24573-38-4

Basic information

• Product Name: 4-chlorophenolate
• Synonyms: 4-chlorophenolate
• CAS NO: 24573-38-4
• Molecular Weight: 127.55
• Mol File: 24573-38-4.mol

Chemical Properties

• CAS DataBase Reference: 4-chlorophenolate(CAS DataBase Reference)
• NIST Chemistry Reference: 4-chlorophenolate(24573-38-4)
• EPA Substance Registry System: 4-chlorophenolate(24573-38-4)

Safety Data

• Hazardous Substances Data: 24573-38-4(Hazardous Substances Data)

Upstream product

• 83491-06-9 4-chlorophenyl dodecanoate 
• 110-86-1 pyridine 
• 135263-40-0 4-chlorophenyl bis(4-methoxyphenyl) phosphate 
• 288-32-4 1H-imidazole 
• 876-27-7 4-chlorophenyl acetate 
• 16984-48-8 fluoride 
• 21713-55-3 O-4-chlorophenyl diphenylphosphinate 
• 67-56-1 methanol 
• 73789-34-1 cinnamic acid 4-chlorophenyl ester 
• 124-40-3 dimethyl amine 
• 128886-84-0 p-Chlorophenyl p-nitrobenzenesulphonate 
• 74104-89-5 p-nitrophenyl picolinate 
• 6317-27-7 p-chlorophenyl mesylate 
• 110-89-4 piperidine 

Downstream Products

• 876-27-7 4-chlorophenyl acetate 
• 16554-54-4 3-nitrophenolate anion 
• 79456-21-6 1-(4-Chlorophenoxy)-3-methyl-4-isoquinoline Acetic Acid 
• 102690-38-0 (2S,3S)-2-tert-Butyl-3-(4-chloro-phenoxy)-oxirane 
• 56961-58-1 4-chlorophenyl diphenyl phosphate 
• 20350-26-9 2,4-dinitrophenolate 
• 288-32-4 1H-imidazole 
• 5076-63-1 (4-chlorophenyl)diethyl phosphate 
• 106-48-9 4-chloro-phenol 
• 1988-22-3 4-chlorophenyl formate 
• 60154-37-2 3,4-dinitrophenoxide ion 
• 6961-42-8 4-chlorophenyl 4-chlorobenzoate 
• 14609-74-6 p-nitrophenolate 
• 32792-59-9 4-cyano-benzoic acid-(4-chloro-phenyl ester) 

Relevant articles and documents

Kinetic study on aminolysis of aryl X-substituted-cinnamates in acetonitrile: Differential medium effect determines reactivity and reaction mechanism

A kinetic study on nucleophilic substitution reactions of 2,4-dinitrophenyl X-substituted-cinnamates (1a-1f) and Y-substituted-phenyl cinnamates (2a-2g) with a series of alicyclic secondary amines in MeCN at 25.0 ± 0.1 °C is reported. The Br?nsted-type pl

Kinetic study on alkaline hydrolysis of Y-substituted phenyl picolinates: Effects of modification of nonleaving group from benzoyl to picolinyl on reactivity and reaction mechanism

Second-order rate constants (kOH-) for alkaline hydrolysis of Y-substituted phenyl picolinates (6a-6i) have been measured spectrophotometrically. A linear Bronsted-type plot is obtained with βlg = -0.34, which is typical for reactions reported previously to proceed through a stepwise mechanism with formation of an addition intermediate being the rate-determining step (RDS). However, σYo constants result in a much poorer Hammett correlation than σY- constants. Furthermore, the Yukawa-Tsuno plot exhibits an excellent linear correlation with ρY = 0.82 and r = 0.72, indicating that a negative charge develops partially on the O atom of the leaving group in the RDS. Thus, the reactions have been concluded to proceed through a forced concerted mechanism with a highly unstable intermediate 7. Comparison of the current kinetic data with those reported previously for the corresponding reactions of Y-substituted phenyl benzoates has revealed that modification of the nonleaving group from benzoyl to picolinyl causes not only an increase in reactivity but also a change in the reaction mechanism (i.e., from a stepwise mechanism to a forced concerted pathway).

Kinetic study on alkaline hydrolysis of Y-substituted phenyl X-substituted benzenesulfonates: Effects of changing nucleophile from azide to hydroxide ion on reactivity and transition-state structure

Second-order rate constants (kOH-) for alkaline hydrolysis of 2,4-dinitrophenyl X-substituted benzenesulfonates (1a-1f) and Y-substituted phenyl 4-nitrobezenesulfonates (2a-2g) have been measured spectrophotometrically. Comparison of kOH/

Structure and mechanism of PhnP, a phosphodiesterase of the carbon-phosphorus lyase pathway

PhnP is a phosphodiesterase that plays an important role within the bacterial carbon-phosphorus lyase (CP-lyase) pathway by recycling a "dead-end" intermediate, 5-phospho-α-d-ribosyl 1,2-cyclic phosphate, that is formed during organophosphonate catabolism

Study on the transesterification of methyl aryl phosphorothioates in methanol promoted by Cd(II), Mn(II), and a synthetic Pd(II) complex

Methanol solutions containing Cd(II), Mn(II), and a palladacycle, (dimethanol bis(N,N-dimethylbenzylamine-2C,N)palladium(II) (3), are shown to promote the methanolytic transesterification of O-methyl O-4-nitrophenyl phosphorothioate (2b) at 25 °C with impressive rate accelerations of 10 6-1011 over the background methoxide promoted reaction. A detailed mechanistic investigation of the methanolytic cleavage of 2a-d having various leaving group aryl substitutions, and particularly the 4-nitrophenyl derivative (2b), catalyzed by Pd-complex 3 is presented. Plots of k obs versus palladacycle [3] demonstrate strong saturation binding to form 2b:3. Numerical fits of the kinetic data to a universal binding equation provide binding constants, Kb, and first order catalytic rate constants for the methanolysis reaction of the 2b:3 complex (kcat) which, when corrected for buffer effects, give corrected (kcat corr) rate constants. A sigmoidal shaped plot of log(k catcorr) versus sspH (in methanol) for the cleavage of 2b displays a broad sspH independent region from 5.6 ≥ sspH ≥ ～10 with a k minimum = (1.45 ± 0.24) × 10-2 s-1 and a [lyoxide] dependent wing plateauing above a kinetically determined sspKa of 12.71 ± 0.17 to give a k maximum = 7.1 ± 1.7 s-1. Bronsted plots were constructed for reaction of 2a-d at sspH 8.7 and 14.1, corresponding to reaction in the midpoints of the low and high s spH plateaus. The Bronsted coefficients (βLG) are computed as -0.01 ± 0.03 and -0.86 ± 0.004 at low and high sspH, respectively. In the low sspH plateau, and under conditions of saturating 3, a solvent deuterium kinetic isotope effect of kH/kD = 1.17 ± 0.08 is observed; activation parameters (ΔHPd? = 14.0 ± 0.6 kcal/mol and ΔSPd?= -20 ± 2 cal/mol?K) were obtained for the 3-catalyzed cleavage reaction of 2b. Possible mechanisms are discussed for the reactions catalyzed by 3 at low and high sspH. This catalytic system is shown to promote the methanolytic cleavage of O,O-dimethyl phosphorothioate in CD3OD, producing (CD3O)2P=O(S-) with a half time for reaction of 34 min.

Pitfalls in assessing the α-effect: Reactions of substituted phenyl methanesulfonates with HOO-, OH-, and substituted phenoxides in H2O

Toward resolving the current controversy regarding the validity of the α-effect, we have examined the reactions of Y-substituted phenyl methanesulfonates 1a-1l with HOO-, OH-, and Z-substituted phenoxides in the gas phase versus solu

Analysis of linear free-energy relationships combined with activation parameters assigns a concerted mechanism to alkaline hydrolysis of X-substituted phenyl diphenylphosphinates

A kinetic study is reported for alkaline hydrolysis of X-substituted phenyl diphenylphosphinates (1a-i). The Bronsted-type plot for the reactions of 1a-i is linear over 4.5 pKa units with βlg= -0.49, a typical βlg value for reactions which proceed through a concerted mechanism. The Hammett plots correlated with σo and σ- constants are linear but exhibit many scattered points, while the corresponding Yukawa-Tsuno plot results in excellent linear correlation with ρ= 1.42 and r=0.35. The r value of 0.35 implies that leaving-group departure is partially advanced at the rate-determining step (RDS). A stepwise mechanism, in which departure of the leaving group from an addition intermediate occurs in the RDS, is excluded since the incoming HO - ion is much more basic and a poorer nucleofuge than the leaving aryloxide. A dissociative (DN + AN) mechanism is also ruled out on the basis of the small βlg value. As the substituent X in the leaving group changes from H to 4-NO2 and 3,4-(NO2)2, ΔH≠ decreases from 11.3 kcal mol-1 to 9.7 and 8.7 kcal mol-1, respectively, while ΔS≠ varies from -22.6 cal mol-1 K-1 to -21.4 and -20.2 cal mol-1 K-1, respectively. Analysis of LFERs combined with the activation parameters assigns a concerted mechanism to the current alkaline hydrolysis of 1a-i.

Aminolyses of aryl diphenylphosphinates and diphenylphosphinothioates: Effect of modification of electrophilic center from P=O to P=S

(Chemical Equation Presented) A kinetic study is reported for aminolysis of aryl diphenylphosphinothioates (2a-i). The phosphinothioates 2a-i are less reactive than aryl diphenylphosphinates (1a-i), the oxygen analogues of 2a-i, regardless of the basicity

Alkaline phosphatase mono- and diesterase reactions: Comparative transition state analysis

Enzyme-catalyzed phosphoryl transfer reactions have frequently been suggested to proceed through transition states that are altered from their solution counterparts. Previous work with Escherichia coli alkaline phosphatase (AP), however, suggests that thi

Mechanistic change in the reactivity of substituted phenyl acetates over phenyl thiolacetates toward imidazole in aqueous phase

The kinetics of aminolysis of several substituted phenyl acetates by imidazole is studied in aqueous medium at 20°C and an ionic strength of 0.1 M (KCl). By following the leaving groups spectrophotometrically (λ max = 272-401 nm), under excess free imidazole, pseudo-first-order rate constants (κobs) are obtained. For the esters with good nucleofuges, the reaction follows clean second-order kinetics and the plots of (κobs - κH) against free imidazole concentration are linear at constant pH. The macroscopic nucleophilic substitution rate constants (κN) are obtained as the slopes of these plots and found to be pH independent. For the esters with poor nucleofuges, a rate dependence on more than first power of the free imidazole and a linear dependence of κ′2 on free imidazole is observed. Accordingly, the microscopic rate constants for the assisted paths viz. κga and κgb have been disseminated besides for simple bimolecular attack. The Broensted-type plots and Hammett plots were constructed whose slope values are consistent with a stepwise mechanism through a bipolar tetrahedral addition intermediate whose formation or breakdown being rate determining for various paths. Comparison of this reaction of oxyesters with the earlier reported works on similar reaction of analogue thiolesters under identical reaction conditions showed remarkable mechanistic differences which are discussed in detail. The discussion is extended to include the details on previously studied ammonolysis of these two types of esters wherein thiolesters showed differed reactivity than that reported in the present study.