3-Oxo­cy­clobu­tanecar­boxylic acid CAS 23761-23-1

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• Prop­er­ties
• Safe­ty Data
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Iden­ti­fi­ca­tion

CAS Number

23761-23-1

Name

3-oxo­­cy­­clobu­­tanecar­boxylic acid

Syn­onyms

2078401 [Beil­stein]
23761-23-1 [RN]
3-Oxo­­cy­­clobu­­tan­­car­bon­säure [Ger­man] [ACD/IUPAC Name]
3-Oxo­­cy­­clobu­­tane-1-car­boxylic acid [ACD/IUPAC Name]
3-Oxo­­cy­­clobu­­tanecar­boxylic acid [ACD/IUPAC Name]
Acide 3-oxo­­cy­­clobu­­tanecar­boxylique [French] [ACD/IUPAC Name]
Cyclobu­tanecar­boxylic acid, 3-oxo- [ACD/​Index Name]
L4VTJ CVQ [WLN]
(3-Oxocyclobutyl)carboxylic acid
[23761-23-1] [RN]
1-Car­boxy-3-oxo­­cy­­clobu­­tane
2-Eth­yl­­sul­­fonylethanol
3-​ox­o­­cy­­clobu­­tanecar­box​ylic acid
3-keto­­cy­­clobu­­tanecar­boxylic acid
3-Oxo­­cy­­clobu­­tane-1-car­boxylic acid|1-Carboxy-3-oxocyclobutane
95%
AC1NKHBV
AGN-PC-0LJAYC
BR-25641
cyclobu­­tanone-3-car­boxylic acid
MFCD00100900 [MDL num­ber]
OS-7697
PS-5042
PubChem14220

SMILES

C1C(CC1=O)C(=O)O

Std­InChI

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

Std­InChIKey

IENOFR­JPUPTE­­MI-UHF­F­­FAOYSA-N

Mol­e­c­u­lar Formula

C₅H₆O₃

Mol­e­c­u­lar Weight

114.099

MDL Number

MFCD00100900

Prop­er­ties

Appear­ance

Off-white sol­id

Safe­ty Data

Sym­bol

GHS07

Sig­nal Word

Warn­ing

Haz­ard statements

Pre­cau­tion­ary Statements

WGK Germany

3

MSDS Download

Spec­i­fi­ca­tions and Oth­er Infor­ma­tion of Our 3-oxo­­cy­­clobu­­tanecar­boxylic acid CAS 23761-23-1

Iden­ti­fi­ca­tion Methods

HNMR, GC

Puri­ty

98% min

K.F

≤1.0%

Shelf Life

2 years

Stor­age

Under room tem­per­a­ture away from light

Known Appli­ca­tion

3-Oxo­­cy­­clobu­­tanecar­boxylic acid is a very impor­tant phar­ma­ceu­ti­cal inter­me­di­ate. It is wide­ly used in the syn­the­sis of dozens of APIs, such as ACK1 anti­bod­ies, MDM2 antag­o­nists, JAK inhibitors, CETP inhibitors, kinase inhibitors, PDE10 inhibitors, throm­bin inhibitors, and in autoim­mune chron­ic inflam­ma­tion and anti-tumor drugs. In the phar­ma­ceu­ti­cal field, it is often used in the fol­low­ing aspects : 

1. Syn­the­sis of antibi­otics and antivi­ral drugs : As an inter­me­di­ate con­tain­ing a ring struc­ture, it can be used to syn­the­size com­pounds with antibac­te­r­i­al or antivi­ral activ­i­ty. Its ring struc­ture can improve the bio­log­i­cal activ­i­ty and cell mem­brane per­me­abil­i­ty of the mol­e­cule in some cas­es, there­by enhanc­ing the efficacy. 

2. Syn­the­sis of unnat­ur­al amino acids : 3-Oxo­­cy­­clobu­­tanecar­boxylic acid is often used to syn­the­size unnat­ur­al amino acids. These spe­cial amino acids are used to devel­op pep­tide drugs, which helps to improve the sta­bil­i­ty, selec­tiv­i­ty and meta­bol­ic half-life of the drug. 

3. Anti­cancer drug devel­op­ment : Due to its unique mol­e­c­u­lar struc­ture, 3-Oxo­­cy­­clobu­­tanecar­boxylic acid is used as a key skele­ton in the design of some anti­cancer drugs. Its ring struc­ture can help drug mol­e­cules bind to spe­cif­ic pro­tein tar­gets, help­ing to inhib­it the pro­lif­er­a­tion of can­cer cells. 

4. Syn­the­sis of enzyme inhibitors : 3-Oxo­­cy­­clobu­­tanecar­boxylic acid can be used as an inter­me­di­ate for syn­the­siz­ing enzyme inhibitors to help design drugs for reg­u­lat­ing the activ­i­ty of bio­log­i­cal enzymes. Such drugs have poten­tial in the treat­ment of meta­bol­ic dis­eases and neu­rode­gen­er­a­tive dis­eases such as Alzheimer’s disease.

5. Oth­er drug mol­e­c­u­lar mod­i­fi­ca­tions : It can also be used to intro­duce cyclobu­tane struc­tures into exist­ing drug mol­e­cules to opti­mize phar­ma­co­ki­net­ic prop­er­ties, such as increas­ing bioavail­abil­i­ty or reduc­ing toxicity. 

It has some poten­tial appli­ca­tion val­ues​in the field of poly­mer mate­ri­als and poly­mers, includ­ing the fol­low­ing aspects : 

1. Cross-link­ing agent or chain trans­fer agent : Its cyclobu­tane struc­ture helps to intro­duce reac­tive sites into the poly­mer sys­tem, which is used to adjust the mol­e­c­u­lar weight and chain struc­ture of the poly­mer chain, there­by opti­miz­ing the mechan­i­cal prop­er­ties, ther­mal sta­bil­i­ty and sol­vent resis­tance of the mate­r­i­al. As a cross-link­ing agent, it can help form a three-dimen­­sion­al net­work struc­ture, there­by enhanc­ing the strength and heat resis­tance of the polymer.

2. Poly­mer mod­i­fi­er : 3-Oxo­­cy­­clobu­­tanecar­boxylic acid can be used to mod­i­fy exist­ing poly­mer mate­ri­als to improve their per­for­mance. For exam­ple, intro­duc­ing it into polyamide, poly­ester or polyurethane can improve the tough­ness, wear resis­tance and chem­i­cal resis­tance of the mate­r­i­al, while its ring struc­ture helps to improve the rigid­i­ty of the material. 

3. Pre­cur­sor of pho­to­sen­si­tive poly­mers : Its ring struc­ture and car­bonyl group can be used as pre­cur­sors of pho­to­sen­si­tive poly­mers, and ring cleav­age reac­tions can be induced by light or heat treat­ment to achieve spe­cif­ic func­tions. The poly­mers pre­pared in this way can be used in fields such as lith­o­g­ra­phy and micro­elec­tron­ic materials. 

4. Syn­the­sis of func­tion­al­ized monomers : 3-Oxo­­cy­­clobu­­tanecar­boxylic acid can be used as an inter­me­di­ate of func­tion­al­ized monomers to pre­pare poly­mers with spe­cif­ic prop­er­ties. These poly­mers may have spe­cif­ic ther­mal prop­er­ties or chem­i­cal activ­i­ties and have poten­tial appli­ca­tions in cut­t­ing-edge mate­ri­als such as self-heal­ing mate­ri­als and bio­mimet­ic materials. 

5. Flame retar­dant mate­ri­als : In the design of flame retar­dant poly­mers, the ring struc­ture of 3-Oxo­­cy­­clobu­­tanecar­boxylic acid may help improve the ther­mal sta­bil­i­ty of poly­mers and reduce the risk of com­bus­tion. It can be used as a flame retar­dant addi­tive or par­tic­i­pate in poly­mer­iza­tion reac­tions to make the final mate­r­i­al have bet­ter sta­bil­i­ty at high temperatures.

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This prod­uct is devel­oped by our R&D com­pa­ny Cam­ing Phar­ma­ceu­ti­cal Lim­it­ed (http://​www​.cam​ing​.com/).

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