(S)-(-)-3-CYCLOHEXENECARBOXYLIC ACID Chemical Properties

Melting point:

19°C(lit.)

Boiling point:

118°C/6mmHg(lit.)

Density 

1.126±0.06 g/cm3(Predicted)

refractive index 

1.4780 to 1.4820

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

clear liquid

pka

4.67±0.20(Predicted)

color 

Colorless to Almost colorless

InChI

InChI=1S/C7H10O2/c8-7(9)6-4-2-1-3-5-6/h1-2,6H,3-5H2,(H,8,9)/t6-/m1/s1

InChIKey

VUSWCWPCANWBFG-ZCFIWIBFSA-N

SMILES

[C@H]1(C(O)=O)CCC=CC1

Safety Information

Hazard Codes 

C

Risk Statements 

34

Safety Statements 

26-36/37/39-45

RIDADR 

UN 3265 8 / PGIII

HazardClass 

8

PackingGroup 

III

HS Code 

2916200090

(S)-(-)-3-CYCLOHEXENECARBOXYLIC ACID Usage And Synthesis

Uses

(S)-(-)-3-CYCLOHEXENECARBOXYLIC ACID can be used as organic synthesis intermediates and pharmaceutical intermediates, mainly used in laboratory research and development processes and chemical production processes.

Uses

(S)-3-Cyclohexene-1-carboxylic Acid has been used as a reactant for the preparation of N-[(1R,2S,5S)-2-{[(5-chloroindol-2-yl)carbonyl]amino}-5-(dimethylcarbamoyl)cyclohexyl]-5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxamide hydrochloride, a potent and orally active direct inhibitor of factor Xa.

Synthesis

54.94 g of cyclohex-3-ene-1(S)-carboxylic acid (R)-(+)-methylbenzylamine salt and 18.2 volumes of H2O were charged to a flask at 20-25°C and stirred. To the mixture obtained further 6.7 volumes of H2O and 10 volumes of EtOAc were added. The mixture obtained was stirred for 15 min, the phases were separated and the organic layer was discarded. The aqueous layer was treated with 10 volumes of MTBE and 2.5 equivalents of 6M HCI were added slowly. The mixture obtained was stirred and two layers were formed, separated and the aqueous layer was extracted with MTBE. The organic layers obtained were combined and washed with aqueous, 30percent NaCl solution. The organic phase obtained was dried over Na2S04, filtered, and from the filtrate obtained solvent was removed in vacuo. Cyclohex-3-ene-1(S)-carboxylic acid in the form of a clear oil was obtained. Yield: 26.13 g (93.3percent of theory).

References

[1] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 3, p. 1193 - 1206
[2] Patent: EP2390245, 2011, A1. Location in patent: Page/Page column 15
[3] Patent: EP2399904, 2011, A1. Location in patent: Page/Page column 25
[4] Patent: EP1577301, 2005, A1. Location in patent: Page/Page column 191
[5] Patent: EP1405852, 2004, A1. Location in patent: Page 175

(S)-(-)-3-CYCLOHEXENECARBOXYLIC ACID(5708-19-0)Related Product Information

• Cyclohexene
• 3-Cyclohexenecarboxylic acid