tri-tert-butylphosphane

• ChemBase ID: 78240
• Molecular Formular: C12H27P
• Molecular Mass: 202.316541
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

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

Database IDs

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

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 2.3845654
• LogD (pH = 7.4): 2.3847759
• Log P: 2.5937
• Molar Refractivity: 68.517 cm^3
• Polarizability: 25.590317 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Solid
• Melting Point: 30°C; 30°C; 30-35 °C(lit.)
• Boiling Point: 102-103 °C/13 mmHg(lit.); 102-103°C/13mm; 102-103°C/13mm
• Flash Point: 1.4 °F; -16°C(-3°F); -17 °C; 39.2 °F; 4 °C
• Density: 0.834 g/mL at 20 °C(lit.); 0.861 g/mL at 25 °C
• Ligand For: Addition Reactions; Buchwald-Hartwig Cross Coupling Reaction; Heck Reaction; Negishi Coupling; Sonogashira Coupling; Stille Coupling; Suzuki-Miyaura Coupling

Safety Information

• Storage Warning: Air & Moisture Sensitive; Highly Flammable/Corrosive/Lachrymatory/Air Sensitive/Moisture Sensitive/Store under Argon
• European Hazard Symbols: Corrosive (C); Flammable (F)
• UN Number: 2845; 2846; UN2845
• German water hazard class: 3
• Hazard Class: 4.2
• Packing Group: 1; I
• Risk Statements: 17-34; 63-11-17-34-48/20-65-67
• Safety Statements: 16-26-27-36/37/39-43-45; 16-26-36/37/39-45-62; 26-36/37/39-45
• TSCA Listed: 否
• GHS Pictograms: GHS02; GHS05; GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H250-H304-H314-H336-H361d-H373; H250-H252-H314-H318; H250-H314
• GHS Precautionary statements: P210-P222-P231-P261-P280-P422; P210-P303+P361+P353-P305+P351+P338-P405-P422A-P501A; P222-P231-P280-P305 + P351 + P338-P310-P422
• Personal Protective Equipment: 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

Product Information

• Purity: ≥97.0% (31P-NMR); 90%; 96%; 98%
• Concentration: 1.0 M in toluene
• Grade: purum; technical grade
• Linear Formula: [(CH3)3C]3P
• Empirical Formula (Hill Notation): C12H27P

DETAILS

Sigma Aldrich - 336955

Packaging
1, 5 g in glass bottle

Sigma Aldrich - 655325

Packaging
10, 50 mL in glass bottle

Sigma Aldrich - 570958

Application
Preferred ligand in the palladium-catalyzed coupling of arylboronic acids with phenyliodonium ylides of hydroxyquinones.1 Also used with Pd2(dba)3 for the α-arylation of trimethylsilyl enol ethers with aryl halides.2
Packaging
1, 5, 10 g in glass bottle

REFERENCES

• 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).