107873-03-0

Basic information

• Product Name: 2,2-DIFLUOROCYCLOPROPANECARBOXYLIC ACID
• Synonyms: 2,2-DIFLUOROCYCLOPROPANECARBOXYLIC ACID;Cyclopropanecarboxylic acid, 2,2-difluoro- (9CI);2,2-Difluorocyclopropanecarboxylic acid, GC 97%;2,2-DIFLUOROCYCLOPROPANECARBOXYLIC ACID, 90% TECH;2,2-difluorocyclopropane-1-carboxylic acid;2-Carboxy-1,1-difluorocyclopropane;Cyclopropanecarboxylic acid, 2,2-difluoro-;2,2-Difluorocyclopropanecarboxylic acid 97%
• CAS NO: 107873-03-0
• Molecular Formula: C₄H₄F₂O₂
• Molecular Weight: 122.07
• Product Categories: CARBOXYLICACID;C1 to C5;Carbonyl Compounds;Carboxylic Acids
• Mol File: 107873-03-0.mol

Chemical Properties

• Melting Point: 55-60°C
• Boiling Point: 70°C 7mm
• Flash Point: 70°C/7mm
• Appearance: /
• Density: 1.527g/cm³
• Vapor Pressure: 0.264mmHg at 25°C
• Refractive Index: 1.409
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 3.22±0.22(Predicted)
• Water Solubility: Soluble in water.
• CAS DataBase Reference: 2,2-DIFLUOROCYCLOPROPANECARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-DIFLUOROCYCLOPROPANECARBOXYLIC ACID(107873-03-0)
• EPA Substance Registry System: 2,2-DIFLUOROCYCLOPROPANECARBOXYLIC ACID(107873-03-0)

Safety Data

• Hazard Codes: C,Xi
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: 3265
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 107873-03-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,2-Difluorocyclopropanecarboxylic acid is used as an intermediate for the synthesis of various pharmaceutical compounds. Its unique structure and reactivity allow for the development of novel drugs with improved properties, such as enhanced bioavailability and selectivity.
Used in Chemical Synthesis:
In the field of chemical synthesis, 2,2-difluorocyclopropanecarboxylic acid is used as a versatile building block for the creation of a wide range of organic compounds. Its ability to participate in various chemical reactions, such as Friedel-Crafts reactions, enables the preparation of aryl 2,2-difluorocyclopropyl ketones and other valuable compounds.
Used in Friedel-Crafts Reactions:
2,2-Difluorocyclopropanecarboxylic acid is used as a reagent in Friedel-Crafts reactions with various arenes to prepare aryl 2,2-difluorocyclopropyl ketones. These reactions are important in the synthesis of complex organic molecules, particularly in the field of pharmaceuticals and materials science. The introduction of the 2,2-difluorocyclopropyl group can significantly alter the properties of the resulting compounds, making them more stable or bioavailable.

InChI:InChI=1/C4H4F2O2/c5-4(6)1-2(4)3(7)8/h2H,1H2,(H,7,8)

Upstream product

• 694-34-8 1,1-difluoro-2-vinylcyclopropane 
• 260352-79-2 2,2-difluorocyclopropanecarboxylic acid butyl ester 

Downstream Products

• 1005784-96-2 N-{5-[(2-{[(2,2-difluorocyclopropyl)carbonyl]amino}imidazo[1,2-b]pyridazin-6-yl)oxy]-2-methylphenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamide 
• 1382838-23-4 2,2-difluoro-N-(7-(5-fluoro-2-methylphenyl)isoquinolin-3-yl)cyclopropanecarboxamide 
• 1883301-82-3 (1R)-2,2-difluorocyclopropanecarboxylic acid 
• 1333213-87-8 7-(2-chloro-5-methylphenylamine)-N-(2,2-difluorocyclopropylcarbamoyl)-6-[4-(4-fluorophenyl)piperidine-1-carbonyl]pyrazolo[1,5-a]pyrimidine-3-sulfonamide 
• 1610051-22-3 phenyl 2,2-difluorocyclopropanecarboxylate 
• 1374342-35-4 [4-(4-bromophenyl)piperazin-1-yl](2,2-difluorocyclopropyl)methanone 
• 1374342-34-3 [4-(4-bromophenyl)piperazin-1-yl](2,2-difluorocyclopropyl)methanone 
• 1426449-92-4 5-(2,2-difluorocyclopropyl)-3-(2,4-dimethyl-5-nitrophenyl)-1,2,4-oxadiazole 
• 1426448-55-6 N-{5-[5-(2,2-difluorocyclopropyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl}imidazo[1,2-a]pyridine-3-carboxamide 
• 1032187-46-4 N-((R)-2-(5-chloropyridin-2-yl)-2-(3-fluoro-5-(2,2,3,3-tetrafluoropropyl)phenyl)-3-phenylpropyl)-2,2-difluorocyclopropanecarboxamide 
• 1163794-04-4 4-{(S)-2-({5-[2-((S)-2-cyclobutylcarbamoyl-pyrrolidin-1-yl)-2-oxo-ethoxy]-1-phenyl-1H-pyrazole-3-carbonyl}-amino)-4-[(2,2-difluoro-cyclopropanecarbonyl)-amino]-butyryl}-piperazine-1-carboxylic acid ethyl ester 
• 1092391-64-4 N-{5-[(2-{[(2,2-difluorocyclopropyl)carbonyl]amino}[1,2,4]triazolo[1,5-a]pyridin-6-yl)oxy]-2-fluorophenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamide 

Relevant articles and documents

Competitive kinetic processes in the thermal rearrangement of 1,1-difluoro-2-(dideuteriomethylene)-cyclopropane

The synthesis of 1,1-difluoro-2-(dideuteriomethylene)-cyclopropane is reported along with the kinetics of its competing, reversible, first order rearrangements: (a) the degenerate rearrangement to 1,1-difluoro-3,3-dideuterio- 2-methylene-cyclopropane, and

PREPARATION OF A PYRIMIDINYL-3,8-DIAZABICYCLO[3.2.1]OCTANYLMETHANONE DERIVATIVE AND SALT THEREOF

Methods for preparing ((S)-2,2-difluorocyclopropyl)-((1R,5S)-3-(2-((1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)-3,8-diazabicyclo[3.2.1]-octan-8-yl)methanone and intermediates used in the processes of preparation thereof.

Large-Scale Cyclopropanation of Butyl Acrylate with Difluorocarbene and Classical Resolution of a Key Fluorinated Building Block

To address challenges in the preparation of a key building block containing a difluorocyclopropane moiety, we have developed a new protocol for difluorocarbene generation that relies on a Krapcho-type dealkylation of ethyl bromodifluoroacetate (EBDFA), an inexpensive and readily available fluorinated feedstock. Application of DoE and kinetic modeling was used to understand key reaction parameters and identify an optimal process. We report two variants of this procedure that offer different processing advantages and that have both been scaled successfully multiple times to deliver hundreds of kilograms of the resulting difluorocyclopropane. To access a single enantiomer of the target compound, we have also developed a classical resolution strategy and recycling protocol for the undesired enantiomer to replace previous chromatographic methods for separation.

Transition Metal-free gem-difluorocyclopropanation of Alkenes with CF3SiMe3?NaI System: a Recipe for Electron-deficient Substrates

Reaction of various electron-deficient alkenes, as well as functionalized styrene derivatives with CF3SiMe3?NaI system is studied. Relative reactivity of the substrates is established. It is shown that many α,β-unsaturated esters can

PYRIMIDINE AND TRIAZINE DERIVATIVES AND THEIR USE AS AXL INHIBITORS

Compounds of the general formula(I): (I) processes for the preparation of these compounds, compositions containing these compounds, and the uses of these compounds.

Friedel-Crafts reactions of 2,2-difluorocyclopropanecarbonyl chloride: Unexpected ring-opening chemistry

The Friedel-Crafts reactions of 2,2-difluorocyclopropanecarbonyl chloride with various arenes did not lead to the straightforward formation of the expected aryl 2,2-difluorocyclopropyl ketones. Instead the reactions proceeded, to various degrees depending on the reactivity of the arene, via an apparent rearrangement of the initially formed acylium ion to form novel aryl 3-chloro-3,3-difluoropropyl ketones. The ring-opened product was formed exclusively, and therefore the reaction may be synthetically useful when relatively unreactive arene substrates such as benzene, toluene, and p-xylene are used. No conditions were found where ring-intact products could be formed exclusively when using substituted benzenes as substrates, with the very reactive substrate thiophene being most selective in that regard, favoring ring intact product 3 with a selectivity of 98:2. The regioselectivity of ring-opening was examined and compared with other related systems computationally.

Fungicides which are N-pyridyl-cyclopropane carboxamides or derivatives thereof

Compounds of having the general formula (I): STR1 and stereoisomers thereof, wherein R1 is hydrogen, halogen, C1-4 alkoxy, C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl, C1-4 haloalkyl, C1-4 haloalkoxy, COR or cyano; R2, R3 and R4 are independently hydrogen, halogen or methyl, provided that R2, R3 and R4 are not all hydrogen and provided that when one of them is methyl then at least one of the other two is not hydrogen; STR2 wherein R5 is hydrogen, C1-4 alkyl (optionally substituted by hydrogen or cyano), optionally substituted benzyl, C2-4 alkenyl, C2-4 alkynyl, cyano, COR, C1-4 thioalkoxy, C1-4 thiohaloalkoxy or SNR7 R8 ; R7 and R8 are independently C1-4 alkyl or CO2 R; Y is oxygen or sulphur; R6 is C1-4 alkoxy, C1-4 thioalkoxy or --NR9 R10 ; and R9 and R10 are independently hydrogen, C1-4 alkyl, aryl or aralkyl or R9 and R10 join to form an optionally substituted heterocyclic ring and R is C1-4 alkyl or C3-7 cycloalkyl . These compounds are fungicidally active.

Fluorinated cyclopropanecarboxylic acids and their derivatives

The addition of halofluorocarbenes such as :CF2, :CClF or :CBrF, generated from the appropriate halofluoromethanes with bases, to butadiene or isoprene gives the corresponding l-vinyl substituted halofluorocyclopropanes in moderate to good yield. The vinyl group facilitates the carbene addition and permits a subsequent wide derivatisation. Several transformations including hydroboration, oxidation and Curtius degradation are presented. Furthermore, replacement of the chlorine atom in 2-chloro-2-fluorocyclopropanecarboxylic acid derivatives by hydrogen is achieved catalytically with Raney nickel. This sequence provides a convenient route to mono-fluorine substituted cyclopropane carboxylic acids.