1031-15-8

Basic information

• Product Name: Methyl triphenyl phosphonium chloride
• Synonyms: Triphenylmethylchlorophosphine;PHOSPHONIUM,METHYLTRIPHENYL-,CHLORIDE;Methyl triphenyl phosphonium chloride;[Ph3MP]Cl;methyl(triphenyl)phosphanium chloride;METHYL TRIPHENYL PHOSPHONIUM CHLORIDE MTPPC
• CAS NO: 1031-15-8
• Molecular Formula: C₁₉H₁₈P*Cl
• Molecular Weight: 312.77
• EINECS: 418-400-2
• Product Categories: C-C Bond Formation;Olefination;Wittig Reagents
• Mol File: 1031-15-8.mol
• Article Data: 17

Chemical Properties

• Melting Point: 221°C (dec.)
• Boiling Point: 332.65℃ at 101.3kPa
• Appearance: White crystalline powder
• Density: 1.22 at 23℃
• Vapor Pressure: 0.001Pa at 40℃
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Soluble in methanol.
• Sensitive: Hygroscopic
• CAS DataBase Reference: Methyl triphenyl phosphonium chloride(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl triphenyl phosphonium chloride(1031-15-8)
• EPA Substance Registry System: Methyl triphenyl phosphonium chloride(1031-15-8)

Safety Data

• Hazard Codes: Xn;N,N,Xn
• Statements: 21/22-38-41-51/53
• Safety Statements: 22-26-36/37/39-61
• RIDADR: UN 3077
• WGK Germany: 2
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 1031-15-8(Hazardous Substances Data)

Usage

Uses

Methyltriphenylphosphonium chloride is used as a phase transfer catalyst in synthetic chemistry. It acts as a catalyst for regio-controlled ring-opening polymerization of substituted epoxides. It is utilized for controlling the corrosion iron. It acts as a reactant for intramolecular nitrone cycloaddition. In addition to this, it is used for neoplasm inhibition through antimitochondrial effect.

InChI:InChI=1/C19H18P.ClH/c1-20(17-11-5-2-6-12-17,18-13-7-3-8-14-18)19-15-9-4-10-16-19;/h2-16H,1H3;1H/q+1;/p-1

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 19493-09-5 Methylenetriphenylphosphorane 
• 712-48-1 chlorodiphenylarsine 
• 96254-26-1 Triphenylphosphonium-(diphenylarsino)methylid 
• 18147-18-7 tert-butyldichloromethylsilane 
• 18395-90-9 Di-tert-butyldichlorosilane 
• 3739-97-7 (trimethylsilyl)methylenetriphenylphosphorane 
• 15424-14-3 N-phenylbenzohydrazonoyl chloride 
• 104438-92-8 <2-(4-Methoxyphenyl)-2-(phenylimino)ethyliden>triphenylphosphoran 
• 64723-81-5 <2-Phenyl-2-(phenylimino)ethyliden>triphenylphosphoran 
• 75624-72-5 <4-(4-Nitrophenyl)-2,4-dioxobutyl>triphenylphosphonium-chlorid 
• 603-35-0 triphenylphosphine 
• 54446-70-7 trimethyl-methylenearsorane 
• 74-87-3 methylene chloride 

Downstream Products

• 1174-61-4 (Benzylcarbonylmethylene)triphenylphosphorane 
• 98-83-9 isopropenylbenzene 
• 827-54-3 2-naphthylethylene 
• 3867-18-3 2-vinylaniline 
• 56100-22-2 6-methyl-2,2'-bipyridine 
• 915944-59-1 C₁₁H₁₁ClO₂ 
• 915944-51-3 C₈H₄BrF₃ 
• 257928-44-2 1-(benzyloxy)-4-(prop-1-en-2-yl)benzene 
• 156441-18-8 (2S,4R)-1-benzyl-4-tert-butyldimethylsilyloxy-2-vinylpyrrolidine 
• 40001-26-1 methyltriphenylphosphonium tetrahydroborate 
• 188999-31-7 5-methoxy-2-vinyl-4-azaindole 
• 127214-37-3 (2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-methoxy-6-vinyl-tetrahydro-pyran 

Relevant articles and documents

Long sought synthesis of quaternary phosphonium salts from phosphine oxides: Inverse reactivity approach

Quaternary phosphonium salts (QPS), a key class of organophosphorus compounds, have previously only been available by routes involving nucleophilic phosphorus. We report the realisation of the opposite approach to QPS utilising phosphine oxides as the electrophilic partner and Grignard reagents as nucleophiles. The process is enabled through the crucial intermediacy of the derived halophosphonium salts. The route does not suffer from the slow kinetics and limited availability of many parent phosphines and a broad range of QPS were prepared in excellent yields.

Exploring an Umpolung strategy for quaternization of phosphorus

We propose a new, potentially widely-applicable, Umpolung approach for the synthesis of quaternary phosphonium salts R3PR1 X (X = Cl, Br) from phosphine oxides R3PO. The new organic group R1 is introduced via nucleophilic attack on an intermediate halophosphonium salt using a Grignard reagent R1MgX and replaces the traditional phosphine quaternization approach. Consequently, the new method does not suffer from the limited availability of many parent phosphines and is much faster than standard quaternization.

Practical synthesis of phosphonium salts with orthoformates and their application as flame retardants in polycarbonate

An efficient and practical approach to phosphonium salts has been developed. By the reaction of phosphines and different acid sources with orthoformates in one-step operation, the process allowed rapid access to phosphonium salts with diverse counterions in high yield after the purification by recrystallization. The flame retardant performance in PC has also been examined by blending several phosphonium salts to PC respectively. Phosphonium phosphates showed excellent flame retardancy in PC with only 2 phr blending.