cyclohexanecarboxylic acid

{{Chembox

| ImageFile = Cyclohexanecarboxylic acid.svg

| ImageSize = 200px

| PIN = Cyclohexanecarboxylic acid{{cite book | title =Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = The Royal Society of Chemistry | date = 2014 | location = Cambridge | pages = 303,639 | doi = 10.1039/9781849733069-00648 | isbn = 978-0-85404-182-4 }}

| OtherNames =

| Section1 = {{Chembox Identifiers

| CASNo = 98-89-5

| CASNo_Ref = {{cascite|correct|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = H9VKD9VL18

| PubChem = 7413

| ChemSpiderID = 7135

| ChEBI = 36096

| SMILES = O=C(O)C1CCCCC1

| InChI = 1/C7H12O2/c8-7(9)6-4-2-1-3-5-6/h6H,1-5H2,(H,8,9)

| InChIKey = NZNMSOFKMUBTKW-UHFFFAOYAH

| StdInChI = 1S/C7H12O2/c8-7(9)6-4-2-1-3-5-6/h6H,1-5H2,(H,8,9)

| StdInChIKey = NZNMSOFKMUBTKW-UHFFFAOYSA-N

}}

| Section2 = {{Chembox Properties

| C=7 | H=12 | O=2

| Appearance = white solid

| Density = 1.0274 g/cm3

| MeltingPtC = 30–31

| BoilingPtC = 232–234

| Solubility =

| MagSus = −83.24·10−6 cm3/mol

}}

| Section3 = {{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

}}

}}

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.{{Ullmann|doi=10.1002/14356007.a03_555|title=Benzoic Acid and Derivatives|last1=Maki|first1=Takao|last2=Takeda|first2=Kazuo}}.

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.

Cyclohexanecarboxylic acid exhibits the reactions typical of carboxylic acids, including its conversion to the acid chloride cyclohexanecarbonyl chloride.{{cite journal|title=Cyclohexylidenecyclohexane|first1=Nicholas J.|last1=Turro|first2=Peter A.|last2=Leermakers|first3=George F.|last3=Vesley|journal=Org. Synth.|year=1967|volume=47|page=34|doi=10.15227/orgsyn.047.0034}}{{cite journal |first1=Arthur C.|last1=Cope|first2=Engelbert|last2=Ciganek|doi=10.15227/orgsyn.039.0019|title=N,N-Dimethylcyclohexylmethylamine|journal=Organic Syntheses|year=1959|volume=39|page=19

}}

Related compounds

Derivatives related to cyclohexanecarboxylic acid include:

Quinic acid flat.svg|Quinic acid

Shikimi.svg|Shikimic acid

Chorisminsäure.svg|Chorismic acid

References