3-Oxocyclobutanecarboxylic acid

CAS NO.：23761-23-1
Empirical Formula: C5H6O3
Molecular Weight: 114.1
MDL number: MFCD00100900
EINECS: 639-432-5
SAFETY DATA SHEET (SDS)
Update Date: 2024-11-14 20:10:21

What is 3-Oxocyclobutanecarboxylic acid?

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

The Uses of 3-Oxocyclobutanecarboxylic acid

3-oxo cyclobutane-carboxylic acid is a very important medicine intermediate, it is widely used 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, etc.

What are the applications of 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.

Preparation

The preparation method of 3-Oxocyclobutanecarboxylic acid comprises the following steps: (1) preparing methyl triphenylphosphine iodide ; (2) preparing 3-benzal cyclobutanol ; (3) preparing methyl-benzenesulfonic acid-3-benzal cyclobutanol ester ; (4) preparing 3-benzal cyclobutanecarbonitrile ; (5) preparing 3-benzal cyclobutylcarboxylic acid ; (6) preparing 3-oxocyclobutanecarboxylic acid.

Synthesis Reference(s)

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

Properties of 3-Oxocyclobutanecarboxylic acid

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)
CAS DataBase Reference	23761-23-1(CAS DataBase Reference)

Safety information for 3-Oxocyclobutanecarboxylic acid

Signal word	Danger
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. P304+P340:IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. P405:Store locked up.