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247049

Tributylphosphine

97%, liquid, mixture of isomers

Synonym(s):

P(n-Bu)3, TBP

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About This Item

Linear Formula:
[CH3(CH2)3]3P
CAS Number:
998-40-3
Molecular Weight:
202.32
NACRES:
NA.22
PubChem Substance ID:
329752742
UNSPSC Code:
12352128
EC Number:
213-651-2
MDL number:
MFCD00009462
Beilstein/REAXYS Number:
1738261
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Product Name

Tributylphosphine, mixture of isomers, 97%

vapor density

9 (vs air)

Quality Level

200

assay

97%

form

liquid

autoignition temp.

392 °F

reaction suitability

reaction type: Buchwald-Hartwig Cross Coupling Reaction, reaction type: Heck Reaction, reaction type: Hiyama Coupling, reaction type: Negishi Coupling, reaction type: Sonogashira Coupling, reaction type: Stille Coupling, reaction type: Suzuki-Miyaura Coupling, reagent type: ligand
reaction type: Acetylations, reagent type: ligand
reaction type: Addition Reactions, reagent type: ligand
reaction type: Stille Coupling

impurities

<1% TBP oxide, 5% TBP isomers

refractive index

n20/D 1.462 (lit.)

bp

150 °C/50 mmHg (lit.)

density

0.81 g/mL at 25 °C (lit.)

functional group

phosphine

SMILES string

CCCCP(CCCC)CCCC

InChI

1S/C12H27P/c1-4-7-10-13(11-8-5-2)12-9-6-3/h4-12H2,1-3H3

InChI key

TUQOTMZNTHZOKS-UHFFFAOYSA-N

Application

Used with platinum (II) or (IV) in an intermolecular hydroamination of unactivated alkenes.
1,4-addition catalyst; used with disulfides for the thioetherification of alcohols; acylation catalyst; used to prepare active esters.

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Danger

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 2 - Eye Dam. 1 - Pyr. Liq. 1 - Skin Corr. 1A

Storage Class

4.2 - Pyrophoric and self-heating hazardous materials

wgk

WGK 2

flash_point_f

242.6 °F - closed cup

flash_point_c

117 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
SHBT3647
SDBB4930
SDBB3685
SDBB3131
SHBR5334

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Phosphine Ligand Application Guide

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J. Mol. Catal. A: Chem., 271, 145-145 (2007)
Yin-Wei Sun et al.
Organic letters, 12(24), 5664-5667 (2010-11-13)
P(n)Bu(3)-catalyzed cyclization reactions of salicylaldimines and salicylaldehydes with ethyl 2,3-butadienoate gave the corresponding functionalized chromans in moderate to good yields in THF under mild conditions. The new reaction provides a new method for the synthesis of biologically active chroman products.
E Kaniowska et al.
Journal of chromatography. A, 798(1-2), 27-35 (1998-05-02)
Several human diseases, in particular metabolic disorders, often lead to the accumulation of characteristic metabolites in plasma, urine and cells. The selected diseases of this type include cystinuria and homocystinuria. In the typical laboratory diagnosis of these two diseases, a
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Global Trade Item Number

SKUGTIN
247049-100G04061838125927
247049-500G04061838125934
247049-PZ04061823820707