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Iodomethyl triphenylphosphonium iodide

Catalog Number
ACM3020288
Product Name
Iodomethyl triphenylphosphonium iodide
Structure
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CAS
3020-28-8
  • Product Overview
  • Usage
Synonyms
Iodomethyl-Triphenyl-Phosphonium Iodide
IUPAC Name
iodomethyl(triphenyl)phosphanium;iodide
Molecular Weight
530.12
Molecular Formula
C19H17I2P
Canonical SMILES
C1=CC=C(C=C1)[P+](CI)(C2=CC=CC=C2)C3=CC=CC=C3.[I-];
InChI
NAVMMSRRNOXQMJ-UHFFFAOYSA-M
InChI Key
InChI=1S/C19H17IP.HI/c20-16-21(17-10-4-1-5-11-17,18-12-6-2-7-13-18)19-14-8-3-9-15-19;/h1-15H,16H2;1H/q+1;/p-1
Melting Point
194-197 °C(lit.)
Purity
98%
Appearance
Solid
Complexity
253
Covalently-Bonded Unit Count
2
Exact Mass
529.916g/mol
H-Bond Acceptor
1
Heavy Atom Count
22
Isomeric SMILES
C1=CC=C(C=C1)[P+](CI)(C2=CC=CC=C2)C3=CC=CC=C3.[I-]
Monoisotopic Mass
529.916g/mol
NSC Number
116665
Rotatable Bond Count
4
Topological Polar Surface Area
0A^2
Application
Iodomethyl triphenylphosphonium iodide serves a pivotal role in chemical synthesis, offering versatility as a reactant or reagent across various applications. This compound is integral in creating phosphacyclic compounds through oxidative dimerizations and synthesizing enamides via cross-coupling methods. It also facilitates the production of cyclopeptide alkaloids, which have potential antibacterial or cytotoxic applications. Moreover, it is employed in forming terminal alkynes through the dehydrohalogenation of aldehydes and is utilized in vinylcyclopropanation or cyclopentenation reactions of strained alkenes using a sequential carborhodation process. Additionally, it acts as an olefination agent in the Lewis acid-catalyzed electrocyclization of trienes, underscoring its broad applicability in complex organic synthesis.
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