2305-32-0

Basic information

• Product Name: trans-1,2-Cyclohexanedicarboxylic acid
• Synonyms: TRANS-HEXAHYDRO-PHTHALIC ACID;TRANS-CYCLOHEXANE-1,2-DICARBOXYLIC ACID;TRANS-1,2-CYCLOHEXANEDICARBOXYLIC ACID;trans-1,2-Cyclohexanedicarboxylic acid, remainder cis, 95%;TRANS-1,2-CYCLOHEXANEDICARBOXYLIC ACDI;trans-Cyclohexane-1,2-dicarboxylic acid, trans-Hexahydrophthalic acid;TRANS-1,2-CYCLOHEXANEDICARBOXYLIC ACID, 95%, REMAINDER CIS;rel-(1R*)-1β*,2α*-Cyclohexanedicarboxylic acid
• CAS NO: 2305-32-0
• Molecular Formula: C₈H₁₂O₄
• Molecular Weight: 172.18
• EINECS: 218-975-8
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts
• Mol File: 2305-32-0.mol
• Article Data: 15

Chemical Properties

• Melting Point: 228-230 °C(lit.)
• Boiling Point: 262.49°C (rough estimate)
• Flash Point: 200.254 °C
• Appearance: white crystalline powder
• Density: 1.2104 (rough estimate)
• Vapor Pressure: 5.78E-07mmHg at 25°C
• Refractive Index: 1.4450 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: Acetone (Slightly), DMSO (Slightly)
• PKA: pK1:4.18;pK2: 5.93 (20°C)
• Water Solubility: 2g/L(20 oC)
• BRN: 3200609
• CAS DataBase Reference: trans-1,2-Cyclohexanedicarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: trans-1,2-Cyclohexanedicarboxylic acid(2305-32-0)
• EPA Substance Registry System: trans-1,2-Cyclohexanedicarboxylic acid(2305-32-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: GU9065000
• TSCA: Yes
• Hazardous Substances Data: 2305-32-0(Hazardous Substances Data)

Usage

Chemical Properties

white crystalline powder

Uses

Different sources of media describe the Uses of 2305-32-0 differently. You can refer to the following data:
1. trans-1,2-cyclohexanedicarboxylic acid be used as organic intermediates.
2. trans-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 Methods

It 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.]

InChI:InChI=1/C8H12O4/c9-7(10)5-3-1-2-4-6(5)8(11)12/h5-6H,1-4H2,(H,9,10)(H,11,12)/p-2/t5-,6-/m1/s1

Synthetic route

C16H21NO4 (97185-53-0, 97233-91-5) → trans-1,2-cyclohexanedicarboxylic acid (2305-32-0)

Conditions	Yield
With barium hydroxide octahydrate In water for 2h; Heating;	99%

(2E)-but-2-enedioic acid (110-17-8) → trans-1,2-cyclohexanedicarboxylic acid (2305-32-0)

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol for 24h;	98%

(1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3) → trans-1,2-cyclohexanedicarboxylic acid (2305-32-0)

Conditions	Yield
With sodium hydroxide In water at 150℃; under 2280.15 Torr; for 72h; Reagent/catalyst; Concentration; Autoclave;	95.5%
With hydrogenchloride at 180℃;
With phosphoric acid
With sulfuric acid

(+/-)-trans-1,2-cyclohexanedicarboxylic anhydride (14166-21-3) → trans-1,2-cyclohexanedicarboxylic acid (2305-32-0)

Conditions	Yield
With potassium superoxide; tetraethylammonium bromide In N,N-dimethyl-formamide at 25℃; for 12h; Ring cleavage;	41%

cyclohex-1-ene-1,2-dicarboxylic acid (635-08-5) → (1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3) + trans-1,2-cyclohexanedicarboxylic acid (2305-32-0)

Conditions	Yield
With sodium amalgam; sodium carbonate

cyclohex-1-ene-1,2-dicarboxylic acid (635-08-5) → trans-1,2-cyclohexanedicarboxylic acid (2305-32-0)

Conditions	Yield
With hydrogen iodide at 230℃; im geschlossenen Rohr;
Multi-step reaction with 2 steps 1: natrium carbonate; sodium amalgam 2: concentrated hydrochloric acid / 180 °C View Scheme
Multi-step reaction with 2 steps 1: natrium carbonate; sodium amalgam 2: concentrated hydrochloric acid / 180 °C View Scheme

cyclohexane-1,2-dicarboxylic acid (1687-30-5) → trans-1,2-cyclohexanedicarboxylic acid (2305-32-0)

Conditions	Yield
With hydrogen bromide im geschlossenen Rohr; man laesst auf das Bromwasserstoffadditionsprodukt Natriumamalgam einwirken;

dimethyl cis-1,2-cyclohexanedicarboxylate (1687-29-2) → trans-1,2-cyclohexanedicarboxylic acid (2305-32-0)

Conditions	Yield
With potassium hydroxide

diethyl 1,2-cyclohexanedicarboxylate (10138-59-7) + sodium ethanolate (141-52-6) → trans-1,2-cyclohexanedicarboxylic acid (2305-32-0)

Conditions	Yield
cis-hexahydrophthalic acid diethyl ester;

cyclohexane-1,1,2,2-tetracarboxylic acid tetraethyl ester (50708-48-0) → trans-1,2-cyclohexanedicarboxylic acid (2305-32-0)

Conditions	Yield
With hydrogenchloride at 150℃;

cyclohex-2-ene-1,2-dicarboxylic acid (38765-78-5) → trans-1,2-cyclohexanedicarboxylic acid (2305-32-0)

Conditions	Yield
With hydrogen iodide; acetic acid at 150℃; Behandeln des Produktes mit Natriumamalgam;

2-hydroxymethyl-cyclohexanecarboxylic acid (93379-40-9) → trans-1,2-cyclohexanedicarboxylic acid (2305-32-0)

Conditions	Yield
With potassium permanganate

(+/-)-trans-cyclohexene-(3)-dicarboxylic acid-(1.2) (25079-83-8, 38765-76-3, 38765-77-4) → trans-1,2-cyclohexanedicarboxylic acid (2305-32-0)

Conditions	Yield
With acetic acid; platinum Hydrogenation;

trans-cyclohex-4-ene-1,2-dicarboxylic acid (88-98-2, 2305-26-2, 15573-40-7, 50987-15-0, 51096-07-2, 51096-08-3) → trans-1,2-cyclohexanedicarboxylic acid (2305-32-0)

Conditions	Yield
With palladium on activated charcoal Hydrogenation;
With methanol; palladium Hydrogenation;
With hydrogen; palladium In methanol at 30 - 35℃;

rac-(1S,2S)-dimethyl 4-oxocyclohexane-1,2-dicarboxylate (13990-96-0, 13991-44-1, 90927-39-2) → trans-1,2-cyclohexanedicarboxylic acid (2305-32-0)

Conditions	Yield
With hydrogenchloride; zinc

o-(N,N-Diethyl-aminomethyl)-benzoesaeure (55741-02-1) → trans-1,2-cyclohexanedicarboxylic acid (2305-32-0)

Conditions	Yield
With pentan-1-ol; sodium
Multi-step reaction with 2 steps 1: sodium; amyl alcohol 2: KMnO4 View Scheme

benzene-1,2-dicarboxylic acid (88-99-3) → trans-1,2-cyclohexanedicarboxylic acid (2305-32-0)

Conditions	Yield
With sodium hydroxide; nickel at 160℃; under 18387.7 Torr; Hydrogenation;

(E)-2,4-pentadienoic acid (21651-12-7) + acrylic acid (79-10-7) → cyclohexane-1,3-dicarboxylic acid (3971-31-1) + trans-1,2-cyclohexanedicarboxylic acid (2305-32-0)

Conditions	Yield
With sodium carbonate at 215 - 225℃; anschliessendes Hydrieren an Raney-Nickel bei 150grad/150 at;

oxalyl dichloride (79-37-8) + cyclohexanylcarbonyl chloride (2719-27-9) → trans-1,2-cyclohexanedicarboxylic acid (2305-32-0)

Conditions	Yield
With Perbenzoic acid anschliessendes Hydrolysieren;

carbon dioxide (124-38-9) + cyclohexene (110-83-8) → (1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3) + trans-1,2-cyclohexanedicarboxylic acid (2305-32-0)

Conditions	Yield
With In tetrahydrofuran under 760 Torr; Mechanism; Irradiation;
With Ni3(Ph2PCH2PPh2)3I2 Product distribution; Mechanism; Irradiation;

trans-hexahydrophthalide (144540-72-7) + KOH-solution → trans-1,2-cyclohexanedicarboxylic acid (2305-32-0)

Conditions	Yield
durch Oxydation mit Permanganat;

N-hydroxyphthalimide (524-38-9) + ethanol (64-17-5) + sodium → trans-1,2-cyclohexanedicarboxylic acid (2305-32-0)

cyclohex-1-ene-1,2-dicarboxylic acid (635-08-5) + hydrogen iodide (10034-85-2) → trans-1,2-cyclohexanedicarboxylic acid (2305-32-0)

Conditions	Yield
at 230℃;

cyclohex-1-ene-1,2-dicarboxylic acid (635-08-5) + sodium amalgam → (1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3) + trans-1,2-cyclohexanedicarboxylic acid (2305-32-0)

2-hydroxymethyl-cyclohexanecarboxylic acid (93379-40-9) + alkaline permanganate → trans-1,2-cyclohexanedicarboxylic acid (2305-32-0)

1-cyano-cyclohexane-dicarboxylic acid-(1.2)-diethyl ester → trans-1,2-cyclohexanedicarboxylic acid (2305-32-0)

Conditions	Yield
With hydrogenchloride Erhitzen des Reaktionsprodukts mit wss. Salzsaeure auf 160grad;

3.6-dibromo-trans-hexahydrophthalic acid → trans-1,2-cyclohexanedicarboxylic acid (2305-32-0)

Conditions	Yield
With acetic acid; zinc
With sodium amalgam

phthalate potassium → trans-1,2-cyclohexanedicarboxylic acid (2305-32-0)

Conditions	Yield
With nickel(III) oxide; hydrogen at 300℃;

3,5-dibromo-cyclohexane-1,2-dicarboxylic acid + sodium amalgam → trans-1,2-cyclohexanedicarboxylic acid (2305-32-0)

Conditions	Yield
3.5-dibromo-trans-hexahydrophthalic acid;

methanol (67-56-1) + trans-1,2-cyclohexanedicarboxylic acid (2305-32-0) → dimethyl cyclohexane-trans-1,2-dicarboxylate (3205-35-4)

Conditions	Yield
With camphor-10-sulfonic acid Heating;	96%

n-Octylamine (111-86-4) + trans-1,2-cyclohexanedicarboxylic acid (2305-32-0) → 2-octylhexahydroisoindole-1,3-dione

Conditions	Yield
With niobium(V) oxide In hexane for 18h; Inert atmosphere; Reflux; Microwave irradiation;	91%

n-butyl formate (592-84-7) + trans-1,2-cyclohexanedicarboxylic acid (2305-32-0) → trans-Cyclohexane-1,2-dicarboxylic acid monobutyl ester + trans-Cyclohexane-1,2-dicarboxylic acid dibutyl ester

Conditions	Yield
With Dowex 50Wx2 In octane at 100℃; for 9h; Esterification;	A 88% B 5%

cobalt(II) chloride hexahydrate + trans-1,2-cyclohexanedicarboxylic acid (2305-32-0) → Co3(μ3-hydroxy)(trans-1,2-cyclohexane-dicarboxylate)2

Conditions	Yield
With triethylamine In water High Pressure; CoCl2, ligand, triethylamine 2:1:1 in H2O heated in a stainless steel autoclave at 220°C for 7 d; elem. anal.;	88%

cobalt(II) chloride hexahydrate + trans-1,2-cyclohexanedicarboxylic acid (2305-32-0) → Co(trans-1,2-cyclohexadicarboxylate)

Conditions	Yield
With triethylamine In water High Pressure; mixt. sealed in teflon-lined autoclave and heated at 160°C for 5 d; elem. anal.; powder XRD;	87%

[2,2]bipyridinyl (366-18-7) + uranyl nirate hexahydrate + trans-1,2-cyclohexanedicarboxylic acid (2305-32-0) → O2U(2+)*C8H10O4(2-)*C10H8N2

Conditions	Yield
In water at 140℃; Autoclave; High pressure;	84%

trans-1,2-cyclohexanedicarboxylic acid (2305-32-0) → (+/-)-trans-2-(hydroxymethyl)cyclohexylmethanol (76155-27-6)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 75℃; for 16h; Schlenk technique;	81%
With lithium aluminium tetrahydride In tetrahydrofuran at 75℃; for 16h; Schlenk technique;	81%
With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether a) RT, 3h, b) reflux, 8 h;	79%

trans-1,2-cyclohexanedicarboxylic acid (2305-32-0) → trans-1,2-cyclo-hexanedicarboxylic acid dichloride (33209-25-5, 34684-19-0, 36909-95-2, 46021-27-6, 60901-05-5, 65653-82-9)

Conditions	Yield
With thionyl chloride; N,N-dimethyl-formamide for 41h;	77%
With phosphorus pentachloride
With thionyl chloride

trans-1,2-cyclohexanedicarboxylic acid (2305-32-0) → (+/-)-trans-1,2-cyclohexanedicarboxylic anhydride (14166-21-3)

Conditions	Yield
With acetyl chloride for 4h; Heating;	76%
With acetic anhydride
With 4-methyl-morpholine; methyl chloroformate In tetrahydrofuran at 20℃; for 0.25h;

sodium nitrate (7631-99-4) + uranyl nirate hexahydrate + trans-1,2-cyclohexanedicarboxylic acid (2305-32-0) → 2O2U(2+)*3C8H10O4(2-)*2Na(1+)*2H2O

Conditions	Yield
With 18-crown-6 ether In water; acetonitrile at 140℃; Autoclave; High pressure;	69%

ferrous(II) sulfate heptahydrate + trans-1,2-cyclohexanedicarboxylic acid (2305-32-0) → [Fe(II)(e,e-trans-cyclohexane-1,2-dicarboxylate)]

Conditions	Yield
With Et3N In water High Pressure; under hydrothermal conditions; mixt. of FeSO4*7H2O, ligand, Et3N and deionized H2O sealed in autoclave; heated at 160°C for 2 d; crystals isolated; elem. anal.;	65%

tetrahydrofuran (109-99-9) + uranyl nirate hexahydrate + trans-1,2-cyclohexanedicarboxylic acid (2305-32-0) → O2U(2+)*C8H10O4(2-)*C4H8O

Conditions	Yield
With manganese (II) nitrate tetrahydrate In water at 140℃; Autoclave; High pressure;	62%

trans-1,2-cyclohexanedicarboxylic acid (2305-32-0) + phenyllithium (591-51-5) → trans-1,2-dibenzoylcyclohexane (104722-26-1)

Conditions	Yield
In tetrahydrofuran; diethyl ether for 16h; Ambient temperature;	53%

caesium nitrate + uranyl nirate hexahydrate + trans-1,2-cyclohexanedicarboxylic acid (2305-32-0) → [(UO2)4Cs4(rac-trans-1,2-cyclohexanedicarboxylate)6(H2O)3]·H2O

Conditions	Yield
In methanol; water at 150℃; High pressure;	48%

4,4'-bipyridine (553-26-4) + cadmium(II) nitrate tetrhydrate + trans-1,2-cyclohexanedicarboxylic acid (2305-32-0) + water (7732-18-5) → ([Cd2(trans-1,2-a,a-cyclohexanedicarboxylate)(trans-1,2-e,e-cyclohexanedicarboxylic acid-H)2(4,4'-bipyridine)2]*8H2O)n

Conditions	Yield
With KOH In ethanol; water (C6H10)(COOH)2 (0.29 mmol) dissolved in mixt. of EtOH and H2O (1:1) containing KOH (0.38 mmol); Cd(NO3)2*4H2O (0.19 mmol) and 4,4'-bipyridine (0.19 mmol) in EtOH added; evapd. slowly (room temp., 1 wk); elem. anal.;	45%

trans-1,2-cyclohexanedicarboxylic acid (2305-32-0) + isopropyl alcohol (67-63-0) → diisopropyl trans-cyclohexane-1,2-dicarboxylate

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 60℃; Inert atmosphere; Sealed tube;	45%

1-methyl-pyrrolidin-2-one (872-50-4) + uranyl nirate hexahydrate + trans-1,2-cyclohexanedicarboxylic acid (2305-32-0) → O2U(2+)*C8H10O4(2-)*C5H9NO

Conditions	Yield
In water at 140℃; Autoclave; High pressure;	39%

18-crown-6 ether (17455-13-9) + uranyl nirate hexahydrate + trans-1,2-cyclohexanedicarboxylic acid (2305-32-0) + water (7732-18-5) + potassium nitrate → [(uranyl)10(potassium)5(rac-trans-1,2-cyclohexanedicarboxylate)4(oxalate)10(18-crown-6)5(OH)(H2O)3] tetrahydrate

Conditions	Yield
at 140℃; for 1461h; High pressure;	34%

uranyl nirate hexahydrate + trans-1,2-cyclohexanedicarboxylic acid (2305-32-0) + silver nitrate → 2O2U(2+)*3C8H10O4(2-)*2Ag(1+)*2H2O

Conditions	Yield
In water; acetonitrile at 140℃; Autoclave; High pressure;	30%

[2,2]bipyridinyl (366-18-7) + copper nitrate hemi(pentahydrate) + uranyl nirate hexahydrate + trans-1,2-cyclohexanedicarboxylic acid (2305-32-0) → O2U(2+)*2C8H10O4(2-)*C10H8N2*Cu(2+)*2H2O

Conditions	Yield
In methanol; water at 140℃; Autoclave; High pressure;	30%

dihydroxyacetone (96-26-4) + trans-1,2-cyclohexanedicarboxylic acid (2305-32-0) → (4aS,11aS)-Hexahydro-6,10-dioxa-benzocyclononene-5,8,11-trione

Conditions	Yield
With 2-chloro-1-methyl-pyridinium iodide; triethylamine In acetonitrile for 15h; Heating;	24%

3-amino-7,8-bis(methoxymethoxy)-2H-chromen-2-one (1610522-97-8) + trans-1,2-cyclohexanedicarboxylic acid (2305-32-0) → trans-N1,N2-bis(7,8-bis(methoxymethoxy)-2-oxo-2H-chromen-3-yl)cyclohexane-1,2-dicarboxamide

Conditions	Yield
With pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 50℃; for 40h;	23.7%

trans-1,2-cyclohexanedicarboxylic acid (2305-32-0) → (1S,2S)-cyclohexane-1,2-dicarboxylic acid (610-10-6, 1687-30-5, 2305-32-0, 21963-41-7, 46022-05-3, 610-09-3)

Conditions	Yield
With (S)-1-phenyl-ethylamine In ethanol; toluene Heating;	19%

uranyl nirate hexahydrate + trans-1,2-cyclohexanedicarboxylic acid (2305-32-0) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → O2U(2+)*C8H10O4(2-)*C3H7NO

Conditions	Yield
With [2,2]bipyridinyl; lead(II) nitrate In water at 140℃; Reagent/catalyst; Autoclave; High pressure;	19%

uranyl nirate hexahydrate + trans-1,2-cyclohexanedicarboxylic acid (2305-32-0) + guanidine nitrate (506-93-4) → [NH4]4[(UO2)4(rac-trans-1,2-cyclohexanedicarboxylate)6]

Conditions	Yield
In water; acetonitrile at 150℃; High pressure;	16%

uranyl nirate hexahydrate + [Ni(1,4,8,11-tetra-azacyclotetradecane)(NO3)2] + trans-1,2-cyclohexanedicarboxylic acid (2305-32-0) → [(UO2)2(rac-trans-1,2-cyclohexanedicarboxylate)2(rac-trans-1,2-cyclohexanedicarboxylate-H)2Ni(1,4,8,11-tetraazacyclotetradecane)]

Conditions	Yield
In water; acetonitrile at 140℃; for 336h; High pressure;	13%

Upstream product

• 635-08-5 cyclohex-1-ene-1,2-dicarboxylic acid 
• 1687-29-2 dimethyl cis-1,2-cyclohexanedicarboxylate 
• 10138-59-7 diethyl 1,2-cyclohexanedicarboxylate 
• 141-52-6 sodium ethanolate 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 21651-12-7 (E)-2,4-pentadienoic acid 
• 79-10-7 acrylic acid 
• 79-37-8 oxalyl dichloride 
• 2719-27-9 cyclohexanylcarbonyl chloride 
• 110-17-8 (2E)-but-2-enedioic acid 
• 144540-72-7 trans-hexahydrophthalide 
• 524-38-9 N-hydroxyphthalimide 
• 64-17-5 ethanol 
• 10034-85-2 hydrogen iodide 

Downstream Products

• 13149-00-3 1,2-cis-cyclohexanedicarboxylic anhydride 
• 33209-25-5 trans-1,2-cyclo-hexanedicarboxylic acid dichloride 
• 14166-21-3 (+/-)-trans-1,2-cyclohexanedicarboxylic anhydride 
• 76155-27-6 (+/-)-trans-2-(hydroxymethyl)cyclohexylmethanol 
• 108-94-1 cyclohexanone 
• 98-89-5 Cyclohexanecarboxylic acid 
• 161117-07-3 7,7,9,9-tetrafluoro-cis-8-oxabicyclo<4.3.0>nonane 
• 161117-11-9 trans-2-trifluoromethylcyclohexanecarbonyl fluoride 
• 161117-10-8 (1S,2S)-Cyclohexane-1,2-dicarbonyl difluoride 
• 161117-10-8 (1S,2R)-Cyclohexane-1,2-dicarbonyl difluoride 
• 610-10-6 (1S,2S)-cyclohexane-1,2-dicarboxylic acid 
• 46021-27-6 (1S,2S)-cyclohexane-1,2-dicarbonyl dichloride 

Relevant articles and documents

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2 or 4-substituted cyclohexane a acrylic compound-trans isomerization method of the

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