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Bis(diphenylphosphino)methane

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Name

Bis(diphenylphosphino)methane

EINECS 218-194-2
CAS No. 2071-20-7 Density N/A
PSA 27.18000 LogP 5.20970
Solubility insoluble in water Melting Point 118-119 °C(lit.)
Formula C25H22P2 Boiling Point 497.2 °C at 760 mmHg
Molecular Weight 384.397 Flash Point 270.2 °C
Transport Information N/A Appearance White powder or crystalline powder
Safety 22-24/25-37/39-26 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 2071-20-7 (Bis(diphenylphosphino)methane) Hazard Symbols IrritantXi
Synonyms

Phosphine,methylenebis[diphenyl- (6CI,7CI,8CI,9CI);DPPM;DPPM (phosphine derivative);Methanediylbis[diphenylphosphine];Methylenebis[diphenylphosphine];NSC 147767;Tetraphenylmethylenediphosphine;

Article Data 43

Bis(diphenylphosphino)methane Synthetic route

67-56-1

methanol

24442-15-7

methylenebis(diphenylphosphane)-borane(1:2)

A

121-43-7

Trimethyl borate

B

2071-20-7

bis-diphenylphosphinomethane

Conditions
ConditionsYield
In toluene at 100℃; Inert atmosphere;A n/a
B 100%
829-85-6

diphenylphosphane

74-95-3

1,1-dibromomethane

2071-20-7

bis-diphenylphosphinomethane

Conditions
ConditionsYield
With cesium hydroxide; 4 Angstroem MS In N,N-dimethyl-formamide at 23℃; for 16h;95%
With cesium hydroxide; 4 A molecular sieve In N,N-dimethyl-formamide at 23℃; for 16h;95%
Stage #1: diphenylphosphane With cesiumhydroxide monohydrate In N,N-dimethyl-formamide at 20℃; for 1h; Molecular sieve; Inert atmosphere;
Stage #2: 1,2-dibromomethane In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere; Molecular sieve;
95%
64-17-5

ethanol

24442-15-7

methylenebis(diphenylphosphane)-borane(1:2)

A

150-46-9

triethyl borate

B

2071-20-7

bis-diphenylphosphinomethane

Conditions
ConditionsYield
Inert atmosphere; Reflux;A n/a
B 91%
2096-83-5

tetraphenyldiphosphine oxide

Cp2Ti=CH2

Cp2Ti=CH2

2071-20-7

bis-diphenylphosphinomethane

Conditions
ConditionsYield
Stage #1: tetraphenyldiphosphine oxide; Cp2Ti=CH2 In benzene at 50℃;
Stage #2: at 80℃;
66%
75-09-2

dichloromethane

829-85-6

diphenylphosphane

2071-20-7

bis-diphenylphosphinomethane

Conditions
ConditionsYield
With tris(dimethylamino)(methylimino)phosphorane In tetrahydrofuran; diethyl ether for 24h; Ambient temperature;50%
With potassium hydroxide; potassium carbonate 1.) HMPT, 20 deg C, 2.) 40 - 45 deg C, 1 h; Yield given. Multistep reaction;
With potassium hydroxide; potassium carbonate 1) HMPA, 20 deg C, 2) HMPA, 40-45 deg C, 1 h; Yield given. Multistep reaction;
67-66-3

chloroform

15475-27-1, 4346-39-8

potassium diphenylphosphine

A

1101-41-3

Tetraphenyldiphosphin

B

2071-20-7

bis-diphenylphosphinomethane

Conditions
ConditionsYield
In ammonia at -50℃;A n/a
B 45%
In ammonia at -50℃; Product distribution; Mechanism; another solvent;A n/a
B 45%
1079-66-9

chloro-diphenylphosphine

2071-20-7

bis-diphenylphosphinomethane

Conditions
ConditionsYield
With sodium und Umsetzung mit CH2Cl2;
54006-28-9

(diphenylphosphinomethyl)diphenylphosphine sulphide

A

14633-92-2

bis(diphenylthiophosphoryl)methane

B

2071-20-7

bis-diphenylphosphinomethane

Conditions
ConditionsYield
at 150℃; vacuum;
at 150℃; vacuum sublimation;
28926-61-6

Lithium-bis(diphenylphosphanyl)methanid

<18>Krone-6-Kaliumdicyanphosphid

A

C26H21NP3(1-)*C12H24O6*K(1+)

B

2071-20-7

bis-diphenylphosphinomethane

Conditions
ConditionsYield
In tetrahydrofuran for 0.25h; Ambient temperature;
80359-57-5

C25H21CsP2

108-91-8

cyclohexylamine

A

4820-05-7

Caesium-cyclohexylamid

B

2071-20-7

bis-diphenylphosphinomethane

Conditions
ConditionsYield
Equilibrium constant; pK;

Bis(diphenylphosphino)methane Specification

The Methylenebis(diphenylphosphine), with the CAS registry number 2071-20-7, is also known as Bis(diphenylphosphino)methane. It belongs to the product categories of Phosphines; Ligand; Phosphine Ligands; Synthetic Organic Chemistry. Its EINECS registry number is 218-194-2. This chemical's molecular formula is C25H22P2 and molecular weight is 384.39. Its IUPAC name is called diphenylphosphanylmethyl(diphenyl)phosphane. What's more, this chemical is white to light yellow crystal powder, which is used in inorganic and organometallic chemistry as a ligand. It is more specifically a chelating ligand because it is a ligand that is attached to the central metals (the phosphorus) by bonds from two or more donor atoms.

Physical properties of Methylenebis(diphenylphosphine): (1)ACD/LogP: 8.57; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 8.57; (4)ACD/LogD (pH 7.4): 8.57; (5)ACD/BCF (pH 5.5): 1000000; (6)ACD/BCF (pH 7.4): 1000000; (7)ACD/KOC (pH 5.5): 1090949.38; (8)ACD/KOC (pH 7.4): 1090949.38; (9)#Freely Rotating Bonds: 6; (10)Flash Point: 270.2 °C; (11)Enthalpy of Vaporization: 73.61 kJ/mol; (12)Boiling Point: 497.2 °C at 760 mmHg; (13)Vapour Pressure: 1.55E-09 mmHg at 25°C.

Preparation: this chemical can be prepared by diphenylphosphane and dichloromethane. This reaction will need reagent (Me2N)3P=NMe and solvents diethyl ether, tetrahydrofuran. The reaction time is 24 hours at ambient temperature. The yield is about 50%.

Methylenebis(diphenylphosphine) can be prepared by diphenylphosphane and dichloromethane

Uses of Methylenebis(diphenylphosphine): it can be used to produce 1,1,3,3-tetraphenyl-[1,3]diphosphinanediium; dibromide. This reaction will need solvent dimethylformamide.

Methylenebis(diphenylphosphine) can be used to produce 1,1,3,3-tetraphenyl-[1,3]diphosphinanediium; dibromide

When you are using this chemical, please be cautious about it as the following:
This chemical may cause inflammation to the skin or other mucous membranes. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective gloves and eye/face protection.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C1=CC=C(C=C1)P(CP(C2=CC=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4
(2)InChI: InChI=1S/C25H22P2/c1-5-13-22(14-6-1)26(23-15-7-2-8-16-23)21-27(24-17-9-3-10-18-24)25-19-11-4-12-20-25/h1-20H,21H2
(3)InChIKey: XGCDBGRZEKYHNV-UHFFFAOYSA-N

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