873-92-7

Basic information

• Product Name: 1-chloro-1-nitrocyclohexane
• CAS NO: 873-92-7
• Molecular Formula: C₆H₁₀ClNO₂
• Molecular Weight: 163.6021
• Mol File: 873-92-7.mol

Chemical Properties

• Boiling Point: 242.2°C at 760 mmHg
• Flash Point: 100.3°C
• Density: 1.22g/cm³
• Vapor Pressure: 0.0344mmHg at 25°C
• Refractive Index: 1.49
• CAS DataBase Reference: 1-chloro-1-nitrocyclohexane(CAS DataBase Reference)
• NIST Chemistry Reference: 1-chloro-1-nitrocyclohexane(873-92-7)
• EPA Substance Registry System: 1-chloro-1-nitrocyclohexane(873-92-7)

Safety Data

• Hazardous Substances Data: 873-92-7(Hazardous Substances Data)

Usage

Physical state

Viscous, colorless liquid

Uses

Intermediate in the production of pharmaceuticals and agrochemicals

Reactivity

Highly reactive

Environmental impact

Potential environmental hazard due to toxic properties and potential to bioaccumulate in the food chain

Health hazards

Harmful if inhaled, swallowed, or absorbed through the skin; can cause irritation to the eyes and skin

Handling and disposal

Proper handling and disposal are essential to minimize impact on human health and the environment

Upstream product

• 695-64-7 1-chloro-1-nitrosocyclohexane 
• 100-64-1 cyclohexanone-oxime 
• 1122-60-7 1-nitrocyclohexane 
• 7697-37-2 nitric acid 
• 64-19-7 acetic acid 
• 64-17-5 ethanol 

Downstream Products

• 100-64-1 cyclohexanone-oxime 
• 2211-64-5 N-cyclohexyl-hydroxylamine 
• 62479-69-0 ethyl 2-cyclohexylidenebutanoate 
• 62479-70-3 2-Cyclohexylidene-hexanoic acid ethyl ester 
• 77850-74-9 2-Cyclohexylidene-3-oxo-butyric acid ethyl ester 
• 77850-75-0 2-Cyclohexylidene-1-phenyl-butane-1,3-dione 
• 108-94-1 cyclohexanone 
• 1122-60-7 1-nitrocyclohexane 
• 58102-55-9 1-nitrocyclohexylcarbonitrile 

Relevant articles and documents

New reagent for a one-step synthesis of gem-chloronitro compounds from oximes

The use of chlorine bleach (5% NaOCl) for the halogenation-oxidation of oximes to gem-chloronitro compounds is reported. Chlorine bleach afforded satisfactory yields when employed alone either at room temperature or under ultrasonic irradiation.

Oxidation of gem-chloronitroso- and vic-chloronitroso-alkanes and -cycloalkanes to respective chloronitro compounds by novel cetyltrimethylammonium hypochlorite reagent

Cetyltrimethylammonium hypochlorite (CTAHC) is prepared and used as an oxidizing agent for nitroso group to nitro group. The gem-chloronitroso and vic-chloronitroso compounds are prepared respectively from ketoximes and olefins by reacting with NOCl generated in situ from chlorotrimethylsilane (TMSC1 (l) and iso-amyl nitrite. CTAHC oxidizes gem-chloronitroso and vic-chloronitroso compounds to the corresponding chloronitro derivatives. While gem-chloronitro compounds are obtained in good yields, the vic-chloronitro derivatives are formed in moderate yields, because of the propensity of the vic-chloronitroso group to tautomerize to α-chlorooxime. The present method is simple and practical, particularly for the preparation of vic-chloronitro compounds, considering the fact that the known methods of their preparation are few and quite involved. Indian Academy of Sciences.

Generation of nitryl chloride from chlorotrimethylsilane-acetyl nitrate reaction: A one-pot preparation of gem-chloronitro compounds from oximes

While iso-amyl nitrite reacts with chlorotrimethylsilane to give NOCl, iso-amyl nitrate does not yield NO 2Cl with silicon reagent. However, acetyl nitrate reacts successfully with chlorotrimethylsilane to give nitryl chloride, which is charact

Chlorination of oximes with aqueous H2O2/HCl system: Facile synthesis of gem-chloronitroso- and gem-chloronitroalkanes, gem-chloronitroso- and gem-chloronitrocycloalkanes

Chlorination of cyclic and linear ketone oximes with aqueous H 2O2/HCl in a two-phase dichloromethane-water system selectively affords gem-chloronitroso compounds in yields of up to 94%. One-pot oxidation of the resulting gem-chloronitroso compounds with peracetic acid, prepared in situ, gives gem-chloronitroalkanes and cycloalkanes in yields of up to 82%. The advantages of the method are that it is facile and environmentally benign and does not require gaseous chlorine. Georg Thieme Verlag Stuttgart.

Electrooxidative coupling of salts of nitro compounds with halide, nitrite, cyanide, and phenylsulfinate anions

Electrolysis of salts of primary and secondary nitro compounds (nitroethane, 1- and 2-nitropropanes, nitrocyclohexane, and nitrocycloheptane) in the presence of excess halide, nitrite, cyanide, and phenylsulfinate anions under undivided and divided amperostatic electrolysis conditions in a two-phase medium (CH2Cl2/H2O) produces geminal nitrohalides (35-85% yields), dinitro compounds (15-51%), nitronitriles (6-27%), and nitrosulfones (50-70%). The salts of secondary nitro compounds form the products of oxidative coupling with halide and phenylsulfinate anions under the undivided electrolysis conditions. In all other cases, divided electrolysis is required.

A new method for the one-step conversion of oximes into gem-halo-nitro derivatives

A mild and efficient process for one-step conversion of oximes into gem- halo-nitro compounds using Oxone and sodium chloride or potassium bromide is described.

Synthesis of α-Chloronitro Compounds

Treatment of acetone oxime, cyclohexanone oxime, bicyclo[3.3.1]nonane-2,6-dione dioxime, 2-adamantanone oxime, and 1,3-dicarboxyadamantane-2,6-dione dioxime with a mixture of hydrochloric acid and 30 percent hydrogen peroxide gave 2-chloro-2-nitropropane, 1-chloro-1-nitrocyclohexane, 2,6-dichloro-2,6-dinitrobicyclo[3.3.1]nonane, 2-chloro-2-nitroadamantane, and 2,6-dichloro-2,6-dinitroadamantane-1,3-dicarboxylic acid.

One-step conversion of oximes to gem-chloro-nitro derivatives

a new method for one-pot conversion of oximes to gem-chloro-nitro compounds using Oxone and sodium chloride is described.