3-Oxocyclobutanecarboxylic acid Chemical Properties

Melting point:

69-70℃

Boiling point:

296°C

Density 

1.431

Flash point:

147°C

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

Solid

pka

4.35±0.20(Predicted)

color 

Off-white

Water Solubility 

Slightly soluble in water.

InChI

InChI=1S/C5H6O3/c6-4-1-3(2-4)5(7)8/h3H,1-2H2,(H,7,8)

InChIKey

IENOFRJPUPTEMI-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

23761-23-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

Safety Statements 

26-37-60

TSCA 

No

HS Code 

29189900

3-Oxocyclobutanecarboxylic acid Usage And Synthesis

Description

3-Oxocyclobutanecarboxylic acid is an organic common intermediate compound used in pharmaceuticals, organic synthesis and organic light-emitting diode (OLED) intermediates. Abrocitinib, prepared from 3-Oxocyclobutanecarboxylic acid, is approved for the treatment of adult patients with atopic dermatitis (AD), as well as patients with refractory moderate to severe AD who have had limited or minimal response to other systemic medications.

Chemical Properties

White solid

Uses

3-Oxocyclobutanecarboxylic Acid (cas# 23761-23-1) is a compound useful in organic synthesis.

Application

3-Oxocyclobutanecarboxylic acid is a very important medicine intermediate, it is widely applied in the synthetic of tens kinds of bulk drugs, such as ACK1 antibody, the MDM2 antagonist, the JAK inhibitor, CETP inhibitor, kinase inhibitor, the PDE10 inhibitor, thrombin inhibitors and in autoimmunization chronic inflammatory diseases and antitumor drug, all being used to.

Preparation

The target product 3-oxocyclobutanecarboxylic acid is obtained by adopting acetone, bromine, and malononitrile as raw materials, adopting ethanol, DMF (dimethyl formamide), and water as solvents, adopting sodium iodide as an activating agent and tetrabutylammonium bromide (TBAB) as a phase transfer catalyst through three-step reaction.

Synthesis Reference(s)

The Journal of Organic Chemistry, 53, p. 3841, 1988 DOI: 10.1021/jo00251a033

Synthesis

General procedure for the synthesis of 3-oxocyclobutanecarboxylic acid from 3,3-dimethoxycyclobutane-1,1-dicarboxylic acid diisopropyl ester: the product of step A (4.8 g, 17 mmol) was mixed with 20% HCl (20 mL) and the reaction was stirred under refluxing conditions for 60 hours. After completion of the reaction, the mixture was cooled to room temperature. Ether was added to the reaction mixture and stirred vigorously for 24 hours. The ether layer was separated and the aqueous layer was extracted with ether three times (3×). All organic layers were combined and dried with anhydrous MgSO4 and subsequently concentrated under vacuum to give Intermediate 1 (1.84 g, 96.8% yield). This crude product was used directly in the next step of the reaction. The NMR hydrogen spectrum (400 MHz, CDCl3) data of intermediate 1 were as follows: δ 3.52-3.26 (m, 5H).

References

[1] Journal of Organic Chemistry, 1988, vol. 53, # 16, p. 3841 - 3843
[2] Patent: WO2004/82682, 2004, A1. Location in patent: Page 35-36
[3] Synlett, 2009, # 11, p. 1827 - 1829
[4] Chemistry - A European Journal, 2011, vol. 17, # 2, p. 468 - 480
[5] Patent: US2009/233903, 2009, A1. Location in patent: Page/Page column 46

3-Oxocyclobutanecarboxylic acid(23761-23-1)Related Product Information

• 1-DODECANESULFONIC ACID SODIUM SALT
• TRIMETHYLENE OXIDE
• 1-Bromobutane
• Sodium dodecyl sulfate
• Cyclopropane
• 1-Hexadecylpyridinium bromide
• 2-Bromo-2-methylpropane
• 1-Chloro-2-methylpropane
• Folic acid
• Oxygen-fluorine acid
• Stearic acid
• Ethyl 2-(Chlorosulfonyl)acetate
• Levofloxacin carboxylic acid
• 2-Chloro-2-methylpropane
• Citric acid
• Ascoric Acid
• Cyclobutanecarboxylic acid
• Cyclobutanemethanol