1,4-Bis(diphenylphosphino)butane

Base Information

• Chemical Name: 1,4-Bis(diphenylphosphino)butane
• CAS No.: 7688-25-7
• Molecular Formula: C28H28P2
• Molecular Weight: 426.478
• Hs Code.: 29319090
• European Community (EC) Number: 231-698-7
• UNII: 35HP6LTD2D
• DSSTox Substance ID: DTXSID4064769
• Nikkaji Number: J133.188D
• Wikipedia: 1,4-Bis(diphenylphosphino)butane
• Wikidata: Q27256466
• ChEMBL ID: CHEMBL71648
• Mol file: 7688-25-7.mol

Synonyms:1,4-Bis(diphenylphosphino)butane;7688-25-7;dppb;Phosphine, 1,4-butanediylbis[diphenyl-;4-diphenylphosphanylbutyl(diphenyl)phosphane;MFCD00003051;1,4-Bis(diphenylphosphino)butane (DPPB);Tetramethylenebis(diphenylphosphine);[4-(diphenylphosphanyl)butyl]diphenylphosphane;C28H28P2;UNII-35HP6LTD2D;35HP6LTD2D;1,4-BUTYLENEBIS(DIPHENYLPHOSPHINE);1,4-bis-(diphenylphosphino)butane;EINECS 231-698-7;Phosphine, 1,1'-(1,4-butanediyl)bis(1,1-diphenyl-;Butane-1,4-diylbis(diphenylphosphine);Phosphine, 1,4-butanediylbis(diphenyl-;1,4-BUTANEDIYLBIS[DIPHENYLPHOSPHINE];1,4-BUTANEDIYLBIS(DIPHENYLPHOSPHINE);BUTANE-1,4-DIYLBIS[DIPHENYLPHOSPHINE];1,4-Bis(diphenylphosphino)butane, 98%;DPPB [MI];4-di(phenyl)phosphanylbutyl-di(phenyl)phosphane;SCHEMBL29179;CHEMBL71648;1,4-bisdiphenylphosphinobutane;1,4-bis(diphenylphospino)butane;DTXSID4064769;BCJVBDBJSMFBRW-UHFFFAOYSA-;Bis(1,4-diphenylphosphino)butane;1,4-bis(di-phenylphosphino)butane;1,4-bis(diphenyl phosphino)butane;1,4-Bis(diphenyl-phosphino)butane;AMY39344;BCP22582;1,4-bis-(diphenylphosphino) butane;1,4-bis-(diphenylphosphino)-butane;butane, 1,4-bis(diphenylphosphino)-;Phosphine, tetramethylenebis[diphenyl-;AKOS004908986;AC-4222;C28-H28-P2;CS-W007569;FD14029;GC10108;GS-3096;1,4-BIS(DIPHENYLPHOSPHINE)BUTANE;BP-10035;SY009758;B1246;FT-0606800;EN300-108128;[4-(Diphenylphosphino)butyl](diphenyl)phosphine #;W-104340;Q27256466

Chemical Property of 1,4-Bis(diphenylphosphino)butane

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 2.92E-11mmHg at 25°C
• Melting Point: 132-136 °C(lit.)
• Boiling Point: 542 °C at 760 mmHg
• Flash Point: 299.5 °C
• PSA: 27.18000
• LogP: 6.03240
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility.: Soluble in chloroform. Slightly soluble in water
• XLogP3: 6.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 9
• Exact Mass: 426.16662489
• Heavy Atom Count: 30
• Complexity: 362

Purity/Quality:

99% ^*data from raw suppliers

1,4-Bis(diphenylphosphino)butane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,F
• Hazard Codes: Xi,F
• Statements: 36/38-36/37/38-11
• Safety Statements: 26-36-37/39-33-16-7/9

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Phosphorus Compounds
• Canonical SMILES: C1=CC=C(C=C1)P(CCCCP(C2=CC=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4
• General Description: 1,4-Bis(diphenylphosphino)butane (dppb) is a bidentate diphosphine ligand commonly used in rhodium-catalyzed reactions, such as hydrothiolation, where it contributes to high Z-selectivity and enantioselectivity. Its flexible butane backbone allows for adaptable coordination geometry, making it effective in forming stable metal complexes for catalytic applications, including dynamic kinetic resolution and the synthesis of bioactive molecules.

Technology Process of 1,4-Bis(diphenylphosphino)butane

There total 18 articles about 1,4-Bis(diphenylphosphino)butane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

1,4-bis(diphenylphosphinyl)butane (4151-27-3) → 1,4-di(diphenylphosphino)-butane (7688-25-7)

Guidance literature:

With 1,1,3,3-Tetramethyldisiloxane; titanium(IV) isopropylate; In various solvent(s); at 100 ℃; for 7h;

DOI:10.1055/s-2007-982536

Reference yield: 94.0%

1,4-bis(diphenylphosphinyl)butan-1-one → 1,4-di(diphenylphosphino)-butane (7688-25-7)

Guidance literature:

With tetramethyldisilazane; isopropyl titanoate(IV); In methyl cyclohexane; at 60 ℃;

Reference yield: 87.0%

1,4-dibromo-butane (110-52-1) + diphenylphosphane (829-85-6) → 1,4-di(diphenylphosphino)-butane (7688-25-7)

Guidance literature:

With cesium hydroxide; 4 Angstroem MS; In N,N-dimethyl-formamide; at 23 ℃; for 47h;

DOI:10.1016/j.tetlet.2003.09.117

upstream raw materials:

tetrachlorure d'octaphenyl-1,1,4,4,9,9,12,12 tetraphosphonia-1,4,9,12 cyclohexadecane

1,4-dibromo-butane

chloro-diphenylphosphine

1,4-dichlorobutane

Downstream raw materials:

4,4,9,9-tetraphenyl-4,9-diphosphonia-dodecadioic acid dichloride

C₂₂H₂₃P₂^(1-)*Li⁽¹⁺⁾

1,4-bis(dicyclohexylphosphino)butane

phenyllithium

Refernces

New rhodium(I) supramolecular structures containing pyridyl and bipyridyl ligands

10.1016/j.jorganchem.2009.08.014

The research explores the self-assembly of rhodium(I) metallosupramolecular structures using [RhCl(CO)2]2 as an acceptor unit. Key chemicals involved in the research include [RhCl(CO)2]2, alkynylgold complex [Au(C?CC5H4N)(CNC6H4O(O)CC6H4OC10H21)], 4-ethynylpyridine, 4,4'-bipyridine, and diphosphines such as 1,4-bis(diphenylphosphino)butane (dppb) and 1,1-bis-(diphenylphosphino)methane (dppm). The study investigates the formation of various rhodium complexes through reactions with these chemicals, resulting in the creation of mono-, bi-, and three-dimensional structures. Notably, an unexpected isonitrile transfer from gold to rhodium centers was observed, and the influence of diphosphine bite angles on the final product structures was demonstrated. The research also includes the use of PM3 semi-empirical methods to optimize the geometry of the synthesized compounds, particularly focusing on the potential applications of these structures in catalysis and molecular recognition.

Z-Selective Hydrothiolation of Racemic 1,3-Disubstituted Allenes: An Atom-Economic Rhodium-Catalyzed Dynamic Kinetic Resolution

10.1002/anie.201507623

The research explores a novel rhodium-catalyzed hydrothiolation process for 1,3-disubstituted allenes, aiming to develop an atom-economic and highly selective method for synthesizing Z-allylic sulfones. The study utilizes bidentate ligands such as 1,4-bis(diphenylphosphino)butane (dppb) and (S,S)-Me-DuPhos to achieve high Z-selectivity and enantioselectivity in the presence of various aromatic and aliphatic thiols. The purpose is to create a versatile synthetic pathway for producing bioactive compounds containing α-stereogenic C–S bonds, which are important in pharmaceuticals. The method demonstrated excellent Z/E-selectivities up to >99:1 and enantioselectivities up to 96% ee, tolerating a wide range of functionalized thiols and allene substrates. The research concludes that this rhodium-catalyzed hydrothiolation is a powerful and efficient approach for the synthesis of Z-allylic sulfones, with potential applications in the synthesis of complex bioactive molecules.