Tri(o-tolyl)phosphine
- 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
| Product description | Number | Pack Size | Price |
| Tri(o-tolyl)-phosphine for synthesis | 8.41817 | 1g | $41 |
| Tri(o-tolyl)-phosphine for synthesis | 8.41817 | 10g | $237 |
| Tri(o-tolyl)phosphine 97% | 287822 | 1g | $66.5 |
| Tri(o-tolyl)phosphine 97% | 287822 | 10g | $363 |
| Tri(o-tolyl)phosphine >97.0%(GC) | T1024 | 5g | $65 |
| More product size | |||
| 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) |  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 |
|
Tri(o-tolyl)phosphine price More Price(102)
| 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 |
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
6163-63-9
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 Preparation Products And Raw materials
Raw materials
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Preparation Products
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| career henan chemical co | +86-0371-86658258 | sales@coreychem.com | China | 29812 | 58 |
| Tangshan Moneide Trading Co., Ltd. | +86-315-8309571 +86-15633399667 | sales@moneidechem.com | China | 574 | 58 |
| Hebei Chuanghai Biotechnology Co., Ltd | +86-15350571055 | Sibel@chuanghaibio.com | China | 8738 | 58 |
| Shanghai UCHEM Inc. | +86-18930848214 +86-021-56762820 | sales@myuchem.com | China | 8834 | 58 |
| Henan Research New Materials Co., Ltd. | +86-18903931628 +86-18903931531 | sales036@researchvip.com | China | 303 | 58 |
| Frapp's ChemicalNFTZ Co., Ltd. | +86 (576) 8169-6106 | sales@frappschem.com | China | 880 | 50 |
| Capot Chemical Co.,Ltd. | +86-（0）57185586718 +86-13336195806 | sales@capot.com | China | 29640 | 60 |
| Shanghai Daken Advanced Materials Co.,Ltd | +86-2158073036 | info@dakenam.com | China | 14026 | 58 |
| Henan Tianfu Chemical Co.,Ltd. | +86-0371-55170693 +86-19937530512 | info@tianfuchem.com | China | 21585 | 55 |
| ATK CHEMICAL COMPANY LIMITED | +undefined-21-51877795 | ivan@atkchemical.com | China | 33024 | 60 |
Related articles
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- Sep 29，2025
View Lastest Price from Tri(o-tolyl)phosphine manufacturers
| Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
|---|---|---|---|---|---|---|---|---|
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2026-07-29 | TRI-O-TOLYLPHOSPHINE
6163-58-2
|
$22.00-259.00 | 25g | 0.98 | 25kg | Shanghai UCHEM Inc. | |
 |
2026-07-29 | Tri(o-tolyl)phosphine
6163-58-2
|
1KG | 98%min | 30tons/month | WUHAN FORTUNA CHEMICAL CO., LTD | ||
 |
2026-07-15 | Tri-o-tolylphosphine
6163-58-2
|
$33.00-70.00 | 10g | TargetMol Chemicals Inc. |
-
- TRI-O-TOLYLPHOSPHINE
6163-58-2
- $22.00-259.00
- 0.98
- Shanghai UCHEM Inc.
-
- Tri(o-tolyl)phosphine
6163-58-2
- $0.00
- 98%min
- WUHAN FORTUNA CHEMICAL CO., LTD
-
- Tri-o-tolylphosphine
6163-58-2
- $33.00-70.00
- TargetMol Chemicals Inc.
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