18583-55-6

Basic information

• Product Name: (2-CHLOROBENZYL)TRIPHENYLPHOSPHONIUM CHLORIDE HYDRATE
• Synonyms: (2-CHLOROBENZYL)TRIPHENYLPHOSPHONIUM CHLORIDE HYDRATE 98%;(2-Chlorobenzyl)triphenylphosphonium chloridehydrate,98%;(2-CHLOROBENZYL)TRIPHENYLPHOSPHONIUM CHLORIDE;(2-CHLOROBENZYL)TRIPHENYLPHOSPHONIUM CHLORIDE HYDRATE;(O-CHLOROBENZYL)TRIPHENYLPHOSPHONIUM CHLORIDE;TRIPHENYL(2-CHLOROBENZYL)PHOSPHONIUM CHLORIDE
• CAS NO: 18583-55-6
• Molecular Formula: C₂₅H₂₁ClP*Cl
• Molecular Weight: 423.32
• Product Categories: Phosphonium Compounds;Synthetic Organic Chemistry;Wittig & Horner-Emmons Reaction;Wittig Reaction
• Mol File: 18583-55-6.mol
• Article Data: 4

Chemical Properties

• Melting Point: 243-245 °C
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: (2-CHLOROBENZYL)TRIPHENYLPHOSPHONIUM CHLORIDE HYDRATE(CAS DataBase Reference)
• NIST Chemistry Reference: (2-CHLOROBENZYL)TRIPHENYLPHOSPHONIUM CHLORIDE HYDRATE(18583-55-6)
• EPA Substance Registry System: (2-CHLOROBENZYL)TRIPHENYLPHOSPHONIUM CHLORIDE HYDRATE(18583-55-6)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-20/22
• Safety Statements: 36/37/39-26
• Hazardous Substances Data: 18583-55-6(Hazardous Substances Data)

Usage

Description

(2-Chlorobenzyl)triphenylphosphonium Chloride Hydrate is a white to light yellow crystalline powder that serves as a reagent in the Wittig reaction, a widely used method for the synthesis of alkenes from aldehydes and ketones.

Uses

Used in Pharmaceutical Industry:
(2-Chlorobenzyl)triphenylphosphonium Chloride Hydrate is used as a reagent for the synthesis of various pharmaceutical compounds, particularly in the Wittig reaction with imidazolecarboxaldehyde to produce level 4-(5)arylethenylimidazoles. These synthesized compounds have potential applications in the development of new drugs and therapeutic agents.
Used in Chemical Synthesis:
In the field of chemical synthesis, (2-Chlorobenzyl)triphenylphosphonium Chloride Hydrate is used as a versatile reagent for the preparation of a wide range of organic compounds, including alkenes, which are essential building blocks in the synthesis of various chemicals, materials, and pharmaceuticals.
Used in Research and Development:
(2-Chlorobenzyl)triphenylphosphonium Chloride Hydrate is also utilized in research and development laboratories for the exploration of new synthetic pathways and the development of innovative chemical processes. Its application in the Wittig reaction allows researchers to access a diverse array of alkenes, which can be further modified and functionalized to create novel compounds with potential applications in various industries.

InChI:InChI=1/C25H21ClP.ClH/c26-25-19-11-10-12-21(25)20-27(22-13-4-1-5-14-22,23-15-6-2-7-16-23)24-17-8-3-9-18-24;/h1-19H,20H2;1H/q+1;/p-1

Upstream product

• 611-19-8 1-chloro-2-(chloromethyl)benzene 
• 603-35-0 triphenylphosphine 

Downstream Products

• 85676-74-0 (E)-1-chloro-2-(4-methoxystyryl)benzene 
• 25144-38-1 (E)-2,2'-dichlorostilbene 
• 20657-43-6 (Z)-1,2-bis(2-chlorophenyl)ethene 
• 112704-51-5 E-2-(4-fluorophenyl)-3-(2-chlorophenyl)-propenal 
• 869106-82-1 5-[2-(2-chlorophenyl)vinyl]-1-(3-methoxypropyl)-1H-pyrrole-2-carboxylic acid ethyl ester 
• 869106-77-4 2-[2-(2-chlorophenyl)vinyl]-1-(3-methoxypropyl)-1H-pyrrole 
• 908863-91-2 (E)-2-[2-(2-chlorophenyl)ethenyl]-5-methoxy-1H-indole 
• 75961-25-0 5-[(Z)-2-(2-Chloro-phenyl)-vinyl]-1H-imidazole 

Relevant articles and documents

Chiral Imidodiphosphoric Acid-Catalyzed Highly Diastereo- and Enantioselective Synthesis of Poly-Substituted 3,4-Dihydro-2 H-pyrans: [4 + 2] Cycloadditions of β,γ-Unsaturated α-Ketoesters and 3-Vinylindoles

Imidodiphosphoric acids were employed to catalyze inverse-electron-demand hetero-Diels-Alder reaction of β,γ-unsaturated α-ketoesters and 3-vinylindoles. A series of optically active 3,4-dihydro-2H-pyran derivatives with three contiguous stereogenic centers was synthesized in excellent yields (70-99%), diastereoselectivities (>20:1), and enantioselectivities (73-99%). The resulting indole containing 3,4-dihydro-2H-pyran could be converted to tetrahydropyran derivatives, which appear in several biological active compounds by simple hydrogenation reduction.

Kinetic Study of the Substitution Reactions of Triphenylphosphine with Chlorobenzyl Chlorides, Dimethylbenzyl Chloride, and Methylbenzyl Bromides in Various Two-Phase Organic Solvent/Water Media

The kinetics of the substitution reactions of triphenylphosphine (TP) with chlorobenzyl chlorides (CBC), 2,5-dimethylbenzyl chloride (DMBC), and methylbenzyl bromides (MBB) in aprotic organic solvent was studied under the extraction by water. The effects of water, agitation, organic solvent, reactant, and temperature were investigated. These reactions take place via the SN2 mechanism and exhibit large and negative entropy of activation. The order of relative activity of solvents is CHCl3 > CH2Cl2 >> C6H6. In CHCl3, the order of relative reactivity of benzyl chloride (BC), benzyl bromide (BB), CBC, DMBC, and MBB toward reaction with TP is 2-MBB > 4-MBB > 3-MBB > BB > DMBC > BC > 2-CBC > 4-CBC > 3-CBC. These reactions produce quantitatively benzyltriphenylphosphonium salts, which are useful for synthesizing Z-form isomers of stilbenes via the two-phase Wittig reaction.