4-Oxoisocrotonic acid

Base Information

• Chemical Name: 4-Oxoisocrotonic acid
• CAS No.: 4437-06-3
• Molecular Formula: C4H4O3
• Molecular Weight: 100.074
• Hs Code.: 2918300090
• European Community (EC) Number: 216-402-6
• DSSTox Substance ID: DTXSID701023311
• Nikkaji Number: J1.574.956C,J650.552J
• Mol file: 4437-06-3.mol

Synonyms:4-oxo-2-butenoic acid;fumaraldehydic acid;fumaraldehydic acid, (Z)-isomer;malealdehydic acid

Chemical Property of 4-Oxoisocrotonic acid

Chemical Property:

• Boiling Point: 271.2°Cat760mmHg
• Flash Point: 132.1°C
• PSA: 54.37000
• Density: 1.248g/cm³
• LogP: -0.17390
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 100.016043985
• Heavy Atom Count: 7
• Complexity: 104

Purity/Quality:

>95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(=CC(=O)O)C=O
• Isomeric SMILES: C(=C/C(=O)O)\C=O

Technology Process of 4-Oxoisocrotonic acid

There total 11 articles about 4-Oxoisocrotonic 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: 57.0%

furan (110-00-9) → trans-β-formylacrylic acid (4437-06-3)

Guidance literature:

With (tetramethylammonium)4[(iron)4((C₅H₄NCHNC₆H₃SO₃)2)6]; oxygen; methylene blue; acetic acid; In water; at 25 ℃; for 9h; pH=4; Irradiation;

DOI:10.1021/ja412235e

Reference yield:

furan (110-00-9) → 5-hydroxy-2-(5H)-furanone (14032-66-7) + 5-ethoxy-2,5-dihydrofuran-2-one (2833-30-9) + trans-β-formylacrylic acid (4437-06-3) + cis-2,5-diethoxy-2,5-dihydrofuran

Guidance literature:

With oxovanadium(IV) sulfate; ethanol; dihydrogen peroxide; at 20 ℃; for 6h; Further byproducts given;

DOI:10.1007/BF02311323

Reference yield:

5-hydroxy-2-(5H)-furanone (14032-66-7) → trans-β-formylacrylic acid (4437-06-3)

Guidance literature:

With (tetramethylammonium)4[(iron)4((C₅H₄NCHNC₆H₃SO₃)2)6]; acetic acid; In water-d2; at 20 ℃; pH=4; Reagent/catalyst;

DOI:10.1021/ja412235e

upstream raw materials:

(E)-4-Methoxy-4-((Z)-1-methoxy-3-methoxycarbonyl-allyloxy)-but-2-enoic acid methyl ester

furan

5-hydroxy-2-(5H)-furanone

furfural

Downstream raw materials:

1-<<2-(Trimethylsilyl)ethoxy>carbonyl>-4-carboxy-1,3-(Z,E)-butadiene

Mono-2-(trimethylsilyl)ethyl (E,E)-Muconate

methyl (E)-4-oxo-2-butenoate

(2E)-but-2-enedioic acid

Refernces

• 1、 Salles, Airton G.,Zarra, Salvatore,Turner, Richard M.,Nitschke, Jonathan R.. "A self-organizing chemical assembly line". supporting information. p. 19143 - 19146. Retrieved 2014/01/17.
• 2、 Fell, Stephen C. M.,Harbridge, John B.. "2,5-Dimethoxy-2,5-dihydrofuran: A convenient synthon for a novel mono-protected glyoxal; synthesis of 4-hydroxybutenolides". . p. 4227 - 4228. Retrieved 2007/10/02.