119-56-2

Usage

Chemical Properties

white crystalline powder

Uses

4-Chlorobenzhydrol was used as internal standard to measure the N-demethyl antipyrine metabolite in urine by gas chromatography-mass spectrometry. It was also used in the identification of the antihistamine cetirizine as a relevant cross-reactant for the carbamazepine-specific enzyme-linked immunosorbent assay .

Preparation

Preparation of 4-Chlorobenzhydrol(4-CB):about 5.0g(0.023 mol) of 4-chloro benzophenone was dissolved in 15 mL of isopropyl alcohol (IPA) and heated to 50°C followed by the addition of 0.265g(0.007 mol) of sodium borohydride as a lot with the temperature maintained at 65°C for 2 h. The reaction mixture was distilled to expel isopropyl alcohol up to 90 %. The resulting solution was cooled and treated with dil HCl (5 mL of conc. HCl in 20 mL of water). Finally the reaction mass was extracted with 15 mL of toluene. The toluene extract was washed withwater to pH-7. The compound obtained in this step was taken to next step without isolation but aliquot sample was concentrated, isolated and checked for melting point (m.p. = 58-60°C).

InChI:InChI=1/C13H11ClO/c14-12-8-6-11(7-9-12)13(15)10-4-2-1-3-5-10/h1-9,13,15H/t13-/m1/s1

Upstream product

• 104-88-1 4-chlorobenzaldehyde 
• 100-52-7 benzaldehyde 
• 7270-47-5 4-chlorophenylmagnesium iodide 
• 683-60-3 sodium isopropylate 
• 134-85-0 4-chlorobenzophenone 
• 67-63-0 isopropyl alcohol 
• 555-31-7 aluminum isopropoxide 
• 912-17-4 1,2-diphenyl-1,2-bis-(4-chlorophenyl)-ethanediol 
• 103-73-1 Phenetole 
• 67-56-1 methanol 
• 134-83-8 1-chloro-4-(chloro(phenyl)methyl)benzene 
• 64-17-5 ethanol 
• 10557-71-8 4-chlorophenyltrimethylsilane 
• 109-72-8 n-butyllithium 

Downstream Products

• 132301-85-0 (+/-)-phthalic acid mono-(4-chloro-benzhydryl ester) 
• 102078-57-9 p-chlorophenyl(phenyl)methyl p-tolyl sulfone 
• 22808-17-9 (+/-)-[2-(4-chloro-benzhydryloxy)-ethyl]-dimethyl-amine 
• 134-83-8 1-chloro-4-(chloro(phenyl)methyl)benzene 
• 134-85-0 4-chlorobenzophenone 
• 15545-16-1 4-[3-(4-chloro-benzhydryloxy)-propyl]-morpholine 
• 3326-55-4 -phenyl-thiocarbonat 
• 948-54-9 4-chlorodiphenylmethyl bromide 
• 3326-54-3 -methyl-thiocarbonat 
• 119-56-2 (4-Chloro-phenyl)-phenyl-methanol 
• 90500-04-2 5-[(4-Chloro-phenyl)-phenyl-methyl]-furan-2-carboxylic acid ethyl ester 
• 81505-86-4 4-chlorobenzhydryl-4-nitrobenzoic carbonic anhydride 
• 958-06-5 (+/-)-(4-chlorophenyl)(phenyl)methyl acetate 
• 90296-26-7 2-<(p-chlorophenyl)phenylmethoxy>acetic acid 

Relevant academic research and scientific papers

Novel reduction of carbonyl compounds with Al/NH3/halide under irradiation of ultrasonic wave

Various carbonyl compounds, such as benzophenones and acetophenones, were reduced by Al/NH3/halide under ultrasonic wave irradiation to give the corresponding monohydric alcohols and/or pinacols in satisfactory yields. The addition of inorganic halides improved the selectivity in the formation of monohydric alcohols and pinacols.

Efficient synthesis of antihistamines clocinizine and chlorcyclizine

A simple and efficient route has been developed for the synthesis of anti-histamine drugs clocinizine and chlorcyclizine. The common intermediate 1-[(4-chloro phenyl) (phenyl)-methyl]-piperazine (8), is prepared from (4-chlorophenyl) (phenyl)-methanone (5), in three steps with excellent yields. All the reactions proceeded smoothly and the products were also isolated easily. Springer Science+Business Media, LLC 2011.

Novel azolinium/rhodium system catalyzed addition of arylboronic acids to aldehydes

There novel 1,3-dialkylperhydrobenzimidazolinium (2a-c) and two 1,3-dialkylimidazolinium salts (4a,b) as NHC precursors were synthesized from N,N′-dialkyl-1,2-cyclohexanediamine dihydrochloride and 1,2-dialkylpropanediamine dihydrochloride. The in situ prepared three component system [RhCl(COD)]2 / imidazolinium salts (2, 4) and KOBut catalyses the addition of phenylboronic acid to sterically hindered aldehydes affording the corresponding arylated secondary alcohols in good yields.

Surface modification of CdS quantum dots with fluorinated thiophenol

CdS nanocrystallites prepared by capping with pentafluorothiophenol, 2,3,5,6-tetrafluorothiophenol or 4-fluorothiophenol are characterized as quantum dots by TEM, FTIR, NMR, UV-VIS and fluorescence spectroscopy. The crystalline size tends to increase with an increase in the number of fluorine atoms in the capping molecules while maintaining high solubility in organic solvents, with solubility in alcohols depending on the number of fluorine atoms in the capping molecules. Pentafluorophenyl-capped CdS nanocrystallites have the highest solubilities in alcohols, and exhibit quantum dot photocatalysis in methanol, leading to the efficient two-electron transfer photoreduction under visible-light irradiation.

Three-component coupling of aryl iodides, allenes, and aldehydes catalyzed by a Co/Cr-hybrid catalyst

The cobalt/chromium-catalyzed three-component coupling of aryl iodides, allenes, and aldehydes has been developed to afford multi-substituted homoallylic alcohols in a diastereoselective manner. Control experiments for understanding the reaction mechanism reveal that the cobalt catalyst is involved in the oxidative addition and carbometalation steps in the reaction, whereas the chromium salt generates highly nucleophilic allylchromium intermediates from allylcobalt species, without the loss of stereochemical information, to allow the addition to aldehydes.

Tuning the reactivity of dirhodium(II) complexes with axial N-heterocyclic carbene ligands: The arylation of aldehydes

(Chemical Equation Presented) Efficient dinuclear catalysts: A complex of {Rh2(OAc)4} with two N-heterocyclic carbenes (NHCs) at the axial positions catalyzes the arylation of aldehydes (see picture; R = alkyl, aryl). DFT calculations reveal subtle stereoelectronic effects resulting from the NHC coordination to the dirhodium(II) complex and suggest that complexes with one axial NHC ligand are the catalytically active species.

Nucleofugality of aliphatic carboxylates in mixtures of aprotic solvents and water

The leaving group ability (nucleofugality) of fluoroacetate, chloroacetate, bromoacetate, dichloroacetate, trifluoroacetate, trichloroacetate, heptafluorobutyrate, formate, isobutyrate, and pivalate have been derived from the solvolysis rate constants of the corresponding X,Y-substituted benzhydryl carboxylates in 60 % and 80 % aqueous acetonitrile and 60 % aqueous acetone, applying the LFER equation: log k = sf(Ef + Nf). The experimental barriers (ΔG?,exp) for solvolyses of 11 reference dianisylmethyl carboxylates in these solvents correlate very well (r = 0.994 in all solvents) with ΔG?,model of the model σ-assisted heterolytic displacement reaction of cis-2,3-dihydroxycyclopropyl trans-carboxylates calculated earlier. Linear correlation observed between the log k for the reference dianisylmethyl carboxylates and the sf values enables estimation of the reaction constant (sfestim). Using the ΔG?,exp vs. ΔG?,model correlation, and taking the estimated sfestim, the nucleofugality parameters for other 34 aliphatic carboxylates have been determined in 60 % and 80 % aqueous acetonitrile and 60 % aqueous acetone. The most important variable that determines the reactivity of aliphatic carboxylates in aprotic solvent/water mixtures is the inductive effect of the group(s) attached onto the carboxylate moiety.

Semiconductor Photocatalysis: Size Control of Surface-Capped CdS Nanocrystallites and the Quantum Size Effect in Their Photocatalysis

Size-controlled CdS nanocrystallites were prepared by using thiophenol or hexanethiol as a capping reagent by controlling the ratio of Cd2+ to bis(trimethylsilyl) sulfide (S(TMS)2) as a source of the sulfide ion in reversed micelles.Their solubility and photocatalysis were examined.A series of size-controlled phenyl-capped CdS nanocrystallites catalyze the photoreduction of aromatic ketones in the presence of triethylamine as an electron donor under visible-light irradiation.The photocatalytic activity is affected by the particle size, i.e., the reducing power of the photogenerated electron on CdS nanocrystallites toward the ketones increases with decreasing the particle size.The enhancement of photocatalytic activity observed by reducing the particle size should be ascribed to not only a negative shift of the conduction band edge, but also suppression of the formation of surface defects.

Comparative Mechanistic Study of the Reaction of Benzophenone with n-BuMgBr and n-BuLi

Substituent effects on reactivity and product distribution (addition vs reduction) were determined for the reactions of benzophenones with n-BuMgBr and n-BuLi at 0 deg C.In case of the reaction with n-BuMgBr, meta and para-substituted benzophenones gave a reasonably linear Hammet plot, from which the ρ value of 1.45 was calculated, while ortho-substituted derivatives deviated downward from the correlation line.In contrast, the reaction with n-BuLi exhibit very small substituent effects on reactivity.The product distrubution is highly dependent on substituents in the n-BuMgBr reaction, whereas it is essentially independent of substituents in the n-BuLi reaction.Mechanistic differences between the reactions of these two reagents are discussed on the basis of these experimental results.

Novel rhodium-1,3-dialkyl-3,4,5,6-tetrahydropyrimidin-2-ylidene complexes as catalysts for arylation of aromatic aldehydes

Six new rhodium-tetrahydropyrimidin-2-ylidene complexes (2a-f) have been prepared and characterized by C, H, N analysis, 1H NMR and 13C NMR. Phenylboronic acid reacts with aldehydes in the presence of a catalytic amount of the new rhodium(I)-carbene complexes, RhCl(COD)(1,3- dialkyl-3,4,5,6-tetrahydropyrimidin-2-ylidene), (2a-f), to give the corresponding secondary aryl alcohols in good yields (72-96%).