4-Chlorobenzyl alcohol

Base Information

• Chemical Name: 4-Chlorobenzyl alcohol
• CAS No.: 873-76-7
• Molecular Formula: C7H7ClO
• Molecular Weight: 142.585
• Hs Code.: 29062900
• European Community (EC) Number: 212-852-2
• NSC Number: 5286
• UNII: GF8BS53B6V
• DSSTox Substance ID: DTXSID7073937
• Nikkaji Number: J141.587E
• Wikidata: Q27279073
• ChEMBL ID: CHEMBL1224554
• Mol file: 873-76-7.mol

Synonyms:4-Chlorobenzyl alcohol;(4-Chlorophenyl)methanol;873-76-7;P-CHLOROBENZYL ALCOHOL;Benzenemethanol, 4-chloro-;4-Chlorobenzenemethanol;4-Chlorobenzylalcohol;Benzyl alcohol, p-chloro-;4-Chlorobenzylic alcohol;MFCD00004652;CCRIS 5120;NSC 5286;EINECS 212-852-2;UNII-GF8BS53B6V;(4-chloro-phenyl)-methanol;GF8BS53B6V;AI3-20628;CHEMBL1224554;NSC-5286;p-chlorotoluol;p-chloro-benzylalcoho;4-chlorophenylmethanol;p-chlorobenzyl-alcohol;4-chloro-benzyl alcohol;para-chlorobenzyl alcohol;(4-chlorophenyl) methanol;(4-chlorophenyl)-methanol;(4-Chlorophenyl)methanol #;SCHEMBL50385;4-Chlorobenzyl alcohol, 99%;1-chloro-4-hydroxymethylbenzene;DTXSID7073937;NSC5286;Benzenemethanol, 4-chloro- (9CI);CS-D1681;AC7505;BBL011936;BDBM50325563;STL163452;AKOS000119500;PS-5314;BP-10435;LS-42763;SY001234;4-Chlorobenzyl alcohol, analytical standard;FT-0656712;EN300-20398;A842116;AB-131/40228314;W-104027;Q27279073;Z104478032;4JL

Chemical Property of 4-Chlorobenzyl alcohol

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 0.0299mmHg at 25°C
• Melting Point: 68-71 °C(lit.)
• Refractive Index: 1.566
• Boiling Point: 234.069 °C at 760 mmHg
• PKA: 14.16±0.10(Predicted)
• Flash Point: 95.362 °C
• PSA: 20.23000
• Density: 1.237 g/cm³
• LogP: 1.83230
• Storage Temp.: Store below +30°C.
• Solubility.: 2.5g/l
• Water Solubility.: Soluble in water (2.5 mg/ml at 20°C), and methanol.
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 142.0185425
• Heavy Atom Count: 9
• Complexity: 77

Purity/Quality:

98% ^*data from raw suppliers

4-Chlorobenzyl Alcohol ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=CC=C1CO)Cl
• Description: It is usually used as the intermediate in organic synthesis and pharmaceutical industry. Specifically, this chemical can react with o-xylene in the presence of HAuCl4 or AuCl3 at 80 ℃ to generate the corresponding benzylated product.1 Moreover, the acetylation of 4-chlorobenzyl alcohol in presence of catalytic amounts of Ce(OTf)4 has been performed in acetic acid to produce the desired esters in the excellent yields.2 In addition, this chemical may function as the raw material to produce its corresponding carboxylic acids and ketones in good yields through the oxidation reaction by using hydrogen peroxide and cobalt(Ⅱ) complex.3 Besides, the formylation and acetylation of 4-chlorobenzyl alcohol may be carried out in the presence of Silphos [PCl3?n(SiO2)n] in ethyl formate and ethyl acetate.4
• Uses: Reagent for carboxyl group protection. 4-Chlorobenzyl alcohol acts as a reagent for the protection of carboxyl groups as their 4-chlorobenzyl esters, more stable to acid than the corresponding benzyl esters. It is used as solvent in paint stripper and waterborne coatings. It acts as curing agent. It is also used in pharmaceuticals, cosmetics, preservatives, and flavoring & fragrance agents.

Technology Process of 4-Chlorobenzyl alcohol

There total 197 articles about 4-Chlorobenzyl alcohol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

4-chlorobenzaldehyde (104-88-1) + aniline (62-53-3) → 4-chlorobenzanilide (6833-15-4) + para-Chlorobenzyl alcohol (873-76-7)

Guidance literature:

aniline; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 20 ℃; Inert atmosphere;

4-chlorobenzaldehyde; With yttrium(III) chloride; In toluene; at 20 ℃; for 48h; Inert atmosphere;

With hydrogenchloride; In water; toluene; at 20 ℃; Inert atmosphere;

DOI:10.1016/j.tet.2009.09.101

Reference yield: 95.0%

benzyloxy-trimethylsilane (14642-79-6) + 4-chloro-1-[(ethoxymethoxy)methyl]benzene (1202-68-2) → para-Chlorobenzyl alcohol (873-76-7) + benzyl alcohol (100-51-6,185532-71-2)

Guidance literature:

With 1-methylimidazole hydrogen sulfate; at 120 ℃; for 0.0166667h; chemoselective reaction; Microwave irradiation;

DOI:10.1007/s00706-010-0373-6

Reference yield: 95.0%

Benzyl acetate (140-11-4) + 4-chloro-1-[(ethoxymethoxy)methyl]benzene (1202-68-2) → para-Chlorobenzyl alcohol (873-76-7) + benzyl alcohol (100-51-6,185532-71-2)

Guidance literature:

With 1-methylimidazole hydrogen sulfate; at 120 ℃; for 0.0166667h; chemoselective reaction; Microwave irradiation;

DOI:10.1007/s00706-010-0373-6

upstream raw materials:

phosgene

diethyl ether

1-chloro-4-{[(phenylmethyl)oxy]methyl}benzene

isopropylmagnesium bromide

Downstream raw materials:

(4-chloro-benzyl)-(6-methyl-[2]pyridyl)-amine

(4-chloro-benzyl)-trityl ether

4-chloro-N-(4-chlorobenzyl)aniline

1-(butoxymethyl)-4-chlorobenzene

Refernces

• 1、 -. "A method of synthesis of alcohols". Paragraph 0067-0072. . Retrieved 2022/01/10.
• 2、 Sharifi, Sina,Sharifi, Hannah,Koza, Darrell,Aminkhani, Ali. "Disproportionation of aliphatic and aromatic aldehydes through Cannizzaro, Tishchenko, and Meerwein–Ponndorf–Verley reactions". . p. 803 - 808. Retrieved 2021/07/20.