trans-3-Methylenecyclopropane-1,2-dicarboxylic acid

Base Information

• Chemical Name: trans-3-Methylenecyclopropane-1,2-dicarboxylic acid
• CAS No.: 499-02-5
• Molecular Formula: C6H6 O4
• Molecular Weight: 142.111
• Hs Code.: 29172000
• European Community (EC) Number: 207-874-4
• DSSTox Substance ID: DTXSID801215743
• Nikkaji Number: J232.227G
• Mol file: 499-02-5.mol

Synonyms:499-02-5;trans-3-Methylenecyclopropane-1,2-dicarboxylic acid;(1S,2S)-3-methylidenecyclopropane-1,2-dicarboxylic acid;SCHEMBL712898;XZVHROKAQFFOCA-QWWZWVQMSA-;DTXSID801215743;MFCD00001312;STK330638;AKOS005438118;trans-3-Methylenecyclopropane-1,2-dicarboxylicacid;3-Methylene-1beta,2alpha-cyclopropanedicarboxylic acid;trans-3-Methylidenecyclopropane-1,2-dicarboxylic acid;(1S,2S)-3-Methylene-1,2-cyclopropanedicarboxylic acid;148152-68-5

Chemical Property of trans-3-Methylenecyclopropane-1,2-dicarboxylic acid

Chemical Property:

• Vapor Pressure: 0.000145mmHg at 25°C
• Melting Point: 197-201 °C
• Refractive Index: 1.5800 (estimate)
• Boiling Point: 309.2°Cat760mmHg
• PKA: 3.48±0.40(Predicted)
• Flash Point: 155°C
• Density: 1.49g/cm³
• Storage Temp.: -20°C
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 142.02660867
• Heavy Atom Count: 10
• Complexity: 196

Purity/Quality:

99% ^*data from raw suppliers

3-Methylenecyclopropane-trans-1,2-dicarboxylicAcid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: C,Xi
• Statements: 34-36/37/38
• Safety Statements: 24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=C1C(C1C(=O)O)C(=O)O
• Isomeric SMILES: C=C1[C@H]([C@@H]1C(=O)O)C(=O)O
• 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.

Technology Process of trans-3-Methylenecyclopropane-1,2-dicarboxylic acid

There total 8 articles about trans-3-Methylenecyclopropane-1,2-dicarboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 68.0%

ethyl 3-bromo-4,6-dimethyl-2-oxo-2H-pyran-5-carboxylate (18152-79-9) → Feist's acid (499-02-5)

Guidance literature:

With potassium hydroxide; In 1,4-dioxane; at 105 ℃; for 0.833333h;

DOI:10.1002/hlca.201100305

Reference yield: 19.0%

ethyl acetoacetate (141-97-9) → Feist's acid (499-02-5)

Guidance literature:

ethyl acetoacetate; With hydrogenchloride; for 336h; Darkness;

With bromine; In chloroform; at 20 ℃; for 24h;

With potassium hydroxide; at 105 ℃; for 1h;

DOI:10.3390/molecules17055550

Reference yield:

ethyl isodehydroacetate (3385-34-0) → Feist's acid (499-02-5)

Guidance literature:

Multi-step reaction with 2 steps

1: bromine / chloroform / 24 h / 0 - 20 °C

2: potassium hydroxide / 1,4-dioxane / 0.83 h / 105 °C

With bromine; potassium hydroxide; In 1,4-dioxane; chloroform;

DOI:10.1002/hlca.201100305

upstream raw materials:

(1R,2R)-(+)-3-methylenecyclopropane-1,2-dicarboxylic acid (R)-(+)-α-methylbenzammonium salt

(1S,2S)-(-)-3-methylenecyclopropane-1,2-dicarboxylic acid (R)-(+)-α-methylbenzammonium salt

ethyl 3-bromo-4,6-dimethyl-2-oxo-2H-pyran-5-carboxylate

ethyl isodehydroacetate

Downstream raw materials:

(1R,2R)-(+)-3-methylenecyclopropane-1,2-dicarboxylic acid

(1S,2S)-3-methylene-cyclopropane-1,2-dicarboxylic acid

levulinic acid

(1R,2R)-N₁,N₂-benzyl-3-methylenecyclopropane-1,2-dicarboxamide

Refernces

• 1、 Al-Majid, Abdullah M. A.,Al-Othman, Zeid A.,Islam, Mohammad Shahidul. "Synthesis of some C2-symmetric bidentate ligands and their complexes derived from Feist's acid". experimental part. p. 268 - 277. Retrieved 2012/04/10.
• 2、 -. "Process for the preparation of an antiviral agent". . . Retrieved 2008/06/13.