39720-27-9

Basic information

• Product Name: 4-(CHLOROMETHYL)PHENYL ACETATE
• Synonyms: 4-(chloromethyl)-phenoacetate;p-(chloromethyl)phenylacetate;p-acetoxybenzylchloride;4-(CHLOROMETHYL)PHENOL ACETATE;4-(CHLOROMETHYL)PHENYL ACETATE;Brn 2440833;Ccris 5104;Phenol, 4-(chloromethyl)-, acetate
• CAS NO: 39720-27-9
• Molecular Formula: C₉H₉ClO₂
• Molecular Weight: 184.62
• Product Categories: Aromatic Esters;C8 to C9;Carbonyl Compounds;Esters;Building Blocks;C8 to C9;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 39720-27-9.mol

Chemical Properties

• Melting Point: 31.5 °C
• Boiling Point: 240 °C(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.201 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00674mmHg at 25°C
• Refractive Index: n20/D 1.53(lit.)
• CAS DataBase Reference: 4-(CHLOROMETHYL)PHENYL ACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(CHLOROMETHYL)PHENYL ACETATE(39720-27-9)
• EPA Substance Registry System: 4-(CHLOROMETHYL)PHENYL ACETATE(39720-27-9)

Safety Data

• Hazard Codes: C
• Statements: 34-43-22
• Safety Statements: 26-27-36/37/39-45
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• RTECS: SK4956000
• Hazardous Substances Data: 39720-27-9(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
4-(Chloromethyl)phenyl acetate is used as a reagent in chemical synthesis for the production of various pharmaceuticals, agrochemicals, and other specialty chemicals. Its chloromethyl group can be easily substituted with other functional groups, making it a valuable building block for the creation of complex molecules.
Used in 4-(Chloromethyl)phenyl Acetate Assay:
4-(Chloromethyl)phenyl acetate is used as a reagent in the 4-(chloromethyl)phenyl acetate assay, which is a method for determining the presence and concentration of 4-(CHLOROMETHYL)PHENYL ACETATE in a sample. This assay is essential for quality control and monitoring the purity of the compound in various applications.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-(Chloromethyl)phenyl acetate is used as an intermediate in the synthesis of various drugs. Its unique reactivity allows for the creation of new drug candidates with potential therapeutic benefits.
Used in Agrochemical Industry:
4-(Chloromethyl)phenyl acetate is also used in the agrochemical industry for the synthesis of pesticides and other crop protection agents. Its versatility in chemical reactions enables the development of new compounds with improved efficacy and selectivity.
Used in Research and Development:
In the field of research and development, 4-(Chloromethyl)phenyl acetate is employed as a reagent for studying various chemical reactions and mechanisms. Its unique properties make it an interesting subject for scientific investigation, potentially leading to new discoveries and applications.

InChI:InChI=1/C9H9ClO2/c1-7(11)12-9-4-2-8(6-10)3-5-9/h2-5H,6H2,1H3

Upstream product

• 623-05-2 (4-hydroxyphenyl)methanol 
• 106-44-5 p-cresol 
• 123-08-0 4-hydroxy-benzaldehyde 
• 878-00-2 4-formylphenyl acetate 
• 6309-46-2 4-acetoxybenzyl alcohol 
• 75-36-5 acetyl chloride 

Downstream Products

• 5355-17-9 4-hydroxybenzyl methyl ether 
• 144868-68-8 4,5-bis(p-acetoxybenzylsulfanyl)-1,3-dithiole-2-thione 
• 94348-39-7 4-(2-oxo-2-phenylethyl)phenyl acetate 
• 894356-87-7 4-(morpholinomethyl)phenyl acetate 
• 1070293-27-4 N-cyclopropyl-3-(2-(4-hydroxybenzyl)-1-oxo-1,2-dihydroisoquinolin-6-yl)-4-methylbenzamide 
• 56071-69-3 acetic acid 4-(3-bromo-2-oxo-propyl)phenyl ester 
• 101-53-1 p-benzylphenol 
• 21388-77-2 4-[(4-methoxyphenyl)methyl]phenol 
• 1323942-07-9 Acetic acid 4-[(4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS,12S)-4b,12-difluoro-5-hydroxy-6b-(2-hydroxy-acetyl)-4a,6a-dimethyl-2-oxo-2,4b,5,6,6a,6b,7,9,9a,10,10a,10b,11,12-tetradecahydro-4aH-8-aza-pentaleno[2,1-a]phenanthren-8-ylmethyl]-phenyl ester 
• 682754-96-7 1-(4-hydroxybenzyl)-3-{1-[2-(3-methyl-3H-diazirin-3-yl)-ethyl]-2,3-dihydro-1H-benzo-imidazol-2-ylmethyl}-1,3-dihydrobenzoimidazol-2-one 

Relevant articles and documents

Fluorescent labeling of s2T-incorporated DNA and m5s2U-modified RNA

We report herein comprehensive investigations of alkylation/sulfur exchange reactions of sulfur-containing substrates including nucleosides such as s2U, m5s2U, s4U, s2A and s2T-incorporated DNA enable by comprehensive screenings of the reagents (2a–2h). It has been proven that iodoacetamide (2a) displays the most promising feasibility toward sulfur-containing substrates including s2T, s2U, m5s2U, s4U and s2A. In sharp contrast, the alkylation process with S-benzyl methanethiosulfonate (BMTS, 2h) displays the best application potential only for s4U. Based on these results, the fluorescent labeling of s2T-incorporated DNA and m5s2U-modified RNA has been achieved. Supplemental data for this article is available online at https://doi.org/10.1080/15257770.2021.1942044.

Natural Product Evodiamine with Borate Trigger Unit: Discovery of Potent Antitumor Agents against Colon Cancer

In order to improve the antitumor potency of the natural product evodiamine, novel boron-containing evodiamine derivatives were designed by incorporating boronic acid and boronate as trigger units. Boronate derivative 13a could be triggered by reactive oxygen species (ROS) in the HCT116 colon cancer cell line and showed excellent antitumor activity in vitro and in vivo. It induced apoptosis in HCT116 cancer cells in a dose-dependent manner and cell growth arrest at the G2 phase.

Palladium-catalyzed carboxylative coupling of benzyl chlorides with allyltributylstannane: Remarkable effect of palladium nanoparticles

Palladium-catalyzed carboxylative coupling of benzyl chlorides with allyltributylstannane was successfully conducted to produce benzyl but-3-enoates in satisfactory to good yields. The carboxylative coupling reaction occurred smoothly under mild conditions in the presence of palladium nanoparticles in tetrahydrofuran.

Regio- and chemoselective palladium-catalyzed benzylallylation of activated olefins: The remarkable effect of palladium nanoparticles

The palladium-catalyzed three-component reactions of benzyl halides, activated olefins, and allyltributylstannane were successfully conducted to produce the corresponding benzylallylation products in satisfactory to high yields. The benzylallylation reaction proceeded smoothly under mild conditions in the presence of palladium nanoparticles in tetrahydrofuran. The Royal Society of Chemistry 2013.

A highly chemoselective and rapid chlorination of benzyl alcohols under neutral conditions

A rapid and highly selective chlorination method has been developed using 2,4,6-trichloro-1,3,5-triazine (TCT) catalyzed by dimethyl sulfoxide. The reactions take 10 to 40 minutes, and the yields are almost quantitative. The neutral reaction conditions are compatible with substrates bearing acid-labile functional groups. Both competitive intramolecular and intermolecular reactions for benzyl alcohols in the presence of aliphatic alcohols indicate high selectivity. The procedure has been successfully used in the selective chlorination of gastrodin, a clinically used neuromedicine. This procedure represents a useful new tool in organic and medicinal chemistry. Georg Thieme Verlag Stuttgart.

Chemical insights in the concept of hybrid drugs: The antitumor effect of nitric oxide-donating aspirin involves a quinone methide but not nitric oxide nor aspirin

Hybrid drug 1 (NO-ASA) continues to attract intense research from chemists and biologists alike. It consists of ASA and a -ONO2 group connected through a spacer and is in preclinical development as an antitumor drug. We report that, contrary to current beliefs, neither ASA nor NO contributes to this antitumor effect. Rather, an unsubstituted QM was identified as the sole cytotoxic agent. QM forms from 1 after carboxylic ester hydrolysis and, in accordance with the HSAB theory, selectively reacts with cellular GSH, which in turn triggers cell death. Remarkably, a derivative lacking ASA and the -ONO 2 group is 10 times more effective than 1. Thus, our data provide a conclusive molecular mechanism for the antitumor activity of 1. Equally importantly, we show for the first time that a "presumed invisible" linker in a hybrid drug is not so invisible after all and is in fact solely responsible for the biological effect.

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