tert-butyl(chloro)diphenylsilane

• ChemBase编号: 90053
• 分子式: C16H19ClSi
• 平均质量: 274.86056
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: tert-butyl(chloro)diphenylsilane
• IUPAC传统名: tert-butyl(chloro)diphenylsilane
• 别名: 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; 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

登记号

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

理论计算性质

• 质子受体: 0
• 质子供体: 0
• LogD (pH = 5.5): 5.8932
• LogD (pH = 7.4): 5.8932
• Log P: 5.8932
• 摩尔折射率: 76.5872 cm^3
• 极化性: 32.05464 Å^3
• 极化表面积: 0.0 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: false

分子性质

理化性质

• 沸点: 40 °C; 90 °C/0.01 mmHg(lit.); 90°C; 90-92°C/0.01mm; 90-92°C/0.01mm
• 闪点: >110 °C; >230 °F; 112 °C; 112°C(233°F); 233.6 °F
• 密度: 1.057; 1.057 g/mL at 25 °C(lit.); 1.068 g/ml; 1.072; 1.249 g/mL at 25 °C
• 折射率: 1.568; 1.5680; n20/D 1.567; n20/D 1.568(lit.)

安全信息

• 保存条件: 2-8°C, Desiccate, Store Under Nitrogen
• 保存注意事项: Corrosive/Moisture Sensitive/Store under Argon; Moisture Sensitive
• 欧盟危险性物质标志: 腐蚀性(Corrosive) (C)
• 联合国危险货物编号: 2922; 2987; UN2987
• 德国WGK号: 3
• 联合国危险货物等级: 8
• 联合国危险货物包装类别(PG): 2; II
• 澳大利亚Hazchem: 4WE
• 危险公开号: 34; 34-37; 34-37-40; R:34
• 安全公开号: 26-36/37/39-45; S:26-27/28-36/37/39-46-64
• 欧盟危险货物分类: C3
• 欧盟危险识别号(EUHIN): 8B
• 美国ERG指导号: 156
• TSCA收录: 是
• GHS危险品标识: GHS05; GHS08
• GHS警示词: Danger
• GHS危险声明: H314; H314-H318; H314-H351
• GHS警示性声明: P280-P303+P361+P353-P305+P351+P338-P310; P280-P305 + P351 + P338-P310
• 个人保护装置: 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

产品相关信息

• 纯度: ≥97.0% (GC); 97%; 98%
• 浓度: 1 M in methylene chloride
• 级别: purum
• 线性分子式: (CH3)3CSi(C6H5)2Cl
• Empirical Formula (Hill Notation): C16H19ClSi

详细说明

MP Biomedicals - 02154908

1 ml = approx. 1.06 g

Sigma Aldrich - 195537

包装
2, 10 g in glass bottle
50, 250 g in Sure/Seal™
Application
用于保护醇1,2以及制备硅基醚的硅烷化试剂。3

Sigma Aldrich - 702730

包装
100, 500 mL in Sure/Seal™

Sigma Aldrich - 19938

Other Notes
用于引入选择性 TBDPS 基团的硅烷化试剂1,2,3

参考文献

• 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).