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Tri(o-tolyl)phosphine

Tri(o-tolyl)phosphine Structure
Tri(o-tolyl)phosphine structure
CAS No.
6163-58-2
Chemical Name:
Tri(o-tolyl)phosphine
Synonyms
P(o-tol)3;TRI-O-TOLYLPHOSPHINE;P(o-tolyl)3;Tri-o-tolylphosphane;TRIS(2-METHYLPHENYL)PHOSPHINE;TRIS(O-TOLYL)PHOSPHINE;TRI-O-TOLYPHOSPHINE;tris(2-Methylphenyl)phosphane;Tri-ortho-tolylphosphine;Tris(o-methylphenyl)phosphine
CBNumber:
CB8128012
Molecular Formula:
C21H21P
Molecular Weight:
304.37
MDL Number:
MFCD00008514
MOL File:
6163-58-2.mol
MSDS File:
SDS
TDS File:
TDS
Last updated:2026-07-16 07:06:08
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Tri(o-tolyl)phosphine Properties

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
InChI 1S/C21H21P/c1-16-10-4-7-13-19(16)22(20-14-8-5-11-17(20)2)21-15-9-6-12-18(21)3/h4-15H,1-3H3
InChIKey COIOYMYWGDAQPM-UHFFFAOYSA-N
SMILES Cc1ccccc1P(c2ccccc2C)c3ccccc3C
LogP 7.2
CAS DataBase Reference 6163-58-2(CAS DataBase Reference)
FDA UNII 5M32DK8XA8
NIST Chemistry Reference Phosphine, tris(2-methylphenyl)-(6163-58-2)
EPA Substance Registry System Phosphine, tris(2-methylphenyl)- (6163-58-2)
UNSPSC Code 12352128
NACRES NA.22

SAFETY

Risk and Safety Statements

Symbol(GHS)  Exclamation Mark (GHS07)
GHS07
Signal word  Warning
Hazard statements  H315-H319-H335
Precautionary statements  P261-P280a-P304+P340-P305+P351+P338-P405-P501a
PPE dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes  Xi
Risk Statements  36/37/38
Safety Statements  26-36-37/39
WGK Germany  3
F  10-23
TSCA  TSCA listed
HS Code  29319090
Storage Class 11 - Combustible Solids
REACH Registrations Active
NFPA 704
1
2 0

Tri(o-tolyl)phosphine price More Price(88)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 8.41817 Tri(o-tolyl)-phosphine for synthesis 6163-58-2 1g $41 2026-04-30 Buy
Sigma-Aldrich 8.41817 Tri(o-tolyl)-phosphine for synthesis 6163-58-2 10g $237 2026-04-30 Buy
Sigma-Aldrich 287822 Tri(o-tolyl)phosphine 97% 6163-58-2 1g $66.5 2026-04-30 Buy
Sigma-Aldrich 287822 Tri(o-tolyl)phosphine 97% 6163-58-2 10g $363 2026-04-30 Buy
TCI Chemical T1024 Tri(o-tolyl)phosphine >97.0%(GC) 6163-58-2 5g $65 2026-04-30 Buy
Product number Packaging Price Buy
8.41817 1g $41 Buy
8.41817 10g $237 Buy
287822 1g $66.5 Buy
287822 10g $363 Buy
T1024 5g $65 Buy

Tri(o-tolyl)phosphine Chemical Properties, Uses, 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

reaction suitability

reagent type: ligand

Synthesis

Phosphine oxide, tris (2-methylphenyl)-

6163-63-9

Tri(o-tolyl)phosphine

6163-58-2

The general procedure for the synthesis of tris(o-methylphenyl)phosphorus from pabuxilib impurities was as follows: 2a (2 mmol) was added to a mixture containing magnesium powder (8 mmol, 4 eq.), trimethylchlorosilane (6 mmol, 3 eq.) and 1,3-dimethyl-2-imidazolidinone (DMI, 8 mL), and the whole mixture was stirred for 2 h at room temperature. After completion of the reaction, saturated aqueous ammonium carbonate solution was added to the reaction mixture and the mixture was extracted with ether (10 mL × 3). The combined organic layers were washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and subsequently concentrated under reduced pressure. The resulting product was analyzed by 31P NMR and was found to be in the ratio of 97:3 for 1a to 2a. After purification by silica gel column chromatography (eluent: hexane/ethyl acetate = 5:1), the target product 1a was obtained in 96% yield (Table 1, entry 1).

Purification Methods

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

References

[1] Tetrahedron Letters, 2015, vol. 56, # 7, p. 918 - 920
[2] Synthesis, 2011, # 24, p. 4091 - 4098
[3] Angewandte Chemie - International Edition, 2018, vol. 57, # 46, p. 15253 - 15256
[4] Angew. Chem., 2018, vol. 130, # 46, p. 15473 - 15476,4

Tri(o-tolyl)phosphine synthesis

6163-61-7
6163-58-2
Synthesis of Tri(o-tolyl)phosphine from Phosphine sulfide, tris(2-methylphenyl)-

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

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Preparation Products

5-Methylindole BIS(O-TOLYL)PHOSPHINE

Tri(o-tolyl)phosphine Suppliers

Global Suppliers ( 532)
Supplier Tel Email Country ProdList Advantage
Hubei Xishaonian biotechnology co., ltd 0711-3700636 18827410479 xujin@boronicgroup.com China 50 58
Puyang Huicheng Electronic Material Co. Ltd. 0393-0393-8910800 15039333257 info@huichengchem.com China 588 64
BeiJing Greenchem Technology Co.,Ltd. 131-21959385 18804271668 chemrocking@bjgreenchem.com China 272 58
Aikon International Limited 025-58859352 13913916777 dt3@aikonchem.com China 15490 58
Wuhan Pengo Technology.,Ltd. 027-60707801 13628634921 sunny.w@boronicgroup.com China 168 56
Creasyn Finechem(Tianjin) Co., Ltd. 022-83946278 13820372920 sales@creasyn.com China 968 68
J & K SCIENTIFIC LTD. 18210857532 18210857532 jkinfo@jkchemical.com China 96815 76
Meryer (Shanghai) Chemical Technology Co., Ltd. 4006356688 18621169109 market03@meryer.com China 40202 62
Beijing Donghualituo Techonlogy Development Co.,Ltd. 010-88425576 sales@dhltchem.com China 793 59
INTATRADE GmbH +49 3493/605464 sales@intatrade.de Germany 3563 66
Supplier Advantage
Hubei Xishaonian biotechnology co., ltd 58
Puyang Huicheng Electronic Material Co. Ltd. 64
BeiJing Greenchem Technology Co.,Ltd. 58
Aikon International Limited 58
Wuhan Pengo Technology.,Ltd. 56
Creasyn Finechem(Tianjin) Co., Ltd. 68
J & K SCIENTIFIC LTD. 76
Meryer (Shanghai) Chemical Technology Co., Ltd. 62
Beijing Donghualituo Techonlogy Development Co.,Ltd. 59
INTATRADE GmbH 66

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View Latest Price from Tri(o-tolyl)phosphine manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
TRI-O-TOLYLPHOSPHINE pictures 2026-09-16 TRI-O-TOLYLPHOSPHINE
6163-58-2
 $22.00-259.00 25g 0.98 25kg Shanghai UCHEM Inc.
Tri(o-tolyl)phosphine pictures 2026-09-16 Tri(o-tolyl)phosphine
6163-58-2
 1KG 98%min 30tons/month WUHAN FORTUNA CHEMICAL CO., LTD
Tri-o-tolylphosphine pictures 2026-08-07 Tri-o-tolylphosphine
6163-58-2
 $1.00 1KG 99% 20 tons Shaanxi Dideu Medichem Co. Ltd

Tri(o-tolyl)phosphine Spectrum

Tri(o-tolyl)phosphine(6163-58-2)MSTri(o-tolyl)phosphine(6163-58-2)1HNMRTri(o-tolyl)phosphine(6163-58-2)13CNMRTri(o-tolyl)phosphine(6163-58-2)31PNMRTri(o-tolyl)phosphine(6163-58-2)IR1Tri(o-tolyl)phosphine(6163-58-2)IR2

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