trans-1,2-Cyclohexanedicarboxylic acid

trans-1,2-Cyclohexanedicarboxylic acid Basic information
Product Name:trans-1,2-Cyclohexanedicarboxylic acid
Synonyms:trans-Cyclohexane-1,2-dicarboxylic acid for synthesis;TRANS-1,2-CYCLOHEXANEDICARBOXYLIC ACID;TRANS-1,2-CYCLOHEXANEDICARBOXYLIC ACID, 95%, REMAINDER CIS;rel-(1R*)-1β*,2α*-Cyclohexanedicarboxylic acid;rel-(1R*,2R*)-1,2-Cyclohexanedicarboxylic acid;rel-Cyclohexane-1β*,2α*-dicarboxylic acid;trans-1,2-Cyclohexanedicarboxylic acid, remainder cis, 95%;TRANS-1,2-CYCLOHEXANEDICARBOXYLIC ACDI
CAS:2305-32-0
MF:C8H12O4
MW:172.18
EINECS:218-975-8
Product Categories:Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts
Mol File:2305-32-0.mol
trans-1,2-Cyclohexanedicarboxylic acid Structure
trans-1,2-Cyclohexanedicarboxylic acid Chemical Properties
Melting point 228-230 °C (lit.)
Boiling point 262.49°C (rough estimate)
density 1.2104 (rough estimate)
refractive index 1.4450 (estimate)
storage temp. Store below +30°C.
solubility Acetone (Slightly), DMSO (Slightly)
form Solid
pkapK1:4.18;pK2: 5.93 (20°C)
color White
Water Solubility 2g/L(20 ºC)
BRN 3200609
InChIKeyQSAWQNUELGIYBC-WDSKDSINSA-N
CAS DataBase Reference2305-32-0(CAS DataBase Reference)
NIST Chemistry Reference1,2-Cyclohexanedicarboxylic acid, trans-(2305-32-0)
EPA Substance Registry System1,2-Cyclohexanedicarboxylic acid, (1R,2R)-rel- (2305-32-0)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36
WGK Germany 3
RTECS GU9065000
TSCA Yes
HS Code 29172000
MSDS Information
ProviderLanguage
trans-Hexahydrophthalic acid English
SigmaAldrich English
ACROS English
ALFA English
trans-1,2-Cyclohexanedicarboxylic acid Usage And Synthesis
Chemical Propertieswhite crystalline powder
Usestrans-1,2-cyclohexanedicarboxylic acid be used as organic intermediates.
Usestrans-1,2-Cyclohexanedicarboxylic Acid is used as a reagent in the synthesis of enantiopure (α-cyanoalkyl)(tetrahydropyrido[4,3-b]indolecarbonyl)cyclohexanecarboxamides and its analogs as selective cathepsin K inhibitors for the treatment of osteoarthritis. Also used as a reagent in the synthesis of novel cyclopentanedicarboxamide sodium channel blockers as a potential treatment for chronic pain.
Purification MethodsIt is purified by recrystallisation from EtOH or H2O. It is formed by hydrolyzing the anhydride with water. The dimethyl ester has m 95-96o (from *C6H6/pet ether). [Abell J Org Chem 22 769 1957, Smith & Byrne J Am Chem Soc 72 4406 1950, Linstead et al. J Am Chem Soc 64 2093 1942, Beilstein 9 III 3812, 9 IV 2801.] The 1R,2R-(-)-trans-cyclohexane-1,2-acid [46022-05-3] has m 171-182o and [ ] D -20o (c 1, Me2CO). cis-Cyclohexane-1,2-dicarboxylic anhydride (cis-hexahydrophthalic anhydride) [85-42-7, 13149-00-3] M 154.2, m 32-34o, b 158o/17mm. It has been obtained by heating the trans-acid or anhydride at 200o. Crystallise it from *C6H6/Et2O or distil it. [Kohler & Jansen J Am Chem Soc 60 2145 1938, Abell J Org Chem 22 769 1957, Beilstein 17 II 452, 17 III/IV 5931.]
trans-1,2-Cyclohexanedicarboxylic acid Preparation Products And Raw materials
Preparation Products(1R,2R)-(-)-1,2-CYCLOHEXANEDICARBOXYLIC ACID-->1,3-Cyclohexanedicarboxylic acid-->CIS-1,2-CYCLOHEXANEDICARBOXYLIC ANHYDRIDE
(3aR,4S,7R,7aS) 4,7-Methano-1H-isoindole-1,3(2H)-dione Cyclobutane-1α,3β-dicarboxylic acid (1R,2R)-1,2-CYCLOHEXANEDIMETHANOL 1,2,3,4,5,6-Cyclohexanehexacarboxylic acid 1,2-CYCLOHEXANEDICARBOXYLIC ACID (1R-trans)-1,2-Cyclohexanedicarboxylic acid (1S,2S)-1,2-CYCLOHEXANEDICARBOXYLIC ACID LABOTEST-BB LT00453217 trans-1,2-Cyclohexanedicarboxylic Acid Dimethyl Ester TRANS-1,2-CYCLOHEXANEDICARBOXYLIC ACID DIETHYL ESTER TRANS-1,4-CYCLOHEXANEDICARBOXYLIC ACID MONOMETHYL ESTER TRANS-1,4-CYCLOHEXANEDICARBOXYLIC ACID DIETHYL ESTER TRANS-1,4-CYCLOHEXANEDICARBOXYLIC ACID CIS/TRANS-1,4-CYCLOHEXANEDICARBOXYLIC ACID = HEXAHYDROTEREPHTHALIC ACID trans,trans-2,4-Undecadienal TRANS-1,4-CYCLOHEXANEDICARBOXYLIC ACID MONOMETHYL ESTER CHLORIDE TRANS-2-CARBOMETHOXYCYCLOHEXANE-1-CARBOXYLIC ACID CIS/TRANS-1,2-CYCLOHEXANEDICARBOXYLIC ACID = HEXAHYDROPHTHALIC ACID

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