2-Propan-2-ylbut-2-enedioic acid

Base Information

• Chemical Name: 2-Propan-2-ylbut-2-enedioic acid
• CAS No.: 44976-69-4
• Molecular Formula: C7H10O4
• Molecular Weight: 158.15200
• DSSTox Substance ID: DTXSID50282273
• Mol file: 44976-69-4.mol

Synonyms:2-propan-2-ylbut-2-enedioic acid;44976-69-4;DTXSID50282273

Chemical Property of 2-Propan-2-ylbut-2-enedioic acid

Chemical Property:

• Melting Point: 54 °C
• Boiling Point: 331.5±25.0 °C(Predicted)
• PSA: 74.60000
• Density: 1.1312 g/cm3
• LogP: 0.73800
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 158.05790880
• Heavy Atom Count: 11
• Complexity: 203

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(=CC(=O)O)C(=O)O

Technology Process of 2-Propan-2-ylbut-2-enedioic acid

There total 1 articles about 2-Propan-2-ylbut-2-enedioic 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:

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + ethyl 3-methyl-2-oxobutanoate (20201-24-5) → (Z)-2-isopropyl-but-2-enedioic acid (44976-69-4) + 2-isopropylfumaric acid (7596-39-6) + 2-isopropylidenesuccinic acid (584-27-0)

Guidance literature:

With potassium hydroxide; sodium hydride; Yield given. Multistep reaction. Yields of byproduct given; 1.) diethyl ether, -78 deg C, 3 h then room temperature, 2.) ethanol-water 1 : 1, reflux;

DOI:10.1016/S0040-4020(01)85677-5

Reference yield: 10.0%

(Z)-2-isopropyl-but-2-enedioic acid (44976-69-4) → 2-isopropylfumaric acid (7596-39-6)

Guidance literature:

Irradiation;

DOI:10.1016/S0040-4020(01)85677-5

Reference yield:

(Z)-2-isopropyl-but-2-enedioic acid (44976-69-4) → farinomalein A (1175521-35-3)

Guidance literature:

Multi-step reaction with 2 steps

1: trifluoroacetic anhydride / 20 °C / Inert atmosphere

2: acetic acid / Inert atmosphere; Reflux

With acetic acid; trifluoroacetic anhydride;

DOI:10.1080/00397911.2011.640969

upstream raw materials:

diethoxyphosphoryl-acetic acid ethyl ester

ethyl 3-methyl-2-oxobutanoate

Downstream raw materials:

2-isopropylfumaric acid

(2S*,3R*)-2,3-epoxy-2-isopropylbutane-1,4-dioic acid

farinomalein A

Refernces