1,3,5-Cyclohexanetricarboxylic acid Chemical Properties

Melting point:

216-220 °C

Boiling point:

372.4±42.0 °C(Predicted)

Density 

1.509±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

3.45±0.10(Predicted)

color 

White to Almost white

BRN 

3120108

InChI

InChI=1/C9H12O6/c10-7(11)4-1-5(8(12)13)3-6(2-4)9(14)15/h4-6H,1-3H2,(H,10,11)(H,12,13)(H,14,15)/t4-,5+,6-

InChIKey

FTHDNRBKSLBLDA-FPFOFBBKSA-N

SMILES

[C@@H]1(C(=O)O)C[C@@H](C[C@H](C(=O)O)C1)C(=O)O |&1:0,5,7,r|

CAS DataBase Reference

16526-68-4

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

29172090

MSDS

• Language:English Provider:SigmaAldrich

1,3,5-Cyclohexanetricarboxylic acid Usage And Synthesis

Uses

Used as an organic intermediate.

Synthesis

A mixture of 18 g (85 mmol) of trimesic acid, 2 g (10% mass equiv) of 5% rhodium on alumina,22 and 300 mL of water was hydrogenated at 70 °C and 50 psi. Uptake was complete in 7 h and the yield was almost quantitative. The filtrate was concentrated to give a white solid. The acid obtained was mostly the cis,cis form (cis,cis/cis,trans = 7:1). Recrystalization from ethanol-toluene solution gave the cis,cis isomer, 1,3,5-Cyclohexanetricarboxylic acid, quantitative yield mp 218-219 °C (lit.23 mp 218 °C); 1H NMR (500 MHz, CDCl3) δ11.51 (br s, 3H), 1.91 (dd, J = 5.5 Hz, J = 5.0 Hz, 3H), 1.83 (dd, J = 13.0 Hz, J = 5.0 Hz, 3H), 1.02 (dd, J = 13.0 Hz, J = 5.5 Hz, 3H); 13C NMR (500 MHz, CDCl3) δ175.44, 40.79, 29.91; IR (cm-1) 2917, 2850, 1708, 1616, 1418, 1289, 1261.

Purification Methods

Purify it also by conversion to the triethyl ester b 217-218o/10mm, 151o/1mm, the distillate solidifies on cooling, m 36-37o, which is hydrolysed by boiling in aqueous HCl. The trimethyl ester can be distilled and recrystallised from Et2O, m 48-49o. [Newman & Lawrie J Am Chem Soc 76 4598 1954, Lukes &S Galik Coll Czech Chem Comm 19 712 1954, Beilstein 9 III 4749.]

1,3,5-Cyclohexanetricarboxylic acid(16526-68-4)Related Product Information

• Methyl cyclohexanecarboxylate
• CIS,CIS-1,3,5-CYCLOHEXANETRICARBOXYLIC ACID TECHNICAL, ≥90% (T),CIS,CIS-1,3,5-CYCLOHEXANETRICARBOXYLIC ACID TECHNICAL, ≥90% (T)
• 1,1,3-Cyclohexanetricarboxylic acid
• (1α,2α,4α)-1,2,4-Cyclohexanetricarboxylic Acid
• cis,cis-1,3,5-Tripropyl-1,3,5-cyclohexanetricarboxylic acid
• 1,3,5-Cyclohexanetricarboxylic acid
• 1,3,5-CYCLOHEXANETRICARBOXYLIC ACID,1,3,5-Cyclohexanetricarboxylic Acid (cis- and trans- mixture)
• 1,3,5,7-ADAMANTANETETRACARBOXYLIC ACID
• PENTAMETHYL CYCLOHEXANE-1,1,3,3,5-PENTACARBOXYLATE
• Trimethyl cis,cis-1,3,5-cyclohexanetricarboxylate
• cis,cis-1,3,5-Trimethyl-1,3,5-cyclohexanetricarboxylic acid (Kemp''s triacid)
• TRIMETHYL CIS,CIS-1,3,5-TRIPROPYL-1,3,5-CYCLOHEXANETRICARBOXYLATE
• 1,2,3,4,5,6-Cyclohexanehexacarboxylic acid
• LABOTEST-BB LT00453217