384-67-8

Basic information

• Product Name: 2-CHLORO-2,2-DIFLUOROACETOPHENONE
• Synonyms: CHLORODIFLUOROACETOPHENONE;2-CHLORO-2,2-DIFLUOROACETOPHENONE;A-CHLORO-A,A-DIFLUOROACETOPHENONE;ALPHA-CHLORO-ALPHA,ALPHA-DIFLUOROACETOPHENONE;alpha,alpha-Difluorophenacyl chloride;à,à-difluorophenacyl chloride;à-chloro-à,à-difluoroacetophene;2-Chloro-2,2-difluoroacetophenone 97%
• CAS NO: 384-67-8
• Molecular Formula: C₈H₅ClF₂O
• Molecular Weight: 190.57
• EINECS: -0
• Product Categories: Fluorine series
• Mol File: 384-67-8.mol
• Article Data: 11

Chemical Properties

• Melting Point: 102-103 °C
• Boiling Point: 94-96 °C35 mm Hg(lit.)
• Flash Point: 163 °F
• Appearance: /
• Density: 1.293 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.01E-05mmHg at 25°C
• Refractive Index: n20/D 1.497(lit.)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: Difficult to mix.
• BRN: 2251448
• CAS DataBase Reference: 2-CHLORO-2,2-DIFLUOROACETOPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLORO-2,2-DIFLUOROACETOPHENONE(384-67-8)
• EPA Substance Registry System: 2-CHLORO-2,2-DIFLUOROACETOPHENONE(384-67-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37
• RIDADR: UN 3334
• WGK Germany: 3
• F: 19
• Hazardous Substances Data: 384-67-8(Hazardous Substances Data)

Usage

Description

2-Chloro-2,2-difluoroacetophenone is a difluorocarbene reagent characterized by its unique chemical structure and reactivity. It is a versatile compound utilized in various synthetic applications due to its ability to form aryl difluoromethyl ethers, gem-difluoromethene derived compounds, and other valuable intermediates.

Uses

Used in Chemical Synthesis:
2-Chloro-2,2-difluoroacetophenone is used as a reagent for the difluoromethylation of various phenols to yield aryl difluoromethyl ethers. This application is significant because it allows for the creation of new compounds with distinct properties, which can be further utilized in various chemical and pharmaceutical processes.
Used in the Baylis-Hillman Reaction:
In the field of organic chemistry, 2-chloro-2,2-difluoroacetophenone serves as a precursor in the Baylis-Hillman reaction of fluoroalkyl ketones. This reaction leads to the formation of chlorodifluoromethyl containing products, which are valuable intermediates in the synthesis of complex organic molecules.
Used in the Synthesis of Propargyl Alcohols:
2-Chloro-2,2-difluoroacetophenone is also employed as a substrate in the synthesis of propargyl alcohols using a novel ruthenium catalyst. This application highlights the compound's versatility and its ability to participate in various catalytic reactions, leading to the formation of important chemical building blocks.

InChI:InChI=1/C9H10FNO2/c10-7-3-1-2-4-8(7)11-6-5-9(12)13/h1-4,11H,5-6H2,(H,12,13)

Upstream product

• 591-51-5 phenyllithium 
• 76-04-0 2-chloro-2,2-difluoroacetic acid 
• 2902-69-4 2,2,2-trichloroacetophenone 
• 383-62-0 ethyl 2-chloro-2,2-difluoroacetate 
• 677-67-8 fluorosulfonyldifluoroacetyl fluoride 
• 71-43-2 benzene 
• 20488-54-4 trans-1,2-difluoro-1,2-diphenylethylene 
• 86340-78-5 2,2-difluoro-1-phenyl-1-trimethylsiloxyethene 
• 100-58-3 phenylmagnesium bromide 
• 108-86-1 bromobenzene 
• 134918-42-6 epoxide of α,β-difluoro-β-chlorostyrene 
• 145693-39-6 epoxide of trans-α,β-difluorostyrene 
• 1514-87-0 metyhyl chlorodifluoroacetate 

Downstream Products

• 115818-56-9 2,2-difluoro-3-hydroxy-3-methyl-1-phenyl-6-hepten-1-one 
• 384-64-5 3,3,3-trifluoro-2-phenylpropene 
• 74492-31-2 α-(Chlorodifluoromethyl)styrene 
• 119454-39-6 (R)-2-chloro-2,2-difluoro-1-phenylethanol 
• 124095-23-4 (S)-2-chloro-2,2-difluoro-1-phenylethan-1-ol 
• 378-99-4 α,α,β-trichloro-β,β-difluoroethylbenzene 
• 192862-16-1 2,2-difluoro-2-(methylthio)acetophenone 
• 5905-69-1 1-bromo-4-(difluoromethoxy)benzene 
• 128140-82-9 1-(difluoromethoxy)-4-iodobenzene 
• 175278-33-8 1-bromo-2-(dilfluoromethoxy)benzene 
• 920981-13-1 1,3,5-tribromo-2-(difluoromethoxy)benzene 
• 458-92-4 (difluoromethoxy)benzene 
• 947504-27-0 (E)-N-(2-chloro-2,2-difluoro-1-phenylethylidene)propylamine 
• 947504-26-9 (E)-N-(2-chloro-2,2-difluoro-1-phenylethylidene)isopropylamine 

Relevant articles and documents

Unusual reactions of Grignard reagents toward fluoroalkylated esters

Fluorine-containing esters were demonstrated to be convenient substrates for construction of the corresponding ketones by low temperature reaction with Grignard reagents followed by warming up to 0 °C, while heating the mixture up to 80 °C readily promoted the reduction of the ketones obtained by the generated magnesium alkoxides whose mechanism was speculated as Meerwein-Ponndorf-Verley type reduction by computational technique.

2-Chloro-2,2-difluoroacetophenone: A non-ODS-based difluorocarbene precursor and its use in the difluoromethylation of phenol derivatives

A novel and non-ODS-based (ODS = ozone-depleting substance) preparation of 2-chloro-2,2-difluoroacetophenone (1) was achieved in high yield by using 2,2,2-trifluoroacetophenone as the starting material. Compound 1 was found to act as a good difluorocarbene reagent, which readily reacts with a variety of structurally diverse phenol derivatives 4 in the presence of potassium hydroxide or potassium carbonate to produce aryl difluoromethyl ethers 5 in good yields. This new and easy-to-handle synthetic methodology offers an environmentally friendly alternative to other Freon- or Halon-based difluoromethylating approaches.

Lewis Acid Catalyzed Aldol-Type Reaction of 1,1-Difluorovinyl Methyl Ether Derivatives

In the presence of Lewis acid, such as SbCl5, SbCl6*NAr3 or Cu(OTf)2, difluorovinyl methyl ether (1,1-difluoro-2-methoxy-1-alkene) 1 reacted with carbonyl compounds to give O-methylated aldol-type products 3 in good yields, while Lewis acid, such as TMSOT