Cyclohexylamine is an

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

, belonging to the

aliphatic In organic chemistry, hydrocarbons ( compounds composed solely of carbon and hydrogen) are divided into two classes: aromatic compounds and aliphatic compounds (; G. ''aleiphar'', fat, oil). Aliphatic compounds can be saturated (in which all ...

amine In chemistry, amines (, ) are organic compounds that contain carbon-nitrogen bonds. Amines are formed when one or more hydrogen atoms in ammonia are replaced by alkyl or aryl groups. The nitrogen atom in an amine possesses a lone pair of elec ...

class. It is a colorless liquid, although, like many amines, samples are often colored due to contaminants. It has a fishy odor and is miscible with water. Like other amines, it is a

weak base A weak base is a base that, upon dissolution in water, does not dissociate completely, so that the resulting aqueous solution contains only a small proportion of hydroxide ions and the concerned basic radical, and a large proportion of undissocia ...

, compared to

strong base In chemistry, there are three definitions in common use of the word "base": '' Arrhenius bases'', '' Brønsted bases'', and '' Lewis bases''. All definitions agree that bases are substances that react with acids, as originally proposed by G. ...

s such as

NaOH Sodium hydroxide, also known as lye and caustic soda, is an inorganic compound with the formula . It is a white solid ionic compound consisting of sodium cations and hydroxide anions . Sodium hydroxide is a highly corrosive base and alkali t ...

, but it is a stronger base than its

aromatic In organic chemistry, aromaticity is a chemical property describing the way in which a conjugated system, conjugated ring of unsaturated bonds, lone pairs, or empty orbitals exhibits a stabilization stronger than would be expected from conjugati ...

analog,

aniline Aniline (From , meaning ' indigo shrub', and ''-ine'' indicating a derived substance) is an organic compound with the formula . Consisting of a phenyl group () attached to an amino group (), aniline is the simplest aromatic amine. It is an in ...

. It is a useful intermediate in the production of many other organic compounds (e.g.

cyclamate Cyclamate is an artificial sweetener. It is 30–50 times sweeter than sucrose (table sugar), making it the least potent of the commercially used artificial sweeteners. It is often used with other artificial sweeteners, especially saccharin; the ...

)

Preparation

Cyclohexylamine is produced by two routes, the main one being the complete hydrogenation of

using some cobalt- or nickel-based catalysts: :C₆H₅NH₂ + 3 H₂ → C₆H₁₁NH₂ It is also prepared by

alkylation Alkylation is a chemical reaction that entails transfer of an alkyl group. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene (or their equivalents). Alkylating agents are reagents for effecting al ...

of ammonia using

cyclohexanol Cyclohexanol is the organic compound with the formula HOCH(CH2)5. The molecule is related to cyclohexane by replacement of one hydrogen atom by a hydroxyl group. This compound exists as a deliquescent colorless solid with a camphor-like odor, whi ...

Applications

Cyclohexylamine is used as an intermediate in synthesis of other organic compounds. It is the precursor to sulfenamide-based reagents used as accelerators for

vulcanization Vulcanization (British English: vulcanisation) is a range of processes for hardening rubbers. The term originally referred exclusively to the treatment of natural rubber with sulfur, which remains the most common practice. It has also grown to ...

. The amine itself is an effective

corrosion inhibitor A corrosion inhibitor or anti-corrosive is a chemical compound added to a liquid or gas to decrease the corrosion rate of a metal that comes into contact with the fluid. The effectiveness of a corrosion inhibitor depends on fluid composition and ...

. It has been used as a flushing aid in the

printing ink Ink is a gel, sol, or solution that contains at least one colorant, such as a dye or pigment, and is used to color a surface to produce an image, text, or design. Ink is used for drawing or writing with a pen, brush, reed pen, or quill. ...

industry. {{Cite book , last = Apps , first = E. A. , title = Printing Ink Technology , publisher = Leonard Hill ooks/nowiki> Limited , year = 1958 , location = London , pages = ix , url =https://archive.org/details/printinginktechn00apps , url-access = registration

Drugs List

It is a building block for pharmaceuticals (e.g.,

mucolytic Mucoactive agents are a class of pharmacologic agents that include expectorants, mucolytics, mucoregulators, and mucokinetics that can affect the volume, viscosity, transportation, and composition of mucus or sputum. They often aid in clearing ...

analgesic An analgesic drug, also called simply an analgesic, antalgic, pain reliever, or painkiller, is any member of the group of drugs used for pain management. Analgesics are conceptually distinct from anesthetics, which temporarily reduce, and in s ...

s, and

bronchodilator A bronchodilator or broncholytic (although the latter occasionally includes secretory inhibition as well) is a substance that dilates the bronchi and bronchioles, decreasing resistance in the respiratory airway and increasing airflow to the lun ...

s). Most of the drugs in the following list fall into the arena of sulfonamide hypoglycemics though: #

Acetohexamide Acetohexamide (trade name Dymelor) is a first-generation sulfonylurea medication used to treat diabetes mellitus type 2, particularly in people whose diabetes cannot be controlled by diet alone. Mechanism of action Acetohexamide binds to an A ...

# Amesergide #

Bromhexine Bromhexine is a mucolytic drug used in the treatment of respiratory disorders associated with viscid or excessive mucus. It was developed in the research laboratory of Boehringer Ingelheim in the late 1950s as an active ingredient for pharmaceut ...

# Brovanexine # CGP-11112 (not actually made from CyNH2 but CyN containing). #

Cilostazol Cilostazol, sold under the brand name Pletal among others, is a medication used to help the symptoms of intermittent claudication in peripheral vascular disease. If no improvement is seen after 3 months, stopping the medication is reasonable. It ...

# Clorexolone #

Cyclamate Cyclamate is an artificial sweetener. It is 30–50 times sweeter than sucrose (table sugar), making it the least potent of the commercially used artificial sweeteners. It is often used with other artificial sweeteners, especially saccharin; the ...

# Enpromate # Esaprazole #

Glibenclamide Glibenclamide, also known as glyburide, is an antidiabetic medication used to treat type 2 diabetes. It is recommended that it be taken together with diet and exercise. It may be used with other antidiabetic medication. It is not recommended ...

# Glicaramide # Gliquidone #

Glipizide Glipizide, sold under the brand name Glucotrol among others, is an anti-diabetic medication of the sulfonylurea class used to treat type 2 diabetes. It is used together with a diabetic diet and exercise. It is not indicated for use by itself i ...

# Glisindamide # Glisolamide # Glycyclamide # Glyhexamide # Hexazinone #

Hexylcaine Hexylcaine hydrochloride, also called cyclaine ( Merck) or osmocaine, is a short-acting local anesthetic. It acts by inhibiting sodium channel conduction. Overdose can lead to headache, tinnitus, numbness and tingling around the mouth and tongu ...

# Hydroxyhexamide #

lomustine Lomustine ( INN; abbreviated as CCNU; original brand name CeeNU, now marketed as Gleostine) is an alkylating nitrosourea compound used in chemotherapy. It is closely related to semustine and is in the same family as streptozotocin. It is a hig ...

# Metahexamide # Timegadine # Thiohexamide # U-37883A

Toxicity

Cyclohexylamine has a low acute toxicity with LD₅₀ (rat; p.o.) = 0.71 ml/kg''The Merck Index, 10th Ed.'' (1983) p.392, Rahway: Merck & Co. Like other amines, it is corrosive. Cyclohexylamine is listed as an extremely hazardous substance as defined by Section 302 of the U.S.

Emergency Planning and Community Right-to-Know Act The Emergency Planning and Community Right-to-Know Act of 1986 is a United States federal law passed by the 99th United States Congress located at Title 42, Chapter 116 of the U.S. Code, concerned with emergency response preparedness. On Octobe ...

. The

National Institute for Occupational Safety and Health The National Institute for Occupational Safety and Health (NIOSH, ) is the List of United States federal agencies, United States federal agency responsible for conducting research and making recommendations for the prevention of work-related occ ...

has suggested workers not be exposed to a

recommended exposure limit A recommended exposure limit (REL) is an occupational exposure limit that has been recommended by the United States National Institute for Occupational Safety and Health. The REL is a level that NIOSH believes would be protective of worker safety ...

of over 10 ppm (40 mg/m³) over an eight-hour workshift.

References

Amines Cyclohexyl compounds