ChemicalBook > CAS DataBase List > Tri(o-tolyl)phosphine

Tri(o-tolyl)phosphine

Product Name
Tri(o-tolyl)phosphine
CAS No.
6163-58-2
Chemical Name
Tri(o-tolyl)phosphine
Synonyms
P(o-tol)3;TRI-O-TOLYLPHOSPHINE;Tri-o-tolylphosphane;TRIS(2-METHYLPHENYL)PHOSPHINE;TRI-O-TOLYPHOSPHINE;TRIS(O-TOLYL)PHOSPHINE;tris(2-Methylphenyl)phosphane;tri-o-tolyl phopine;Tri-ortho-tolylphosphine;TRI(2-METHYLPHENYL)PHOSPHINE
CBNumber
CB8128012
Molecular Formula
C21H21P
Formula Weight
304.37
MOL File
6163-58-2.mol
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Tri(o-tolyl)phosphine Property

Melting point:
123-125 °C(lit.)
Boiling point:
412.4±44.0 °C(Predicted)
Density 
1.16[at 20℃]
vapor pressure 
0Pa at 20℃
Flash point:
198°C (388°F)
storage temp. 
Store below +30°C.
solubility 
Chloroform, Ethyl Acetate
form 
Crystalline Powder
color 
White
Water Solubility 
Soluble in alcohol. Slightly soluble in cold water. Insoluble in water.
Sensitive 
air sensitive
Hydrolytic Sensitivity
7: reacts slowly with moisture/water
BRN 
661212
InChIKey
COIOYMYWGDAQPM-UHFFFAOYSA-N
LogP
7.2
CAS DataBase Reference
6163-58-2(CAS DataBase Reference)
NIST Chemistry Reference
Phosphine, tris(2-methylphenyl)-(6163-58-2)
EPA Substance Registry System
Phosphine, tris(2-methylphenyl)- (6163-58-2)
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36-37/39
WGK Germany 
3
F 
10-23
TSCA 
Yes
HS Code 
29319090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
8.41817
Product name
Tri(o-tolyl)-phosphine
Purity
for synthesis
Packaging
1g
Price
$37.5
Updated
2024/03/01
Sigma-Aldrich
Product number
8.41817
Product name
Tri(o-tolyl)-phosphine
Purity
for synthesis
Packaging
10g
Price
$217
Updated
2024/03/01
Sigma-Aldrich
Product number
287822
Product name
Tri(o-tolyl)phosphine
Purity
97%
Packaging
1g
Price
$60.6
Updated
2024/03/01
Sigma-Aldrich
Product number
287822
Product name
Tri(o-tolyl)phosphine
Purity
97%
Packaging
10g
Price
$331
Updated
2024/03/01
TCI Chemical
Product number
T1024
Product name
Tri(o-tolyl)phosphine
Purity
>97.0%(GC)
Packaging
5g
Price
$65
Updated
2024/03/01
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Tri(o-tolyl)phosphine Chemical Properties,Usage,Production

Description

Tris(o-tolyl)phosphine is an organophosphorus compound. This compound is a white, water-insoluble solid that is soluble in organic solvents. In solution, it slowly converts to the phosphine oxide. As a phosphine ligand, it has a wide cone angle of 194°. Consequently, it tends to cyclometalate when treated with metal halides and metal acetates. Complexes of this ligand are common in homogeneous catalysis.

Chemical Properties

white to light yellow crystal powder.

Uses

Tri(o-tolyl)phosphine is used in a ruthenium-catalyzed direct amination of alcohols. It is also used in Suzuki reaction. Further, it is used in the preparation of tri-ortho-phosphinselenide by reacting with selenium as a reagent. In addition to this, it acts as a ligand in coordination chemistry.

Application

Tris(2-methylphenyl)phosphine (Eletriptan Impurity 13) is a phosphine catalyst. It can be used in the rhodium-catalyzed hydrogenation, Suzuki-Miyaura cross-coupling reactions and Heck reactions.

Preparation

Tri(o-tolyl)phosphine can be obtained by the reduction of tris(o-tolyl)phosphine oxide or prepared by the 2-bromotoluene Grignard reaction.
Procedure: To a solution of magnesuim turnings (3.11 g, 128 mmol, 3.5 equiv) in THF (50 mL) was added a small amount of 2-bromotoluene (1 mL) and 1 iodine crystal. The reaction vessel was heated until initiation occurred, where upon a solution of the remaining 2-bromotoluene (20 g, 117 mmol, 3.2 equiv in total) in THF (100 mL) was added. The reaction was set to reflux for 2 hours (colour change to black solution), after which it was cooled to 0 oC and a solution of phosphorus trichloride (5.01 g, 36.5 mmol, 1 equiv) in THF (30 mL) was added dropwise. Upon addition completion the reaction was set to reflux for 18 hours. The reaction was allowed to cool to room temperature, whereupon NH4Cl solution was added with care. The resulting solution was extracted with ether (3 x 100 mL), dried over MgSO4, filtered and concentrated in vacuo. The resulting white solid was recrystalised from ethanol to yield Tri(o-tolyl)phosphine as a white solid. (6.8 g, 62 %)

Reactivity Profile

Tri(o-tolyl)phosphine is suitable for the following reaction types: Cross Couplings, Silylations, Buchwald-Hartwig Cross Coupling Reaction, Heck Reaction, Negishi Coupling, Stille Coupling, Suzuki-Miyaura Coupling.

Flammability and Explosibility

Not classified

Purification Methods

It crystallises from EtOH [Boert et al. J Am Chem Soc 109 7781 1987]. [Beilstein 16 III 835.]

Tri(o-tolyl)phosphine Preparation Products And Raw materials

Raw materials

Ethanol Sodium sulfate Sodium chloride Phosphorus trichloride 1,2-Dibromoethane Tetrahydrofuran Diethyl ether Ammonium chloride Iodine Ethyl acetate Hydrochloric acid Dichloromethane Sodium hydroxide L(+)-Tartaric acid 2-Bromotoluene PETROLEUM ETHER Magnesium

Preparation Products

5-Methylindole
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View Lastest Price from Tri(o-tolyl)phosphine manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
Tri(o-tolyl)phosphine 6163-58-2
Price
US $0.00/KG
Min. Order
1KG
Purity
98%min
Supply Ability
30tons/month
Release date
2023-01-29
Shanghai UCHEM Inc.
Product
TRI-O-TOLYLPHOSPHINE 6163-58-2
Price
US $22.00-259.00/g
Min. Order
25g
Purity
0.98
Supply Ability
25kg
Release date
2023-12-19
Hebei Weibang Biotechnology Co., Ltd
Product
TRI-O-TOLYLPHOSPHINE 6163-58-2
Price
US $10.00/KG
Min. Order
100KG
Purity
99%
Supply Ability
100 mt
Release date
2021-07-29

6163-58-2, Tri(o-tolyl)phosphineRelated Search:

TRI-M-TOLYLPHOSPHINE Aluminum trifluoromethanesulfonate Eletriptan hydrobromide TRI(2-FURYL)PHOSPHINE TRIS(2-CYANOETHYL)PHOSPHINE Dibromobis(tri-o-tolylphosphine)palladium(II), Pd 12% Tri(o-tolyl)phosphine DICHLOROBIS(TRI-O-TOLYLPHOSPHINE)PALLADIUM(II) TRIS(4,6-DIMETHYL-3-SULFANATOPHENYL)PHOSPHINE TRISODIUM SALT HYDRATE TRIS(2,4-DIMETHYLPHENYL)PHOSPHINE TRANS-DI(MU-ACETATO)BIS[O-(DI-O-TOLYLPHOSPHINO)BENZYL]DIPALLADIUM (II) TRI(2,5-XYLYL)PHOSPHINE TRIMESITYLPHOSPHINE TRI-4-TOLYLPHOSPHINE,TRI-P-TOLYLPHOSPHINE,Tri-para-tolylphosphine,Tri-p-tolylphosphine,98% Phosphine (FORMYLMETHYLENE)TRIPHENYLPHOSPHORANE Rizatriptan TRI-P-TOLYLPHOSPHINE OXIDE

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  • Tri-ortho-tolylphosphine
  • tris(2-methylphenyl)-phosphin
  • PHOSPHORUS TRI-O-TOLYL
  • TRIS(O-TOLYL)PHOSPHINE
  • TRIS(2-METHYLPHENYL)PHOSPHINE
  • TRIS(2-TOLYL)PHOSPHINE
  • TRI-O-TOLYPHOSPHINE
  • TRI-O-TOLYLPHOSPHINE
  • TRI-2-TOLYLPHOSPHINE
  • TRI(2-METHYLPHENYL)PHOSPHINE
  • Tris (o-methylphenyl) phosphorus
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  • 6163-58-2
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