6961-42-8

Upstream product

• 122-01-0 4-chloro-benzoyl chloride 
• 106-48-9 4-chloro-phenol 
• 74-11-3 para-chlorobenzoic acid 
• 6264-29-5 4-nitrophenyl 4-chlorobenzoate 
• 24573-38-4 4-chlorophenolate 
• 7553-56-2 iodine 
• 108-90-7 chlorobenzene 
• 1679-18-1 4-Chlorophenylboronic acid 
• 104-88-1 4-chlorobenzaldehyde 

Downstream Products

• 2005-08-5 4-chlorophenyl benzoate 
• 62066-31-3 4-[2-(4-chlorophenyl)-2-oxoethyl]benzonitrile 
• 1387574-39-1 4-chlorophenyl nonanate 
• 1186436-48-5 [5-chloro-2-(4-nitro-benzyloxy)-phenyl] (4-chloro-phenyl) methanone 
• 61785-37-3 (5-chloro-2-hydroxy-phenyl)-(4-chloro-phenyl)-methanone 
• 1121-75-1 lithium 4-chlorophenolate 

Relevant academic research and scientific papers

Studies of hydrogen isotope scrambling during the dehalogenation of aromatic chloro-compounds with deuterium gas over palladium catalysts

Catalytic dehalogenation of aromatic halides using isotopic hydrogen gas is an important strategy for labelling pharmaceuticals, biochemicals, environmental agents and so forth. To extend, improve and further understand this process, studies have been carried out on the scrambling of deuterium isotope with protium during the catalytic deuterodehalogenation of model aryl chlorides using deuterium gas and a palladium on carbon catalyst in tetrahydrofuran solution. The degree of scrambling was greatest with electron-rich chloroarene rings. The tetrahydrofuran solvent and the triethylamine base were not the source of the undesired protium; instead, it arose, substantially, from the water content of the catalyst, though other sources of protium may also be present on the catalyst. Replacement of the Pd/C catalyst with one prepared in situ by reduction of palladium trifluoroacetate with deuterium gas and dispersed upon micronised polytetrafluoroethylene led to much reduced scrambling (typically 0–6% compared with up to 40% for palladium on carbon) and to high atom% abundance, regiospecific labelling. The improved catalytic system now enables efficient polydeuteration via the dehalogenation of polyhalogenated precursors, making the procedure viable for the preparation of MS internal standards and, potentially, for high specific activity tritium labelling.

N-Heterocyclic carbene catalysed aerobic oxidation of aromatic aldehydes to aryl esters using boronic acids

The organocatalytic behavior of N-heterocyclic carbenes in the aerobic oxidation of aromatic aldehydes to esters with boronic acids has been explored. This transition metal-free protocol allows access to a wide variety of aromatic esters in good to excellent yields under mild reaction conditions.

Preparation of benzoyloxy benzophenone derivatives and their inhibitory effects of ICAM-1 expression

Benzoyloxy benzophenone derivatives were prepared in 3 steps including DCC coupling, Fries rearrangement and esterification from benzoic acids in 24-89% total yields. Among the prepared 12 benzophenone analogues 1a-1l, the compound 1b having three chloro groups at the para position showed maximum inhibitory effects of ICAM-1 expression but, 1a which have no substituents at all showed no inhibitory activity. This study provides the evidences that benzoyloxy benzophenone derivative, 1b may exert its anti-inflammatory activity by suppressing IFN-γ-induced ICAM-1 expression.

Synthesis and crystal structure of [5-Chloro-2-(4-nitro-benzyloxy)-phenyl]- (4-chloro-phenyl) methanone

The title compound, C20H13Cl2NO4, crystallizes in the monoclinic crystal system and space group P21/n with cell parameters a=9.434(2)A, b=13.167(3)A, c=15.087(4)A, β=105.289(8)°, V=1807.7(7)A3 for Z=4. The structure exhibits inter-molecular hydrogen bonds

Synthesis and crystal structure of [5-chloro-2-(4-nitrobenzyloxy)-phenyl]- (4-chloro-phenyl) methanone

The title compound, C20H13Cl2NO 4, crystallizes in the monoclinic crystal system and space group P21/n with cell parameters a = 9.434(2) A, b = 13.167(3) A, c = 15.087(4) A, β = 105.289(8)°, V = 1807.

Evidence of substituent-induced electronic interplay. Effect of the remote aromatic ring substituent of phenyl benzoates on the sensitivity of the carbonyl unit to electronic effects of phenyl or benzoyl ring substituents

Carbonyl carbon 13C NMR chemical shifts δC(C=O) measured in this work for a wide set of substituted phenyl benzoates p-Y-C 6H4CO2C6H4-p-X (X = NO2, CN, Cl, Br, H, Me, or MeO; Y = NO2, Cl, H, Me, MeO, or NMe2) have been used as a tool to study substituent effects on the carbonyl unit. The goal of the work was to study the cross-interaction between X and Y in that respect. Both the phenyl substituents X and the benzoyl substituents Y have a reverse effect on δC(C=O). Electron-withdrawing substituents cause shielding while electron-donating ones have an opposite influence, with both inductive and resonance effects being significant. The presence of cross-interaction between X and Y could be clearly verified. Electronic effects of the remote aromatic ring substituents systematically modify the sensitivity of the C=O group to the electronic effects of the phenyl or benzoyl ring substituents. Electron-withdrawing substituents in one ring decrease the sensitivity of δC(C=O) to the substitution of another ring, while electron-donating substituents inversely affect the sensitivity. It is suggested that the results can be explained by substituent-sensitive balance of the contributions of different resonance structures (electron delocalization, Scheme 1).

The effect of acyl substituents on the α-effect: Contrasting α-effect profiles for reactions of 4-nitrophenyl substituted benzoates with neutral and anionic nucleophiles

The magnitude of the α-effect for reactions of 4-nitrophenyl substituted benzoates with a pair of anionic nucleophiles is independent of the electronic nature of the acyl substituent, while the one for the corresponding reactions with a pair of neutral nucleophiles increases as the acyl substituent changes from a strong electron withdrawing substituent to electron donating ones.

Evidence of a stepwise acyl-transfer reaction mechanism: Nonlinear hammett plots for reactions of p-nitrophenyl substituted benzoates with hydroxide and p-chlorophenoxide

The Hammett plots obtained for the title-reactions exhibit a break, i.e. ρ acyl values decrease from 2.21 ~ 2.44 to 1.45 ~ 1.52 as the acyl substituent becomes a strong electron withdrawing group (σ > 0.6). Such a break in the Hammett plots is suggestive of a change in the reaction mechanism and strong evidence of a stepwise mechanism for the acyl-transfer reaction.