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:

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organophosphorus ligand

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