931-97-5

Basic information

• Product Name: 1-HYDROXY-1-CYCLOHEXANECARBONITRILE
• Synonyms: CYCLOHEXANONE CYANOHYDRIN;1-HYDROXY-1-CYCLOHEXANECARBONITRILE;1-HYDROXY-CYCLOHEXANECARBONITRILE;1-Hydroxy-cyclohexancarbonitril;1-hydroxy-cyclohexanecarbonitril;CYCLOHEXANECARBONITRILE,1-HYDROXY-;1-Cyano-1-hydroxycyclohexane;1-Hydroxy-1-cyanocyclohexane
• CAS NO: 931-97-5
• Molecular Formula: C₇H₁₁NO
• Molecular Weight: 125.17
• EINECS: 213-246-0
• Product Categories: Cycloalkanes;Miscellaneous
• Mol File: 931-97-5.mol

Chemical Properties

• Melting Point: 32-35 °C(lit.)
• Boiling Point: 132 °C19 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Colourless solid. Typical sharp nitrile odor
• Density: 1.031
• Vapor Pressure: 0.0113mmHg at 25°C
• Refractive Index: 1.4693
• Storage Temp.: 2-8°C
• PKA: 11.45±0.20(Predicted)
• CAS DataBase Reference: 1-HYDROXY-1-CYCLOHEXANECARBONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-HYDROXY-1-CYCLOHEXANECARBONITRILE(931-97-5)
• EPA Substance Registry System: 1-HYDROXY-1-CYCLOHEXANECARBONITRILE(931-97-5)

Safety Data

• Hazard Codes: T+
• Statements: 28
• Safety Statements: 45
• RIDADR: UN 2811 6.1/PG 2
• WGK Germany: 3
• RTECS: GU7710000
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 931-97-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-HYDROXY-1-CYCLOHEXANECARBONITRILE is used as a key intermediate in the synthesis of various pharmaceuticals, including antibiotics and antifungal agents. Its unique structure allows for the development of new drugs with improved efficacy and reduced side effects.
Used in Agrochemical Industry:
1-HYDROXY-1-CYCLOHEXANECARBONITRILE is used as a starting material for the production of agrochemicals, such as insecticides and herbicides. Its ability to form stable derivatives makes it suitable for the development of effective and environmentally friendly pesticides.
Used in High-Throughput Screening Assays:
1-HYDROXY-1-CYCLOHEXANECARBONITRILE is used as a substrate during high-throughput screening assays for hydroxynitrile lyase activity. This allows researchers to identify and optimize enzymes that can efficiently catalyze the conversion of cyclohexanone cyanohydrin into other valuable compounds.
Used in the Preparation of 1-Aminomethyl Cyclohexanol:
1-HYDROXY-1-CYCLOHEXANECARBONITRILE is used in the preparation of 1-aminomethyl cyclohexanol via catalytic hydrogenation reaction. 1-HYDROXY-1-CYCLOHEXANECARBONITRILE has potential applications in the synthesis of pharmaceuticals and other specialty chemicals, further expanding the utility of cyclohexanone cyanohydrin.

Synthesis Reference(s)

Tetrahedron Letters, 19, p. 3773, 1978 DOI: 10.1016/S0040-4039(01)95055-5

Air & Water Reactions

Water soluble. Reacts slowly with water .

Reactivity Profile

1-HYDROXY-1-CYCLOHEXANECARBONITRILE is an a-hydroxonitrile. Incompatible with acids; mixing nitriles with strong oxidizing acids can lead to violent reactions. Incompatible with oxidizing agents such as peroxides and epoxides. Mixing with bases can produce poisonous and flammable hydrogen cyanide. May be hydrolyzed exothermically in both aqueous acid and base to give carboxylic acids (or salts of carboxylic acids). May react vigorously with reducing agents.

Fire Hazard

Flash point data regarding 1-HYDROXY-1-CYCLOHEXANECARBONITRILE are not available, however, 1-HYDROXY-1-CYCLOHEXANECARBONITRILE is probably combustible.

InChI:InChI=1/C7H11NO/c8-6-7(9)4-2-1-3-5-7/h9H,1-5H2

Upstream product

• 123-91-1 1,4-dioxane 
• 74-90-8 hydrogen cyanide 
• 108-94-1 cyclohexanone 
• 60-29-7 diethyl ether 
• 24731-36-0 1-trimethylsilanyloxycyclohexanecarbonitrile 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 2094-98-6 1,1'-azobis(1-cyanocyclohexanenitrile) 
• 5804-85-3 diethylaluminium cyanide 
• 773837-37-9 sodium cyanide 
• 1123-28-0 1-hydroxy-cyclohexanecarboxylic acid 
• 151-50-8 potassium cyanide 
• 7677-24-9 trimethylsilyl cyanide 
• 143-33-9 sodium cyanide 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 

Downstream Products

• 1206-23-1 1-tetrahydropyran-2-yloxy-cyclohexanecarbonitrile 
• 51939-79-8 ethyl 2-cyano-2-(1-cyanocyclohexyl)acetate 
• 74-90-8 hydrogen cyanide 
• 108-94-1 cyclohexanone 
• 1123-27-9 1-(1-hydroxycyclohexyl)ethan-1-one 
• 855425-07-9 1,1'-(4-methyl-m-phenylenediamino)-bis-cyclohexanecarbonitrile 
• 2103-37-9 2-cyano-2-(1-cyano-cyclohexyl)-propionic acid ethyl ester 
• 2103-35-7 2-cyano-2-(1-cyano-cyclohexyl)-3-phenyl-propionic acid ethyl ester 
• 947-19-3 1-hydroxycyclohexyl phenyl ketone 
• 7500-69-8 1-hydroxycyclohexanecarboxamide 
• 4000-72-0 1-aminomethylcyclohexanol 
• 1123-28-0 1-hydroxy-cyclohexanecarboxylic acid 
• 702-62-5 spiro(imidazolidine-4,1'-cyclohexane)-2,5-dione 
• 636-82-8 cyclohexene-1-carboxylic acid 

Relevant articles and documents

Radical-mediated aerobic oxidation of substituted styrenes and stilbenes

A 2,2-azobis(isobutyronitrile)-catalyzed oxidative cleavage of alkenes with molecular oxygen as the oxidant was described. Carbonyl compounds and oxiranes were obtained in moderate yield under mild conditions. This study provided useful insights into the mechanism of aerobic oxidative cleavage of alkenes.

CO2-Enabled Cyanohydrin Synthesis and Facile Iterative Homologation Reactions**

Thermodynamic and kinetic control of a chemical process is the key to access desired products and states. Changes are made when a desired product is not accessible; one may manipulate the reaction with additional reagents, catalysts and/or protecting groups. Here we report the use of carbon dioxide to accelerate cyanohydrin synthesis under neutral conditions with an insoluble cyanide source (KCN) without generating toxic HCN. Under inert atmosphere, the reaction is essentially not operative due to the unfavored equilibrium. The utility of CO2-mediated selective cyanohydrin synthesis was further showcased by broadening Kiliani–Fischer synthesis under neutral conditions. This protocol offers an easy access to a variety of polyols, cyanohydrins, linear alkylnitriles, by simply starting from alkyl- and arylaldehydes, KCN and an atmospheric pressure of CO2.

Production process of high-purity and high-yield spirodiclofen

The invention relates to the technical field of synthesis of compounds and specifically relates to a production process of high-purity and high-yield spirodiclofen. The production process comprises the following steps: performing an addition reaction on cyclohexanone which is taken as a starting material, so as to obtain 1-cyano-cyclohexanol; hydrolyzing and esterifying the 1-cyano-cyclohexanol, so as to obtain 1-hydroxylethyl formate; performing a condensation ring-closing reaction on the 1-hydroxylethyl formate, so as to obtain an intermediate caproate; and performing a reaction on the caproate and 2, 2-dimethylbutyryl chloride, so as to obtain the spirodiclofen. According to the production process, the problem in the prior art that the prepared spirodiclofen is low in purity and yield is solved; the spirodiclofen prepared by adopting the production process is high in purity and yield; and in addition, the raw material for preparing the spirodiclofen is easily obtained, and the operation is convenient.

A magnetic nanoparticle catalyzed eco-friendly synthesis of cyanohydrins in a deep eutectic solvent

Magnetic Fe3O4 nanoparticles in deep eutectic solvents (DESs) have been regard as excellent catalysts for highly efficient cyanosilylation of various aldehydes and epoxides using trimethylsilyl cyanide TMSCN in high yields with excellent selectivity. Fe3O4 nanoparticles were synthesized and applied as a catalyst for the preparation of a wide variety of cyanohydrins (α-hydroxy nitriles and β-hydroxy nitriles) in readily available urea-choline chloride deep eutectic solvent DES as the most promising environmentally benign and cost-effective green solvent. Magnetic DES operates at very mild reaction conditions and can be easily recycled without significant loss of its catalytic activity.

SPIRO-OXAZOLONES

The present invention provides spiro-oxazolones, which act as V1a receptor modulators, and in particular as V1a receptor antagonists, their manufacture, pharmaceutical compositions containing them and their use as medicaments. The present compounds are useful as therapeutics acting peripherally and centrally in the conditions of inappropriate secretion of vasopressin, anxiety, depressive disorders, obsessive compulsive disorder, autistic spectrum disorders, schizophrenia, aggressive behavior and phase shift sleep disorders, in particular jetlag.

The continuous reaction device and method of using the continuous composite (by machine translation)

PROBLEM TO BE SOLVED: compounds with high productivity can be generated. SOLUTION: 1 the raw material supply section 12 and a first, a second and 2 the raw material supply section 14, and a reaction part 18, the first reaction part 1 from the raw material supply section 1 and a second quantity of raw material, the raw material supply section 2 from the first reaction part 2 and a second quantity of raw material, the raw material supply section 1 from the first reaction part 1 and a second temperature of the raw material, the raw material supply section 2 from the first reaction part 2 and supplied to the temperature of the raw material, and having a control part 22, a continuous reaction device as shown in the drawing. Selected drawing: fig. 1 (by machine translation)

Anesthetic compounds and related methods of use

Provided herein are compounds according to formula (I): Provided herein is also a pharmaceutical composition comprising a compound according to formula (I) and a pharmaceutically acceptable carrier, and a method for providing anesthesia in a subject by administering such a pharmaceutical composition.

Synthesis, spectral, and structural characteristics of cyanohydrines derived from aliphatic cyclic ketones1

A series of cyanohydrines derived from cyclic aliphatic ketones was synthesized by acid-catalyzed nucleophilic addition reaction under the action of potassium cyanide. The products were characterized by means of multi-nuclear NMR spectroscopy (1H, 13C, 14N, 15N), mass spectrometry, elemental analysis, UV-Vis spectroscopy, refraction index measurements as well as vibrational spectroscopy. The structure of the cyanohydrine of cyclohexanone was elucidated by means of single crystal X-ray diffraction.

Novel 4H-1,2,4-triazol-3-yl cycloalkanols as potent antitubercular agents

Enzymes of shikimate pathway, dehydroquinase and shikimate kinase represent comparatively newer targets for antitubercular research. Molecular hybridization approach was implemented by integrating the essential features of inhibitors acting on these enzymes of shikimate pathway. Considering the flexibility of alicyclic ring of reported dehydroquinase (DHQ) inhibitors and triazole ring, key feature of the virtual hits of Mtb shikimate kinase, a series of structurally novel, substituted 4H-1,2,4-triazol-3-yl cycloalkanols were designed as antimycobacterial agents. Docking studies of the molecules was carried out on the enzyme DHQ. All the synthesized compounds exhibited promising activity (MIC 0.59-15.5 μg/ml) against H37Rv strains of Mycobacterium tuberculosis using resazurin microtiter assay. Five of the evaluated compounds exhibit MIC 50 values indicate compounds are non-toxic, with selectivity indices >28. These compounds could serve as leads for further optimization to obtain novel antimycobacterial agents.

ANESTHETIC COMPOUNDS AND RELATED METHODS OF USE

Provided herein are compounds according to formula (I): Provided herein is also a pharmaceutical composition comprising a compound according to formula (I) and a pharmaceutically acceptable carrier, and a method for providing anesthesia in a subject by administering such a pharmaceutical composition.