10602-04-7

Basic information

• Product Name: 4-ETHYNYLBENZYL ALCOHOL 97
• Synonyms: 4-ETHYNYLBENZYL ALCOHOL 97;(4-ethynylphenyl)Methanol;1-Ethynyl-4-(hydroxymethyl)benzene;4-Hydroxymethylphenylacetylene;4-Ethynyl-benzeneMethanol;4-Ethynylbenzyl alcohol 97%;Benzenemethanol,4-ethynyl-
• CAS NO: 10602-04-7
• Molecular Formula: C₉H₈O
• Molecular Weight: 132.161
• Product Categories: Alkynes;Organic Building Blocks;Terminal;Building Blocks;Chemical Synthesis;Organic Building Blocks
• Mol File: 10602-04-7.mol
• Article Data: 41

Chemical Properties

• Melting Point: 40-44 °C(lit.)
• Boiling Point: 239.6±23.0℃ (760 Torr)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.08±0.1 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 0.0216mmHg at 25°C
• Refractive Index: 1.572
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 14.13±0.10(Predicted)
• CAS DataBase Reference: 4-ETHYNYLBENZYL ALCOHOL 97(CAS DataBase Reference)
• NIST Chemistry Reference: 4-ETHYNYLBENZYL ALCOHOL 97(10602-04-7)
• EPA Substance Registry System: 4-ETHYNYLBENZYL ALCOHOL 97(10602-04-7)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36-42/43
• Safety Statements: 26-36
• WGK Germany: 2
• Hazardous Substances Data: 10602-04-7(Hazardous Substances Data)

Usage

Description

4-Ethynylbenzyl alcohol, also known as 4-ETHYNYLBENZYL ALCOHOL 97, is an organic compound characterized by its unique structure that features an ethynyl group attached to a benzyl alcohol moiety. 4-ETHYNYLBENZYL ALCOHOL 97 is known for its versatile chemical properties and reactivity, making it a valuable building block in various synthetic applications.

Uses

Used in Chemical Synthesis:
4-Ethynylbenzyl alcohol is used as a key intermediate in the synthesis of complex organic molecules, such as platinum-acetylide dendrimers, rotaxanes, and arylacetylenes. Its unique structure allows for the formation of diverse molecular architectures with potential applications in various fields.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-Ethynylbenzyl alcohol is used as a precursor to synthesize arylalkyne-tagged sugars, which are essential for the photoinduced glycosylation of cysteine-containing peptides. This process plays a crucial role in the development of novel drug candidates and therapeutic agents.
Used in Material Science:
4-Ethynylbenzyl alcohol can also act as a precursor to synthesize fluorescent probes through a Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) click reaction. These fluorescent probes are valuable tools in material science, as they can be used to study various biological processes and interactions at the molecular level.
Overall, 4-Ethynylbenzyl alcohol 97 is a versatile and valuable compound with a wide range of applications in chemical synthesis, pharmaceuticals, and material science, making it an essential component in the development of new technologies and products.

InChI:InChI=1/C9H8O/c1-2-8-3-5-9(7-10)6-4-8/h1,3-6,10H,7H2

Upstream product

• 63697-96-1 4-Ethynylbenzaldehyde 
• 889361-56-2 1-(triisopropylsilyl)-2-[4-(hydroxymethyl)phenyl]ethyne 
• 18282-51-4 4-iodo-benzyl alcohol 
• 1066-54-2 trimethylsilylacetylene 
• 3034-86-4 4-ethynylbenzoic acid methyl ester 
• 619-44-3 methyl 4-iodobenzoate 
• 77123-57-0 4-[(trimethylsilyl)ethynyl]bezaldehyde 
• 115-19-5 2-methyl-but-3-yn-2-ol 
• 766-96-1 4-bromo-1-ethynylbenzene 
• 117569-57-0 4-(3-hydroxy-3-methylbut-1-ynyl)benzaldehyde 
• 1122-91-4 4-bromo-benzaldehyde 
• 75867-41-3 4-trimethylsilanylethynyl-benzoic acid methyl ester 
• 619-42-1 4-methoxycarbonylphenyl bromide 
• 873-75-6 4-bromobenzenemethanol 

Downstream Products

• 113331-97-8 methyl 5-hydroxy-7-<4-(1-hydroxymethyl)phenyl>hept-6-ynoate 
• 870719-33-8 4-ethynylbenzyl 3,5-bis[3',4'-di(octan-1-yloxy)benzyloxy]benzoate 
• 870719-39-4 4-ethynylbenzyl 3,5-bis[3',4'-di((S)-3,7-dimethyloctan-1-yloxy)benzyloxy]benzoate 
• 870719-35-0 4-ethynylbenzyl 3,5-bis[3',4'-di(decan-1-yloxy)benzyloxy]benzoate 
• 870719-59-8 4-ethynylbenzyl 3,5-bis[3',4'-di(tetradecan-1-yloxy)benzyloxy]benzoate 
• 1013026-53-3 (4-dodeca-1,3-diynyl-phenyl)-methanol 
• 1019336-34-5 C₂₅H₂₁N₃O₂ 
• 1019336-67-4 C₂₅H₁₈N₄O 
• 1019336-92-5 C₂₄H₁₉N₃O 
• 1134374-46-1 (E)-S-(2-diphenylthiophosphinyl-1-(4-hydroxymethylphenyl)ethenyl) O-ethyl dithiocarbonate 
• 1084329-02-1 5,7-dihydroxy-2-(4-((4-(hydroxymethyl)phenyl)ethynyl)phenyl)-4H-chromen-4-one 
• 1262105-91-8 (4-(1-(4-nitrobenzyl)-1H-1,2,3-triazol-4-yl)phenyl)methanol 
• 1093190-17-0 tert-butyl[(4-ethynylphenyl)methoxy]dimethylsilane 
• 1224841-01-3 {4-[6-chloro-2-methanesulfonyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazol-5-ylethynyl]-phenyl}-methanol 

Relevant articles and documents

Synthesis of chiral helical poly(hydroxyl-containing phenylacetylene) membranes by in-situ depinanylsilylation and their enantioselective permeabilities

Two new chiral helical poly(hydroxyl-containing phenylacetylene) membranes without the coexistence of any other chiral moieties were prepared in the following manner: (1) synthesis and homo-or copolymerization of two new chiral pinanylsiloxy-containing ph

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Small interfering RNA (siRNA) can be used as an innovative next-generation drug. However, there are several challenges in the therapeutic application of siRNAs, including their low cell membrane permeability. In this study, we designed and synthesized siR

Chelation control through the coordination of Lewis acids to an acetylenic π-bond

-

Design, synthesis and antitumor evaluations of nucleoside base hydroxamic acid derivatives as DNMT and HDAC dual inhibitors

DNA methyltransferase (DNMT) and histone deacetylase (HDAC) are well recognized epigenetic targets for discovery of antitumor agents. In this study, we designed and synthesized a series of nucleoside base hydroxamic acid derivatives as DNMT and HDAC dual inhibitors. MTT assays and enzymatic inhibitory activity tests indicated that compound 204 exhibited potent DNMT1 and HDAC1/6 inhibitory potency simultaneously in enzymatic levels and at cellular levels, inducing hypomethylation of p16 and hyperacetylation of histones H3K9 and H4K8. Besides, 204 remarkably inhibited proliferation against cancer cells U937 by prompting G0/G1 cell cycle arrest. Molecular docking models explained the functional mechanism of 204 inhibiting DNMT1 and HDAC. Preliminary studies on metabolic profiles revealed that 204 showed desirable stability in liver microsomes. Our study suggested that 204 inhibiting DNMT and HDAC concurrently can be a potential lead compound for epigenetic cancer therapy.

Electrochemical Difunctionalization of Terminal Alkynes: Access to 1,4-Dicarbonyl Compounds

1,4-Dicarbonyl compounds are versatile scaffolds for the heterocycle synthesis, including the Paal-Knorr reaction. Herein, a feasible electrosynthesis method to access 1,4-dicarbonyl compounds has been developed from simple alkynes and 1,3-dicarbonyl compounds. When the undivided cell is combined with the constant current mode, aryl alkynes containing numerous medicinal motifs with 1,3-dicarbonyl esters or ketones react smoothly. External oxidant and catalyst-free conditions conform to the requirements of green synthesis.

Iron-Catalyzed Tertiary Alkylation of Terminal Alkynes with 1,3-Diesters via a Functionalized Alkyl Radical

Direct oxidative C(sp)?H/C(sp3)?H cross-coupling offers an ideal and environmentally benign protocol for C(sp)?C(sp3) bond formations. As such, reactivity and site-selectivity with respect to C(sp3)?H bond cleavage have remained a persistent challenge. Herein is reported a simple method for iron-catalyzed/silver-mediated tertiary alkylation of terminal alkynes with readily available and versatile 1,3-dicarbonyl compounds. The reaction is suitable for an array of substrates and proceeds in a highly selective manner even employing alkanes containing other tertiary, benzylic, and C(sp3)?H bonds alpha to heteroatoms. Elaboration of the products enables the synthesis of a series of versatile building blocks. Control experiments implicate the in situ generation of a tertiary carbon-centered radical species.