Mass: 274.09445482
• SMILES: [Si](c1ccccc1)(c1ccccc1)(Cl)C(C)(C)C
• Canonical SMILES: CC([Si](c1ccccc1)(c1ccccc1)Cl)(C)C
• InChI: InChI=1S/C16H19ClSi/c1-16(2,3)18(17,14-10-6-4-7-11-14)15-12-8-5-9-13-15/h4-13H,1-3H3
• InChIKey: MHYGQXWCZAYSLJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tert-butyl(chloro)diphenylsilane
• IUPAC Traditional name: tert-butyl(chloro)diphenylsilane
• Synonyms: Tert-Butylchlorodiphenylsilane; TBDPSCl; tert-Butyldiphenylchlorosilane; tert-Butyl(chloro)diphenylsilane; tert-Butylchlorodiphenylsilane solution; (tert-Butyl)diphenylsilyl chloride; (tert-Butyl)(chloro)diphenylsilane; t-BUTYLCHLORODIPHENYL-SILANE; tert-Butylchlorodiphenylsilane; tert-Butyldiphenylsilyl chloride; tert-Butyldiphenylchlorosilane; 叔丁基二苯基氯硅烷; 叔丁基(氯)二苯基硅烷; 叔丁基氯二苯基硅烷 溶液; 叔丁基二苯基氯硅烷

Database IDs

• CAS Number: 58479-61-1
• EC Number: 261-282-0
• MDL Number: MFCD00000497
• Beilstein Number: 644023
• PubChem SID: 162076908; 24851697; 24851910
• PubChem CID: 94078

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 5.8932
• LogD (pH = 7.4): 5.8932
• Log P: 5.8932
• Molar Refractivity: 76.5872 cm^3
• Polarizability: 32.05464 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Boiling Point: 40 °C; 90 °C/0.01 mmHg(lit.); 90°C; 90-92°C/0.01mm; 90-92°C/0.01mm
• Flash Point: >110 °C; >230 °F; 112 °C; 112°C(233°F); 233.6 °F
• Density: 1.057; 1.057 g/mL at 25 °C(lit.); 1.068 g/ml; 1.072; 1.249 g/mL at 25 °C
• Refractive Index: 1.568; 1.5680; n20/D 1.567; n20/D 1.568(lit.)

Safety Information

• Storage Condition: 2-8°C, Desiccate, Store Under Nitrogen
• Storage Warning: Corrosive/Moisture Sensitive/Store under Argon; Moisture Sensitive
• European Hazard Symbols: Corrosive (C)
• UN Number: 2922; 2987; UN2987
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; II
• Australian Hazchem: 4WE
• Risk Statements: 34; 34-37; 34-37-40; R:34
• Safety Statements: 26-36/37/39-45; S:26-27/28-36/37/39-46-64
• EU Classification: C3
• EU Hazard Identification Number: 8B
• Emergency Response Guidebook(ERG) Number: 156
• TSCA Listed: 是
• GHS Pictograms: GHS05; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H314; H314-H318; H314-H351
• 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); Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2922 8/PG 2; UN 2987 8/PG 2

Product Information

• Purity: ≥97.0% (GC); 97%; 98%
• Concentration: 1 M in methylene chloride
• Grade: purum
• Linear Formula: (CH3)3CSi(C6H5)2Cl
• Empirical Formula (Hill Notation): C16H19ClSi

DETAILS

MP Biomedicals - 02154908

1 ml = approx. 1.06 g

Sigma Aldrich - 195537

Packaging
2, 10 g in glass bottle
50, 250 g in Sure/Seal™
Application
Silylating reagent used in the protection of alcohols1,2 and the preparation of silyl ethers.3

Sigma Aldrich - 702730

Packaging
100, 500 mL in Sure/Seal™

Sigma Aldrich - 19938

Other Notes
Silylating agent for the introduction of the selective TBDPS group1,2,3

REFERENCES

• Silylating agent (see Appendix 4) for the formation, with e.g. imidazole, of t-butyldiphenylsilyl (TBDPS) ethers of alcohols: Can. J. Chem., 53, 2975 (1975); Org. Synth. Coll., 9, 139 (1998). Alternative to tert-Butyldimethylchlorosilane, A13064, allowing selective protection of primary alcohols in the presence of secondary, using DMAP/pyridine: Helv. Chim. Acta, 69, 1273 (1986), or DMAP/triethylamine: Tetrahedron Lett., 99 (1979); 26, 1185 (1985). TBDPS ethers tend to be more crystalline and are much more stable to acidic conditions than TBDMS. They can also survive acetal formation and cleavage, as well as the acidic conditions required for cleavage of trityl and THP ethers. Silylation rates of hindered alcohols have been increased in the presence of silver nitrate: J. Am. Chem. Soc., 116, 5050 (1994).
• Cleavage occurs readily with TBAF in THF: Org. Synth. Coll., 9, 4 (1998). For use of K10 clay in aqueous MeOH, see: J. Org. Chem., 61, 9026 (1996). Cleavage with BBr₃ leads directly to the corresponding alkyl bromides: J. Org. Chem., 53, 3111 (1988).
• The silyl copper species derived from the lithio-derivative and CuCN adds to terminal alkynes, giving vinyl copper intermediates which react with electrophiles to give vinyl silanes. The presence of the hindered TBDPS group confers some useful differences in comparison with less hindered silyl groups: J .Chem. Soc., Perkin 1., 1525 (1995); compare Chlorodimethylphenylsilane, A15638. The hindered TBDPS group has also been utilized in the Peterson olefination reaction to promote high (Z)-selectivity: Synthesis, 1223 (2000).