tri-tert-butylphosphane

• ChemBase编号: 78240
• 分子式: C12H27P
• 平均质量: 202.316541
• 单一同位素质量: 202.18503749
• SMILES: P(C(C)(C)C)(C(C)(C)C)C(C)(C)C
• Canonical SMILES: CC(P(C(C)(C)C)C(C)(C)C)(C)C
• InChI: InChI=1S/C12H27P/c1-10(2,3)13(11(4,5)6)12(7,8)9/h1-9H3
• InChIKey: BWHDROKFUHTORW-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: tri-tert-butylphosphane
• IUPAC传统名: tri-tert-butylphosphane
• 别名: 三叔丁基膦 溶液; 三叔丁基膦; 三特丁基膦; P(t-Bu)3; Tri-tert-butylphosphine solution; Tri-tert-butylphosphine; Tris(tert-butyl)phosphine, 50% solution in toluene; Tris(tert-butyl)phosphine 95%

登记号

• CAS号: 13716-12-6
• EC号: 237-266-4
• MDL号: MFCD00015006
• Beilstein号: 1738613
• PubChem SID: 24860444; 24884097; 24880600; 162043030
• PubChem CID: 83681

理论计算性质

• 质子受体: 0
• 质子供体: 0
• LogD (pH = 5.5): 2.3845654
• LogD (pH = 7.4): 2.3847759
• Log P: 2.5937
• 摩尔折射率: 68.517 cm^3
• 极化性: 25.590317 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: true

分子性质

理化性质

• 外观: Solid
• 熔点: 30°C; 30°C; 30-35 °C(lit.)
• 沸点: 102-103 °C/13 mmHg(lit.); 102-103°C/13mm; 102-103°C/13mm
• 闪点: 1.4 °F; -16°C(-3°F); -17 °C; 39.2 °F; 4 °C
• 密度: 0.834 g/mL at 20 °C(lit.); 0.861 g/mL at 25 °C
• 作为配体的用途: Addition Reactions; Buchwald-Hartwig Cross Coupling Reaction; Heck Reaction; Negishi Coupling; Sonogashira Coupling; Stille Coupling; Suzuki-Miyaura Coupling

安全信息

• 保存注意事项: Air & Moisture Sensitive; Highly Flammable/Corrosive/Lachrymatory/Air Sensitive/Moisture Sensitive/Store under Argon
• 欧盟危险性物质标志: 腐蚀性(Corrosive) (C); 易燃性(Flammable) (F)
• 联合国危险货物编号: 2845; 2846; UN2845
• 德国WGK号: 3
• 联合国危险货物等级: 4.2
• 联合国危险货物包装类别(PG): 1; I
• 危险公开号: 17-34; 63-11-17-34-48/20-65-67
• 安全公开号: 16-26-27-36/37/39-43-45; 16-26-36/37/39-45-62; 26-36/37/39-45
• TSCA收录: 否
• GHS危险品标识: GHS02; GHS05; GHS07; GHS08
• GHS警示词: Danger
• GHS危险声明: H225-H250-H304-H314-H336-H361d-H373; H250-H252-H314-H318; H250-H314
• GHS警示性声明: P210-P222-P231-P261-P280-P422; P210-P303+P361+P353-P305+P351+P338-P405-P422A-P501A; P222-P231-P280-P305 + P351 + P338-P310-P422
• 个人保护装置: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges; Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2845 4.2/PG 1; UN 2846 4.2/PG 1

产品相关信息

• 纯度: ≥97.0% (31P-NMR); 90%; 96%; 98%
• 浓度: 1.0 M in toluene
• 级别: purum; technical grade
• 线性分子式: [(CH3)3C]3P
• Empirical Formula (Hill Notation): C12H27P

详细说明

Sigma Aldrich - 336955

包装
1, 5 g in glass bottle

Sigma Aldrich - 655325

包装
10, 50 mL in glass bottle

Sigma Aldrich - 570958

Application
芳基硼酸与羟基醌的苯基碘叶立德进行钯催化的偶联反应时的首选配体。1还可与 Pd2(dba)3 一起用于三甲基甲硅烷基烯醇醚与芳基卤化物的 α-芳基化。2
包装
1, 5, 10 g in glass bottle

参考文献

• For a brief feature on uses of the reagent in synthesis, see: Synlett, 709 (2005).
• Ligand which has been used in conjunction with Tris(dibenzylideneacetone)dipalladium(0), 12760 in promoting Suzuki cross-coupling reactions of arylboronic acids with aryl and vinyl halides under mild conditions. The system is particularly recommended for coupling reactions with normally unreactive aryl chlorides: J. Am. Chem. Soc., 4070 (2000). The same catalyst system has been found to be effective in the room-temperature cyanation of aryl bromides using zinc cyanide: Synlett, 2237 (2003).
• Efficient catalyst for the trifluoromethylation of aldehydes, ketones, imides and imines with (Trifluoromethyl)trimethylsilane, B20347: Synlett, 267 (2006).