Pent-2-ene-1,5-dioic acid

Base Information

• Chemical Name: Pent-2-ene-1,5-dioic acid
• CAS No.: 1724-02-3
• Molecular Formula: C5H6O4
• Molecular Weight: 130.1
• Hs Code.: 2917190090
• DSSTox Substance ID: DTXSID40862740
• Wikidata: Q27109839
• Mol file: 1724-02-3.mol

Synonyms:Glutaconicacid (6CI,7CI,8CI);1,3-Propenedicarboxylic acid;1-Propene-1,3-dicarboxylicacid;Pentenedioic acid;

Chemical Property of Pent-2-ene-1,5-dioic acid

Chemical Property:

• Vapor Pressure: 5.23E-08mmHg at 25°C
• Melting Point: 137-139 °C(lit.)
• Refractive Index: 1.516
• Boiling Point: 413.8 °C at 760 mmHg
• PKA: 4.21±0.10(Predicted)
• Flash Point: 218.2 °C
• PSA: 74.60000
• Density: 1.384g/cm³
• LogP: 0.10190
• Storage Temp.: Amber Vial, Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 130.02660867
• Heavy Atom Count: 9
• Complexity: 147

Purity/Quality:

98%,99%, ^*data from raw suppliers

Glutaconic acid ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C=CC(=O)O)C(=O)O
• Uses: Glutaconic acid has been used in the preparation of CoA-substrate glutaconyl-CoA by reacting with acetyl-CoA. It may be used in the preparation of 6-chloro-2(2H)-pyranone by reacting with phosphorus pentachloride (PCl5).

Technology Process of Pent-2-ene-1,5-dioic acid

There total 50 articles about Pent-2-ene-1,5-dioic 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: 92.5%

chloroform (67-66-3,8013-54-5) + malonic acid dimethyl ester (108-59-8) → glutaconic acid (1724-02-3)

Guidance literature:

malonic acid dimethyl ester; With sodium ethanolate; In ethanol; at 70 ℃; for 1h; Large scale;

chloroform; In methanol; for 2h; Reflux; Large scale;

With hydrogenchloride; In water; at 0 - 90 ℃; for 3h; Large scale;

Reference yield:

2-monochlorophenol (95-57-8) → glutaconic acid (1724-02-3) + ortoquinone (583-63-1) + 2-hydroxyterephthalic acid (636-94-2) + oxalic acid (144-62-7,97993-78-7) + benzene-1,2-diol (120-80-9,19481-10-8,37349-32-9) + maleic acid (110-16-7,26099-09-2) + phenol (108-95-2,27073-41-2)

Guidance literature:

With sodium sulfate; at 30 ℃; Reagent/catalyst; Kinetics; Electrolysis;

DOI:10.1016/j.electacta.2017.04.114

Reference yield:

dimethyl 3-hydroxypentanedioate (7250-55-7) → diethyl 3-hydroxypentanedioate (638-18-6) + glutaconic acid (1724-02-3)

Guidance literature:

dimethyl 3-hydroxypentanedioate; With potassium hydroxide; In methanol; at 0 - 20 ℃;

With hydrogenchloride; In water;

DOI:10.1021/ja908191k

upstream raw materials:

2H-pyran-2-one-5-carboxylic acid

diethyl 3-hydroxypentanedioate

diethyl 3-hydroxyglutarate

3-hydroxyglutaronitrile

Downstream raw materials:

(E)-diethyl glutaconate

Glutaconsaeureanhydrid

1,5-pentanedioic acid

diethyl 3-hydroxypentanedioate

Refernces

• 1、 -. "Preparation method of 3-substituted dimethyl glutarate and dimethyl glutaconate". Paragraph 0032-0034. . Retrieved 2018/09/08.
• 2、 Corr, Michael J.,Roydhouse, Mark D.,Gibson, Kirsty F.,Zhou, Sheng-Ze,Kennedy, Alan R.,Murphy, John A.. "Amidine dications as superelectrophiles". supporting information; experimental part. p. 17980 - 17985. Retrieved 2010/04/01.