2-Pentenoic acid

Base Information

• Chemical Name: 2-Pentenoic acid
• CAS No.: 13991-37-2
• Molecular Formula: C5H8O2
• Molecular Weight: 100.117
• Hs Code.: 29161900
• European Community (EC) Number: 237-791-9,210-975-6
• UNII: 1RG66883CF
• DSSTox Substance ID: DTXSID30893700
• Nikkaji Number: J49.966H,J97.997J
• Wikidata: Q27117596
• Metabolomics Workbench ID: 440
• ChEMBL ID: CHEMBL115668
• Mol file: 13991-37-2.mol

Synonyms:pent-2-enoic acid;pent-2-enoic acid, (E)-isomer

Chemical Property of 2-Pentenoic acid

Chemical Property:

• Appearance/Colour: clear, colorless clear liquid.
• Vapor Pressure: 0.107mmHg at 25°C
• Melting Point: 9-11 °C
• Refractive Index: n20/D 1.452(lit.)
• Boiling Point: 204.7 °C at 760 mmHg
• PKA: pK1:4.70 (25°C)
• Flash Point: 97.7 °C
• PSA: 37.30000
• Density: 1.008 g/cm³
• LogP: 1.03720
• Storage Temp.: Store below +30°C.
• Solubility.: 60g/l
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 100.052429494
• Heavy Atom Count: 7
• Complexity: 84.1

Purity/Quality:

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

trans-2-Pentenoic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 22-34
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCC=CC(=O)O
• Isomeric SMILES: CC/C=C/C(=O)O
• Uses: 2-Pentenoic acid has been used in preparation of new nonsteroidal human androgen receptor (hAR) agonists from an hAR antagonist pharmacophore, 2(1H)-piperidino[3,2-g]quinolinone.

Technology Process of 2-Pentenoic acid

There total 61 articles about 2-Pentenoic 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: 93.0%

malonic acid (141-82-2) + propionaldehyde (123-38-6) → pent-2-enoic acid (626-98-2,13991-37-2,16666-42-5)

Guidance literature:

With pyridine; for 3h; Heating;

Reference yield:

(E/Z)-2-buten-1-ol (6117-91-5,542-72-3) + carbon monoxide (201230-82-2) → Adipic acid (124-04-9) + pent-4-enoic acid (591-80-0) + pent-2-enoic acid (626-98-2,13991-37-2,16666-42-5) + 2-methylglutaric acid (18069-17-5) + monoethylsuccinic acid (636-48-6) + 3-pentenoic acid (5204-64-8)

Guidance literature:

With α,α′-bis(2-pyridyl(tert-butyl)phosphino)-o-xylene; water; toluene-4-sulfonic acid; palladium dichloride; In tetrahydrofuran; at 125 ℃; for 24h; under 30003 Torr; Reagent/catalyst; regioselective reaction; Autoclave; Green chemistry;

DOI:10.1002/anie.202008916

Reference yield:

5-methyl-dihydro-furan-2-one (108-29-2) → 1-butylene (106-98-9,9003-28-5) + (Z)-2-Butene (590-18-1) + trans-2-Butene (624-64-6) + pent-2-enoic acid (626-98-2,13991-37-2,16666-42-5)

Guidance literature:

With silica-alumina; at 280 ℃; under 24002.4 Torr;

upstream raw materials:

quinoline

malonic acid

propionaldehyde

3-hydroxyvaleric acid

Downstream raw materials:

propionic acid

Tiglic acid

butanone

(+/-)-trans-6-ethyl-cyclohex-3-enecarboxylic acid

Refernces

• 1、 Greenwood. "-". . p. 2308. Retrieved 1962.
• 2、 Beller, Matthias,Ge, Yao,Huang, Weiheng,Jackstell, Ralf,Liu, Jiawang,Neumann, Helfried,Yang, Ji. "Direct and Selective Synthesis of Adipic and Other Dicarboxylic Acids by Palladium-Catalyzed Carbonylation of Allylic Alcohols". supporting information. p. 20394 - 20398. Retrieved 2020/09/21.
• 3、 Kaur, Paranjeet,Khatik, Gopal L.. "Lithium perchlorate catalyzed electrophilic activation: A convenient one-pot synthesis of trans-cinnamic acids". . p. 688 - 692. Retrieved 2018/07/13.