| Identification | Back Directory | [Name]
CIS,CIS-1,3,5-CYCLOHEXANETRICARBOXYLIC ACID | [CAS]
16526-68-4 | [Synonyms]
5&alpha
Cyclohexanetricarboxylicaicd
1,3,5-CYCLOHEXANETRICARBOXYLIC ACID
CIS,CIS-1,3,5-CYCLOHEXANETRICARBOXYLIC
CIS-1,3,5-CYCLOHEXANETRICARBOXYLIC ACID
CIS,CIS-1,3,5-CYCLOHEXANETRICARBOXYLIC ACID
1,3,5-Cyclohexanetricarboxylic acid cis 90 %
Cis,cis-cyclohexane-1,3,5-tricarboxylic acid
1,3,5-CYCLOHEXANETRICARBOXYLIC ACID, 95% CIS
1,3,5-CYCLOHEXANETRICARBOXYLIC ACID, 90% CIS
(1α,3α,5α)-1,3,5-Cyclohexanetricarboxylic acid
1,3,5-Cyclohexanetricarboxylicacid, (1a,3a,5a)-
(1ALPHA,3ALPHA,5ALPHA)-1,3,5-CYCLOHEXANETRICARBOXYLIC ACID
1,3,5-Cyclohexanetricarboxylic acid, (1.alpha.,3.alpha.,5.alpha.)-
1,3,5-Cyclohexanetricarboxylic acid,cis,cis-1,3,5-Cyclohexanetricarboxylic acid | [Molecular Formula]
C9H12O6 | [MDL Number]
MFCD00075294 | [MOL File]
16526-68-4.mol | [Molecular Weight]
216.19 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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.] |
| Spectrum Detail | Back Directory | [Spectrum Detail]
1,3,5-Cyclohexanetricarboxylic acid(16526-68-4)MS
1,3,5-Cyclohexanetricarboxylic acid(16526-68-4)1HNMR
1,3,5-Cyclohexanetricarboxylic acid(16526-68-4)13CNMR
1,3,5-Cyclohexanetricarboxylic acid(16526-68-4)IR
1,3,5-Cyclohexanetricarboxylic acid(16526-68-4)Raman
|
|
|