trimethyl(trifluoromethyl)silane

• ChemBase编号: 8668
• 分子式: C4H9F3Si
• 平均质量: 142.1949696
• 单一同位素质量: 142.04256148
• SMILES: C[Si](C)(C(F)(F)F)C
• Canonical SMILES: FC([Si](C)(C)C)(F)F
• InChI: InChI=1S/C4H9F3Si/c1-8(2,3)4(5,6)7/h1-3H3
• InChIKey: MWKJTNBSKNUMFN-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: trimethyl(trifluoromethyl)silane
• IUPAC传统名: trifluoromethyltrimethylsilane
• 别名: 三氟甲基三甲基硅烷 溶液; Ruppert 试剂; (三氟甲基)三甲基硅烷; (三氟甲基)三甲基硅烷, 0.5M THF溶液; Ruppert-Prakash reagent; Trifluoromethyltrimethylsilane; Trimethyl(trifluoromethyl)silane solution; Ruppert′s reagent; (Trifluoromethyl)trimethylsilane; Ruppert’s Reagent; Trimethyl(trifluoromethyl)silane; (Trifluoromethyl)trimethylsilane 99%; (Trifluoromethyl)trimethylsilane; Trifluoromethyltrimethylsilane; (Trimethylsilyl)trifluoromethane; (Trifluoromethyl)trimethylsilane 98%, 0.5M solution in THF; Ruppert's Reagent; TFMTMS; (Trifluoromethyl)trimethylsilane, 0.5M soln. in THF; (Trifluoromethyl)trimethylsilane

登记号

• CAS号: 81290-20-2
• EC号: 000-000-0
• MDL号: MFCD00145454
• Beilstein号: 4241868
• PubChem SID: 24872418; 160971975; 24862831; 24889567
• PubChem CID: 552549
• 维基百科标题: Trifluoromethyltrimethylsilane

理论计算性质

• 质子受体: 0
• 质子供体: 0
• LogD (pH = 5.5): 3.6948
• LogD (pH = 7.4): 3.6948
• Log P: 3.6948
• 摩尔折射率: 22.423 cm^3
• 极化性: 10.52733 Å^3
• 极化表面积: 0.0 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

分子性质

理化性质

• 外观: colorless liquid
• 沸点: 40 °C; 40°C; 40°C; 54-55 °C; 54-55 °C(lit.); 54-55°C; 54-55°C
• 闪点: 1.4 °F; -10°C(14°F); -17 °C; -17°C; -20°C
• 密度: 0.895; 0.895 g/mL at 25 °C; 0.91 g/mL at 20 °C; 0.962; 0.962 g/mL at 20 °C(lit.); 0.9626 g/cm^3 @ 20 °C
• 折射率: 1.330; 1.3305; 1.332; n20/D 1.332; n20/D 1.386
• 蒸汽压: 10.98 psi ( 55 °C); 2.8 psi ( 20 °C)

安全信息

• 保存注意事项: FLAMMABLE; Highly Flammable/Harmful/Irritant/Hygroscopic/Moisture Sensitive/Light Sensitive/Keep Cold/Store under Argon; Highly Flammable/Keep Cold; Moisture Sensitive
• 欧盟危险性物质标志: 易燃性(Flammable) (F); 刺激性(Irritant) (Xi)
• 联合国危险货物编号: 1993; UN1993
• 德国WGK号: 3
• 联合国危险货物等级: 3
• 联合国危险货物包装类别(PG): 2; II
• 危险公开号: 11; 11-19-36/37; 11-36/37/38
• 安全公开号: 16-26; 16-33; 23-26; 9-16-23-26-33-37
• TSCA收录: false; 否
• GHS危险品标识: GHS02; GHS07
• GHS警示词: Danger
• GHS危险声明: H225; H225-H315-H319-H335; H225-H319-H335
• GHS警示性声明: P210; P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A; P210-P261-P305 + P351 + P338
• 个人保护装置: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US); Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1993 3/PG 2
• 欧盟补充危害声明: May form explosive peroxides.
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥98.0% (GC); 97%; 98%; 99%
• 浓度: ~2.0 M in THF; 0.5 M in THF; 0.5M soln. in THF
• 级别: purum
• 线性分子式: (CH3)3SiCF3

详细说明

Apollo Scientific Ltd - PC7779

Ruppert's reagent - valuable trifluoromethylating agent of electrophilic compounds. Trifluoromethylates carbonyl compounds in high yield: JACS., 1989, 111, 393

Sigma Aldrich - 488712

Application
参与三氟甲基的亲核加成反应生成醛和酮。1
包装
5, 25 mL in glass bottle

Sigma Aldrich - 91862

包装
10, 50 mL in glass bottle
Application
Reactant for:
• Silver-mediated C-H trifluoromethylation of arenes1
• Preparation of trifluoromethyl ketone analog of L-arginine having contrasting inhibitory activity against human arginase I and histone deacetylase 82
• Organocatalyzed regio- and enantioselective allylic trifluoromethylation of Morita-Baylis-Hillman adducts3
• Palladium-catalyzed oxidative trifluoromethylation of indoles4
• Preparation of 5-HT1A antagonists5
• Used as difluorocarbene source6

Sigma Aldrich - 367737

Application
参与三氟甲基的亲核加成反应生成醛和酮。7
Reactant for:
• Silver-mediated C-H trifluoromethylation of arenes1
• Preparation of trifluoromethyl ketone analog of L-arginine having contrasting inhibitory activity against human arginase I and histone deacetylase 82
• Organocatalyzed regio- and enantioselective allylic trifluoromethylation of Morita-Baylis-Hillman adducts3
• Palladium-catalyzed oxidative trifluoromethylation of indoles4
• Preparation of 5-HT1A antagonists5
• Used as difluorocarbene source6
包装
25 mL in Sure/Seal™
5 mL in glass bottle

Sigma Aldrich - 91873

Other Notes
各种化合物的 F- 诱导亲核三氟甲基化反应试剂1,2,3,4,5

参考文献

• Valuable reagent for trifluoromethylation of electrophilic substrates.
• In the presence of F^-, aldehydes and ketones give, after hydrolysis of the intermediate silyl ethers, the trifluoromethyl carbinols: J. Am. Chem. Soc., 111, 393 (1989); J. Org. Chem., 56, 984 (1991); Org. Synth. Coll., 9, 711 (1998):
  
• Alternatively, rapid and efficient trifluoromethylation of carbonyl compounds can be carried out at room temperature in DMSO, in the presence of molecular sieves, without fluoride or other basic catayst: Synlett, 112 (2006). The use of Tri-tert-butylphosphine, 10178 as a catalyst has also been advocated: Synlett, 267 (2006).
• In the presence of CsF and TMS-imidazole, aldimines are converted to ɑ-trifluoromethyl amines: Tetrahedron Lett., 40, 5475 (1999).
• With a catalytic amount of TBAF, excellent yields of trifluoromethyl ketones can be obtained from methyl esters: Angew. Chem. Int. Ed., 37, 820 (1998).
• Similarly, alkyl or aryl thiocyanates are converted to the corresponding trifluoromethyl sulfides in generally good yields: Tetrahedron Lett., 38, 65 (1997). Selenocyanates behave similarly. Trifluoromethylation of aromatics bearing electron-withdrawing groups can be effected in the presence of KF, by displacement of nitro-, cyano- or chloro-substituents: J. Chem. Soc., Perkin 1, 3081 (1998).
• For reviews of this and similar reagents, see: Chem. Rev., 97, 757 (1997); J. Fluorine Chem., 112, 123 (2001).