18113-03-6

Basic information

• Product Name: 2-CHLORO-4-METHOXYPHENOL
• Synonyms: 3-CHLORO-4-HYDROXYANISOLE;2-CHLORO-4-METHOXYPHENOL;2-Chlorohydroquinonemonomethylether;2-chloro-4-methoxylphenol ;2-Chloro-4-methoxyphenol,97%;2-Chloro-4-Methoxyphenol, 97% 5GR;3-Chloro-4-hydroxyanisole, 2-Chloro-p-guaiacol
• CAS NO: 18113-03-6
• Molecular Formula: C₇H₇ClO₂
• Molecular Weight: 158.58
• EINECS: 242-007-3
• Product Categories: Aromatic Hydrocarbons (substituted) & Derivatives;Phenol&Thiophenol&Mercaptan;Anisoles, Alkyloxy Compounds & Phenylacetates;Chlorine Compounds;Phenols;Organic Building Blocks;Oxygen Compounds;NULL
• Mol File: 18113-03-6.mol

Chemical Properties

• Melting Point: 41-44 °C(lit.)
• Boiling Point: 241°C (rough estimate)
• Flash Point: 185 °F
• Appearance: White to light yellow/Crystalline Low Melting Solid
• Density: 1.153 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0184mmHg at 25°C
• Refractive Index: 1.554
• Storage Temp.: 0-10°C
• PKA: 8.98±0.18(Predicted)
• BRN: 1936412
• CAS DataBase Reference: 2-CHLORO-4-METHOXYPHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLORO-4-METHOXYPHENOL(18113-03-6)
• EPA Substance Registry System: 2-CHLORO-4-METHOXYPHENOL(18113-03-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 18113-03-6(Hazardous Substances Data)

Usage

Chemical Properties

WHITE TO LIGHT YELLOW CRYST. LOW MELTING SOLID

InChI:InChI=1/C7H7ClO2/c1-10-5-2-3-7(9)6(8)4-5/h2-4,9H,1H3

Upstream product

• 150-76-5 4-methoxy-phenol 
• 21306-21-8 2,2,3,4,5,6-hexachloro-cyclohexa-2,4-dien-1-one 
• 150-78-7 1,4-dimethoxybezene 
• 1131890-97-5 2-chloro-4-methoxyphenyl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate 
• 60672-33-5 4-methyl-N'-(1-(p-tolyl)ethylidene)benzenesulfonohydrazide 
• 935-50-2 4,4-dimethoxycyclohexa-2,5-dienone 
• 64-17-5 ethanol 
• 73010-52-3 4-ethoxy-4-methoxycyclohexa-2,5-dien-1-one 
• 73010-54-5 4-isopropoxy-4-methoxycyclohexa-2,5-dien-1-one 
• 139139-72-3 4-methoxy-4-(prop-2-yn-1-yloxy)cyclohexa-2,5-dien-1-one 
• 108534-51-6 4-((tert-butyldimethylsilyl)oxy)-4-methoxycyclohexa-2,5-dienone 
• 108-95-2 phenol 
• 1746-23-2 4-tert-Butylstyrene 
• 98-83-9 isopropenylbenzene 

Downstream Products

• 57197-15-6 2-chloro-4,4-dimethoxycyclohexa-2,5-dien-1-one 
• 56219-58-0 1-bromo-6-(2-chloro-4-methoxyphenoxy)hexane 
• 62489-69-4 3-[6-(2-Chloro-4-methoxy-phenoxy)-hexyl]-pentane-2,4-dione 
• 62489-74-1 4-[4-(2-chloro-4-methoxyphenoxy)butyl]-3,5-heptanedione 
• 62489-75-2 4-[5-(2-Chloro-4-methoxy-phenoxy)-pentyl]-heptane-3,5-dione 
• 62489-84-3 4-[8-(2-Chloro-4-methoxyphenoxy)octyl]-3,5-heptanedione 
• 62489-76-3 4-[7-(2-chloro-4-methoxyphenoxy)heptyl]-3,5-heptanedione 
• 62489-77-4 4-[9-(2-Chloro-4-methoxy-phenoxy)-nonyl]-heptane-3,5-dione 
• 99179-70-1 2-Acetoxy-4-methoxy-phenol 
• 132806-87-2 Acetic acid 3-chloro-2-hydroxy-5-methoxy-phenyl ester 
• 67205-86-1 1-(4-Bromomethyl-cyclohexylmethoxy)-2-chloro-4-methoxy-benzene 
• 175907-64-9 2-Chloro-6-dimethylaminomethyl-4-methoxy-phenol 
• 1007853-31-7 2-chloro-6-(hydroxymethyl)-4-methoxyphenol 
• 475040-00-7 2-bromobenzyl 2-chloro-4-methoxyphenyl ether 

Relevant articles and documents

Unprecedented Regioregular Poly(1,4-arylene)s Prepared by Nickel(II)-Catalyzed Cross-Coupling Polymerization of 2,5-Disubstituted Bromo(chloro)arylene

The unprecedented synthesis of regioregular head-to-tail-type poly(1,4-arylene)s bearing different substituents at the 2- and 5-positions is described. They were prepared by the polymerization of 2,5-disubstituted bromo(chloro)arylenes by selective halogen–metal exchange with a Grignard reagent and subsequent cross-coupling polymerization with a nickel catalyst [NiCl2(dppp)]. Formation of the regioregular poly(1,4-arylene)s were confirmed by NMR spectroscopy, and showed remarkable differences to those polymers having uncontrolled regioregularity. Polymerization of bromo(chloro)arylenes with a chiral alkoxy substituent also led to the regioregular head-to-tail-type polyarylene, which demonstrated circular dichroism, thus suggesting formation of a structure with higher-order regularity.

Synthetic method 4 - alkoxyphenol compounds

The invention discloses a synthetic method of 4 - alkoxyphenol compounds, and belongs to the field of organic chemical synthesis. The method is as follows: An aryl alkyl ether compound is added to the sealing tube. The catalyst dimerization acetic acid rhodium and the oxidizing agent iodobenzene diethyl ester are added, a solvent trifluoroacetic anhydride is added, and the 4 -alkoxyphenol compound is prepared by heating reaction. To the invention, high regioselectivity direct hydroxylation of the aryl alkyl ether compound is realized, the application range of the substrate is wide, the yield is high, the activity after amplification reaction does not significantly decay, and higher yield is still obtained. The utility model has good practicability and industrial application prospect.

Para -Selective hydroxylation of alkyl aryl ethers

para-Selective hydroxylation of alkyl aryl ethers is established, which proceeds with a ruthenium(ii) catalyst, hypervalent iodine(iii) and trifluoroacetic anhydride via a radical mechanism. This protocol tolerates a wide scope of substrates and provides a facile and efficient method for preparing clinical drugs monobenzone and pramocaine on a gram scale.

Direct Acetoxylation of Arenes

Acetoxylation of arenes is an important reaction and an unmet need in chemistry. We report a metal-free, direct acetoxylation reaction using sodium nitrate under an anhydrous environment of trifluoroacetic acid, acetic acid, and acetic anhydride. Arenes (31 examples), with oxidation potentials (Eox, in V vs SCE) lower than benzene (2.48 V), were acetoxylated with good yields and regioselectivity. A stepwise, single electron-transfer mechanism is proposed.

Regioselective synthesis of gentisyl alcohol-type marine natural products

Gentisyl alcohol-type natural products, possessing various important biological properties, have been synthesized from 4-methoxyphenol by using a selective phenol monohydroxymethylation/monochlorination, a CAN oxidation and a sodium dithionite reduction as the key steps. The natural product synthesis is efficient, atom- and step-economical, and requires no protecting groups.

Regioselective C-H chlorination: Towards the sequential difunctionalization of phenol derivatives and late-stage chlorination of bioactive compounds

We have developed a protocol for the auxillary directed C-H chlorination of phenol derivatives using catalytic amounts of palladium acetate that is amenable to the late-stage chlorination of diflufenican and estrone. The 2-pyridine group allows for a highly efficient palladium-catalyzed chlorination and sequential ortho C-H functionalization reaction of phenol derivatives to produce a variety of symmetrical and unsymmetrical 2,4,6-trisubstituted phenols.

Unanticipated participation of HCl in nucleophilic chlorination reaction: Expedient route to meta chlorophenols

o-Quinone monoketals participated in a 1,4-addition reaction with HCl furnishing m-chlorophenols in high yields. Several readily available o-quinone monoketals were selected to display the generality of this serendipitous and unprecedented reaction and the results are presented herein.

Highly Selective Synthesis of Chlorophenols under Microwave Irradiation

Oxychlorination of various phenols is finished in 60 minutes with high efficiency and perfect selectivity under microwave irradiation. These reactions adopt copper(II) chloride (CuCl2) as the catalyst and hydrochloric acid as chlorine source instead of expensive and toxic ones. Oxychlorination of phenols substituted with electron donating groups (methyl, methoxyl, isopropyl, etc.) at ortho- and meta-positions is accomplished with higher conversion rates, lower reaction time, and excellent selectivity. A proposed reaction mechanism is deduced; one electron transfers from CuCl2 to phenol followed by the formation of tautomeric radical that can be rapidly captured by chlorine atom and converts into para-substituted product.

Metal-Free [3+2] Oxidative Coupling of Phenols with Alkenes: Synthesis of Dihydrobenzofurans

Herein, we demonstrated a benign and metal-free [3+2]-cycloaddition reaction using simple and readily available phenols and styrenes as substrates and sodium persulfate as an inexpensive and environmentally friendly oxidant for the direct synthesis of dih

Synthesis of o-chlorophenols via an unexpected nucleophilic chlorination of quinone monoketals mediated by N,N′-dimethylhydrazine dihydrochloride

An unexpected nucleophilic chlorination of a quinone monoketal while carrying out a pyrazolidine synthesis has led to a general preparation of multisubstituted phenols. The products are obtained in good to high yields under mild conditions. The bridged pyrazolidines that were the original targets are obtained in the presence of a protic solvent. This journal is the Partner Organisations 2014.