• Name

  Diphenylphosphine

• EINECS 212-591-4
• CAS No. 829-85-6
• Article Data143
• CAS DataBase
• Density 1.07 g/cm³
• Solubility Insoluble in water
• Melting Point 65-67oC (338-340 K)
• Formula C₁₂H₁₁P
• Boiling Point 275 °C at 760 mmHg
• Molecular Weight 186.193
• Flash Point 120.1 °C
• Transport Information UN 2845 4.2/PG 1
• Appearance colorless liquid
• Safety 26-36
• Risk Codes 17-36/37/38
• Molecular Structure
• Hazard Symbols F,Xi
• Synonyms NSC 152123;Diphenylphosphin;
• PSA 13.59000
• LogP 2.31590

Synthetic route

603-35-0

triphenylphosphine

829-85-6

diphenylphosphane

Conditions

Conditions	Yield
With sodium In ammonia at -78℃; for 4h;	100%
With lithium In tetrahydrofuran for 27h;	74%
With lithium In tetrahydrofuran; diethyl ether; water cooling;	73%

6002-34-2

tert-butyldiphenylphosphine

829-85-6

diphenylphosphane

Conditions

Conditions	Yield
With ammonia; sodium at -78℃; for 4h;	100%
Multi-step reaction with 2 steps 1: sodium / tetrahydrofuran / 1 h / 25 °C / Inert atmosphere 2: tetrahydrofuran / 25 °C View Scheme
Multi-step reaction with 2 steps 1: sodium / tetrahydrofuran / 1 h / 25 °C / Inert atmosphere 2: tetrahydrofuran / 25 °C View Scheme

793695-34-8

C2H2N2(2,4,6-trimethylbenzene)PPPh2

A

1,3-bis-(2,4,6-trimethyl-phenyl)-1,3-dihydro-[1,3,2]diazaphosphole 2-oxide

B

829-85-6

diphenylphosphane

Conditions

Conditions	Yield
With water at 20℃;	A 100% B n/a

1101-41-3

Tetraphenyldiphosphin

829-85-6

diphenylphosphane

Conditions

Conditions	Yield
With hydrogen; Rh{HC[CMeN(iPr2C6H2)]2}(C8H14)N2 In (2)H8-toluene at 50℃; under 760.051 Torr; for 12h;	95%
protic solvents, electrolysis;
With triethylsilane; gallium(III) trichloride In chlorobenzene at 100℃; for 1h;

766-77-8

Dimethylphenylsilane

1101-41-3

Tetraphenyldiphosphin

A

1009109-32-3

C20H21PSi

B

829-85-6

diphenylphosphane

Conditions

Conditions	Yield
Rh{HC[CMeN(iPr2C6H2)]2}(C8H14)N2 In (2)H8-toluene at 100℃;	A 95% B 5%

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507-20-0

tertiary butyl chloride

4376-01-6

sodium diphenylphosphide

829-85-6

diphenylphosphane

Conditions

Conditions	Yield
In tetrahydrofuran at 25℃;	95%

NiOs3H3(1+)*C5H5(1-)*8CO*PH(C6H5)2=(C5H5)NiOs3H3(CO)8PH(C6H5)2

603-35-0

triphenylphosphine

A

NiOs3H3(1+)*C5H5(1-)*8CO*P(C6H5)3=(C5H5)NiOs3H3(CO)8(P(C6H5)3)

B

829-85-6

diphenylphosphane

Conditions

Conditions	Yield
In hexane The complex and a slight excess of Pp are refluxed in hexane (N2) for 6 min.; The reaction soln. was filtered and concd. to small vol. under reduced pressure then subjected to preparative thin layer chromy.(silica gel; light petroleum/diethyl ether).;	A 90% B n/a

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4559-70-0

Diphenylphosphine oxide

829-85-6

diphenylphosphane

Conditions

Conditions	Yield
Stage #1: Diphenylphosphine oxide With diisobutylaluminium hydride In tetrahydrofuran; toluene at 20℃; Inert atmosphere; Stage #2: With sodium hydroxide In tetrahydrofuran; tert-butyl methyl ether; water; toluene at 5℃;	88%
With diisobutylaluminium hydride In tetrahydrofuran at 25℃; for 0.166667h;	86%
With diisobutylaluminium hydride In tert-butyl methyl ether; cyclohexane at 25℃; for 0.166667h; Inert atmosphere; chemoselective reaction;	86%

1079-66-9

chloro-diphenylphosphine

7429-90-5

aluminium

829-85-6

diphenylphosphane

Conditions

Conditions	Yield
In N,N-dimethyl-formamide; toluene	87%
In N,N-dimethyl-formamide; toluene	84%

7439-96-5

manganese

1079-66-9

chloro-diphenylphosphine

106-93-4

ethylene dibromide

829-85-6

diphenylphosphane

Conditions

Conditions	Yield
With chloro-trimethyl-silane In tetrahydrofuran; nitrogen; toluene	84%

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1079-66-9

chloro-diphenylphosphine

829-85-6

diphenylphosphane

Conditions

Conditions	Yield
With nickel tetrafluoroborate; tetraethylammonium bromide In acetonitrile electrolysis;	82%
With magnesium In N,N-dimethyl-formamide; toluene	81%
With lithium aluminium tetrahydride	68%

108-86-1

bromobenzene

A

603-35-0

triphenylphosphine

B

829-85-6

diphenylphosphane

C

791-28-6

Triphenylphosphine oxide

Conditions

Conditions	Yield
With phosphorous; Ni(0)bipy In N,N-dimethyl-formamide Electrochemical reaction; Zn anode;	A 80% B 9% C 10%
With phosphorous; tris(2,2'-bipyridine)nickel(II) tetrafluoroborate In N,N-dimethyl-formamide at 50℃; Electrochemical reaction; Zn anode;	A 50% B 9% C 10%

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17154-34-6

(trimethylsilyl)diphenylphosphine

A

1101-41-3

Tetraphenyldiphosphin

B

829-85-6

diphenylphosphane

Conditions

Conditions	Yield
With tris(2,3,5,6-tetrafluorophenyl)borane triethylphosphine oxide; 4-heptanone; bromobenzene-d5 at 130℃; for 120h; Concentration; Inert atmosphere; Schlenk technique;	A 12% B 80%

7439-96-5

manganese

1079-66-9

chloro-diphenylphosphine

829-85-6

diphenylphosphane

Conditions

Conditions	Yield
With acetic acid In water; N,N-dimethyl-formamide; toluene	77%
In nitrogen; N,N-dimethyl-formamide; toluene	63%
In tetrahydrofuran; water	60%

776-76-1

methyldiphenylsilane

1101-41-3

Tetraphenyldiphosphin

A

1009109-35-6

C25H23PSi

B

829-85-6

diphenylphosphane

Conditions

Conditions	Yield
Rh{HC[CMeN(iPr2C6H2)]2}(C8H14)N2 In (2)H8-toluene Heating;	A 76% B 17%

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591-50-4

iodobenzene

A

603-35-0

triphenylphosphine

B

638-21-1

phenylphosphane

C

829-85-6

diphenylphosphane

Conditions

Conditions	Yield
With phosphorous; Ni(0)bipy In N,N-dimethyl-formamide Electrochemical reaction; Zn anode;	A 75% B 5% C 10%
With phosphorous; tris(2,2'-bipyridine)nickel(II) tetrafluoroborate In N,N-dimethyl-formamide at 50℃; Electrochemical reaction; Zn anode;	A 65% B 10% C 12%

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Diphenylphosphine Chemical Properties

Diphenylphosphine Safety Profile

Diphenylphosphine Specification