61925-88-0

Usage

Uses

Used in Pesticide Industry:
2,3,5-Trichlorophenol acetate is used as a fungicide, insecticide, and herbicide for controlling pests and unwanted plant growth in agricultural settings. Its chemical properties allow it to effectively target and eliminate a wide range of pests, contributing to improved crop yields and protection against diseases.
Used in Chemical Production:
2,3,5-Trichlorophenol acetate serves as an important intermediate in the synthesis of other chemicals, including pharmaceuticals, dyes, and plastics. Its versatile chemical structure makes it a valuable building block in the development of various industrial products.

InChI:InChI=1/C8H5Cl3O2/c1-4(12)13-7-3-5(9)2-6(10)8(7)11/h2-3H,1H3

Upstream product

• 60386-78-9 4-chloro-2-nitrophenyl acetate 
• 100414-67-3 2,3,5-trichlorophenoxide ion 
• 933-78-8 2,3,5-trichlorophenol 
• 108-24-7 acetic anhydride 
• 830-03-5 4-nitrophenol acetate 
• 4232-27-3 2,4-dinitrophenyl acetate 
• 64-19-7 acetic acid 
• 58200-72-9 potassium salt of 2,3,5-trichlorophenol 

Downstream Products

• 108-24-7 acetic anhydride 
• 58200-72-9 potassium salt of 2,3,5-trichlorophenol 
• 1119-49-9 N-butylacetamide 
• 933-78-8 2,3,5-trichlorophenol 
• 64-19-7 acetic acid 

Relevant academic research and scientific papers

Binding Affinities and Spectroscopy of Complexes Formed by Polysiloxanes with Aniline and Chlorophenol Acetates

Abstract: The theoretical binding energies of the complexes formed by polysiloxanes with aniline and chlorophenol acetates were calculated at B3LYP/6-31G(d, p) level after the basis set superposition error (BSSE) based on B3LYP/6-31G(d) optimized geometri

Effective charge development in the transfer of the acetyl group between nucleophiles in acetonitrile solution: Acetolysis and butylaminolysis of substituted phenyl esters

Equilibrium and rate constants have been measured for the phenolyses of acetic anhydride in acetonitrile solution. Acetolysis of substituted phenyl acetates by acetate ion possesses a Bronsted βlg value of -1.50 which, together with a βeq value of 2.86, indicates substantial fission of the C-OAr bond in the transition structure. The value of βeq is employed to identify the rate-limiting steps in aminolyses in acetonitrile. Butylaminolysis of substituted phenyl acetates in acetonitrile solution yields amide and substituted phenolate anion and the kinetics obey the general rate law: Rate = k1[ester][amine] + k2[ester][amine]2 + k3[ester][amine][18-crown-6] Free energy plots of log k1 and log k2 exhibit breaks near pKaArOH values of 9 and 8, respectively, and these can be interpreted by a mechanism which involves a common zwitterionic adduct T±, which partitions to give the product by two routes: A involving direct expulsion of the phenolate ion leaving group (k1 parameter) and B involving proton transfer prior to phenolate ion expulsion (k2 parameter). The formation of T± is rate-limiting for the A path and C-OAr bond fission is rate-limiting for the B mechanism.

Kinetics and Equilibria of Reactions between Acetic Anhydride and Substituted Phenolate Ions in Aqueous and Chlorobenzene Solutions

Potassium acetate, solubilised in chlorobenzene by 18-crown-6, displaces the phenolate ion from substituted phenyl acetates by a second-order (kCl-2) process.Potassium phenolate ions, under similar conditions, react with acetic anhydride via a second order (kCl2) to yield the phenyl acetate.The concentration of the crown does not affect the reactivity unless it is not sufficient to solubilise the reactants.The rate constants correlate with the ionisation of the substituted phenols in water: log kCl2=1.60+/-0.23pKArOH(aq)a - 9.06+/-1.4 log kCl-2=-0.97+/-0.12pKArOH(aq)a + 4.78+/-0.78.The equilibrium constant for transfer of the acetyl group between phenolate ions and acetic anhydride in chlorobenzene has a Broensted βCleq of 2.6 measured against pKArOH(aq)a.The second-order rate constants (k2aq) have been measured for the reaction of substituted phenolate ions with acetic anhydride in water and they obey the Broensted equation: log (k2aq) = 0.56 +/- 0.06 pKArOH(aq)a - 2.52 +/- 0.51 Comparison of the value of the Broensted exponent for the equilibrium constant in chlorobenzene (β = 2.6) compared with that for aqueous solution (β = 1.7) indicates a greater development of effective charge consistent with the weaker solvating power of chlorobenzene.The reaction of substituted phenoxide ion with acetic anhydride has a Leffler α value of 0.33 and 0.62 for aqueous and chlorobenzene solutions, respectively, indicating a more advanced bond formation in the transition state of the reaction in the latter solvent even though the reactions in chlorobenzene are faster than in water.

Structure-reactivity correlations for reactions of substituted phenolate anions with acetate and formate esters

The reactions of substituted phenolate anions with m-nitrophenyl, p-nitrophenyl, and 3,4-dinitrophenyl formates follow nonlinear Br?nsted-type correlations that might be taken as evidence for a change in the rate-limiting step of a reaction that proceeds through a tetrahedral addition intermediate. However, the correlation actually represents two different Br?nsted lines that are defined by meta- and para-substituted phenolate anions and by meta- and para-substituted o-chlorophenolate anions. A concerted mechanism for both acetyl- and formyl-transfer reactions is supported by the absence of a detectable change in the Br?nsted slope at ΔpK = 0 for the attacking and leaving phenolate anions within each class of Br?nsted correlations. Regular increases in the dependence of log k on the pKa of the nucleophile with increasing pKa of the leaving group correspond to a positive interaction coefficient pxy = ?β1g/?(pKnuc) = ?βnuc/?(pK1g). The observation of two different Br?nsted lines for the reactions of substituted phenolate anions with phenyl acetates is attributed to a steric effect that decreases the rate of reaction of substituted o-chlorophenolate anions by 25-50%. The reactions of meta- and para-substituted phenolate and o-chlorophenolate anions with substituted phenyl acetate esters follow values of βnuc = 0.53-0.66 and -β1g = 0.50-0.63. The reactions of meta- and para-substituted phenolate anions with formate esters are ～ 103 times faster and follow smaller values of βnuc = 0.43-0.64 and -β1g = 0.31-0.48. However, the reactions of meta- and para-substituted o-chlorophenolate anions with the same formate esters follow larger values of βnuc = 0.63-0.90 and -β1g = 0.46-0.90. The large values of βnuc and -β1g for the reactions of substituted o-chlorophenolate anions with formate esters may arise from destabilization by the o-chloro group of a stacking interaction that is present in the transition state for reactions of formate esters, but not acetate esters.

An Open Transition State in Carbonyl Acyl Group Transfer in Aqueous Solution

The second-order rate constants have been measured for the reaction of substituted phenolate ions with 2,4-dinitrophenyl acetate, 2,4-dinitrophenyl 4-methoxy-2,6-dimethylbenzoate and acetic anhydride in aqueous solution at 25 deg C.The data are over a wide range of phenolate ion basicity and obey good Broensted equations which have βnuc values of, respectively, 0.57 +/- 0.03, 0.15 +/- 0.07 and 0.59 +/- 0.05.The principal conclusion of this work is that the identity reaction of 2,4-dinitrophenolate ion with 2,4-dinitrophenyl 4-methoxy-2,6-dimethylbenzoate has anopen transition state, namely one with very weak bonds to entering and departing ligands.The transition state possesses a Kreevoy tightness parameter (τ) of 0.18.The open transition state arises from the stabilising effect of the acyl group substituents on the benzoylium ion and their destabilising effect on the putative tetrahedral intermediate as well as the weak basicities of the nucleophile and nucleofuge.This is the first example of an open transition state in an acyl group transfer which does not require the assistance of a negatively charged internal nucleophile.The data for 2,4-dinitrophenyl acetate may be employed to calculate an identity rate constant (kii) for the reaction of 2,4-dinitrophenolate ion with the ester.This data may be fitted to a theoretical Lewis-Kreevoy plot (log kii vs. pKi) possessing both positive and negative values of βii (slope of the line).Microscopic medium effects place a limit to the accuracy of predictions of rate constants, including kii, from linear free energy relationships.

Reductive Dechlorination of Chloro-phenols and -benzoic acids by Raney Co-Al Alloy in an Alkaline Deuterium Oxide Solution and Preparation of Deuterated Salicylic Acids

Reduction of monochloro-phenols (1a-c) and -benzoic acids (3a-c) by using Raney Co-Al alloy in 10percent NaOD-D2O gave phenols (2a-c) and benzoic acids (4a-c) in 86-93percent isotopic purities.The reduction of di-, tri-, and tetra-chlorinated derivatives, (1) and (3), gave the deuteriated products, (2) and (4), in somewhat low isotopic purities (70-84percent).In the reduction of polychlorinated benzoic acids (3), the use of a mixed solution (1/1 = v/v) of 10percent Na2CO3-D2O and 10percent NaOD-D2O was effective and gave 4 in 80-89percent isotopic purities.The treatment of chlorosalicylic acids (5) with Raney Co-Al alloy in 10percent NaOD-D2O gave 1> (6) - 3> (6) in 91-93percent isotopic purities.

Concerted Acetyl Group Transfer between Substituted Phenolate Ion Nucleophiles: Variation of Transition-State Structure as a Function of Substituent

Second-order rate constants (kArO) have been measured for the concerted displacement of aryl oxide from aryl acetates in aqueous solution by substituted phenoxide ions.Values of kArO obey linear Bronsted correlations when either the leaving group or the attacking phenolate ion structures are varied.The Bronsted coefficients obey the equations βnuc = 0.20pK1g - 0.68 and β1g = 0.15pKnuc - 1.73 to a good degree of precision, and the variation indicates that the structure of the transition-state changes within the range of phenolate ions studied; this alsoprovides confirmation that a concerted mechanism operates.The equations for βnuc and β1g predict the equation (log kii = 0.17pKa2 - 2.41pKa + C) for kii, the rate constant for the reaction of aryl oxide ion with acetates bearing identical aryl oxide leaving groups.The identity rate constants may be interpolated from the observed rate constants (kArO) and exhibit excellent fit to the above equation with the single disposable parameter, C, set at 6.5.This is the first report of curvature in a Bronsted plot of identity rate constants.Effective charge development and loss on leaving and attacking oxyanions is fully balanced in the transition state when entering and leaving nucleophiles have a pKa of 7.1.Tetrahedral or acylium ion-like transition-state structures are predicted for hypothetical phenols with pKa's of 11.7 and 2.0, respectively.

Concertedness in Acyl Group Transfer in Solution: A Single Transition State in Acetyl Group Transfer between Phenolate Ion Nucleophiles

Rate constants have been measured for nucleophilic substitution of 4-nitrophenol from 4-nitrophenyl acetate by a series of phenolate anions.The Bronsted type plot is linear for unhindered phenolate ions with pKa values significantly above and below that of the displaced 4-nitrophenol: (log kArO = 0.75pKArOH - 7.28; n = 17, r = 0.984); this is consistent with a mechanism involving a single transition state or a mechanism with an intermediate that has a very low barrier to decomposition.A small change in effective charge on the carbonyl group from reactant to transition state (measured from βnuc and the known βeq for the overall reaction) points to an almost coupled concerted mechanism for the transfer of acetyl function between phenolate ion nucleophiles.The conclusions of this work are consistent with previous results that indicate relatively stable tetrahedral intermedates in reactions at reactive acyl centers; a spectrum of mechanisms exists for substitution reactions of acyl functions in solution that ranges from SN1 (or ElcB for an ester with an α-carbanion) through concerted to BAc2.