cis-4-Aminocyclohexanecarboxylic acid Chemical Properties

Melting point:

299-301 °C(lit.)

Boiling point:

280.0±33.0 °C(Predicted)

Density 

9 g/cm³

storage temp. 

Inert atmosphere,Room Temperature

Water Solubility 

Soluble in water

solubility 

Methanol (Very Slightly), Water (Sparingly)

form 

Powder

pka

4.62±0.25(Predicted)

color 

Off-white

InChI

InChI=1S/C7H13NO2/c8-6-3-1-5(2-4-6)7(9)10/h5-6H,1-4,8H2,(H,9,10)/t5-,6+

InChIKey

DRNGLYHKYPNTEA-OLQVQODUSA-N

SMILES

[C@@H]1(C(O)=O)CC[C@H](N)CC1

CAS DataBase Reference

3685-23-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29224999

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

cis-4-Aminocyclohexanecarboxylic acid Usage And Synthesis

Chemical Properties

off-white powder

Uses

cis-4-Aminocyclohexanecarboxylic Acid is used as a reagent in the synthesis of thiazolylquinazolines

Synthesis

The general procedure for the synthesis of 4-aminocyclohexanecarboxylic acid and cis-4-aminocyclohexanecarboxylic acid from p-aminobenzoic acid is as follows: p-aminobenzoic acid (10.0 g, 0.07 mol, 1 eq.), 5% Ru/C catalyst (2.50 g), and 10% NaOH solution (100.0 mL) were added in an autoclave. The mixture was stirred to react under 100 bar hydrogen pressure and 15 bar hydrogen atmosphere. After 20 hours of reaction, the progress of the reaction was detected by thin layer chromatography (TLC), the unfolding agent was dichloromethane/methanol/ammonia (5:5:1, v/v/v), and the staining agent was ninhydrin to confirm that the starting material was completely consumed. Nuclear magnetic resonance (NMR) analysis showed that the reaction was fully converted and the ratio of cis to trans product was 1:4.6. After confirming that the reaction was complete, the reaction was stopped.

References

[1] European Journal of Medicinal Chemistry, 2001, vol. 36, # 3, p. 265 - 286
[2] Biochemische Zeitschrift, 1933, vol. 262, p. 462
[3] Journal of the American Chemical Society, 1938, vol. 60, p. 2341,2343
[4] Chemische Berichte, 1942, vol. 75, p. 425,428
[5] Chemische Berichte, 1943, vol. 76, p. 1019,1023

cis-4-Aminocyclohexanecarboxylic acid(3685-23-2)Related Product Information

• Chlorocyclohexane
• Methylcyclohexane
• Cyclohexanecarboxylic acid
• Ethylcyclohexane
• Glycine
• Cyclohexane
• Cyclohexene oxide
• 4-aminocyclohexan-1-ol
• cis-4-Hydroxy-D-proline hydrochloride
• (4S)-4-hydroxy-L-proline hydrochloride
• CIS-4-METHYL-CYCLOHEXYLAMINE HCL
• CIS-4-CYCLOHEXENE-1,2-DICARBOXYLIC ACID
• 4α-Aminocyclohexan-1α-ol
• Cis-4-Aminoadamantan-1-ol hydrochloride
• Methyl cis-4-Aminocyclohexanecarboxylate Hydrochloride
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