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Tris(2-methylphenyl)phosphine

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Name

Tris(2-methylphenyl)phosphine

EINECS 228-193-9
CAS No. 6163-58-2 Density 1.16[at 20℃]
PSA 13.59000 LogP 4.37000
Solubility Soluble in alcohol. Slightly soluble in cold water. Insoluble in water. Melting Point 123-125 °C(lit.)
Formula C21H21P Boiling Point 412.4 °C at 760 mmHg
Molecular Weight 304.371 Flash Point 214.6 °C
Transport Information N/A Appearance white to light yellow crystal powder
Safety 26-36-37/39 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 6163-58-2 (TRI-O-TOLYLPHOSPHINE) Hazard Symbols IrritantXi
Synonyms

Phosphine,tri-o-tolyl- (7CI,8CI);NSC 116667;Tri-2-tolylphosphine;Tri-o-tolylphosphine;Tris(2-toluene)phosphine;Tris(2-tolyl)phosphine;Tris(o-methylphenyl)phosphine;Tris(o-tolyl)phosphine;Tri-(O-Tol)phosphine;

Article Data 31

Tris(2-methylphenyl)phosphine Synthetic route

64-17-5

ethanol

878809-28-0

tris(2-tolyl)phosphane-borane(1:1)

A

150-46-9

triethyl borate

B

6163-58-2

tris-(o-tolyl)phosphine

Conditions
ConditionsYield
Inert atmosphere; Reflux;A n/a
B 96%
95-46-5

2-methylphenyl bromide

6163-58-2

tris-(o-tolyl)phosphine

Conditions
ConditionsYield
Stage #1: 2-methylphenyl bromide With magnesium In tetrahydrofuran Reflux; Inert atmosphere;
Stage #2: With phosphorus trichloride In tetrahydrofuran for 24h; Inert atmosphere;
89%
Stage #1: 2-methylphenyl bromide With magnesium In tetrahydrofuran at 20℃; for 0.666667h;
Stage #2: With phosphorus trichloride In tetrahydrofuran for 1.5h;
85%
Stage #1: 2-methylphenyl bromide With iodine; magnesium In tetrahydrofuran at 20℃; for 2.5h; Schlenk technique; Inert atmosphere;
Stage #2: With phosphorus trichloride In tetrahydrofuran at -40℃; for 0.5h;
Stage #3: In tetrahydrofuran; ethanol for 5h;
75%
6163-63-9

tri-o-tolylphosphine oxide

6163-58-2

tris-(o-tolyl)phosphine

Conditions
ConditionsYield
With chloro-trimethyl-silane; magnesium at 20℃; for 4h;89%
With aluminum (III) chloride; N,N,N,N,-tetramethylethylenediamine; tetrabutyl-ammonium chloride; tert-butylammonium hexafluorophosphate(V) In acetonitrile at 60℃; Inert atmosphere; Glovebox; Electrolysis;69%
With chloro-trimethyl-silane; tetrabutylammomium bromide; copper; zinc In acetonitrile at 45℃; Electrochemical reaction; Inert atmosphere;58%
With oxalyl dichloride; hydrogen In chloroform-d1 at 130℃; under 60006 Torr; for 18h; Reagent/catalyst;51%
615-37-2

ortho-methylphenyl iodide

6163-58-2

tris-(o-tolyl)phosphine

Conditions
ConditionsYield
With white phosphorus; 1,3-dicyano-5-fluoro-2,4,6-tris(diphenylamino)benzene; triethylamine In acetonitrile; benzene for 24h; Inert atmosphere; Glovebox; Sealed tube; Irradiation;43%

di-m-acetato-bis{2-(diortho-tolylphosphino)benzyl-C,P}dipalladium(II)

15475-27-1, 4346-39-8

potassium diphenylphosphine

A

[2-(di-ortho-tolylphosphino)benzyl]diphenylphosphine oxide

B

6163-58-2

tris-(o-tolyl)phosphine

Conditions
ConditionsYield
Stage #1: di-m-acetato-bis{2-(diortho-tolylphosphino)benzyl-C,P}dipalladium(II); potassium diphenylphosphine In tetrahydrofuran at 20℃; for 48h;
Stage #2: With air
A 2%
B 30%
172418-37-0, 199609-05-7

di-m-chloro-bis{2-(di-ortho-tolylphosphino)benzyl-C,P}dipalladium(II)

15475-27-1, 4346-39-8

potassium diphenylphosphine

A

[2-(di-ortho-tolylphosphino)benzyl]diphenylphosphine oxide

B

6163-58-2

tris-(o-tolyl)phosphine

Conditions
ConditionsYield
Stage #1: di-m-chloro-bis{2-(di-ortho-tolylphosphino)benzyl-C,P}dipalladium(II); potassium diphenylphosphine In tetrahydrofuran at 20℃; for 48h; Schlenk technique; Inert atmosphere;
Stage #2: With air In tetrahydrofuran for 48h; Schlenk technique;
A 20%
B 2%
95-52-3

2-Fluorotoluene

6163-58-2

tris-(o-tolyl)phosphine

Conditions
ConditionsYield
With 1-methyl-pyrrolidin-2-one; potassium hydroxide monohydrate; phosphorus at 100 - 120℃; for 1h; Reagent/catalyst; Temperature; Inert atmosphere;19%
932-31-0

ortho-tolylmagnesium bromide

6163-58-2

tris-(o-tolyl)phosphine

Conditions
ConditionsYield
With diethyl ether; hydrogen; phosphorus trichloride

{(pyrimidine-2-thione)(tri-ortho-tolylphosphine)copper(I) chloride}

A

{Cu(C4H3N2(S))Cl}

B

6163-58-2

tris-(o-tolyl)phosphine

Conditions
ConditionsYield
In chloroform Irradiation (UV/VIS); decompn. at room temp. within minutes;

{(1,3-thiazolidine-2-thione)(tri-ortho-tolylphosphine)copper(I) iodide}

A

Cu(1+)*C3H6NS(S)*I(1-) = {Cu(C3H6NS(S))I}

B

6163-58-2

tris-(o-tolyl)phosphine

Conditions
ConditionsYield
In chloroform Irradiation (UV/VIS); decompn. at room temp. within minutes;

Tris(2-methylphenyl)phosphine Specification

The CAS register number of Tris(2-methylphenyl)phosphine is 6163-58-2. It also can be called as Phosphine,tris(2-methylphenyl)- and the IUPAC name about this chemical is tris(2-methylphenyl)phosphane. The molecular formula about this chemical is C21H21P and the molecular weight is 304.37. It belongs to the following product categories, such as Ligand; Phosphine Ligands; Synthetic Organic Chemistry; Benzenes and so on. This chemical is usually used as a ligand for the coupling reaction.

Physical properties about Tris(2-methylphenyl)phosphine are: (1)ACD/LogP: 7.07; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 7.07; (4)ACD/LogD (pH 7.4): 7.07; (5)ACD/BCF (pH 5.5): 139115.45; (6)ACD/BCF (pH 7.4): 139115.45; (7)ACD/KOC (pH 5.5): 167188.17; (8)ACD/KOC (pH 7.4): 167188.17; (9)#Freely Rotating Bonds: 3; (10)Polar Surface Area: 13.59Å2; (11)Flash Point: 214.6 °C; (12)Enthalpy of Vaporization: 63.92 kJ/mol; (13)Boiling Point: 412.4 °C at 760 mmHg; (14)Vapour Pressure: 1.24E-06 mmHg at 25°C.

Uses of p-Chloropropiophenone: it can be used to produce Tri-ortho-phosphinselenid at heating. This reaction will need reagent selenium black and solvent toluene with reaction time of 6 hours. The yield is about 100%.

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable protective clothing, gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: c3(c(P(c1ccccc1C)c2ccccc2C)cccc3)C
(2)InChI: InChI=1/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
(3)InChIKey: COIOYMYWGDAQPM-UHFFFAOYAJ
(4)Std. InChI: 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
(5)Std. InChIKey: COIOYMYWGDAQPM-UHFFFAOYSA-N

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