4-Methylenecyclopentane-1,2-dicarboxylic acid

Base Information

• Chemical Name: 4-Methylenecyclopentane-1,2-dicarboxylic acid
• CAS No.: 90474-14-9
• Molecular Formula: C₈H₁₀O₄
• Molecular Weight: 170.165
• Hs Code.: 2917209090
• DSSTox Substance ID: DTXSID40529169
• Mol file: 90474-14-9.mol

Synonyms:90474-14-9;4-Methylenecyclopentane-1,2-dicarboxylic acid;4-methylidenecyclopentane-1,2-dicarboxylic acid;4-METHYLENE-CYCLOPENTANE-1,2-DICARBOXYLIC ACID;SCHEMBL1030623;DTXSID40529169;AKOS006326421;4-Methylenecyclopentane-1,2-dicarboxylicacid

Chemical Property of 4-Methylenecyclopentane-1,2-dicarboxylic acid

Chemical Property:

• Vapor Pressure: 4.65E-07mmHg at 25°C
• Refractive Index: 1.534
• Boiling Point: 386.8°C at 760 mmHg
• Flash Point: 201.9°C
• PSA: 74.60000
• Density: 1.32g/cm³
• LogP: 0.73800
• Storage Temp.: 2-8°C
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 170.05790880
• Heavy Atom Count: 12
• Complexity: 219

Purity/Quality:

≥99% ^*data from raw suppliers

4-Methylenecyclopentane-1,2-dicarboxylicacid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=C1CC(C(C1)C(=O)O)C(=O)O

Technology Process of 4-Methylenecyclopentane-1,2-dicarboxylic acid

There total 7 articles about 4-Methylenecyclopentane-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:

4-Methylene-cyclopentane-1,2-dicarboxylic acid diethyl ester (343956-49-0) → 4-Methylene-cyclopentane-1,2-dicarboxylic acid (90474-14-9)

Guidance literature:

With potassium hydroxide; In tetrahydrofuran;

DOI:10.1016/S0960-894X(02)00958-7

Reference yield:

1,2,3,4-butanetetracarboxylic acid (4534-68-3) → 4-Methylene-cyclopentane-1,2-dicarboxylic acid (90474-14-9)

Guidance literature:

Multi-step reaction with 6 steps

1: H₂SO₄

2: NaOMe / methanol

3: aq. HCl

4: H₂SO₄

5: KOtBu / tetrahydrofuran

6: aq. KOH / tetrahydrofuran

With hydrogenchloride; potassium hydroxide; sulfuric acid; potassium tert-butylate; sodium methylate; In tetrahydrofuran; methanol;

DOI:10.1016/S0960-894X(02)00958-7

Reference yield:

1,2,3,4-butanetetracarboxylic acid tetraethyl ester (4373-15-3) → 4-Methylene-cyclopentane-1,2-dicarboxylic acid (90474-14-9)

Guidance literature:

Multi-step reaction with 5 steps

1: NaOMe / methanol

2: aq. HCl

3: H₂SO₄

4: KOtBu / tetrahydrofuran

5: aq. KOH / tetrahydrofuran

With hydrogenchloride; potassium hydroxide; sulfuric acid; potassium tert-butylate; sodium methylate; In tetrahydrofuran; methanol;

DOI:10.1016/S0960-894X(02)00958-7

upstream raw materials:

4-Methylene-cyclopentane-1,2-dicarboxylic acid diethyl ester

1,2,3,4-butanetetracarboxylic acid

1,2,3,4-butanetetracarboxylic acid tetraethyl ester

diethyl 4-oxo-1,2-cyclopentanedicarboxylate

Downstream raw materials:

(+)-(1S,2R)-4-methylene-2-[(2E)-3-phenyl-2-propenyloxycarbonyl]cyclopentanecarboxylic acid

(+)-(1R,2S)-4-methylene-2-[(2E)-3-phenyl-2-propenyloxycarbonyl]cyclopentanecarboxylic acid

Refernces

• 1、 Furuta, Kyoji,Ikeda, Nobuo,Yamamoto, Hisashi. "DIANION OF 1,2-BIS(4',4'-DIMETHYL-2'-OXAZOLIN-2'-YL)ETHANE VERSATILE SYNTHETIC REAGENT FOR ANNULATION". . p. 675 - 678. Retrieved 2007/10/02.