(4-Carboxybutyl)triphenylphosphonium bromide

Base Information

• Chemical Name: (4-Carboxybutyl)triphenylphosphonium bromide
• CAS No.: 17814-85-6
• Molecular Formula: C23H24O2P^.Br
• Molecular Weight: 443.32
• Hs Code.: 29310095
• European Community (EC) Number: 241-782-5
• NSC Number: 147756
• UNII: U574RP8CHR
• DSSTox Substance ID: DTXSID6057669
• ChEMBL ID: CHEMBL3250674
• Mol file: 17814-85-6.mol

Synonyms:(4-Carboxybutyl)triphenylphosphonium bromide;17814-85-6;Phosphonium, (4-carboxybutyl)triphenyl-, bromide;4-Carboxybutyl triphenylphosphonium bromide;NSC 147756;4-carboxybutyl(triphenyl)phosphanium;bromide;MFCD00011906;DTXSID6057669;EINECS 241-782-5;NSC-147756;Phosphonium, (4-carboxybutyl)triphenyl-, bromide (1:1);CARBOXYBUTYLTRIPHENYLPHOSPHONIUM BROMIDE;4-(Carboxybutyl)triphenylphosphonium Bromide;5-(TRIPHENYLPHOSPHONIO)PENTANOIC ACID BROMIDE;NSC147756;(4-carboxybutyl)triphenylphosphanium bromide;(4-Carboxybutyl)triphenylphosphoniumBromide;4-carboxybutyl(triphenyl)phosphanium,bromide;(4-carboxybutyl)-triphenylphosphonium bromide;U574RP8CHR;(4-Carboxy-butyl)-triphenyl-phosphonium;C23H24O2P.Br;TRIPHENYL(4-CARBOXYBUTYL)PHOSPHONIUM BROMIDE;SCHEMBL163452;CHEMBL3250674;DTXCID7031458;AMY39331;BCP04324;CS-B1768;Tox21_113895;AKOS015888431;GC10172;NCGC00261975-01;AC-29279;AS-15678;SY036108;4-carboxybutyl-triphenylphosphonium bromide;4-carboxybutyl-triphenylphosphonium-bromide;4-carboxybutyltriphenyl phosphonium bromide;4-carboxybutyltriphenyl-phosphonium bromide;4-carboxybutyl-triphenyl-phosphonium bromide;CAS-17814-85-6;(4-carboxybutyl) triphenylphosphonium bromide;(4-carboxybutyl)triphenyl phosphonium bromide;(4-carboxybutyl)triphenyl-phosphonium bromide;FT-0617958;FT-0617959;triphenyl (4-carboxybutyl)phosphonium bromide;triphenyl-(4-carboxybutyl)-phosphonium bromide;(4-carboxy butyl) triphenyl phosphonium bromide;(4-Carboxy-butyl)-triphenyl-phosphonium bromide;F10042;EN300-7386259;4-hydroxycarbonylbutyl-triphenylphosphonium bromide;A812343;J-501381;(4-CARBOXYBUTYL)TRIPHENYLPHOSPHANIUM BROMIDE;(4-CARBOXYBUTYL)TRIPHENYLPHOSPHONIUM BROMIDE;PHOSPHONIUM,(4-CARBOXYBUTYL)TRIPHENYL-BROMIDE

Chemical Property of (4-Carboxybutyl)triphenylphosphonium bromide

Chemical Property:

• Appearance/Colour: white to almost white crystalline powder
• Vapor Pressure: 0Pa at 25℃
• Melting Point: 204-207 °C(lit.)
• Boiling Point: 324.7-327.4℃ at 101.93-102.15kPa
• Flash Point: 195°(383°F)
• PSA: 50.89000
• Density: 1.371 at 20℃
• LogP: 1.23940
• Storage Temp.: Refrigerator
• Sensitive.: Hygroscopic
• Solubility.: DMSO, Methanol, Water
• Water Solubility.: Soluble in ethanol, methanol and soluble water. Insoluble in toluene and hexane.
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 8
• Exact Mass: 442.06973
• Heavy Atom Count: 27
• Complexity: 372

Purity/Quality:

98% ^*data from raw suppliers

(4-Carboxybutyl)triphenylphosphonium bromide ^*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+](CCCCC(=O)O)(C2=CC=CC=C2)C3=CC=CC=C3.[Br-]
• Uses: suzuki reaction (4-Carboxybutyl)triphenylphosphonium Bromide (cas# 17814-85-6) is a compound useful in organic synthesis. Used as a platform for delivery of pro-apoptotic peptides into the mitochondria of tumor cellsReactant for preparation of:Ring skeletons via ring closing metathesis and double bond migration ring closing metathesis reactionsMethyl alkenyl quinolones as antimycobacterial agentsProstaglandins and their drug analogs via Gold-catalyzed Meyer-Schuster rearrangementDiphenylmethylpiperazines as N-type calcium channel blockers as potential therapeutic agentsFolate receptor-specific glycinamide ribonucleotide formyltransferase (GARFTase) inhibitors with antitumor activityCycloalkylidene alkanols with antileishmanial activity, via Wittig reaction

Technology Process of (4-Carboxybutyl)triphenylphosphonium bromide

There total 14 articles about (4-Carboxybutyl)triphenylphosphonium bromide 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: 96.0%

5-bromopentanoic acid (2067-33-6) + triphenylphosphine (603-35-0) → (4-carboxybutyl)triphenylphosphonium bromide (17814-85-6)

Guidance literature:

In acetonitrile; at 80 ℃; for 24h;

DOI:10.1021/jo982393e

Reference yield: 87.0%

→ (4-carboxybutyl)triphenylphosphonium bromide (17814-85-6)

Guidance literature:

Reference yield:

3,4,5,6-tetrahydro-2H-pyran-2-one (542-28-9,26354-94-9) + triphenylphosphine hydrobromide (6399-81-1) → (4-carboxybutyl)triphenylphosphonium bromide (17814-85-6)

Guidance literature:

at 170 - 180 ℃;

upstream raw materials:

3,4,5,6-tetrahydro-2H-pyran-2-one

triphenylphosphine hydrobromide

5-bromopentanoic acid

triphenylphosphine

Downstream raw materials:

(Z)-methyl 6-(4-(2-aminoethyl)phenyl)-6-(3-pyridyl)hex-5-enoate

6,6-diphenyl hex-5-enoic acid

Triphenylphosphine oxide

Refernces

• 1、 Ye, Yaqing,Zhang, Tao,Yuan, Huiqing,Li, Defeng,Lou, Hongxiang,Fan, Peihong. "Mitochondria-Targeted Lupane Triterpenoid Derivatives and Their Selective Apoptosis-Inducing Anticancer Mechanisms". . p. 6353 - 6363. Retrieved 2017.
• 2、 Bergman, Nils-Ake,Jansson, Marie,Chiang, Yvonne,Kresge, A. Jerry,Yin, Ya. "Synthesis and Kinetic Studies of a Simple Prostacyclin Model". . p. 4449 - 4453. Retrieved 1987.
• 3、 Hamri, Salha,Jouha, Jabrane,Oumessaoud, Asmaa,Pujol,Khouili, Mostafa,Guillaumet, Gérald. "Convenient approach for the synthesis of ONO-LB-457, a potent leukotriene B4 receptor antagonist". . . Retrieved 2020/12/07.
• 4、 -. "A mitochondrial targeting of the nano drug delivery system and its preparation method and application". Paragraph 0046; 0062-0063. . Retrieved 2019/04/18.