499-02-5 Usage
Description
3-METHYLENECYCLOPROPANE-TRANS-1,2-DICARBOXYLIC ACID, also known as (1S,2S)-3-methylidenecyclopropane-1,2-dicarboxylic acid with the CAS number 499-02-5, is an off-white to beige crystalline powder. It is a significant organic compound utilized in the synthesis of various pharmaceuticals and chemicals due to its unique chemical properties and reactivity.
Uses
Used in Pharmaceutical Industry:
3-METHYLENECYCLOPROPANE-TRANS-1,2-DICARBOXYLIC ACID is used as a key intermediate for the synthesis of various antibacterial and antifungal agents. Its application is particularly focused on the regioselective green preparation of (arylnitroethyl)indoles and (arylnitroethyl)pyrroles, which exhibit potent bioactivity against a range of bacterial and fungal pathogens.
3-METHYLENECYCLOPROPANE-TRANS-1,2-DICARBOXYLIC ACID plays a crucial role in the Michael addition of indole and pyrrole to trans-β-nitroolefins, a process catalyzed by hydrogen bond donor Feist's catalyst. This reaction pathway allows for the efficient and environmentally friendly production of biologically active molecules, contributing to the development of novel therapeutic agents in the pharmaceutical industry.
Check Digit Verification of cas no
The CAS Registry Mumber 499-02-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,9 and 9 respectively; the second part has 2 digits, 0 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 499-02:
(5*4)+(4*9)+(3*9)+(2*0)+(1*2)=85
85 % 10 = 5
So 499-02-5 is a valid CAS Registry Number.
InChI:InChI=1/C6H6O4/c1-2-3(5(7)8)4(2)6(9)10/h3-4H,1H2,(H,7,8)(H,9,10)/p-2/t3-,4-/m1/s1
499-02-5Relevant articles and documents
Synthesis of some C2-symmetric bidentate ligands and their complexes derived from Feist's acid
Al-Majid, Abdullah M. A.,Al-Othman, Zeid A.,Islam, Mohammad Shahidul
experimental part, p. 268 - 277 (2012/04/10)
Various new C2-symmetric bidentate ligands, bearing phosphorus, nitrogen, and sulfur, were obtained in an efficient manner, starting from (±)-trans-3-methylidenecyclopropane-1,2-dicarboxylic acid (Feist's acid; (±)-trans-3). The structures of the new bidentate ligands, di(tert-butyl) (±)-[(trans-3-methylidenecyclopropane-1,2-diyl)dimethanediyl] biscarbamate ((±)-9), (±)-(trans-3-methyldienecyclopropane-1,2- diyl)dimethanaminium dichloride ((±)-10), (±)-S,S′-[(trans- 3-methylidenecyclopropane-1,2-diyl)dimethanediyl] diethanethioate ((±)-11), and (±)-[(trans-3-methylidenecyclopropane-1,2-diyl) dimethanediyl]bis(diphenylphosphane) ((±)-12), were fully characterized by standard spectroscopic techniques. These new classes of C2- symmetric bidentate ligands have the potential to be used in asymmetric catalysis. Copyright
C2-Symmetric Ligands for Asymmetric Catalysis based on Feist's Acid
Al-Maijd, Abdullah,Booth, Brian L. M.,Gomes, Jonnes T.
, p. 580 - 589 (2007/10/03)
(2R,3R)-(+)-Feist's acid has been converted via its dimethyl ester into (2R,3R)-(-bis(diphenylmethanol)-1-methylenecyclopropane, the corresponding bisdiol and bismesylate derivatives, and the racemic analogues of these derivatives has been converted into the bisazide, bis amino compounds and a bisindenyl derivative in good yields.