3-METHYLENECYCLOBUTANECARBOXYLIC ACID Chemical Properties

Boiling point:

102.5-103 °C(Press: 11 Torr)

Density 

1.12±0.1 g/cm3(Predicted)

refractive index 

1.46

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

4.52±0.20(Predicted)

form 

liquid

color 

Clear, colourless

InChI

InChI=1S/C6H8O2/c1-4-2-5(3-4)6(7)8/h5H,1-3H2,(H,7,8)

InChIKey

NNKLICLIBKMDOY-UHFFFAOYSA-N

SMILES

C1(C(O)=O)CC(=C)C1

Safety Information

Hazard Codes 

F,Xn

Risk Statements 

22

HazardClass 

IRRITANT

HS Code 

2916399090

Toxicity

mouse,LD50,intraperitoneal,500mg/kg (500mg/kg),National Technical Information Service. Vol. AD430-559,

3-METHYLENECYCLOBUTANECARBOXYLIC ACID Usage And Synthesis

Uses

Because it contains a cyclobutane skeleton, 3-methylenecyclobutane carboxylic acid can be used as a synthetic intermediate for functional organic molecules containing a cyclobutane skeleton. By utilizing the chemical transformation properties of this substance, different functional groups can be introduced onto the cyclobutane skeleton, thereby achieving the regulation of the properties of the target organic molecule.

Synthesis

Step 1: Preparation of 3-methylenecyclobutanecarboxylic acid Potassium hydroxide (264 g, 4.7 mol) was added to a mixed solution of 3-methylenecyclobutanecarbonitrile (110 g, 1.18 mol) in ethanol (500 mL) and water (500 mL), and the resulting mixture was heated to reflux overnight. Upon completion of the reaction, ethanol was removed by distillation under reduced pressure. The remaining solution was cooled to below 10 °C and acidified with concentrated hydrochloric acid to pH 1. The mixture was extracted with ethyl acetate (2 × 500 mL), the organic phases were combined and dried over anhydrous sodium sulfate. The organic phase was concentrated under reduced pressure to give the title compound 3-methylenecyclobutanecarboxylic acid (132 g, 100% yield) as a yellow oil.

References

[1] Patent: US2013/79324, 2013, A1. Location in patent: Paragraph 0934; 0935
[2] Patent: US2014/142081, 2014, A1. Location in patent: Paragraph 0242; 0244
[3] Patent: WO2014/79136, 2014, A1. Location in patent: Page/Page column 89-90
[4] Patent: WO2018/89355, 2018, A1. Location in patent: Page/Page column 221; 222
[5] Patent: WO2015/129926, 2015, A1. Location in patent: Page/Page column 108

3-METHYLENECYCLOBUTANECARBOXYLIC ACID(15760-36-8)Related Product Information

• METHYLENECYCLOBUTANE
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• 3-METHYLENECYCLOBUTANECARBOXYLIC ACID
• Cyclobutanecarboxylic acid