13371-17-0

Basic information

• Product Name: Butyltriphenylphosphonium chloride
• Synonyms: BTC;BUTYLTRIPHENYLPHOSPHONIUM CHLORIDE;TRIPHENYLBUTYLPHOSPHONIUM CHLORIDE;butyltriphenyl-phosphoniuchloride;BUTYLTRIPHENYL PHOSPHONIUM CHLORIDE 98%;Phosphonium, butyltriphenyl-, chloride;(1-Butyl)triphenylphosphonium chloride;Butyltriphenyl phosphonium chloride,98%
• CAS NO: 13371-17-0
• Molecular Formula: C₂₂H₂₄P*Cl
• Molecular Weight: 354.85
• EINECS: 236-443-3
• Product Categories: C-C Bond Formation;Olefination;Wittig Reagents
• Mol File: 13371-17-0.mol
• Article Data: 8

Chemical Properties

• Melting Point: 226-230 °C(lit.)
• Flash Point: >270°C
• Appearance: /solid
• Storage Temp.: Store below +30°C.
• Solubility: soluble in Methanol
• Water Solubility: soluble
• Sensitive: Hygroscopic
• CAS DataBase Reference: Butyltriphenylphosphonium chloride(CAS DataBase Reference)
• NIST Chemistry Reference: Butyltriphenylphosphonium chloride(13371-17-0)
• EPA Substance Registry System: Butyltriphenylphosphonium chloride(13371-17-0)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 6.1
• Hazardous Substances Data: 13371-17-0(Hazardous Substances Data)

Usage

Chemical Properties

white to off-white crystalline powder

InChI:InChI=1/C22H24P.ClH/c1-2-3-19-23(20-13-7-4-8-14-20,21-15-9-5-10-16-21)22-17-11-6-12-18-22;/h4-18H,2-3,19H2,1H3;1H/q+1;/p-1

Upstream product

• 344-07-0 1-chloro-2,3,4,5,6-pentafluorobenzene 
• 1779-51-7 n-butyl(triphenyl)phosphonium bromide 
• 109-69-3 n-Butyl chloride 
• 603-35-0 triphenylphosphine 
• 791-28-6 Triphenylphosphine oxide 
• 1191-47-5 dibutylmagnesium 
• 19171-57-4 dichlorotriphenyl-λ⁴-phosphane 
• 109-72-8 n-butyllithium 
• 693-04-9 butyl magnesium bromide 
• 3728-50-5 butylidenetriphenylphosphorane 
• 1071-38-1 N,N,N',N'-Tetramethylformamidinium chloride 
• 75-45-6 Chlorodifluoromethane 
• 592-34-7 carbonochloridic acid, butyl ester 
• 4342-61-4 1,2-dichlorotetramethylsilane 

Downstream Products

• 538-68-1 pentylbenzene 
• 16002-93-0 (E)-1-phenyl-1-pentene 
• 145091-66-3 (Z)-1-(ortho-pyridyl)-1-pentene 
• 83299-49-4 {(C₆H₅)3PC₄H₉}⁽¹⁺⁾*{FeCl₄}^(1-)={(C₆H₅)3PC₄H₉}{FeCl₄} 
• 3728-50-5 butylidenetriphenylphosphorane 
• 96371-92-5 Triphenylphosphin-<1-hydrocinnamoyl-butylen> 
• 17620-90-5 3-(triphenyl-λ⁵-phosphanylidene)-hexan-2-one 

Relevant articles and documents

A ONE-POT SYNTHESIS OF PENTAFLUORO- AND POLYFLUOROPHENYL ALKYL KETONES

A one-pot synthesis of pentafluoro- and polyfluorophenyl alkyl ketones via ozonolysis of fluorinated phosphoranes is described.In view of the fact that one-pot reaction without isolation of intermediates and the total yield in 3 steps reaches 51-60percent

Toxicity assessment of phosphonium based ionic liquids towards female guppy fish

In this study, two phosphonium based ionic liquids (butyl triphenyl phosphonium chloride and hexyl triphenyl phosphonium bromide) have been synthesized using quarternization process. The toxicities of these ionic liquids are unknown and may be harmful to humans and the environment. Therefore, the toxicity assessment of these ionic liquids was carried out according to the Organization for Economic Cooperation and Development (OECD) guideline 203 using female guppy fish (Poecilia reticulata). The median lethal concentrations (LC50) have been estimated for butyl triphenyl phosphonium chloride and for hexyl triphenyl phosphonium bromide to be 73.35 mg/L and 61.36 mg/L respectively. Both LC50 obtained can be identified as slightly toxic ionic liquids based on Acute Toxicity Rating Scale by by the United States Fish and Wildlife Service (USFWS). The findings from this study can be used for better design of phosphonium-based ionic liquids with consideration of their aquatic toxicities.

Organic phosphine salt and optical physical property regulation and control method and application thereof (by machine translation)

The invention discloses an organic phosphine salt and an optical physical property regulation and control method and application, of the compound, with different alkyl chain lengths through an ion exchange reaction; to obtain the organic phosphine salt, with different alkyl chain lengths through the ion exchange reaction to control the photophysical property (Cl, Br, I), of the compound by using alkyl, chain length and heavy atom, after, ultraviolet irradiation to achieve information, encryption application 300 nm. (by machine translation)

Synthesis of Functional Monosilanes by Disilane Cleavage with Phosphonium Chlorides

The Müller–Rochow direct process (DP) for the large-scale production of methylchlorosilanes MenSiCl4?n (n=1–3) generates a disilane residue (MenSi2Cl6?n, n=1–6, DPR) in thousands of tons annually. This report is on methylchlorodisilane cleavage reactions with use of phosphonium chlorides as the cleavage catalysts and reaction partners to preferably obtain bifunctional monosilanes MexSiHyClz (x=2, y=z=1; x,y=1, z=2; x=z=1, y=2). Product formation is controlled by the reaction temperature, the amount of phosphonium chloride employed, the choice of substituents at the phosphorus atom, and optionally by the presence of hydrogen chloride, dissolved in ethers, in the reaction mixture. Replacement of chloro by hydrido substituents at the disilane backbone strongly increases the overall efficiency of disilane cleavage, which allows nearly quantitative silane monomer formation under comparably moderate conditions. This efficient workup of the DPR thus not only increases the economic value of the DP, but also minimizes environmental pollution.

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.

One alkyl triphenyl substituted group based phosphonium salt preparation method and application

The invention discloses a one alkyl triphenyl substituted group based phosphonium salt preparation method and application. The preparation method includes that a one alkyl triphenyl phosphonium salt halide I is obtained through reaction of several alkyl h

Reactions with Phosphine Alkylenes, XLV. Reactions of Alkylidenetriphenylphosphoranes with Tetramethylformamidinium Chloride. Synthesis of triphenylphosphonium Chloride and (Formylalkylidene)triphenylphosphoranes

Phosphonium ylides 1 react with tetramethylformamidinium chloride (2) to form enamine phosphonium chlorides 8 and the formic orthoamide 7.The salts 8 show temperature depending 1H NMR spectra with respect to the protons of the dimethylamino group (hindered rotation around the C - N(CH3)2 bond).Treatment of 8 with acids and subsequently with bases gives rise to the formation of the formyl ylides 19. 8a is deprotonated with sodium amide to give the phosphaallene ylide 20, which reacts with water to yield the phosphane oxide 21, and with methyl iodide stereospecifically to form 8b.

Ylide-Carbene Chemistry. Synthesis of 1,1-Difluoro-1-alkenes

The reaction between nonstabilized alkylidenetriphenylphosphoranes and chlorodifluoromethane has been found to be a useful alternative to the Wittig reaction for the synthesis of many difluoromethylene olefins.Both primary and secondary ylides which do not contain strongly electron-withdrawing substituents within the alkylidene portion of the ylide react with chlorodifluoromethane to give the corresponding difluoromethylene olefins in yields which are significantly better than those obtained by the Wittig reaction.The formation of triphenylphosphine oxide is avoided, and all phosphorus-containing moieties can be recovered and recycled.The reaction proceeds by initial dehydrochlorination of chlorodifluoromethane by the ylide to generate difluorocarbene.The intermediate difluorocarbene is then trapped by a second equivalent of the nucleophilic ylide.Mechanistic evidence indicates that either a zwitterionic intermediate or a three-membered cyclic phosphorane can account for the 1,1-difluoro-1-alkene products.The isolation of several 1-hydro-1-fluoro-1-alkene products such as FCH=CHPh, FHC=CPh2, and FHC=CHCH=CHPh after steam distillation of the reaction mixtures, however, can only be accounted for via a three-membered cyclic phosphorane.