ChemicalBook > CAS DataBase List > 1,2-Bis(diphenylphosphino)ethane

1,2-Bis(diphenylphosphino)ethane

Product Name: 1,2-Bis(diphenylphosphino)ethane
CAS No.: 1663-45-2
Chemical Name: 1,2-Bis(diphenylphosphino)ethane
Synonyms: DIPHOS;BIS(DIPHENYLPHOSPHINO)ETHANE;1,2-Bis(diphenylphos;1,2-Bis(diphenylphosphono)ethane;1,2-BIS(DIPHENYLPHOSPHINE)ETHANE;98% DPPE;DIPHOS OR DPPE;1,2-()(DPPE) 98%;bis(diphenylphosphine)ethane;1,2-Bis(diphenylphosphino)etha
CBNumber: CB7138139
Molecular Formula: C26H24P2
Formula Weight: 398.42
MOL File: 1663-45-2.mol

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1,2-Bis(diphenylphosphino)ethane Property

Melting point:: 137-142 °C (lit.)
Boiling point:: 514.8±33.0 °C(Predicted)
storage temp.: Inert atmosphere,Room Temperature
solubility: Soluble in acetone, methanol and alcoholic hydrochloric acid.
form: Crystalline Powder or Crystals
color: White to off-white
Sensitive: Air Sensitive
BRN: 761261
Stability:: Stable. Combustible. Incompatible with strong oxidizing agents. May be air-sensitive.
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
InChIKey: QFMZQPDHXULLKC-UHFFFAOYSA-N
SMILES: C1C=CC=CC=1P(CCP(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1
CAS DataBase Reference: 1663-45-2(CAS DataBase Reference)
NIST Chemistry Reference: Phosphine, 1,2-ethanediylbis[diphenyl-(1663-45-2)
EPA Substance Registry System: Phosphine, 1,2-ethanediylbis[diphenyl- (1663-45-2)

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Safety

Hazard Codes: Xi
Risk Statements: 36/37/38
Safety Statements: 22-24/25-37/39-26-36
WGK Germany: 3
F: 9
TSCA: Yes
HS Code: 29310095

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P271Use only outdoors or in a well-ventilated area.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 106496
Product name: Ethylenebis(diphenylphosphine)
Purity: 97%
Packaging: 10g
Price: $62.37
Updated: 2025/07/31

Sigma-Aldrich

Product number: 106496
Product name: Ethylenebis(diphenylphosphine)
Purity: 97%
Packaging: 50g
Price: $324
Updated: 2025/07/31

TCI Chemical

Product number: B1137
Product name: 1,2-Bis(diphenylphosphino)ethane
Purity: >97.0%(GC)(T)
Packaging: 10g
Price: $40
Updated: 2025/07/31

TCI Chemical

Product number: B1137
Product name: 1,2-Bis(diphenylphosphino)ethane
Purity: >97.0%(GC)(T)
Packaging: 25g
Price: $78
Updated: 2025/07/31

Strem Chemicals

Product number: 15-0200
Product name: 1,2-Bis(diphenylphosphino)ethane, 99% DIPHOS
Packaging: 5g
Price: $40
Updated: 2024/03/01

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1,2-Bis(diphenylphosphino)ethane Chemical Properties,Usage,Production

Chemical Properties

white to light yellow crystal powde

Uses

suzuki reaction

Uses

1,2-Bis(diphenylphosphino)ethane is a bidendate ligand used in coordination chemistry to prepare metal complexes. It is involved in the metal-catalyzed allylic alkylation and decarboxylation of allylic esters. It is also used in 1,3-diene synthesis. Further, it is used in cycloaddition reactions and carbonylation reactions. In addition to this, it is used to prepare bis(dicyclohexylphosphino)ethane by hydrogenation.

Definition

ChEBI: 1,2-bis(diphenylphosphino)ethane is a tertiary phosphine and a member of diphosphanes. It has a role as an allergen.

reaction suitability

reagent type: ligand
reaction type: C-C Bond Formation
reagent type: ligand
reaction type: Carbonylations
reagent type: ligand
reaction type: Cycloadditions
reagent type: ligand
reaction type: Decarboxylations
reagent type: ligand
reaction type: Diels-Alder Reaction
reagent type: ligand
reaction type: Heck Reaction
reagent type: ligand
reaction type: Negishi Coupling
reagent type: ligand
reaction type: Suzuki-Miyaura Coupling

Mechanism of action

1,2-Bis(diphenylphosphino)ethane (DPPE) and its synthetic analogues are important structural motifs in organic synthesis, particularly as diphosphine ligands with a C2-alkyl-linker chain. Since DPPE is known to bind to many metal centers in a bidentate fashion to stabilize the corresponding metal complex via the chelation effect originating from its entropic advantage over monodentate ligands, it is often used in transition-metal-catalyzed transformations.

Synthesis

Several synthetic methods to produce 1,2-Bis(diphenylphosphino)ethane (DPPE) exist; however, most of these methods are limited to substitution reactions of highly reactive alkali metal diphenylphosphides (e.g., Ph2PM; M = Li or Cs) with 1,2-dihaloethanes (X−CH2−CH2−X; X = Cl, Br, and I) in an SN2 fashion (Eq. 1). Moreover, there are a few methods using the alkoxide-base (KOt-Bu)-catalyzed hydrophosphination of vinyl phosphines (Eq. 2) with diphenylphosphines9 or the dihydrophosphination of acetylene gas (Eq. 3). [1]

Purification Methods

Recrystallise it from aqueous EtOH or *C6H6. The dimethiodide, when recrystallised from MeOH has m 305-307o, and the dioxide when recrystallised from toluene or DMF (needles), or *C6H6 (plates) has m 252-254o (276-278o) [Isslieb et al. Chem Ber 92 3175 1959, NMR: Aquiar et al. J Org Chem 29 1660 1964, B.ckvall et al. J Org Chem 52 5430 1987]. [Beilstein 16 IV 958.]

References

[1] Takano, H., Katsuyama, H., Hayashi, H. et al. A theory-driven synthesis of symmetric and unsymmetric 1,2-bis(diphenylphosphino)ethane analogues via radical difunctionalization of ethylene. Nat Commun 13, 7034 (2022).

1,2-Bis(diphenylphosphino)ethane Preparation Products And Raw materials

Raw materials

Diphenylphosphine Ethanol Acetone Sodium 1,2-Dibromoethane Tetrahydrofuran Ethyl acetate 1,2-Dichloroethane Hydrochloric acid Dichloromethane Sodium hydroxide Triphenylphosphine Magnesium sulfate PETROLEUM ETHER Lithium n-Butyllithium

Preparation Products

Bis(diphenylphosphino)methane (R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl 1.1'-Binaphthyl-2.2'-diphemyl phosphine

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View Lastest Price from 1,2-Bis(diphenylphosphino)ethane manufacturers

Hebei Chuanghai Biotechnology Co., Ltd

Product: 1,2-Bis(diphenylphosphino)ethane 1663-45-2
Price: US $0.00-0.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 500000kg
Release date: 2024-10-31

Henan Aochuang Chemical Co.,Ltd.

Product: 1,2-Bis(diphenylphosphino)ethane 1663-45-2
Price: US $0.00-0.00/kg
Min. Order: 1kg
Purity: 98%
Supply Ability: 1Ton
Release date: 2022-10-19

Hebei Yanxi Chemical Co., Ltd.

Product: 1,2-Bis(diphenylphosphino)ethane 1663-45-2
Price: US $20.00-7.00/kg
Min. Order: 1kg
Purity: 0.99
Supply Ability: 10 tons
Release date: 2023-10-10

1663-45-2, 1,2-Bis(diphenylphosphino)ethaneRelated Search:

Hexafluoroethane ETHANE 3,4'-DIAMINODIPHENYLMETHANE 1,5-Diphenylcarbazide N-(Carboxymethyl)-N-(phosphonomethyl)-glycine 4,4'-DDT Chlorodiphenylphosphine 1,1'-Bis(diphenylphosphino)ferrocene 1,3-Bis(diphenylphosphino)propane Bis(diphenylphosphino)methane [1,2-Bis(diphenyphosphino)ethane]dichlorocobalt(II) 1,2,3,4-DIEPOXYBUTANE [1,2-Bis(diphenyphosphino)ethane]dichloroiron(II) R-(+)-1,2-BIS(DIPHENYLPHOSPHINO)PROPANE (2R,3R)-(+)-BIS(DIPHENYLPHOSPHINO)BUTANE (2S,3S)-(-)-BIS(DIPHENYLPHOSPHINO)BUTANE ETHYLENEBIS(TRIPHENYLPHOSPHONIUM BROMIDE) (2R,3R)-(-)-2,3-BIS(DIPHENYLPHOSPHINO)BICYCLO[2.2.1]HEPT-5-ENE

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1,2-Bis(diphenylphosphino)ethane,98% DPPE

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1,2-Bis(diphenylphosphino)-ethane for synthesis

[2-(Diphenylphosphino)ethyl](diphenyl)phosphine

1,2-Ethanediylbis(diphenylphosphine)

1,2-ethanediylbis[diphenyl-phosphin

bis(diphenylphosphine)ethane

P,P'-Ethylenebis(diphenylphosphine)

Phosphine, 1,2-ethanediylbis*diphenyl-

Phosphine, ethylenebis*diphenyl-

Phosphine, ethylenebis[diphenyl-

1,2-BIS(DIPHENYLPHOSPHINO)ETHANE

1,2-BIS(DIPHENYLPHOSPHINE)ETHANE

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DIPHOS

BIS(1,2-DIPHENYLPHOSPHINO)ETHANE

BIS(DIPHENYLPHOSPHINO)ETHANE

1,2-Bis(Diphenylphosphor) Ethane

1,2-Bis(diphenylphosphino)ethane(dppe)

1,2-Bis(diphenylphosphino)ethane, 98+%

1,2-bis(diphenyphosphino)ethane

1,2-Bis(diphenylphosphino)ethane,99%DIPHOS

DPPE/ 1,2-BIS(DIPHENY PHOSPHINE)ETHANE

DPPE/1,2-BIS- (DIPHENYLPHOSPHINO)ETHANE

1,2-Bis(dipheny phosphine)ethane

1,2-Bis(diphenylphosphino)ethane, 97+%

1,2-()(DPPE) 98%

DIPHOS OR DPPE

1,2-Bis(diphenylphosphino)ethane, Diphos

2-Di(phenyl)phosphanylethyl-di(phenyl)phosphane

1,2-Bis(diphenylphosphino) ethane,99% Dipltos

1,2-Bis(diphenylphosphino)ethane &gt

1,2-Bis(diphenylphosphino)ethane, 98%, for synthesis

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1,2- bis(diphenylphosphaneyl)ethane (DPPE)

TIANFUCHEM--1663-45-2--2-Aminobenzaldehyde factory price

DPPE (1,2-Bis(Diphenylphosphino)Ethane) extrapure, 98%

1,2-Bis(diphenylphosphanyl)ethane

Ethylenebis(diphenylphosphine), 98%

1,2-Bis(diphenylphosphosphone)ethane

1663-45-2

C6H52PCH2CH2PC6H52

C26H24P2

Catalysis and Inorganic Chemistry

Polydentate Phosphine Ligands

Phosphorus Compounds

Phosphine Ligands

Ligand