39774-18-0

Basic information

• Product Name: 4-CHLOROBENZOIN
• Synonyms: 4-CHLOROBENZOIN;1-(4-CHLOROPHENYL)-2-HYDROXY-2-PHENYLETHANONE;4-Chlorobenzoin,1-(4-Chlorophenyl)-2-hydroxy-2-phenylethanone
• CAS NO: 39774-18-0
• Molecular Formula: C₁₄H₁₁ClO₂
• Molecular Weight: 246.69
• Mol File: 39774-18-0.mol
• Article Data: 11

Chemical Properties

• Melting Point: 89-93 °C(lit.)
• Boiling Point: 407.098 °C at 760 mmHg
• Flash Point: 200.006 °C
• Appearance: /
• Density: 1.286 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.618
• PKA: 11.82±0.20(Predicted)
• CAS DataBase Reference: 4-CHLOROBENZOIN(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLOROBENZOIN(39774-18-0)
• EPA Substance Registry System: 4-CHLOROBENZOIN(39774-18-0)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36/37
• WGK Germany: 3
• Hazardous Substances Data: 39774-18-0(Hazardous Substances Data)

Usage

General Description

4-Chlorobenzoin, also known as p-chlorobenzoin or 4-chlorobenzoyl alcohol, is a chemical compound with the formula C7H5ClO2. It belongs to the class of organic compounds known as benzoins. These are organic compounds containing a 1-hydroxy-2-oxo-1,2-diphenylethane moiety. It is characterized by the presence of a chlorine atom attached to the fourth carbon in the benzene ring. This chemical is generally used in various sectors of the chemical industry, notably in syntheses of other organic chemicals. Its physical properties include a white to light yellow crystalline powder appearance. As with many such chemicals, care must be taken to handle this compound safely, since it may pose hazards upon ingestion, inhalation, or skin contact.

InChI:InChI=1/C14H11ClO2/c15-12-8-6-11(7-9-12)14(17)13(16)10-4-2-1-3-5-10/h1-9,13,16H

Upstream product

• 4998-15-6 4-chlorophenylglyoxal 
• 71-43-2 benzene 
• 106-39-8 bromochlorobenzene 
• 532-28-5 (RS)-mandelonitrile 
• 100-52-7 benzaldehyde 
• 113348-33-7 phosphoric acid (4-chlorophenyl)(cyano)methyl ester diethyl ester 
• 7446-70-0 aluminium trichloride 
• 25438-37-3 phenyl(trimethylsiloxy)acetonitrile 
• 873-77-8 (4-chlorphenyl)magnesium bromide 
• 71292-81-4 2-(4-chlorophenyl)-2-hydroxy-1-phenylethanone 
• 10359-09-8 2-(4-chlorophenyl)-1,3-dithiane 
• 1333394-46-9 (2-(4-chlorophenyl)-1,3-dithian-2-yl)(phenyl)methanol 
• 104-88-1 4-chlorobenzaldehyde 
• 1889-71-0 4'-chloro-2-phenylacetophenone 

Downstream Products

• 75116-28-8 3-[2-(4-chlorophenyl)-2-oxoethyl]-1,3-dimethylindolin-2-one 
• 312523-92-5 5-(4-chlorophenyl)-2-(3,5-dimethoxyphenyl)-4-phenyl-1H-imidazole 
• 22394-04-3 2-(4-chloro-phenyl)-3,4,5-triphenyl-pyrrole 
• 119267-71-9 2-(4-chlorophenyl)-2-oxo-1-phenylethyl acetate 
• 1889-71-0 4'-chloro-2-phenylacetophenone 
• 134-85-0 4-chlorobenzophenone 
• 1379799-72-0 dimethyl 4-(4-chlorophenyl)-5-phenylfuran-2,3-dicarboxylate 
• 1293372-52-7 (4S,5R)-4-(4-chlorophenyl)-5-phenyl-[1,2,3]oxathiazolidine 2,2-dioxide 
• 1293372-40-3 4-(4-chlorophenyl)-5-phenyl-5H-[1,2,3]oxathiazole 2,2-dioxide 

Relevant articles and documents

Green preparation method α - hydroxyketone

The invention relates to a green preparation method of alpha-hydroxyketone. The method comprises the following steps: adding ketone, iodine, 1,4-diazabicyclo[2.2.2]octane and methanol into a glass reaction bottle in sequence; then stirring and reacting for 14 to 30h at room temperature in an air atmosphere under the irradiation of a 23W compact type fluorescent lamp, so as to obtain a reaction mixture; carrying out silica gel column chromatographic separation to obtain the pure alpha-hydroxyketone. The green preparation method provided by the invention has the characteristics of greenness, high efficiency, simplicity in operation, moderate conditions, wide applicability and easiness for industrialization.

Mechanism of α-ketol-type rearrangement of benzoin derivatives under basic conditions

The mechanism of base-catalyzed rearrangement of ring-substituted benzoins in aqueous methanol was examined by kinetic and product analyses. Substituent effects on the rate and equilibrium constants revealed that the kinetic process has a different electron demand compared to the equilibrium process. Reactions in deuterated solvents showed that the rate of H/D exchange of the α-hydrogen is similar to the overall rate toward the equilibrium state. A proton-inventory experiment using partially deuterated solvents showed a linear dependence of the rate on the deuterium fraction of the solvent, indicating that only one deuterium isotope effect contributes to the overall rate process. All these results point to a mechanism in which the rearrangement is initiated by the rate-determining α-hydrogen abstraction rather than a mechanism with initial hydroxyl hydrogen abstraction as in the general α-ketol rearrangement.

Oxidation of benzoins to benzils using sodium hydride

A highly efficient and eco-friendly oxidation of benzoins 1 to benzils 2 using sodium hydride has been developed.