143251-93-8

Basic information

• Product Name: [ethane-1,2-diylbis(oxyethane-2,1-diyl)]bis[tribenzylphosphonium] dibromide
• Synonyms: [ethane-1,2-diylbis(oxyethane-2,1-diyl)]bis[tribenzylphosphonium] dibromide
• CAS NO: 143251-93-8
• Molecular Weight: 884.711
• Mol File: 143251-93-8.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: [ethane-1,2-diylbis(oxyethane-2,1-diyl)]bis[tribenzylphosphonium] dibromide(CAS DataBase Reference)
• NIST Chemistry Reference: [ethane-1,2-diylbis(oxyethane-2,1-diyl)]bis[tribenzylphosphonium] dibromide(143251-93-8)
• EPA Substance Registry System: [ethane-1,2-diylbis(oxyethane-2,1-diyl)]bis[tribenzylphosphonium] dibromide(143251-93-8)

Safety Data

• Hazardous Substances Data: 143251-93-8(Hazardous Substances Data)

Upstream product

• 31255-10-4 1,2-bis-(2-bromo-ethoxy)-ethane 
• 7650-89-7 tribenzylphosphine 

Downstream Products

• 70641-75-7 P,P'-Dibenzyl-<18>-1,4,10,13-tetraoxa-7,16-diphosphino-kronenether 
• 143251-95-0 7,7,16,16-Tetrabenzyl-<18>-1,4,10,13-tetraoxa-7,16-diphosphoniumdibromid-kronenether 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 470454-02-5 [ethane-1,2-diylbis(oxyethane-2,1-diyl)]bis[dibenzylphosphin] dioxide 
• 143251-94-9 [ethane-1,2-diylbis(oxyethane-2,1-diyl)]bis[dibenzylphosphine] 

Relevant articles and documents

Diphosphapodands, [12]-, [15]-, and [18] diphosphacoronands, diphosphacryptand-8, and alkali-metal complexes

The cyclizing bis-phosphonium-salt formation of the open-chain bis-phosphine 17a (1,1,7,7-tetrabenzyl〈P.O.P-podand-7〉) with diethylene glycol derived dibromide 13a yields the 12-membered cyclic bis-phosphonium salt 20 (4,4,10,10-tetrabenzyl-12〈O.P.O.P-coronand-4〉-4,10-diium dibromide) in yields as high as 50-60%. The 1,1,10,10-tetrabenzyl〈P.O2.P-podand-10〉 17b forms with 13a the 15-membered cyclic bis-phosphonium salt 21 (7,7,13,13-tetrabenzyl-15〈O2.P.O.P-coronand-5〉-7, 13-diium dibromide) with the same high yield. By quaternization of the bis-phosphine 17b with triethylene glycol derived dibromide 13b, the 18-membered 7,7,16,16- tetrabenzyl-18〈O2.P.O2.P-coronand-6〉-7, 16-diium dibromide 24 is obtained in 50% yield, too. The Wittig reaction of the cyclic phosphonium salts with benzaldehyde yields the 12-, 15-, and 18-membered cyclic bisbenzylphosphine dioxides 9, 10, and 11 as cis- and trans-isomers beside trans-stilbene. The 7,13-dioxido-7,13dibenzyl-15〈O2.P.O2. P-coronand-5〉 10 forms a crystalline 1:1 Na-complex 23, which exists as a dimer. The structure of 23 was established by an X-ray analysis and spectroscopic data. The 7,16-dibenzyl-18〈O2.P.O2.Pcoronand-6〉 28 that is available by reduction of 11 with CeCl3/LiAlH4 reacts with triethylene glycol derived dibromide 13b under Ruggly-Ziegler8-dilution conditions to give the bicyclic bis-phosphonium salt 29 (1,10- dibenzyl 〈P[O2]3.P-cryptand-8〉-1,10-diium dibromide) in 18% yield. Again, by the Wittig procedure with benzaldehyde, the 7,16-dioxido〈P[O2]3P-cryptand-8〉 12 is obtained as the first diphosphacryptand. The FD-MS (CH2Cl2) of the cyclic bis-phosphine dioxides 10-12 show that they exist as [2M+Na]+ complexes. The complex formation constants Ka of 9-11 with alkali-metal cations are studied and compared with the complex formation of corresponding crown ethers.