499-02-5

Basic information

• Product Name: 3-METHYLENECYCLOPROPANE-TRANS-1,2-DICARBOXYLIC ACID
• Synonyms: 1,2-Cyclopropanedicarboxylic acid, 3-methylene-, trans-;3-Methylene-1,2-cyclopropanedicarboxylic acid;3-Methylenecyclopropane-1,2-dicarboxylic acid, trans-;SALOR-INT L167959-1EA;TIMTEC-BB SBB008097;TRANS-1-METHYLENECYCLOPROPANE-2,3-DICARBOXYLIC ACID;3-METHYLENECYCLOPROPANE-TRANS-1,2-DICARBOXYLIC ACID;3-METHYLIDENECYCLOPROPANE-1,2-DICARBOXYLIC ACID
• CAS NO: 499-02-5
• Molecular Formula: C₆H₆O₄
• Molecular Weight: 142.11
• EINECS: 207-874-4
• Mol File: 499-02-5.mol
• Article Data: 4

Chemical Properties

• Melting Point: 197-201 °C
• Boiling Point: 219.65°C (rough estimate)
• Flash Point: 155°C
• Appearance: /
• Density: 1.3863 (rough estimate)
• Vapor Pressure: 0.000145mmHg at 25°C
• Refractive Index: 1.5800 (estimate)
• Storage Temp.: -20°C
• PKA: 3.48±0.40(Predicted)
• CAS DataBase Reference: 3-METHYLENECYCLOPROPANE-TRANS-1,2-DICARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3-METHYLENECYCLOPROPANE-TRANS-1,2-DICARBOXYLIC ACID(499-02-5)
• EPA Substance Registry System: 3-METHYLENECYCLOPROPANE-TRANS-1,2-DICARBOXYLIC ACID(499-02-5)

Safety Data

• Hazard Codes: C,Xi
• Statements: 34-36/37/38
• Safety Statements: 24/25-36-26
• Hazardous Substances Data: 499-02-5(Hazardous Substances Data)

Usage

Chemical Properties

off-white to beige crystalline powder

Uses

(1S,2S)-3-methylidenecyclopropane-1,2-dicarboxylic acid (cas# 499-02-5) is used in the regioselective green preparation antibacterial and antifungal activity of (arylnitroethyl)indoles and (arylnitroethyl)pyrroles by Michael addition of indole and pyrrole to trans-β-nitroolefins catalyzed by hydrogen bond donor Feist''s catalyst.

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

Upstream product

• 18152-79-9 ethyl 3-bromo-4,6-dimethyl-2-oxo-2H-pyran-5-carboxylate 
• 141-97-9 ethyl acetoacetate 
• 3385-34-0 ethyl isodehydroacetate 
• 148152-70-9 (1S,2S)-(-)-3-methylenecyclopropane-1,2-dicarboxylic acid (R)-(+)-α-methylbenzammonium salt 
• 148082-88-6 (1R,2R)-(+)-3-methylenecyclopropane-1,2-dicarboxylic acid (R)-(+)-α-methylbenzammonium salt 

Downstream Products

• 39653-07-1 (+/-)-methylene-cyclopropane-1r,2t-dicarbonyl chloride 
• 499-02-5 (1R,2R)-(+)-3-methylenecyclopropane-1,2-dicarboxylic acid 
• 499-02-5 (1S,2S)-3-methylene-cyclopropane-1,2-dicarboxylic acid 
• 1391950-67-6 (1R,2R)-N₁,N₂-benzyl-3-methylenecyclopropane-1,2-dicarboxamide 
• 148152-70-9 (1S,2S)-(-)-3-methylenecyclopropane-1,2-dicarboxylic acid (R)-(+)-α-methylbenzammonium salt 
• 148082-88-6 (1R,2R)-(+)-3-methylenecyclopropane-1,2-dicarboxylic acid (R)-(+)-α-methylbenzammonium salt 
• 1391950-71-2 (1S,2S)-N₁,N₂-benzyl-3-methylenecyclopropane-1,2-dicarboxamide 
• 107520-09-2 (+/-)-methylene-cyclopropane-1r,2t-dicarboxylic acid-dianilide 
• 127696-06-4 (2S-trans)-2,3-bis[(t-butyldiphenylsilyloxy)methyl]-cyclobutanone 
• 132164-71-7 C₃₈H₄₆O₂Si₂ 
• 132164-69-3 C₂₀H₂₂O₂ 
• 95898-34-3 (+)-trans-methylenecyclopropane-2,3-dicarboxamide 
• 134716-70-4 [(2S,3S)-2,3-Bis-(tert-butyl-dimethyl-silanyloxymethyl)-cyclopropyl]-carbamic acid benzyl ester 
• 75858-34-3 (1S,2S)-1,2-bis(benzoyloxymethyl)-3-methylcyclopropane 

Relevant articles and documents

Synthesis of some C2-symmetric bidentate ligands and their complexes derived from Feist's acid

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

(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.