Tetramethylenebis(triphenylphosphonium) dibromide

Base Information

• Chemical Name: Tetramethylenebis(triphenylphosphonium) dibromide
• CAS No.: 15546-42-6
• Molecular Formula: C40H38Br2P2
• Molecular Weight: 740.497
• European Community (EC) Number: 239-598-5
• DSSTox Substance ID: DTXSID10935218
• Mol file: 15546-42-6.mol

Synonyms:15546-42-6;Tetramethylenebis(triphenylphosphonium bromide);Tetramethylenebis(triphenylphosphonium) dibromide;680579-51-5;1,4-Bis(triphenylphosphonio)butane dibromide;Butane-1,4-diylbis(triphenylphosphonium) bromide;EINECS 239-598-5;triphenyl(4-triphenylphosphaniumylbutyl)phosphanium;dibromide;Tetramethylenebis(triphenylphosphonium bromide;Tetramethylenebis[triphenylphosphonium] dibromide;SCHEMBL2446042;C40H38P2.2Br;DTXSID10935218;WTFXVDWCEPLDDY-UHFFFAOYSA-L;C40-H38-P2.2Br;MFCD00031714;AKOS017345148;FT-0637242;Butane-1,4-diylbis(triphenylphosphonium)bromide;(Butane-1,4-diyl)bis(triphenylphosphanium) dibromide;Phosphonium,1,1'-(1,4-butanediyl)bis[1,1,1-triphenyl-,bromide(1:2)

Chemical Property of Tetramethylenebis(triphenylphosphonium) dibromide

Chemical Property:

• Melting Point: 292-293 °C
• PSA: 27.18000
• LogP: 1.76280
• Sensitive.: Hygroscopic
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 11
• Exact Mass: 740.07950
• Heavy Atom Count: 44
• Complexity: 585

Purity/Quality:

99% ^*data from raw suppliers

TETRAMETHYLENEBIS(TRIPHENYLPHOSPHONIUM BROMIDE) 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)[P+](CCCC[P+](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6.[Br-].[Br-]
• Uses: Tetramethylenebis(triphenylphosphonium Bromide) is a key intermediate in the one-step synthesis of ocimin by a bis-Wittig reaction.

Technology Process of Tetramethylenebis(triphenylphosphonium) dibromide

There total 6 articles about Tetramethylenebis(triphenylphosphonium) dibromide 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-dibromo-butane (110-52-1) + triphenylphosphine (603-35-0) → [1,1'-(butane-1,4-diyl)bis(triphenylphosphonium)] dibromide (15546-42-6)

Guidance literature:

In methanol; for 24h; Reflux;

DOI:10.1016/j.poly.2010.08.010

Reference yield: 85.2%

→ [1,1'-(butane-1,4-diyl)bis(triphenylphosphonium)] dibromide (15546-42-6)

Guidance literature:

Reference yield:

triphenylphosphine (603-35-0) + succinic acid diethyl ester (123-25-1) → [1,1'-(butane-1,4-diyl)bis(triphenylphosphonium)] dibromide (15546-42-6)

Guidance literature:

With lithium aluminium tetrahydride; sulfuric acid; hydrogen bromide; Yield given. Multistep reaction; 1.) THF, 0 deg C, then reflux, 3 h ; 3 M H₂SO₄ added, reflux overnight, 2.) solvent evaporated, reflux, 6 h, 3.) 190 deg C, 10 min, then 230 deg C, 30 min ; double ⁽¹³⁾C labelling;

DOI:10.1016/S0040-4020(01)87607-9

upstream raw materials:

1,4-dibromo-butane

triphenylphosphine

4-bromobutylphosphonium bromide

tetrahydrofuran

Downstream raw materials:

(4-diphenylphosphinoyl-butyl)-triphenyl-phosphonium; bromide

1,5,9-cyclododecatriene

1,4-bis(triphenylphosphorylidene)butane

1,6-bis-(p-methoxyphenyl)-1,5-(E),(E)-hexadiene

Refernces

• 1、 Delaram, Behnaz,Gholizadeh, Mostafa,Makari, Faezeh,Nokhbeh, Seyed Reza,Salimi, Alireza. "Synthesis, crystal and structural characterization, Hirshfeld surface analysis and DFT calculations of three symmetrical and asymmetrical phosphonium salts". . . Retrieved 2021/07/01.
• 2、 Amirova, Lyaysan R.,Burilov, Alexander R.,Amirova, Liliya M.,Bauer, Ingmar,Habicher, Wolf D.. "Kinetics and mechanistic investigation of epoxy-anhydride compositions cured with quaternary phosphonium salts as accelerators". . p. 1088 - 1097. Retrieved 2016/03/12.