14503-45-8

Basic information

• Product Name: 3-Chloro-4-methoxybenzyl alcohol
• Synonyms: 3-Chloro-4-methoxybenzyl alcohol
• CAS NO: 14503-45-8
• Molecular Formula: C₈H₉ClO₂
• Molecular Weight: 172.60886
• Product Categories: Alcohols;Anisoles, Alkyloxy Compounds & Phenylacetates;Chlorine Compounds
• Mol File: 14503-45-8.mol

Chemical Properties

• Boiling Point: 279.7 °C at 760 mmHg
• Flash Point: >110℃
• Appearance: /
• Density: 1.274 g/mL at 25 °C
• Vapor Pressure: 0.00188mmHg at 25°C
• Refractive Index: n20/D1.566
• PKA: 14.13±0.10(Predicted)
• CAS DataBase Reference: 3-Chloro-4-methoxybenzyl alcohol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Chloro-4-methoxybenzyl alcohol(14503-45-8)
• EPA Substance Registry System: 3-Chloro-4-methoxybenzyl alcohol(14503-45-8)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 14503-45-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
3-Chloro-4-methoxybenzyl alcohol is used as a key intermediate in the synthesis of pharmaceuticals for its versatile reactivity, allowing the creation of more complex molecules that can be used in the development of new drugs.
Used in Agrochemical Production:
In the agrochemical industry, 3-Chloro-4-methoxybenzyl alcohol is utilized as a building block for the synthesis of various agrochemicals, contributing to the development of effective pesticides and other agricultural chemicals.
Used in Organic Synthesis as a Reagent:
3-Chloro-4-methoxybenzyl alcohol is employed as a reagent in various chemical reactions, facilitating the synthesis of a wide range of organic compounds due to its unique functional groups.
Used as a Solvent in Organic Chemistry:
Owing to its properties as a solvent, 3-Chloro-4-methoxybenzyl alcohol is used for dissolving various organic compounds, making it a valuable component in organic synthesis processes and laboratory practices.

InChI:InChI=1/C8H9ClO2/c1-11-8-3-2-6(5-10)4-7(8)9/h2-4,10H,5H2,1H3

Upstream product

• 4903-09-7 3-chloro-4-methoxy-benzaldehyde 
• 37908-96-6 3-chloro-4-methoxy benzoic acid 
• 37908-98-8 methyl 3-chloro-p-anisate 
• 3964-57-6 methyl 4-hydroxy-3-chlorobenzoate 
• 3964-58-7 3-chloro-4-hydroxybenzoic acid 

Downstream Products

• 37908-96-6 3-chloro-4-methoxy benzoic acid 
• 4903-09-7 3-chloro-4-methoxy-benzaldehyde 
• 320407-92-9 4-(bromomethyl)-2-chloro-1-methoxybenzene 
• 13719-57-8 3-chloro-4-methoxybenzyl chloride 
• 115514-77-7 (3-chloro-4-methoxyphenyl)methanamine 
• 1418759-16-6 2-(3-azadicyclo[3.1.0]hexan-3-yl)-4-(3-chloro-4-methoxybenzyloxy)-N-(4-fluorobenzyl)pyrimidine-5-carboxamide 
• 1418759-14-4 2-(3-azadicyclo[3.1.0]hexan-3-yl)-4-(3-chloro-4-methoxybenzyloxy)-N-(pyridin-2-ylmethyl)pyrimidine-5-carboxamide 
• 1418759-40-6 4-(3-chloro-4-methoxybenzyloxy)-2-(methylsulfinyl)-N-(pyridin-2-ylmethyl)pyrimidine-5-carboxamide 
• 1418759-13-3 2-(3-azadicyclo[3.1.0]hexan-3-yl)-4-(3-chloro-4-methoxybenzyloxy)-N-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide 
• 1418759-33-7 ethyl 4-(3-chloro-4-methoxybenzyloxy)-2-(methylmercapto)pyrimidine-5-carboxylate 
• 1418759-45-1 4-(3-chloro-4-methoxybenzyloxy)-2-(methylsulfinyl)-N-(4-fluorobenzyl)pyrimidine-5-carboxamide 
• 1418759-44-0 4-(3-chloro-4-methoxybenzyloxy)-2-(methylmercapto)-N-(4-fluorobenzyl)pyrimidine-5-carboxamide 
• 1418759-39-3 4-(3-chloro-4-methoxybenzyloxy)-2-(methylmercapto)-N-(pyridine-2-ylmethyl)pyrimidine-5-carboxamide 
• 1418759-38-2 4-(3-chloro-4-methoxybenzyloxy)-2-(methylsulfinyl)-N-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide 

Relevant articles and documents

Scope and limitations of biocatalytic carbonyl reduction with white-rot fungi

The reductive activity of various basidiomycetous fungi towards carbonyl compounds was screened on an analytical level. Some strains displayed high reductive activities toward aromatic carbonyls and aliphatic ketones. Utilizing growing whole-cell cultures of Dichomitus albidofuscus, the reactions were up-scaled to a preparative level in an aqueous system. The reactions showed excellent selectivities and gave the respective alcohols in high yields. Carboxylic acids were also reduced to aldehydes and alcohols under the same conditions. In particular, benzoic, vanillic, ferulic, and p-coumaric acid were reduced to benzyl alcohol, vanillin, dihydroconiferyl alcohol and 1-hydroxy-3-(4-hydroxyphenyl)propan, respectively.

Benzylic phosphates as electrophiles in the palladium-catalyzed asymmetric benzylation of azlactones

Palladium-catalyzed asymmetric benzylation has been demonstrated with azlactones as prochiral nucleophiles in the presence of chiral bisphosphine ligands. Benzylic electrophiles are utilized under two sets of reaction conditions to construct a new tetrasubstituted stereocenter. Electron density of the phenyl ring dictates the reaction conditions, including the leaving group. The reported methodology represents a novel asymmetric carbon-carbon bond formation in an amino acid precursor.

Imidazopyridinone derivatives and their use as phosphodiesterase inhibitors

A compound (Ia): wherein the variables are defined in the specification, its prodrug or a pharmaceutically acceptable salt thereof useful in the treatment of angina, hypertension etc.

PYRIMIDINE-5-CARBOXAMIDE COMPOUNDS, PROCESS FOR PRODUCING THE SAME AND USE THEREOF

A compound of the formula wherein R1 is a heterocycle having a skeleton consisting of 3 to 15 atoms including 1 to 5 nitrogen atom(s), which heterocycle is attached by a secondary nitrogen atom constituting the heterocycle; X is an oxygen atom, a nitrogen atom optionally substituted by a hydrocarbon group having 1 to 5 carbon atom(s) or a sulfur atom optionally oxidized with 1 or 2 oxygen, Y is a bond or a C1-5 alkylene group, R2 is (1) a hydrogen atom, (2) a hydroxy group, (3) a C1-5 alkoxy group, (4) a C1-5 alkylthio group, (5) a carbocycle having 3 to 15 carbon atoms or (6) a heterocycle having a skeleton consisting of 3 to 15 atoms including 1 to 5 heteroatom(s), provided that when Y is a bond, R2 is a carbocycle having 3 to 15 carbon atoms or a heterocycle having a skeleton consisting of 3 to 15 atoms including 1 to 5 heteroatom(s) and; one of R3 and R4 is a hydrogen atom or a group of the formula: -Z-R5 (Z is a bond or C1-10 alkylene group optionally having substituent(s) and R5 is (1) a hydrogen atom, (2) a hydroxy group, (3) a C1-5 alkoxy group, (4) a nitrile group, (5) a C1-5 alkoxy-carbonyl group, (6) a carboxyl group, (7) a carbamoyl group, (8) a (mono or di-C1-5 alkyl)carbamoyl group, (9) an amino group, (10) a (di or mono-C1-5 alkyl)amino group, (11) a (C1-5 alkoxy-carbonyl)amino group, (12) a C1-5 alkylthio group, (13) a carbocycle having 3 to 15 carbon atoms or (14) a heterocycle having a skeleton consisting of 3 to 15 atoms including 1 to 5 heteroatom(s)); the other is a group of the formula: -Z-R5 (Z and R5 are as defined above); and R3 and R4 may form, together with the adjacent nitrogen atom, a heterocycle having a skeleton consisting of 3 to 15 atoms, which heterocycle is attached by a secondary nitrogen atom constituting the heterocycle, wherein the above-mentioned heterocycle and a carbocycle having 3 to 15 carbon atoms are each optionally substituted by substituent(s) selected from the group consisting of C1-8 alkyl, C2-8 alkenyl, C2-8 alkynyl, C7-16 aralkyl, C3-8 cycloalkyl, C3-8 cycloalkenyl, C6-14 aryl, C1-8 alkoxy, C1-3 alkylenedioxy, hydroxy, halogen atom, amino, (di or mono-C1-5 alkyl)amino, (C1-5 alkoxy-carbonyl)amino, (C1-5 acyl)amino, (C1-5 acyl) (C1-5 alkyl)amino, C1-5 alkylthio, nitrile, nitro, C1-5 alkoxy-carbonyl, carboxyl, C1-5 alkyl-carbonyloxy, oxo, thioxo, C1-6 acyl group, sulfamoyl and (di or mono-C1-5 alkyl)sulfamoyl, or a salt thereof or a prodrug thereof have a superior cGMP specific phosphodiesterase (PDE) inhibitory activity, and can be used as an agent for the prophylaxis or treatment of cardiovascular diseases such as angina pectoris, heart failure, cardiac infarction, hypertension, arteriosclerosis and the like, allergic diseases such as asthma, or disorders of male or female genital function and the like.

Synthesis of (1R,2S)-1-(3′-chloro-4′-methoxyphenyl)-1,2- propanediol (trametol) and (1R,2S)-1-(3′,5′-dichloro-4′- methoxyphenyl)-1,2-propanediol, chlorinated fungal metabolites in the natural environment

(1R,2S)-1-(3′-Chloro-4′-methoxyphenyl)-1,2-propanediol (Trametol, 3), a metabolite of the fungus Trametes sp. IVP-F640 and Bjerkandera sp. BOS55, was synthesized by employing Sharpless asymmetric dihydroxylation as the key step. Similarly, the (1R,2S)-isomer of 1-(3′,5′-dichloro- 4′-methoxyphenyl)-1,2-propanediol (4), another metabolite of Bjerkandera sp. BOS55, was synthesized by asymmetric dihydroxylation.

Evaluation of isomeric 4-(chlorohydroxyphenyl)-1,2,3,4-tetrahydroisoquinolines as dopamine D-1 antagonists

The isomeric 4-(3-chloro-4-hydroxyphenyl)- and 4-(4-chloro-3-hydroxyphenyl)-1,2,3,4-tetrahydroisoquinolines, the N-methyl derivative of the 4-(4-chloro-3-hydroxyphenyl)isomer, and 4-(3-hydroxyphenyl)-1,2,3,4-tetrahydroisoquinoline were synthesized and evaluated for dopamine D-1 antagonist activity. The 4-(3-chloro-4-hydroxyphenyl) and the 4-(3-hydroxyphenyl) isomer possessed similar potencies as D-1 antagonists. Introduction of the N-methyl group enhanced potency about twofold. The 'pharmacophore' for selective dopamine D-1 antagonist activity appears to be a tertiary 2-(3-hydroxyphenyl)-2-phenethylamine.