Cyclohexanecarboxylic acid

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Cyclohexanecarboxylic acid
Cyclohexanecarboxylic acid.svg
Names
IUPAC name
Cyclohexanecarboxylic acid
Other names
hexahydrobenzoic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.002.465
PubChem CID
UNII
Properties
C7H12O2
Molar mass 128.171 g·mol−1
Appearancewhite solid
Density 1.0274 g/cm3
Melting point 30–31 °C (86–88 °F; 303–304 K)
Boiling point 232–234 °C (450–453 °F; 505–507 K)
-83.24·10−6 cm3/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Cyclohexanecarboxylic acid is the organic compound with the formula C6H11CO2H. It is the carboxylic acid of cyclohexane. It is a colorless oil that crystallizes near room temperature. [1]

Contents

Preparation and reactions

It is prepared by hydrogenation of benzoic acid.

Cyclohexanecarboxylic acid is a precursor to the nylon-6 precursor caprolactam via its reaction with nitrosylsulfuric acid. It can also be oxidized to cyclohexene. [1]

Cyclohexanecarboxylic acid exhibits the reactions typical of carboxylic acids, including its conversion to the acid chloride cyclohexanecarbonyl chloride. [2] [3]

Derivatives related to cyclohexanecarboxylic acid include:

Related Research Articles

Benzoic acid Chemical compound

Benzoic acid is a white (or colorless) solid with the formula C6H5CO2H. It is the simplest aromatic carboxylic acid. The name is derived from gum benzoin, which was for a long time its only source. Benzoic acid occurs naturally in many plants and serves as an intermediate in the biosynthesis of many secondary metabolites. Salts of benzoic acid are used as food preservatives. Benzoic acid is an important precursor for the industrial synthesis of many other organic substances. The salts and esters of benzoic acid are known as benzoates.

Carboxylic acid Oxoacid having the structure RC(=O)OH, used as a suffix in systematic name formation to denote the –C(=O)OH group including its carbon atom

A carboxylic acid is an organic compound that contains a carboxyl group attached to an R-group. The general formula of a carboxylic acid is R–COOH, with R referring to the alkyl group. Carboxylic acids occur widely. Important examples include the amino acids and fatty acids. Deprotonation of a carboxylic acid gives a carboxylate anion.

Ketone Class of organic compounds having structure RCOR´

In chemistry, a ketone is a functional group with the structure RC(=O)R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group (a carbon-oxygen double bond). The simplest ketone is acetone (R = R' = methyl), with the formula CH3C(O)CH3. Many ketones are of great importance in industry and in biology. Examples include many sugars (ketoses), many steroids (e.g., testosterone), and the solvent acetone.

Trichlorosilane chemical compound

Trichlorosilane is an inorganic compound with the formula HCl3Si. It is a colourless, volatile liquid. Purified trichlorosilane is the principal precursor to ultrapure silicon in the semiconductor industry. In water, it rapidly decomposes to produce a silicone polymer while giving off hydrochloric acid. Because of its reactivity and wide availability, it is frequently used in the synthesis of silicon-containing organic compounds.

Chloroacetic acid chemical compound

Chloroacetic acid, industrially known as monochloroacetic acid (MCA), is the organochlorine compound with the formula ClCH2CO2H. This carboxylic acid is a useful building-block in organic synthesis. It is a colorless solid. Related compounds are dichloroacetic acid and trichloroacetic acid.

Acyl chloride any chemical compound having a chlorine atom bonded to a carboacyl group

In organic chemistry, an acyl chloride (or acid chloride) is an organic compound with the functional group -COCl. Their formula is usually written RCOCl, where R is a side chain. They are reactive derivatives of carboxylic acids. A specific example of an acyl chloride is acetyl chloride, CH3COCl. Acyl chlorides are the most important subset of acyl halides.

Acyl halide any chemical compound having a halogen atom bonded to an acyl group

An acyl halide is a chemical compound derived from an oxoacid by replacing a hydroxyl group with a halide group.

Diazomethane chemical compound

Diazomethane is the chemical compound CH2N2, discovered by German chemist Hans von Pechmann in 1894. It is the simplest diazo compound. In the pure form at room temperature, it is an extremely sensitive explosive yellow gas; thus, it is almost universally used as a solution in diethyl ether. The compound is a popular methylating agent in the laboratory, but it is too hazardous to be employed on an industrial scale without special precautions. Use of diazomethane has been significantly reduced by the introduction of the safer and equivalent reagent trimethylsilyldiazomethane.

Aluminium chloride chemical compound

Aluminium chloride (AlCl3), also known as aluminium trichloride, describe compounds with the formula AlCl3(H2O)n (n = 0 or 6). the main aluminium chloride. Both are white solids, but samples are often contaminated with iron(III) chloride, giving a yellow color. The anhydrous material is important commercially. It has a low melting and boiling point. It is mainly produced and consumed in the production of aluminium metal, but large amounts are also used in other areas of the chemical industry. The compound is often cited as a Lewis acid. It is an example of an inorganic compound that reversibly changes from a polymer to a monomer at mild temperature.

Benzoyl chloride chemical compound

Benzoyl chloride, also known as benzenecarbonyl chloride, is an organochlorine compound with the formula C6H5COCl. It is a colourless, fuming liquid with an irritating odour. It is mainly useful for the production of peroxides but is generally useful in other areas such as in the preparation of dyes, perfumes, pharmaceuticals, and resins.

Amidine derivatives of oxoacids RnE(=O)OH in which the hydroxy group is replaced by an amino group and the oxo group is replaced by =NR

Amidines are organic compounds with the functional group RC(NR)NR2, where the R groups can be the same or different. They are the imine derivatives of amides (RC(O)NR2). The simplest amidine is formamidine, HC(=NH)NH2.

Peroxy acid any chemical compound in which an acidic –OH group has been replaced by an –OOH group

A peroxy acid is an acid which contains an acidic –OOH group. The two main classes are those derived from conventional mineral acids, especially sulfuric acid, and the peroxy derivatives of organic carboxylic acids. They are generally strong oxidizers.

In organic chemistry, the Arndt–Eistert reaction is the conversion of a carboxylic acid to its homologue. Named for the German chemists Fritz Arndt (1885–1969) and Bernd Eistert (1902–1978), the method entails treating an acid chlorides with diazomethane. It is a popular method of producing β-amino acids from α-amino acids.

Anthranilic acid chemical compound

Anthranilic acid is an aromatic acid with the formula C6H4(NH2)(CO2H) and has a sweetish taste. The molecule consists of a benzene ring, ortho-substituted with a carboxylic acid and an amine. As a result of containing both acidic and basic functional groups, the compound is amphoteric. Anthranilic acid is a white solid when pure, although commercial samples may appear yellow. The anion [C6H4(NH2)(CO2)], obtained by the deprotonation of anthranilic acid, is called anthranilate. Anthranilic acid was once thought to be a vitamin and was referred to as vitamin L1 in that context, but it is now known to be non-essential in human nutrition.

3-Nitrobenzoic acid is an organic compound with the formula C6H4(NO2)CO2H. It is an aromatic compound and under standard conditions, it is an off-white solid. The two substituents are in a meta position with respect to each other, giving the alternative name of m-nitrobenzoic acid. This compound can be useful as it is a precursor to 3-aminobenzoic acid, which is used to prepare some dyes.

Benzenediazonium chloride chemical compound

Benzenediazonium chloride is an organic compound with the formula [C6H5N2]Cl. It is a salt of a diazonium cation and chloride. It exists as a colourless solid that is soluble in polar solvents including water. It is the parent member of the aryldiazonium compounds, which are widely used in organic chemistry. Because the salt is unstable, it is not commercially available but is prepared upon demand.

In organic synthesis, cyanation is the attachment or substitution of a cyanide group on various substrates. Such transformations are high-value because they generate C-C bond. Furthermore nitriles are versatile functional groups.

4-Nitrobenzoic acid is an organic compound with the formula C6H4(NO2)CO2H. It is a pale yellow solid. It is a precursor to 4-nitrobenzoyl chloride, the precursor to the anesthetic procaine and folic acid. It is also a precursor to 4-aminobenzoic acid.

Thiocarboxylic acids are organosulfur compounds related to carboxylic acids by replacement of one of the oxygen atoms with a sulfur atom. Two tautomers are possible: a thione form (RC OH) and a thiol form (RC SH). These are sometimes also referred to as "carbothioic O-acid" and "carbothioic S-acid" respectively. Of these the thiol form is most common.

2-Methylanthraquinone chemical compound

2-Methylanthraquinone, an organic compound, is a methylated derivative of anthraquinone. An off-white solid, it is an important precursor to many dyes.

References

  1. 1 2 Maki, Takao; Takeda, Kazuo. "Benzoic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a03_555..
  2. Turro, Nicholas J.; Leermakers, Peter A.; Vesley, George F. (1967). "Cyclohexylidenecyclohexane". Org. Synth. 47: 34. doi:10.15227/orgsyn.047.0034.
  3. Cope, Arthur C.; Ciganek, Engelbert (1959). "N,N-Dimethylcyclohexylmethylamine". Organic Syntheses. 39: 19. doi:10.15227/orgsyn.039.0019.