54100-47-9

Basic information

• Product Name: (4-tert-butylphenyl)(oxo)sulfanylphosphonium
• Synonyms: Phosphinothioic acid, P-(1,1-dimethylethyl)-P-phenyl-, [P(R)]-
• CAS NO: 54100-47-9
• Molecular Formula: C₁₀H₁₅OPS
• Molecular Weight: 213.2558
• Mol File: 54100-47-9.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (4-tert-butylphenyl)(oxo)sulfanylphosphonium(CAS DataBase Reference)
• NIST Chemistry Reference: (4-tert-butylphenyl)(oxo)sulfanylphosphonium(54100-47-9)
• EPA Substance Registry System: (4-tert-butylphenyl)(oxo)sulfanylphosphonium(54100-47-9)

Safety Data

• Hazardous Substances Data: 54100-47-9(Hazardous Substances Data)

Usage

Description

(4-tert-butylphenyl)(oxo)sulfanylphosphonium is a phosphonium salt chemical compound characterized by the presence of a sulfur atom and a phosphorus atom bonded to a tert-butylphenyl group. Additionally, it contains an oxo group bonded to the sulfur atom. (4-tert-butylphenyl)(oxo)sulfanylphosphonium is known for its utility in organic synthesis reactions, particularly as a phase transfer catalyst.

Uses

Used in Organic Synthesis:
(4-tert-butylphenyl)(oxo)sulfanylphosphonium is used as a phase transfer catalyst for facilitating the transfer of organic molecules between aqueous and organic phases in chemical reactions. Its application in this context is valuable in various laboratory and industrial processes, enhancing the efficiency and selectivity of the reactions.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (4-tert-butylphenyl)(oxo)sulfanylphosphonium may be utilized as a catalyst in the synthesis of complex organic molecules, including those with potential medicinal properties. Its ability to improve reaction conditions and selectivity can contribute to the development of new drugs and active pharmaceutical ingredients.
Used in Chemical Research:
(4-tert-butylphenyl)(oxo)sulfanylphosphonium is also used in chemical research as a tool to study reaction mechanisms and optimize reaction conditions. (4-tert-butylphenyl)(oxo)sulfanylphosphonium's unique structural features, including the tert-butylphenyl group and the oxo group, can provide insights into the influence of steric hindrance and electronic effects on reaction outcomes.
Used in Material Science:
(4-tert-butylphenyl)(oxo)sulfanylphosphonium may find applications in material science, particularly in the synthesis of novel materials with specific properties. The use of (4-tert-butylphenyl)(oxo)sulfanylphosphonium as a catalyst can help in the development of materials with tailored characteristics for various applications, such as in electronics, coatings, or advanced materials for energy storage and conversion.

Upstream product

• 644-97-3 Dichlorophenylphosphine 
• 98976-30-8 tert-Butylphenylphosphine oxide 
• 6002-45-5 t-butylphenylphosphinothioic acid 
• 6057-79-0 (S)-(-)-t-butyl(phenyl)phosphine oxide 
• 6002-45-5 (+/-)-tert-butyl(phenyl)phosphinothioic O-acid 

Downstream Products

• 38802-08-3 (S)-(-)-tert-butylmethylphenylphosphine oxide 
• 133319-25-2 (S_p)-(E)-But-2-enyl-tert-butylphenylphosphine oxide 
• 21448-79-3 (R_P)-tert-butylphenylmethylphosphine oxide 
• 75213-01-3 t-BuPhP(O)Cl 
• 1345019-56-8 C₁₀H₁₅OPS*C₁₄H₁₉NO₂ 
• 1345019-54-6 C₁₀H₁₅OPS*C₁₄H₁₉NO₂ 
• 51584-29-3 S-methyl tert-(butylphenylphosphino)thiolate 
• 79158-03-5 C₁₉H₂₅N₂OPS 
• 82945-12-8 (-)-S-t-butylphenyl-phosphinothiocyanidate 

Relevant articles and documents

T -Butylphenyl-(1-Naphthyl)Phosphinothioic Acids and Their Selenium Analogs: Synthesis of the Racemic Mixtures and Attempts to Isolate the Enantiomers of t -Butyl-1-Naphthylphosphinothioic Acid

Synthesis of racemic t-butyl-1-naphthylphosphinothio(seleno)ic acids and attempts to isolate the enantiomers of t-butyl-1-naphthylphosphinothioic acid are described.

A new procedure for the synthesis of optically active t-butylphenylphosphinothioic acid

A new procedure for the synthesis of optically active t-butylophenylphosphinothioic acid as an enantiomerically pure dextrorotatory enantiomer having the absolute configuration (R), by a reaction of the racemate of secondary t-butylphenylphosphine oxide with elemental sulfur in the presence of a molar equivalent of the levorotatory enantiomer of enantiomerically pure (S)-α-phenylethylamine, is reported. It is obvious that with the use of the dextrorotatory enantiomer of α-phenylethylamine, the levorotatory enantiomer of this thioacid will be isolated.

Reaction of metallated tert-butyl(phenyl)phosphane oxide with electrophiles as a route to functionalized tertiary phosphane oxides: Alkylation reactions

P-Chiral tertiary phosphane oxides have been prepared from each of the secondary phosphane oxides racemic 1, (S(p))-(-)-4 and (Rp)-(+)-tert-butylphenylphosphane oxide (5) by lithiation with LDA or nBuLi, or sodiation with sodium hydride, in THF, and then by treatment with a series of primary alkyl halides. Doubly P-chiral ditertiary bis(phosphane oxides) are also obtained from these metallated secondary phosphane oxides by treatment with electrophiles based on straight-chain, tartrate-derived, and bishalomethylarene dihalides. In general, the bis-phosphane oxides are obtained in good yields. However, when the α,ω-dihalide bears an embedded heteroatom (O or Si), yields are diminished. The enantiomeric purity of each of the products was assessed through admixture with (R(p))- and (S(p))-tert-butyl(phenyl)phosphanylthioic acids and measurement of the tert-butyl resonances in the 1H-NMR spectra. In all cases, the act of metallation of the enantiomerically pure secondary phosphane oxide followed by its alkylation is not accompanied by detectable racemization. This method for preparing P-chiral tertiary phosphane oxides is therefore more straightforward than those described previously.