1,4-Cyclohexanedicarboxylic acid

1,4-Cyclohexanedicarboxylic acid describes a pair of organic compounds with the formula C₆H₁₀(CO₂H)₂. The CO₂H groups are attached to the opposite carbon centers of the cyclohexane ring. These groups can be cis or trans. Other isomers of cyclohexanedicarboxylic acid are known, but the 1,4- isomers are of greatest interest, perhaps because they are obtainable from a commodity chemical. Specifically, hydrogenation of terephthalic acid affords the title compound:^[1]

C₆H₄(CO₂H)₂ + 3 H₂ → C₆H₁₀(CO₂H)₂.

Quick facts Names, Identifiers ...

1,4-Cyclohexanedicarboxylic acid

Names
Preferred IUPAC name Cyclohexane-1,4-dicarboxylic acid
Identifiers
CAS Number	cis: 619-81-8 trans: 619-82-9 mix: 1076-97-7
3D model (JSmol)	Interactive image cis: Interactive image trans: Interactive image
ChEBI	CHEBI:145052
ChEMBL	ChEMBL3187151
ChemSpider	13484
ECHA InfoCard	100.012.790
EC Number	214-068-6 trans: 210-614-2
PubChem CID	14106
UNII	cis: 68QED0R44U trans: 18W55738KH
CompTox Dashboard (EPA)	DTXSID2038788 cis: DTXSID001290604 trans: DTXSID901031536
InChI InChI=1S/C8H12O4/c9-7(10)5-1-2-6(4-3-5)8(11)12/h5-6H,1-4H2,(H,9,10)(H,11,12) Key: PXGZQGDTEZPERC-UHFFFAOYSA-N cis: InChI=1S/C8H12O4/c9-7(10)5-1-2-6(4-3-5)8(11)12/h5-6H,1-4H2,(H,9,10)(H,11,12)/t5-,6+ Key: PXGZQGDTEZPERC-OLQVQODUSA-N trans: InChI=1S/C8H12O4/c9-7(10)5-1-2-6(4-3-5)8(11)12/h5-6H,1-4H2,(H,9,10)(H,11,12)/t5-,6- Key: PXGZQGDTEZPERC-IZLXSQMJSA-N
SMILES C1CC(CCC1C(=O)O)C(=O)O cis: OC(=O)[C@H]1CC[C@H](CC1)C(O)=O trans: OC(=O)[C@H]1CC[C@@H](CC1)C(O)=O
Properties
Chemical formula	C8H12O4
Molar mass	172.180 g·mol−1
Appearance	white solid
Density	1.36 g/cm3
Melting point	312.5 Â°C (594.5 Â°F; 585.6 K) 168-170°C for cis isomer
Except where otherwise noted, data are given for materials in their standard state (at 25 Â°C [77 Â°F], 100 kPa). Infobox references

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The trans isomer has been more heavily studied. It has been examined as a precursor to polycarbonates^[2] and as a building block for metal-organic frameworks.^[3]