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1,2-Bis(diphenylphosphino)ethane
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Name

1,2-Bis(diphenylphosphino)ethane

 EINECS 216-769-2
CAS No. 1663-45-2 Density N/A
PSA 27.18000 LogP 5.25220
Solubility N/A Melting Point 137-142 °C(lit.)
Formula C26H24P2 Boiling Point 514.815 °C at 760 mmHg
Molecular Weight 398.424 Flash Point 281.728 °C
Transport Information N/A Appearance white to light yellow crystal powder
Safety 26-37/39 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 1663-45-2 (1,2-Bis(diphenylphosphino)ethane) Hazard Symbols IrritantXi
Synonyms

P,P'-Ethylenebis(diphenylphosphine);Phosphine,1,2-ethanediylbis[diphenyl- (9CI);1,2-Ethylenebis(diphenylphosphine);DPPE (ligand);Ethylenebis(diphenylphosphine);NSC 76285;

Article Data 80

1,2-Bis(diphenylphosphino)ethane Synthetic route

15444-66-3

(1,2-bis(diphenylphosphino)ethane)tetracarbonylmolybdenum

38536-63-9

(1,2-bis(diphenylarsino)ethane)molybdenum tetracarbonyl

A

53557-42-9

(1-diphenylphosphino-2-diphenylarsinoethane)molybdenum tetracarbonyl

B

4431-24-7

1,2-bis(diphenylarsino)ethane

C

1663-45-2

1,2-bis-(diphenylphosphino)ethane

Conditions
ConditionsYield
reaction in a calorimeter under argon;A 100%
B n/a
C n/a

cyclopentadienylmolybdenum(III)(bis(diphenylphosphino)ethane)Cl2

594-09-2

trimethylphosphane

cyclopentadienylmolybdenum(III)(PMe3)2Cl2

B

1663-45-2

1,2-bis-(diphenylphosphino)ethane

Conditions
ConditionsYield
In dichloromethane mixing of the Mo compd. with the free phosphine (molar ratio 2.3:1) in CH2Cl2;;A 100%
B n/a
829-85-6

diphenylphosphane

74-86-2

acetylene

1663-45-2

1,2-bis-(diphenylphosphino)ethane

Conditions
ConditionsYield
With potassium hydroxide In water; dimethyl sulfoxide for 1h;97%
4141-50-8

1,2-bis(diphenylphosphinoyl)ethane

1663-45-2

1,2-bis-(diphenylphosphino)ethane

Conditions
ConditionsYield
Stage #1: 1,2-bis(diphenylphosphinoyl)ethane With trityl tetrakis(pentafluorophenyl)borate In (2)H8-toluene at 20℃; Glovebox; Inert atmosphere;
Stage #2: With phenylsilane In (2)H8-toluene at 80℃; for 13.5h; Glovebox; Inert atmosphere; Sealed tube;		97%
With 1,1,3,3-Tetramethyldisiloxane; titanium(IV) isopropylate In various solvent(s) at 100℃; for 7h;95%
With titanium(IV) isopropylate; Triethoxysilane In tetrahydrofuran at 67℃;90%
7615-76-1

1,2-bis(diphenylphosphinothioyl)ethane

1663-45-2

1,2-bis-(diphenylphosphino)ethane

Conditions
ConditionsYield
With Raney-Ni In ethanol; benzene at 20℃; for 3h; Inert atmosphere;97%
984-43-0

1,2-bis(diphenylphosphanyl)ethane monoxide

1663-45-2

1,2-bis-(diphenylphosphino)ethane

Conditions
ConditionsYield
With diethoxymethylane; Bis(p-nitrophenyl) phosphate In toluene at 110℃; Inert atmosphere; chemoselective reaction;96%
With Bis(p-nitrophenyl) phosphate; 1,3-diphenyl-disiloxane In ethyl acetate at 23℃; for 70h; Sealed tube; chemoselective reaction;96%
Stage #1: 1,2-bis(diphenylphosphanyl)ethane monoxide With trityl tetrakis(pentafluorophenyl)borate In (2)H8-toluene at 20℃; Glovebox; Inert atmosphere;
Stage #2: With phenylsilane In (2)H8-toluene at 80℃; for 4h; Glovebox; Inert atmosphere; Sealed tube;		90%
/PBGRG362--165/

/PBGRG362--165/

1663-45-2

1,2-bis-(diphenylphosphino)ethane

Conditions
ConditionsYield
With sodium hydrogencarbonate; tetrafluoroboric acid dimethyl ether complex In dichloromethane 1.) a.) -5 up to 25 deg C; b.) 25 deg C, 12h; 2.) 0 deg C;92%
829-85-6

diphenylphosphane

2155-96-6

Diphenylvinylphosphine

1663-45-2

1,2-bis-(diphenylphosphino)ethane

Conditions
ConditionsYield
With potassium tert-butylate In dimethyl sulfoxide at 20℃;90%

[dppeP][Br]

882-33-7

diphenyldisulfane

A

1095-04-1

triphenyl thiophosphite

B

C32H29P2S(1+)*Br(1-)

C

1663-45-2

1,2-bis-(diphenylphosphino)ethane

Conditions
ConditionsYield
In dichloromethane for 1h; Inert atmosphere;A 90%
B n/a
C n/a
106-93-4

ethylene dibromide

829-85-6

diphenylphosphane

1663-45-2

1,2-bis-(diphenylphosphino)ethane

Conditions
ConditionsYield
With cesium hydroxide; 4 Angstroem MS In N,N-dimethyl-formamide at 23℃; for 36h;78%
With cesium hydroxide; 4 A molecular sieve In N,N-dimethyl-formamide at 23℃; for 36h;78%
Stage #1: diphenylphosphane With cesiumhydroxide monohydrate In N,N-dimethyl-formamide at 20℃; for 1h; Molecular sieve; Inert atmosphere;
Stage #2: ethylene dibromide In N,N-dimethyl-formamide at 20℃; for 36h; Inert atmosphere; Molecular sieve;		78%
With cesiumhydroxide monohydrate In N,N-dimethyl-formamide at 20℃; for 36h; Molecular sieve; Inert atmosphere;78%
With tris(dimethylamino)(methylimino)phosphorane In tetrahydrofuran; diethyl ether for 24h; Ambient temperature;

1,2-Bis(diphenylphosphino)ethane Specification

The 1,2-Bis(diphenylphosphino)ethane, with the CAS registry number 1663-45-2, is also known as 1,2-Ethanediylbis(diphenylphosphine). It belongs to the product categories of Phosphines; Ligand; Phosphine Ligands; Synthetic Organic Chemistry; Organophosphine ligand. Its EINECS registry number is 216-769-2. This chemical's molecular formula is C26H24P2 and molecular weight is 398.42. What's more, its IUPAC name is called 2-Diphenylphosphanylethyl(diphenyl)phosphane. This chemical is a commonly used in coordination chemistry. It is almost invariably chelated, although there are examples of unidentate and of bridging behavior. It is a metal organic catalyst widely used in organic synthesis.

Physical properties about 1,2-Bis(diphenylphosphino)ethane are: (1)ACD/LogP: 6.851; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 6.85; (4)ACD/LogD (pH 7.4): 6.85; (5)ACD/BCF (pH 5.5): 94718.27; (6)ACD/BCF (pH 7.4): 94718.27; (7)ACD/KOC (pH 5.5): 126972.80; (8)ACD/KOC (pH 7.4): 126972.80; (9)#H bond acceptors: 0; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 7; (12)Polar Surface Area: 27.18 Å2; (13)Flash Point: 281.728 °C; (14)Enthalpy of Vaporization: 75.685 kJ/mol; (15)Boiling Point: 514.815 °C at 760 mmHg; (16)Vapour Pressure: 0 mmHg at 25 °C.

Preparation of 1,2-Bis(diphenylphosphino)ethane: this chemical can be prepared by diphenylphosphinous acid chloride with 1,2-dichloro-ethane. This reaction needs reagents Bu4NI, Bu4NBF4, NMP at ambient temperature. The yield is 65 %.

1,2-Bis(diphenylphosphino)ethane can be prepared by diphenylphosphinous acid chloride with 1,2-dichloro-ethane.

Uses of 1,2-Bis(diphenylphosphino)ethane: it is used to produce other chemicals. For example, it can react with 3-bromo-propene to get 1,2-ethanediylbis(allyldiphenylphosphonium) dibromide. The reaction occurs with reagent benzene and other condition of heating for 24 hours. The yield is 70 %.

1,2-Bis(diphenylphosphino)ethane can react with 3-bromo-propene to get 1,2-ethanediylbis(allyldiphenylphosphonium) dibromide.

When you are dealing with this chemical, you should be very careful. This chemical is inflammation to the skin, eyes and respiratory system or other mucous membranes. Therefore, you should wear suitable protective clothing, gloves and eye/face protection. And you must avoid contacting with skin and eyes. In case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1) SMILES: c1ccc(cc1)P(CCP(c2ccccc2)c3ccccc3)c4ccccc4
(2) InChI: InChI=1S/C26H24P2/c1-5-13-23(14-6-1)27(24-15-7-2-8-16-24)21-22-28(25-17-9-3-10-18-25)26-19-11-4-12-20-26/h1-20H,21-22H2
(3) InChIKey: QFMZQPDHXULLKC-UHFFFAOYSA-N

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