1678-18-8

Basic information

• Product Name: BENZOYLMETHYLTRIPHENYLPHOSPHONIUM CHLORIDE
• Synonyms: BENZOYLMETHYLTRIPHENYLPHOSPHONIUM CHLORIDE;Benzoylmethyltriphenylphosphonium chloride, 99 %;phenacyl(triphenyl)phosphanium chloride;phenacyl(triphenyl)phosphonium chloride
• CAS NO: 1678-18-8
• Molecular Formula: C₂₆H₂₂OP*Cl
• Molecular Weight: 416.88
• Mol File: 1678-18-8.mol
• Article Data: 6

Chemical Properties

• Melting Point: 267-271 °C
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• CAS DataBase Reference: BENZOYLMETHYLTRIPHENYLPHOSPHONIUM CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZOYLMETHYLTRIPHENYLPHOSPHONIUM CHLORIDE(1678-18-8)
• EPA Substance Registry System: BENZOYLMETHYLTRIPHENYLPHOSPHONIUM CHLORIDE(1678-18-8)

Safety Data

• Hazardous Substances Data: 1678-18-8(Hazardous Substances Data)

Usage

General Description

Benzoylmethyltriphenylphosphonium chloride is a chemical compound used in organic synthesis as a reagent for the preparation of ylides, which are important intermediates in various chemical reactions. It is a quaternary ammonium salt with a phosphonium cation, and the benzoyl group attached to the phosphorous atom increases the reactivity of the ylide. Benzoylmethyltriphenylphosphonium chloride is commonly used in the Wittig reaction, a method for the synthesis of alkenes from aldehydes or ketones. BENZOYLMETHYLTRIPHENYLPHOSPHONIUM CHLORIDE is a versatile and widely utilized reagent in organic chemistry, particularly in the synthesis of complex organic molecules and pharmaceutical compounds.

InChI:InChI=1/C26H22OP.ClH/c27-26(22-13-5-1-6-14-22)21-28(23-15-7-2-8-16-23,24-17-9-3-10-18-24)25-19-11-4-12-20-25;/h1-20H,21H2;1H/q+1;/p-1

Upstream product

• 532-27-4 1-chloroacetophenone 
• 603-35-0 triphenylphosphine 
• 20913-05-7 (Benzoylmethylene)triphenylphosphorane 
• 103-80-0 phenylacetyl chloride 
• 98-88-4 benzoyl chloride 
• 19493-09-5 Methylenetriphenylphosphorane 

Downstream Products

• 34836-18-5 (α-Nitroso-phenacyl)-triphenylphosphoniumchlorid 
• 20913-05-7 (Benzoylmethylene)triphenylphosphorane 
• 1427349-44-7 2-(2,3-dihydrobenzofuran-2-yl)-1-phenylethanone 
• 1450761-18-8 (R)-2-(2,3-dihydrobenzofuran-2-yl)-1-phenylethanone 
• 1450760-86-7 (S)-2-(2,3-dihydrobenzofuran-2-yl)-1-phenylethanone 
• 24721-26-4 4-chlorochalcone 
• 1245905-80-9 (E)-3-(4-bromophenyl)-4,4,4-trifluoro-1-phenyl-2-buten-1-one 
• 1245905-78-5 (E)-4,4,4-trifluoro-3-(4-fluorophenyl)-1-phenylbut-2-en-1-one 
• 851645-63-1 (E)-4,4,4-trifluoro-3-(4-methoxyphenyl)-1-phenyl-2-buten-1-one 

Relevant articles and documents

ACYLATION OF PHOSPHORUS β-KETOYLIDES BY ACID CHLORIDES

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Inner workings of a cinchona alkaloid catalyzed oxa-Michael cyclization: Evidence for a concerted hydrogen-bond-network mechanism

Cinchona alkaloids catalyze the oxa-Michael cyclization of 4-(2-hydroxyphenyl)-2-butenoates to benzo-2,3-dihydrofuran-2-yl acetates and related substrates in up to 99 % yield and 91 % ee (ee=enantiomeric excess). Catalyst and substrate variation studies reveal an important role of the alkaloid hydroxy group in the reaction mechanism, but not in the sense of a hydrogen-bonding activation of the carbonyl group of the substrate as assumed by the Hiemstra-Wynberg mechanism of bifunctional catalysis. Deuterium labeling at C-2 of the substrate shows that addition of RO-H to the alkenoate occurs with syn diastereoselectivity of ≥99:1, suggesting a mechanism-based specificity. A concerted hydrogen-bond network mechanism is proposed, in which the alkaloid hydroxy group acts as a general acid in the protonation of the α-carbanionic center of the product enolate. The importance of concerted hydrogen-bond network mechanisms in organocatalytic reactions is discussed. The relative stereochemistry of protonation is proposed as analytical tool for detecting concerted addition mechanisms, as opposed to ionic 1,4-additions. Secret of cyclization: The cinchona alkaloid catalyzed asymmetric oxa-Michael cyclization of 2′-hydroxyphenyl-2-butenoates to benzodihydrofurans proceeds by a highly enantio- and diastereoselective syn-specific addition mode (see scheme). Transition-state activation of the carbonyl group by hydrogen bonding to the catalyst is excluded. This represents a clear-cut demonstration of the importance of concerted hydrogen-bond network mechanisms in cinchona-based asymmetric organocatalysis. Copyright

Synthesis of nitrogen heterocycles by intramolecular Michael type of amination via reduction of imines with di-n-butyliodotin hydride (n-Bu2SnIH)

(matrix presented). Novel nitrogen heterocycles were prepared by a one-pot procedure involving the reductive amination of the bifunctional substrates containing an aldehyde and enone groups with di-n-butyliodotin hydride (n-Bu2SnIH).