2257-35-4

Usage

Uses

Used in Pharmaceutical Industry:
Trichloroacrylic acid is used as a raw material for the production of pharmaceuticals, contributing to the synthesis of various medicinal compounds due to its strong acidic properties and reactivity in organic synthesis.
Used in Pesticide and Herbicide Production:
In the agricultural sector, TCAA is employed as a key component in the manufacturing of pesticides and herbicides, enhancing their effectiveness in controlling pests and unwanted plant growth.
Used in Organic Synthesis:
Trichloroacrylic acid serves as a reagent in organic synthesis, facilitating the formation of desired chemical products through its participation in various reaction mechanisms.
Used as a Catalyst in Chemical Reactions:
TCAA is utilized as a catalyst to accelerate chemical reactions, improving the efficiency and speed of processes in the chemical industry.
Given the potential hazards associated with TCAA, it is imperative that it is handled with care and that appropriate safety measures are implemented in all applications.

InChI:InChI=1/C3HCl3O2/c4-1(2(5)6)3(7)8/h(H,7,8)

Upstream product

• 20599-54-6 3H,4H-hexachloro-hexa-1,3t,5-triene 
• 3787-28-8 trichloro-acrylaldehyde 
• 29030-84-0 1,1,2,3,3,4,4,5,6,6-decachloro-hexa-1,5-diene 
• 50565-69-0 hexachloro-cyclopentane-1,3-dione 
• 3047-66-3 trichloro-acrylic acid ethyl ester 
• 1888-71-7 perchloropropene 
• 34947-89-2 octachloro-pent-1-en-3-one 
• 13340-11-9 1,1,1,3,4,4-hexachloro-but-3-en-2-one 
• 55108-38-8 3,4,4-Trichloro-2-nitro-but-3-enoic acid 
• 127-18-4 1,1,2,2-tetrachloroethylene 
• 3875-85-2 tetrachlorosuccinic acid 
• 7664-93-9 sulfuric acid 
• 7697-37-2 nitric acid 
• 949462-28-6 2-(2,3,3-trichloro-1-nitroallylidene)-1,3-dimethyl-imidazolidine 

Downstream Products

• 3880-18-0 trichloro-acrylic acid amide 
• 815-58-7 2,3,3-trichloroacryloyl chloride 
• 24598-45-6 2,2,3,3,3-pentachloropropanoic acid 
• 63979-42-0 trichloroacryloyl-urea 
• 802294-64-0 propionic acid 
• 1101891-14-8 N-(4-(3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl)phenyl)-2,3,3-trichloroacrylamide 
• 80460-18-0 4-chloro-2-nitroanilide of α,β,β-trichloroacrylic acid 

Relevant academic research and scientific papers

Chemistry of polyhalogenated nitrobutadienes, part 5: Synthesis and reactions of dichloromethyl nitrovinylidene ketones of heterocycles

An easy access to dichloromethyl nitrovinylidene ketones of five-membered heterocycles is presented starting from nitroperchlorobutadiene. These complex ketones are valuable starting materials for novel product structures in versatile reactions such as selective reductions, substitutions to give α-nitroacryl cyanides, fragmentations by means of an alkoxide, as well as ring-cleavage/ring-closure steps by the action of hydrazine. Some of the products show biological activity in crop protection. Georg Thieme Verlag Stuttgart.

Reaction of the OH Radical with Tetrachloroethene and Trichloroacetaldehyde (Hydrate) in Oxygen-free Aqueous Solution

Hydroxyl radicals are generated radiolytically in NO2-saturated aqueous solutions and are reacted with either tetrachloroethene or trichloroacetaldehyde hydrate.The primary products after irradiation are tetrachlorosuccinic acid (G = 2.3*10-7 mol J-1 and 2.7*10-7 mol J-1, respectively) and chloride ions (G = 11.6*10-7 mol J-1 and 7.3*10-7 mol J-1, respectively).The former decomposes into trichloroacrylic acid and carbon dioxide (Ea = 115 kJ mol-1).From tetrachloroethene some dichloroacetic acid is also formed (G = 0.2*10-7 mol J-1).Trichloroacetic acid is not among the products.Kinetic studies were carried out by pulse radiolysis.In the case of trichloroacetaldehyde hydrate there is a jump in conductivity increase of G(H+) ca. 2*G((OH(radical)) within not greater than 5 μs and no further increase in conductivity at later times.It is concluded that the OH-radicals abstract the carbon-bound H-atom and the resulting CCl3C(OH)2 radicals rapidly eliminate HCl forming CCl2CO2H radicals which dissociate and dimerize yielding tetrachlorosuccinic acid.In the case of the reaction of the OH-radical with tetrachloroethene the conductivity build-up is biphasic.In the first step one equivalent H+ is formed when the primary CCl2CCl2OH radical eliminates HCl yielding the CCl2C(O)Cl radical (k > 7*105 s-1).Upon dimerization (2 k = 6.9*108 dm3 mol-1 s-1) Cl(O)CCCl2CCl2C(O)Cl is formed which hydrolyses (k = 5 s-1).Only one conductivity equivalent is liberated, and it is concluded that the ensuing monoanion rapidly eliminates a chlorine ion (no conductivity change) yielding tetrachlorosuccinic anhydride.It subsequently hydrolyses at a later stage, not resolved by pulse radiolysis, to tetrachlorosuccinic acid.