90827

Tributylphosphine

≥93.5% (Tri-N-butylphosphine, GC)

• Synonyme(s) : P(n-Bu)₃, TBP
• Formule linéaire : [CH₃(CH₂)₃]₃P
• Numéro CAS: 998-40-3
• Poids moléculaire : 202.32
• Numéro Beilstein : 1738261
• Numéro CE : 213-651-2
• Numéro MDL: MFCD00009462
• Code UNSPSC : 12352128
• ID de substance PubChem : 57653412
• Nomenclature NACRES : NA.22

Propriétés

• Densité de vapeur: 9 (vs air)
• Niveau de qualité: 200
• Pureté: ≥93.5% (Tri-N-butylphosphine, GC); ≥97% (Tri-N-butylphospine + isomers)
• Forme: liquid
• Température d'inflammation spontanée: 392 °F
• Capacité de réaction: reaction type: Acetylations
• Pertinence de la réaction: reagent type: ligand
• Indice de réfraction: n20/D 1.462 (lit.); n20/D 1.463
• Point d'ébullition: 150 °C/50 mmHg (lit.)
• Densité: 0.81 g/mL at 25 °C (lit.)
• Groupe fonctionnel: phosphine
• Chaîne SMILES: CCCCP(CCCC)CCCC
• InChI: 1S/C12H27P/c1-4-7-10-13(11-8-5-2)12-9-6-3/h4-12H2,1-3H3
• Clé InChI: TUQOTMZNTHZOKS-UHFFFAOYSA-N

Description

Description générale

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)dipiperidine (ADDP) constitutes Mitsunobu reagent. This reactive phosphine allows the formation of a strained lactone.

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.

Informations sur la sécurité

• Pictogrammes: GHS02,GHS05,GHS07,GHS09
• Mention d'avertissement: Danger
• Mentions de danger: H250,H302,H314,H411
• Conseils de prudence: P231 + P232 - P273 - P280 - P303 + P361 + P353 - P305 + P351 + P338 - P370 + P378
• Classification des risques: Acute Tox. 4 Oral - Aquatic Chronic 2 - Eye Dam. 1 - Pyr. Liq. 1 - Skin Corr. 1A
• Code de la classe de stockage: 4.2 - Pyrophoric and self-heating hazardous materials
• Classe de danger pour l'eau (WGK): WGK 2
• Point d'éclair (°F): 242.6 °F - closed cup
• Point d'éclair (°C): 117 °C - closed cup
• Équipement de protection individuelle: Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter