1,3,5-Cyclohexanetricarboxylic acid
- CAS NO.:16526-68-4
- Empirical Formula: C9H12O6
- Molecular Weight: 216.19
- MDL number: MFCD00075294
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-03-20 19:26:33
What is 1,3,5-Cyclohexanetricarboxylic acid?
The Uses of 1,3,5-Cyclohexanetricarboxylic acid
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.]
Properties of 1,3,5-Cyclohexanetricarboxylic acid
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- |
CAS DataBase Reference | 16526-68-4 |
Safety information for 1,3,5-Cyclohexanetricarboxylic acid
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P271:Use only outdoors or in a well-ventilated area. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for 1,3,5-Cyclohexanetricarboxylic acid
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| |
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