170859-72-0

Basic information

• Product Name: 3-(3-HYDROXY-PROP-1-YNYL)-BENZONITRILE
• Synonyms: 3-(3-HYDROXY-1-PROPYNYL)BENZONITRILE;3-(3-HYDROXY-PROP-1-YNYL)-BENZONITRILE;AKOS PRN-0100;3-(3-Hydroxyprop-1-yn-1-yl)benzonitrile
• CAS NO: 170859-72-0
• Molecular Formula: C₁₀H₇NO
• Molecular Weight: 157.17
• Mol File: 170859-72-0.mol

Chemical Properties

• Boiling Point: 317.1 °C at 760 mmHg
• Flash Point: 145.6 °C
• Appearance: /
• Density: 1.2g/cm³
• PKA: 13.01±0.10(Predicted)
• CAS DataBase Reference: 3-(3-HYDROXY-PROP-1-YNYL)-BENZONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(3-HYDROXY-PROP-1-YNYL)-BENZONITRILE(170859-72-0)
• EPA Substance Registry System: 3-(3-HYDROXY-PROP-1-YNYL)-BENZONITRILE(170859-72-0)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 170859-72-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
3-(3-Hydroxy-prop-1-ynyl)-benzonitrile is used as a key intermediate in the synthesis of various organic compounds. Its hydroxyl and propynyl groups provide opportunities for further functionalization and modification, enabling the creation of a wide range of chemical products.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-(3-Hydroxy-prop-1-ynyl)-benzonitrile is utilized for the development of new drugs. Its unique structure allows for the design of novel therapeutic agents with potential applications in treating various diseases and medical conditions.
Used in Medicinal Chemistry Research:
3-(3-Hydroxy-prop-1-ynyl)-benzonitrile is employed as a subject of research in medicinal chemistry. Scientists are exploring its potential uses in the discovery and optimization of new pharmaceutical compounds, leveraging its distinctive structural features to enhance drug efficacy and selectivity.
Ongoing research on 3-(3-Hydroxy-prop-1-ynyl)-benzonitrile aims to uncover its full potential in various fields and industries, expanding its applications and contributing to the advancement of science and medicine.

Upstream product

• 69113-59-3 3-iodobenzonitrile 
• 107-19-7 propargyl alcohol 
• 6952-59-6 3-cyanobromobenzene 

Downstream Products

• 171290-53-2 3-ethynylbenzonitrile 
• 1399086-40-8 3-(3-oxoprop-1-yn-1-yl)benzonitrile 
• 352615-74-8 (Z)-3-(3-cyanophenyl)-2-propen-1-ol 
• 83101-13-7 3-(3-cyanophenyl)-1-propanol 
• 98116-50-8 3-(3-cyanophenyl)-2-(E)-propen-1-ol 
• 1620138-04-6 C₂₂H₃₅NOSn 
• 1402044-03-4 C₂₀H₁₃NO 

Relevant articles and documents

Novel Propargyl-Linked Bisubstrate Analogues as Tight-Binding Inhibitors for Nicotinamide N-Methyltransferase

Nicotinamide N-methyltransferase (NNMT) catalyzes the methyl transfer from the cofactor S-adenosylmethionine to nicotinamide and other pyridine-containing compounds. NNMT is an important regulator for nicotinamide metabolism and methylation potential. Aberrant expression levels of NNMT have been implicated in cancer, metabolic, and neurodegenerative diseases, which makes NNMT a potential therapeutic target. Therefore, potent and selective NNMT inhibitors can serve as valuable tools to investigate the roles of NNMT in its mediated diseases. Here, we applied a rational strategy to design and synthesize the tight-binding bisubstrate inhibitor LL320 through a novel propargyl linker. LL320 demonstrates a Ki value of 1.6 ± 0.3 nM, which is the most potent inhibitor to date. The cocrystal structure of LL320 confirms its interaction with both the substrate and cofactor binding sites on NNMT. Importantly, this is the first example of using the propargyl linker to construct potent methyltransferase inhibitors, which will expand our understanding of the transition state of methyl transfer.

Cobalt-catalyzed (Z)-selective semihydrogenation of alkynes with molecular hydrogen

Cobalt-catalyzed highly (Z)-selective semihydrogenation of alkynes using molecular H2 was developed using commercially available and cheap cobalt precursors. A variety of (Z)-alkenes were obtained in moderate to excellent selectivities [(Z)-alkene/(E)-alkene/alkane ratio up to >99 : 1 : 1] and it was found that the readily available ethylenediamine ligand is crucial in determining the selectivity.

Design and synthesis of novel xanthine derivatives as potent and selective A2B adenosine receptor antagonists for the treatment of chronic inflammatory airway diseases

Adenosine induces bronchial hyperresponsiveness and inflammation in asthmatics through activation of A2B adenosine receptor (A2BAdoR). Selective antagonists have been shown to attenuate airway reactivity and improve inflammatory cond

Palladium-catalyzed multicomponent reaction (MCR) of propargylic carbonates with isocyanides

A palladium-catalyzed multicomponent reaction (MCR) of propargylic carbonates with isocyanides is reported. Remarkably, the orderly insertion of isocyanides affords two types of valuable N-heterocyclic products (Z)-6-imino-4,6-dihydro-1H-furo[3,4-b]pyrrol-2-amines and (E)-5-iminopyrrolones in high yields. Systematic analysis of the reaction conditions indicates that the selectivity of these N-heterocyclic products can be controlled by ligands and temperature.

Factor xa inhibitors with aryl-amidines and derivatives, and prodrugs thereof

The present invention relates to a compound with aryl-amidines, particularly amidinoaryl-cyclopropanes, amidinoarylmethyl-pyrroles, amidinoaryl-benzenes, amidinoaryl-pyridines, or amindonoaryl-alanines, represented by formula (1), a pharmaceutically acceptable salt, a prodrug, a hydrate, a solvate or an isomer thereof, which are inhibitors of coagulation enzyme, factor Xa (FXa). The present invention also relates to a pharmaceutical composition containing the compound, and a method of using the same as an anticoagulant agent for treatment and prevention of thrombosis disorders.

Synthesis and Electrochemical Properties of 4-Phenyl-1-buten-3-yne-1,1,2-tricarbonitriles and Tricyanoacrylates

The reaction of phenylacetylenes 4a-h copper(I) acetate (5) and TCNE (tetracyanoethylene) in THF/acetonitrile gave 4-phenyl-1-buten-3-yne-1,1,2-tricarbonitriles 6a-h. 4i did not react to give 6i.The phenylacetylenes 4b-i were prepared by a two-step synthesis starting from the corresponding phenyl halides 1b-i.The tricyanoacrylates 8 were synthesised from the corresponding cyanoacetates 7, TCNE and catalytic amounts of pyridine in THF. - Cyclovoltammetric investigations showed that the butenynes 6 and the tricyanoacrylates 8 are strong electron acceptors which can be easily reduced.The radical anions 6.- are unstable in acetonitrile and react irreversibly with 6 to give oligomeric anions 6.-n.Only 4-(2,4,6-trimethoxyphenyl)-1-buten-3-yne-1,1,2-tricarbonitrile (6h) is reduced to a radical anion 6h.- which associates with 6h in a reversible follow-up process to form a dimeric anion 6h2.-.By contrast, the tricyanoacrylates 8 can be reversibly reduced to their respective radical anions and dianions. - Keywords: Cyano compounds, conjugated / Phenylacetylenes / Radical anions / Electrochemistry