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

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.

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

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

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 
• 123-76-2 levulinic acid 
• 263169-44-4 (2S,2'R,3'R)-N-[(R)-α-phenylglycinyl]-2-(1'-[3H]-2',3'-dicarbomethoxycyclopropyl)glycinonitrile 
• 75858-34-3 (1S,2S)-1,2-bis(benzoyloxymethyl)-3-methylcyclopropane 
• 134716-70-4 [(2S,3S)-2,3-Bis-(tert-butyl-dimethyl-silanyloxymethyl)-cyclopropyl]-carbamic acid benzyl ester 
• 95898-34-3 (+)-trans-methylenecyclopropane-2,3-dicarboxamide 
• 132164-69-3 C₂₀H₂₂O₂ 
• 132164-71-7 C₃₈H₄₆O₂Si₂ 
• 127696-06-4 (2S-trans)-2,3-bis[(t-butyldiphenylsilyloxy)methyl]-cyclobutanone 
• 107520-09-2 (+/-)-methylene-cyclopropane-1r,2t-dicarboxylic acid-dianilide 
• 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 

Relevant articles and documents

Synthesis and characterization of some new c2 symmetric chiral bisamide ligands derived from chiral feist's acid

The hemilabile chiral C2 symmetrical bidentate substituted amide ligands (1R,2R)-5a-d and (1S,2S)-6a-d were synthesized in quantitative yield from (1R,2R)-(+)-3- methylenecyclo-propane-1,2-dicarboxylic acid (1R,2R)-3 and (1S,2S)-(-)-3-methylenecyclopropane- 1,2-dicarboxylic acid (1S,2S)-3, in two steps, respectively. The chiral Feist's acids (1R,2R)-3 and (1S,2S)-3 were obtained in good isomeric purity by resolution of trans-(±)-3-methylene-cyclopropane-1,2-dicarboxylic acid from an 8:2 mixture of tert-butanol and water, using (R)-(+)-α-methylbenzyl amine as a chiral reagent. This process is reproducible on a large scale. All these new synthesized chiral ligands were characterized by 1H-NMR, 13C-NMR, IR, and mass spectrometry, as well as elemental analysis and their specific rotations were measured. These new classes of C2 symmetric chiral bisamide ligands could be of special interest in asymmetric transformations.

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.