Tributylphosphine
ALDRICH/90827 - ≥93.5% (Tri-N-butylphosphine, GC)
Synonym: P(n-Bu)3; TBP
CAS Number: 998-40-3
Empirical Formula (Hill Notation): C12H27P
Molecular Weight: 202.32
EC Number: 213-651-2
MDL Number: MFCD00009462
Linear Formula: [CH3(CH2)3]3P
Product Type: Chemical
| assay | ≥93.5% (Tri-N-butylphosphine, GC) |
| ≥97% (Tri-N-butylphospine + isomers) | |
| autoignition temp. | 392 °F |
| bp | 150 °C/50 mmHg (lit.) |
| density | 0.81 g/mL at 25 °C (lit.) |
| form | liquid |
| functional group | phosphine |
| InChI | 1S/C12H27P/c1-4-7-10-13(1 |
| InChI key | TUQOTMZNTHZOKS-UHFFFAOYSA |
| Quality Level | 200  |
| reaction suitability | reaction type: Acetylations |
| reagent type: ligand | |
| refractive index | n |
| n |
|
| SMILES string | CCCCP(CCCC)CCCC |
| vapor density | 9 (vs air) |
| Application: | Tributylphosphine was used in the preparation of silver nanoparticles (AgNPs) functionalized with an organometallic bifunctional thiol containing Pt(II) centers. It may be used in the following processes: • As reducing agent for alkyl disulfides and aromatic disulfides. • As catalyst for the synthesis of 2-substituted 1,3-benzoselenazoles. • As promoter for the ring opening of epoxides and aziridines with nucleophiles. • As a reagent in the preparation of 6-substituted penicillanate esters by reduction of 6-bromo-6-substituted penicillanate esters in high diastereoselectivity. • As a catalyst in the acylation reaction of alcohols. • As a catalyst to prepare rotaxanes by the acylation of corresponding pseudorotaxanes using 3,5-dimethylbenzoic anhydride. • As a catalyst to prepare vinyl thioethers by the Michael addition of ethanethiol to various alkynyl ketones. • As a promoter in the conjugate addition of non-nucleophilic N-containing compounds with Michael acceptors. |
| General description: | Tributylphosphine (TBP) is a potential nucleophile. It acts as a weak base in organic solvents. It is an important catalyst for the acylation reactions. It is an efficient promoting reagent for the ring-opening reaction of various epoxides and aziridines. TBP in conjugation with 1,1′-(azodicarbonyl)dipip |
| Packaging: | 25, 100, 500 mL in Sure/Seal™ |
| Symbol |     GHS02,GHS05,GHS07,GHS09 |
| Signal word | Danger |
| Hazard statements | H251 - H302 - H314 - H411 |
| Precautionary statements | P235 - P273 - P280 - P301 + P312 - P303 + P361 + P353 - P305 + P351 + P338 |
| Hazard Codes | F,C |
| Risk Statements | 17-21/22-34 |
| Safety Statements | 17-26-36/37/39-43-45 |
| RIDADR | UN 3254 4.2 / PGI |
| WGK Germany | WGK 3 |
| Purity | ≥93.5% (Tri-N-butylphosphine, GC); ≥97% (Tri-N-butylphospine + isomers) |
| bp | 150 °C/50 mmHg (lit.) |
| Density | 0.81 g/mL at 25 °C (lit.) |
| Refractive Index | n |
| UNSPSC | 12352128 |