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- (3-Bromopropyl)triphenylphosphonium bromide
(3-Bromopropyl)triphenylphosphonium bromide
Catalog Number
ACM3607178
Product Name
(3-Bromopropyl)triphenylphosphonium bromide
Structure
![{[CurrentData.Name]}](https://resource.alfachemic.com/structure/3607-17-8.gif)
CAS
3607-17-8
Synonyms
I01-9357; 3-bromopropyl(triphenyl)phosphonium bromide; NSC84074; MFCD00011866; (3-Bromo-propyl)-triphenyl-phosphonium bromide; 3-(Bromopropyl)triphenylphosphonium; EINECS 222-770-9; Bromo(3-bromopropyl)triphenylphosphorus; FT-0604703; Acm³607178;
IUPAC Name
3-bromopropyl(triphenyl)phosphanium;bromide
Molecular Weight
464.18
Molecular Formula
C21H21Br2P
Canonical SMILES
C1=CC=C(C=C1)[P+](CCCBr)(C2=CC=CC=C2)C3=CC=CC=C3.[Br-];
InChI
ZAHUZZUGJRPGKW-UHFFFAOYSA-M
InChI Key
InChI=1S/C21H21BrP.BrH/c22-17-10-18-23(19-11-4-1-5-12-19,20-13-6-2-7-14-20)21-15-8-3-9-16-21;/h1-9,11-16H,10,17-18H2;1H/q+1;/p-1
Melting Point
228-230 °C(lit.)
Purity
98%
Appearance
Solid
Storage
Store below +30°C.
Complexity
279
Covalently-Bonded Unit Count
2
EC Number
222-770-9
Exact Mass
463.973g/mol
H-Bond Acceptor
1
Heavy Atom Count
24
Isomeric SMILES
C1=CC=C(C=C1)[P+](CCCBr)(C2=CC=CC=C2)C3=CC=CC=C3.[Br-]
Monoisotopic Mass
461.975g/mol
NSC Number
84074
Rotatable Bond Count
6
Topological Polar Surface Area
0A^2
Application
(3-Bromopropyl)triphenylphosphonium bromide is a versatile white to off-white crystalline powder used primarily in organic synthesis and rearrangement reactions of cyclic organic molecules. Its applications include serving as a reactant in the synthesis of functionalized polyurethanes via cationic ring-opening polymerization and click chemistry, facilitating semipinacol rearrangement and direct arylation, and enabling the olefination of benzaldehydes. Furthermore, it plays a role in C-H activation and cycloisomerization, assists in intramolecular dehydrobromination, and is instrumental in the cycloisomerizations of bromodienes and enynes.
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