354-24-5

Basic information

• Product Name: CHLORODIFLUOROACETYL CHLORIDE
• Synonyms: chlorodifluoro-acetylchlorid;CHLORODIFLUOROACETYL CHLORIDE;Chlorodifluoroacetylchloride97%;Chlorodifluoroacetyl chloride (CDFAC);acetyl chloride, chlorodifluoro-
• CAS NO: 354-24-5
• Molecular Formula: C₂Cl₂F₂O
• Molecular Weight: 148.92
• EINECS: 206-551-5
• Mol File: 354-24-5.mol

Chemical Properties

• Boiling Point: 20 °C
• Appearance: Colorless volatile liquid with pungent odor.
• Density: 1.612 g/cm³
• Vapor Pressure: 627mmHg at 25°C
• Refractive Index: 1.378
• CAS DataBase Reference: CHLORODIFLUOROACETYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: CHLORODIFLUOROACETYL CHLORIDE(354-24-5)
• EPA Substance Registry System: CHLORODIFLUOROACETYL CHLORIDE(354-24-5)

Safety Data

• Hazard Codes: C
• Statements: 20-35-37
• Safety Statements: 9-26-36-45
• RIDADR: 3265
• HazardClass: CORROSIVE
• Hazardous Substances Data: 354-24-5(Hazardous Substances Data)

Usage

Uses

Chlorodifluoroacetyl Chloride is used as a chemical intermediate for the synthesis of various compounds, particularly in the fields of medicine and pesticides. Its applications can be categorized as follows:
Used in Pharmaceutical Industry:
Chlorodifluoroacetyl Chloride is used as a synthetic building block for the development of pharmaceutical compounds. Its reactivity allows for the creation of new molecules with potential therapeutic properties, contributing to the advancement of drug discovery and development.
Used in Pesticide Industry:
In the pesticide industry, Chlorodifluoroacetyl Chloride serves as a key intermediate in the production of various agrochemicals. Its derivatives are known to possess insecticidal, herbicidal, and fungicidal properties, making them valuable for crop protection and management of pests in agriculture.

InChI:InChI=1/C2Cl2F2O/c3-1(7)2(4,5)6

Upstream product

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• 76-11-9 1,1-difluorotetrachloroethane 
• 354-23-4 1,2-dichloro-1,2,2-trifluoroethane 
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• 76-04-0 2-chloro-2,2-difluoroacetic acid 

Downstream Products

• 652-73-3 2-chloro-1-(2,4-difluoro-phenyl)-2,2-difluoro-ethanone 
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• 7647-01-0 hydrogenchloride 
• 42518-98-9 5-chlorothiophene-2-carbonyl chloride 
• 76-04-0 2-chloro-2,2-difluoroacetic acid 
• 2063-17-4 4-chloro-4,4-difluoro-3-oxo-butyric acid ethyl ester 
• 131153-94-1 1-chloro-4-ethoxy-1,1-difluoro-3-buten-2-one 
• 359-13-7 difluoroethanol 
• 1300698-74-1 2,2-difluoroethyl 2,2-difluoroacetate 
• 478065-02-0 2-chloro-2,2-difluoro-1-(1H-indol-3-yl)ethan-1-one 

Relevant articles and documents

Synthesis, structure and conformational properties of fluoroformylchlorodifluoroacetyl disulfide, FC(O)SSC(O)CF2Cl: Conformational transferability in -C(O)SSC(O)- compounds

Pure fluoroformylchlorodifluoroacetyl disulfide, FC(O)SSC(O)CF 2Cl, has been prepared by the reaction of FC(O)SCl and CF 2ClC(O)SH in quantitative yield. The conformational properties of the novel molecule have been studied by vibrational spectroscopy (IR - gas phase, Raman - liquid phase) and quantum chemical calculations (B3LYP and MP2 methods). The gaseous compound exhibits a conformational equilibrium at room temperature where the most stable form adopts a C1 symmetry and a syn-periplanar (sp) orientation of both carbonyl groups with respect to the disulfide bond. A second form, observed in the IR spectrum of the vapor, corresponds to a conformer in which the carbonyl bond of the FC(O) moiety adopts an anti-periplanar (ap) position with respect to the S-S single bond, and gauche with respect to the ClC-C=O moiety in the chlorodifluoroacetyl group. The experimental free energy difference value ΔG0 = G 0(ap-sp) - G0(sp-sp) = 1.4(3) kcal/mol (IR) is reproduced well by the B3YLP/6-311+G(3df) (1.1 kcal/mol) and the MP2/6-31G* (1.8 kcal/mol) methods. In addition, the structure of a single-crystal, grown in situ, was determined by X-ray diffraction analysis at low temperature. The crystalline solid [monoclinic, P21/n, a = 5.579(3) A, b = 16.615(7), c = 8.455(4) A, β = 106.876(8)°] consists exclusively of molecules with the (sp-sp) conformation and the usual gauche orientation around the disulfide bond [φ(CS-SC) = 84.2°]. Conformational transferability is thus demonstrated once again for species that contain the -C(O)SSC(O)- group as part of a systematic program designed to analyze the behavior of this class of molecules. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

Chlorodifluoroacetyl isothiocyanate, ClF2CC(O)NCS: Preparation and structural and spectroscopic studies

Chlorodifluoroacetyl isothiocyanate, ClF2CC(O)NCS, was synthesized by the reaction of ClF2CC(O)Cl with an excess of AgNCS. The colorless product melts at -85 C, and its vapor pressure follows the equation ln p = -4471.1 (1/T) + 11.35 (p [atm], T [K]) in the range -38 to 22 C. The compound has been characterized by IR (gas phase, Ar matrix, and matrix photochemistry), by liquid Raman, by 19F and 13C NMR, gas UV-vis, and photoelectron spectroscopy (PES), by photoionization mass spectrometry (PIMS), and by gas electron diffraction (GED). The conformational properties of ClF2CC(O)NCS have been analyzed by joint application of vibrational spectroscopy, GED and quantum chemical calculations. The existence of two conformers has been detected in the gas and liquid phases, in which the C-Cl bond adopts a gauche orientation with respect to the C=O group; the C=O group is in syn- or anti-position with respect to the N=C double bond of the NCS group. The computed ΔG difference between these two gauche-syn and gauche-anti forms is ΔG = 0.63 kcal mol-1 in the B3LYP/6-31G(d) approximation. The most significant gas-phase structural parameters for gauche-syn ClF2CC(O)NCS are re(NC=S) 1.559(2) A, re(N=CS) 1.213(2) A, re(N-C) 1.399(7) A, re(C=O) 1.199(2) A, and ∠e(CNC) 134.7(13). Photolysis of ClF2CC(O)NCS using an ArF excimer laser (193 nm) mainly yields ClF2CNCS, CO, and ClC(O)CF2NCS. The valence electronic properties of the title compound were studied using PES and PIMS. The experimental first vertical ionization energy of 10.43 eV corresponds to the ejection primarily of the sulfur lone-pair electrons of the in-plane nonbonding orbital on the NCS group.

Gas phase structures of trifluoroacetyl chloride, CF3C(O)Cl, and chlorodifluoroacetyl chloride, CF2ClC(O)Cl

The geometric structures of trifluoroacetyl chloride, CF3C(O)Cl, and chlorodifluoroacetyl chloride, CF2ClC(O)Cl were determined by gas electron diffraction. The CF3 group in CF3C(O)Cl adopts an eclipsed orientation relative to the C=O double bond. In the predominant conformer of CF2ClC(O)Cl (93(3)%) the two chlorine atoms are gauche to each other (6(ClCCCl) = 75.4(10)°) with a small contribution of the trans form (Θ(ClCCCl) = 180°). The experimental geometric parameters are compared to those obtained by ab initio calculations.

Chlorodifluoroacetyl isocyanate, ClF2CC(O)NCO: Preparation and structural and spectroscopic studies

Chlorodifluoroacetyl isocyanate, ClF2CC(O)NCO, was prepared by the reaction of ClF2CC(O)Cl with excess of AgNCO. The colorless compound melts at -83 °C and the vapor pressure follows the equation ln p = -3868.3 (1/T) + 10.89 (p [Atm], T [K]) in the range -38 to +22 °C, extrapolated bp ca. 82 °C. It has been characterized by IR (gas phase, Ar matrix), liquid Raman, 19F and 13C NMR, gas UV-vis spectrum, photoelectron spectroscopy (PES), photoionization mass spectrometry (PIMS), and gas electron diffraction (GED). The matrix photochemistry has been studied and the conformational properties of ClF2CC(O)NCO have been analyzed by joint application of vibrational spectroscopy, GED, and quantum chemical calculations. Two conformers were detected in gaseous and liquid phases, in which the C-Cl bond adopts a gauche orientation with respect to the C=O group, whereas this group can be in syn or anti orientation with respect to the N=C bond of the NCO group. An enthalpy difference δHexp° = 1.3 ± 0.2 kcal mol-1 between the most stable syn-gauche and the less stable anti-gauche form was derived using the van't Hoff equation, which is in reasonable agreement with the computed difference of δH° = 0.8 kcal mol-1 (B3LYP/6-311+G(3df) approximation). The most significant gas phase structural parameters for gauche-syn ClF2CC(O)NCO are re(NC=O) = 1.157(1) A, re(N=CO) = 1.218(1) A, re(N-C) = 1.378(9) A, re(C=O) = 1.195(1) A,e(CNC) = 128.6(19)°. Photolysis of ClF 2CC(O)NCO using an ArF excimer laser (193 nm) mainly yield ClF 2CNCO along with some ClF2CC(O)N nitrene. The valence electronic properties of the title compound were studied using the PES and PIMS. The experimental first vertical ionization energy of 11.54 eV corresponds to the ejection of a carbonylic oxygen lone pair electron.

Chlorodifluoroacetyl azide, ClF2CC(O)N3: Preparation, properties, and decomposition

Chlorodifluoroacetyl azide, ClF2CC(O)N3, was prepared and characterized by IR (gas, Ar matrix), Raman (liquid), UV-vis (gas), and 19F, 13C NMR spectroscopy. The vibrational spectra were analyzed in terms of a single conformer, gauche-syn, where the Cl-C and the Nα=Nβ bonds are gauche and syn to the C=O bond, respectively. The photo and thermal decomposition reactions of the azide were studied with the aid of matrix isolation. In both cases, a new isocyanate species ClF2CNCO was produced and characterized by matrix IR spectroscopy. The conformational properties and the Curtius rearrangement pathways of this new carbonyl azide were theoretically explored, which suggest the preference of a concerted over stepwise decomposition for the global minimum gauche-syn conformer.

Synthesis of 2-(Chlorodifluoromethyl)indoles for Nucleophilic Halogen Exchange with [18F]Fluoride

The synthesis of 2-[18F]trifluoromethylated indoles from the corresponding chlorodifluoromethyl precursors was found to proceed under milder conditions when compared to known metal-free nucleophilic exchange reactions with [18F]fluoride on chlorodifluoro-methyl arenes. A key element in the reaction course is – most likely – a favorable elimination-addition mechanism on the 2-methyl position of the indole. Given the increasing interest in 18F-labelled compounds, this single step labeling methodology nicely complements the so far existing routes to 2-[18F]trifluoromethylated indoles.

Photooxidation preparation method of haloacetyl chloride

The invention discloses a photooxidation preparation method of haloacetyl chloride. The halogenated alkane is mixed with an oxygen source and vaporized, and then the materials are introduced into a reactor for photooxidation to obtain haloacetyl chloride, the photooxidation reaction temperature is 5 to 60 DEG C, the stay time of the material is 1 to 50 s, and the molar ratio of the oxygen source to the halogenated alkane is 0.1 to 5:1, a quartz cold trap is arranged in the reactor, and the quartz cold trap is composed of a quartz inner shell and a quartz outer shell, a light source is arrangedin the quartz inner shell, and a double-layer cold trap jacket is formed between the quartz inner shell and the quartz outer shell, and the double-layer cold trap jacket is filled with circularly flowed filter liquid, and the filter liquid filters out ultraviolet light generated by the light source in a wavelength band of less than 300 nm. The method has the advantages of simple process, high yield, safety and environmental protection, and continuous operation.

Synthesis production process of difluorochloroacetic acid

The invention discloses a synthesis production process of difluorochloroacetic acid, comprising the following steps: charging sulfur trioxide with nitrogen gas into an oxidation reaction kettle by an intermittent process, starting stirring; after reaching a certain temperature, adding difluorotetrachloroethane and catalyst according to a predetermined ratio into the oxidation reaction kettle; heating for reaction, observing the backflow condition, starting steaming the byproduct sulfuric chloride when the kettle temperature rises to a certain temperature while the backflow is small; after steaming the byproduct sulfuric chloride, carrying out charging for the second time; carrying out three-stage spray hydrolysis and absorption on the product difluorochloracetyl chloride to generate crude product difluorochloroacetic acid, and carrying out defluorination and rectification on the crude product to obtain finished product difluorochloroacetic acid. The synthesis production process of difluorochloroacetic acid disclosed by the invention adopts the difluorotetrachloroethane as a raw material, the finished product difluorochloroacetic acid is prepared by oxidation reaction, the preparation process has reasonable design, high absorption rate, high overall yield and low energy consumption; and the byproduct can be hydrolyzed and reused, so that the production process is clean, environment-friendly, safe and reliable.

DISTILLATION PROCESS COMPRISING AT LEAST TWO DISTILLATION STEPS TO OBTAIN PURIFIED HALOGENATED CARBOXYLIC ACID HALIDE, AND USE OF THE PURIFIED HALOGENATED CARBOXYLIC ACID HALIDE

The present invention concerns a process for the production of a fluorinated carboxylic halide having a reduced content of impurities, a fraction of the fluorinated carboxylic halide having a reduced content of impurities, and its use in the manufacture of agriculturally and pharmaceutically active compounds or their intermediates.

HALOGENATION PROCESS OF 1,1-DIHALOETHENE

The present invention concerns a halogenation process, in which a 1,1- dihaloethene CX2=CH2 (I) with at least one halogenation agent. The invention concerns further a process for the manufacture of chlorodifluoroacetic acid chloride (CDFAC), which comprise the steps of (a) chlorination of VF2, and (b) an oxidation process. Another object of the present invention is a process for the manufacture of agriculturally or pharmaceutically active compounds, comprising the halogenation and/or oxidation process.