2138-22-9

Basic information

• Product Name: 4-Chlorobenzene-1,2-diol
• Synonyms: 4-CHLORO-1,2-DIHYDROXYBENZENE;4-CHLOROCATHECOL;4-CHLOROCATECHOL;4-chloro-2-benzenediol;4-chloro-pyrocatecho;Chlorocatechol;AIDS-017780;4-MONOCHLOROCATECHOL
• CAS NO: 2138-22-9
• Molecular Formula: C₆H₅ClO₂
• Molecular Weight: 144.56
• EINECS: 218-381-9
• Product Categories: Phenol&Thiophenol&Mercaptan;Heterocyclic Compounds;Benzenes;Organic Building Blocks;Oxygen Compounds;Polyols
• Mol File: 2138-22-9.mol
• Article Data: 53

Chemical Properties

• Melting Point: 90-94 °C(lit.)
• Boiling Point: 140°C 10,5mm
• Flash Point: 115.328 °C
• Appearance: /
• Density: 1.2558 (rough estimate)
• Vapor Pressure: 0.00505mmHg at 25°C
• Refractive Index: 1.4620 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 8.84±0.10(Predicted)
• CAS DataBase Reference: 4-Chlorobenzene-1,2-diol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chlorobenzene-1,2-diol(2138-22-9)
• EPA Substance Registry System: 4-Chlorobenzene-1,2-diol(2138-22-9)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 1759 8/PG 2
• WGK Germany: 3
• RTECS: UX1490000
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 2138-22-9(Hazardous Substances Data)

Usage

Definition

ChEBI: A chlorocatechol that is catechol substituted by a chloro group at position 4.

Synthesis Reference(s)

Tetrahedron Letters, 33, p. 865, 1992 DOI: 10.1016/S0040-4039(00)91561-2

General Description

4-chlorocatechol was a major degradation product of 4-chloro-2-aminophenol (4C2AP). The degradation of 4-chlorocatechol was catalyzed by cphA-I enzyme.

InChI:InChI=1/C6H5ClO2/c7-4-1-2-5(8)6(9)3-4/h1-3,8-9H

Upstream product

• 635-93-8 5-chlorosalicyclaldehyde 
• 36637-30-6 O-(4-chlorophenyl)hydroxylamine 
• 407-25-0 trifluoroacetic anhydride 
• 106-48-9 4-chloro-phenol 
• 31222-02-3 4-chlorocyclohexa-3,5-diene-1,2-dione 
• 94-75-7 2,4-Dichlorophenoxyacetic acid 
• 89-64-5 p-chloro-o-nitrophenol 
• 7791-25-5 sulfuryl dichloride 
• 60-29-7 diethyl ether 
• 120-80-9 benzene-1,2-diol 
• 56-23-5 tetrachloromethane 
• 7722-84-1 dihydrogen peroxide 
• 1193-00-6 sodium 4-chlorophenolate 
• 452-81-3 2-fluoro-4-methylphenole 

Downstream Products

• 106063-57-4 (5-chloro-2-phenyl-1,3-benzodioxol-2-yl)propan-2-one 
• 106063-52-9 (Z)-3-(5-chloro-2-hydroxyphenoxy)-4-phenyl-3-buten-2-one sodium salt 
• 121185-70-4 2-(2-oxy-4-chloro)phenyleneoxy-7-chlorobenzo-1,3,2-dioxaarsole 
• 852434-12-9 [Fe(III)(bis(4-chloropyridin-2-ylmethyl)(pyridin-2-ylmethyl)amine)(4-chlorocatecholate)]BPh₄ 
• 852434-10-7 [Fe(III)(bis(4-methoxypyridin-2-ylmethyl)(pyridin-2-ylmethyl)amine)(4-chlorocatecholate)]BPh₄ 
• 852434-18-5 [Fe(III)(bis(4-nitropyridin-2-ylmethyl)(pyridin-2-ylmethyl)amine)(4-chlorocatecholate)]BPh₄*MeOH 
• 86873-60-1 5-chloropicolinic acid 
• 16766-27-1 4-chloro-1,2-dimethoxybenzene 
• 121451-57-8 1-(5-Chloro-2-hydroxy-phenoxy)-propan-2-one 
• 57744-68-0 6-chloro-2,3-dihydrobenzo[b][1,4]dioxine 
• 126644-73-3 1,2-bis<(tert-butyldimethylsilyl)oxy>-4-chlorobenzene 
• 75484-25-2 7-Chloro-3-methyl-3,4-dihydro-2H-benzo[b][1,4]dioxepin-3-ol 
• 75484-28-5 Toluene-4-sulfonic acid 6-chloro-2-methyl-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl ester 
• 855872-11-6 4-(4-chloro-2-hydroxy-phenoxy)-[1,2]benzoquinone 

Relevant articles and documents

Facile synthesis of visible-light-driven Cu2O/BiVO4 composites for the photomineralization of recalcitrant pesticides

Cu2O/BiVO4 composites with different Cu2O co-catalysts were synthesized by a simple impregnation method at 200 °C for 4 h under N2 atmosphere. The Cu2O powder was obtained through the chemical reduction of copper sulfate using different reducing reagents such as ascorbic acid, glucose or fructose. The as-synthesized samples were characterized by X-ray powder diffraction, scanning and transmission electron microscopies, UV-vis diffuse reflection absorption and electrochemical impedance spectroscopy. The photoactivities of the Cu2O/BiVO4 composites were evaluated in terms of the mineralization of 4-chlorophenol (4-CP) in aqueous solutions under visible-light irradiation. The role of experimental variables including the preparation method of the co-catalyst, catalyst concentration, and 4-chlorophenol initial concentration in the photocatalytic performance of Cu2O/BiVO4 catalysts was analyzed. Likewise, the viability to recover and reuse these photocatalysts was also tested. It was found that the complete abatement of 4-CP led to the formation of chlorocatechol (4-CC) without concomitantly involving the formation pathway of hydroquinone/p-benzoquinone, 4-CC was identified in the light of experimental evidence (UV-vis) and spectral simulation done by using time-dependent density functional theory (TD-DFT) with the polarized continuum model.

Method for hydrolyzing diarylether compound to generate aryl phenol compound

The invention discloses a method for hydrolyzing a diarylether compound to generate an arylphenol compound. According to the method, visible light is utilized to excite a photosensitizer for catalysis. In a reaction solvent, the raw material in the formula (1) breaks a C (sp2)-O bond under the auxiliary action of acid, and hydrolysis is performed to obtain the bimolecular aryl phenol compounds in the formula (3) and the formula (4). The method can catalyze the reaction at room temperature, is green and environment-friendly, and is easy to operate; the universality is wide, the reaction yield is relatively high, and the tolerance of functional groups is strong; the synthesis method not only can realize small-scale hydrolysis conversion of various diarylether compounds, but also can realize hydrolysis of herbicidal ether, triclosan and a lignin template substrate, and even can realize large-scale hydrolysis of triclosan and the lignin template substrate to realize gram-level degradation. A new strategy is provided for recovering phenol derivatives through lignin hydrolysis, degrading pesticides and purifying wastewater containing a degerming agent or herbicide. The method has wide application prospect and use value.

Isosteres of ester derived glucose uptake inhibitors

Glucose transporters (GLUTs) facilitate glucose uptake and are overexpressed in most cancer cells. Inhibition of glucose transport has been shown to be an effective method to slow the growth of cancer cells both in vitro and in vivo. We have previously reported on the anticancer activity of an ester derived glucose uptake inhibitor. Due to the hydrolytic instability of the ester linkage we have prepared a series of isosteres of the ester moiety. Of all of the isosteres prepared, the amine linkage showed the most promise. Several additional analogues of the amine-linked compounds were also prepared to improve the overall activity.

Anchimerically Assisted Selective Cleavage of Acid-Labile Aryl Alkyl Ethers by Aluminum Triiodide and N, N-Dimethylformamide Dimethyl Acetal

Aluminum triiodide is harnessed by N,N-dimethylformamide dimethyl acetal (DMF-DMA) for the selective cleavage of ethers via neighboring group participation. Various acid-labile functional groups, including carboxylate, allyl, tert-butyldimethylsilyl (TBS), and tert-butoxycarbonyl (Boc), suffer the conditions intact. The method offers an efficient approach to cleaving catechol monoalkyl ethers and to uncovering phenols from acetal-type protecting groups such as methoxymethyl (MOM), methoxyethoxymethyl (MEM), and tetrahydropyranyl (THP) chemoselectively.