51336-94-8

Basic information

• Product Name: 2-Chloro-2',4'-difluoroacetophenone
• Synonyms: [2-(2,4-difluorophenyl)-2-oxoethyl]chloranuide;2-Chloro-2',4'-difluoroacetophenone, 2-Chloro-1-(2,4-difluorophenyl)ethan-1-one;2-Chloro-2',4'-difluoroacetophenone, 97+%;2-Chloro-2',4'-difluoroacetophenone 98%;Voriconazole Impurity 6;2-CHLORO-1-(2,4-DIFLUOROPHENYL)ETHANONE;2'-CHLORO-2,4-DIFLUOROACETOPHENONE;2-CHLORO-2',4'-DIFLUOROACETOPHENONE
• CAS NO: 51336-94-8
• Molecular Formula: C₈H₅ClF₂O
• Molecular Weight: 190.57
• EINECS: 1592732-453-0
• Product Categories: blocks;FluoroCompounds;Benzene series;C7 to C8;Carbonyl Compounds;Ketones;Acetophenone series;Aromatics;Inhibitors
• Mol File: 51336-94-8.mol
• Article Data: 65

Chemical Properties

• Melting Point: 44-48 °C(lit.)
• Boiling Point: 240.877 °C at 760 mmHg
• Flash Point: >230 °F
• Appearance: white crystalline powder
• Density: 1.3544 (estimate)
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility: Chloroform (Slightly)
• Sensitive: Lachrymatory
• BRN: 1943217
• CAS DataBase Reference: 2-Chloro-2',4'-difluoroacetophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-2',4'-difluoroacetophenone(51336-94-8)
• EPA Substance Registry System: 2-Chloro-2',4'-difluoroacetophenone(51336-94-8)

Safety Data

• Hazard Codes: C,Xi
• Statements: 34-37
• Safety Statements: 26-36/37/39-45-25-27
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• F: 10-21
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 51336-94-8(Hazardous Substances Data)

Usage

Description

2-Chloro-2′,4′-difluoroacetophenone was used in the synthesis of allyl alcohol1. It can also be tested for inhibition of protein tyrosine phosphatases SHP-1 and PTP1B2.

Chemical Properties

white crystalline powder

Uses

Different sources of media describe the Uses of 51336-94-8 differently. You can refer to the following data:
1. A α-haloacetophenone derivatives tested for inhibition of protein tyrosine phosphatases SHP-1 and PTP1B.
2. 2-Chloro-2′,4′-difluoroacetophenone was used in the synthesis of allyl alcohol.

Upstream product

• 372-18-9 1,3-Difluorobenzene 
• 79-04-9 chloroacetyl chloride 
• 1440-61-5 N-chloroacetylmorpholine 
• 348-57-2 2,4-difluorobromobenzene 
• 79-11-8 chloroacetic acid 
• 106614-28-2 methyl 2,4-difluorobenzoate 
• 364-83-0 2',4'-difluoroacetophenone 
• 78-95-5 chloroacetone 

Downstream Products

• 134071-11-7 1‐(2,4‐difluorophenyl)‐2‐(1H‐imidazol‐1‐yl)ethan‐1‐one 
• 142657-56-5 1-(2,4-difluorophenyl)-1-(4-bromophenyl)epoxyethane 
• 169218-76-2 <3(2S,3S),4S>-4-Benzyl-3-<4-chloro-3-(2,4-difluorophenyl)-3-hydroxy-2-methyl-1-oxobutyl>-2-oxazolidinone 
• 169218-76-2 <3(2R,3S),4S>-4-Benzyl-3-<4-chloro-3-(2,4-difluorophenyl)-3-hydroxy-2-methyl-1-oxobutyl>-2-oxazolidinone 
• 169218-76-2 <3(2S,3R),4S>-4-Benzyl-3-<4-chloro-3-(2,4-difluorophenyl)-3-hydroxy-2-methyl-1-oxobutyl>-2-oxazolidinone 
• 169218-76-2 <3(2R,3R),4S>-4-Benzyl-3-<4-chloro-3-(2,4-difluorophenyl)-3-hydroxy-2-methyl-1-oxobutyl>-2-oxazolidinone 
• 1027900-87-3 2-[2-(2,4-Difluoro-phenyl)-2-oxo-ethyl]-2-[2-(4-methanesulfonyl-phenyl)-2-oxo-ethyl]-malonic acid dimethyl ester 
• 1026500-07-1 4-{5-[2-Chloro-1-(2,4-difluoro-phenyl)-1-hydroxy-ethyl]-thiazol-2-yl}-benzonitrile 
• 1025877-72-8 2-Chloro-1-(2,4-difluoro-phenyl)-1-[4-(2,4-difluoro-phenyl)-thiazol-2-yl]-ethanol 
• 308368-72-1 [2-(4-{4-[4-(2,4-difluoro-phenyl)-thiazol-2-yl]-benzenesulfonylamino}-phenyl)-ethyl]-(2-hydroxy-2-pyridin-3-yl-ethyl)-carbamic acid tert-butyl ester 
• 330156-49-5 (S)-2-chloro-1-(2’,4’-difluorophenyl)ethanol 
• 234759-78-5 2-(cyclopropylthio)-2',4'-difluoroacetophenone 
• 185302-85-6 methyl 3-(2,4-difluorophenyl)-3-oxopropanoate 

Relevant articles and documents

Discovery of potential antifungal triazoles: Design, synthesis, biological evaluation, and preliminary antifungal mechanism exploration

A series of triazoles as miconazole analogues was designed, synthesized and characterized by IR, NMR, MS and HRMS. All the newly prepared compounds were screened for their antifungal activities against five kinds of fungi. The bioactive assay showed that most of the synthesized compounds exhibited good or even stronger antifungal activities in comparison with the reference drugs miconazole and fluconazole. In particular, the 3,4-dichlorobenzyl derivative 5b showed a comparable or superior activity against all the tested fungal strains to standard drugs, and formed a supramolecular complex with CYP51 via the hydrogen bond between the 4-nitrogen of the triazole nucleus and the histidine residue. Preliminary experiments revealed that both of the active molecules 5b and 9c could intercalate into calf thymus DNAs, which might block DNA replication to exhibit their powerful antifungal abilities. Further studies indicated that compound 5b might be stored and transported by human serum albumin through hydrophobic interactions, specific electrostatic interactions and hydrogen bonds. These results strongly suggested that compound 5b could serve as a promising antifungal candidate.

Design, synthesis, and biological evaluation of novel miconazole analogues containing selenium as potent antifungal agents

Herein, based on the theory of bioisosterism, a series of novel miconazole analogues containing selenium were designed, synthesized and their inhibitory effects on thirteen strains of pathogenic fungi were evaluated. It is especially encouraging that all the novel target compounds displayed significant antifungal activities against all tested strains. Furthermore, all the target compounds showed excellent inhibitory effects on fluconazole-resistant fungi. Subsequently, preliminary mechanistic studies indicated that the representative compound A03 had a strong inhibitory effect on C.alb. CYP51. Moreover, the target compounds could prevent the formation of fungi biofilms. Further hemolysis test verified that potential compounds had higher safety than miconazole. In addition, molecular docking study provided the interaction modes between the target compounds and C.alb. CYP51. These results strongly suggested that some target compounds are promising as novel antifungal drugs.

Continuous Flow Synthesis of Terminal Epoxides from Ketones Using in Situ Generated Bromomethyl Lithium

A scalable procedure for the direct preparation of epoxides from ketones has been developed. The method is based on the carefully controlled generation of (bromomethyl)lithium (LiCH2Br) from inexpensive CH2Br2 and MeLi in a continuous flow reactor. The reaction has shown excellent selectivity for a variety of substrates, including α-chloroketones, which typically fail under classic Corey-Chaykovsky conditions. This advantage has been used to develop a novel route toward the drug fluconazole.