3-Pentenoic acid

Base Information

• Chemical Name: 3-Pentenoic acid
• CAS No.: 1617-32-9
• Molecular Formula: C5H8 O2
• Molecular Weight: 100.117
• European Community (EC) Number: 216-573-7,628-465-0
• DSSTox Substance ID: DTXSID20902436
• Nikkaji Number: J97.999F,J98.000E
• Wikidata: Q27117626
• Metabolomics Workbench ID: 441
• Mol file: 1617-32-9.mol

Synonyms:3-PENTENOIC ACID;trans-3-Pentenoic Acid;1617-32-9;(E)-pent-3-enoic acid;5204-64-8;(E)-3-pentenoic acid;beta-penteic acid;beta-pentenoic acid;3-PENTENOICACID;trans-pent-3-enoic acid;3-Pentenoic acid, (3E)-;(E)-Pent-3-en-1-oic acid;pent-3-enoic acid;3-Pentenoic acid, (E)-;C5:1n-2;EINECS 216-573-7;(3E)-pent-3-enoic acid;CH3CH=CHCH2COOH;Pent-3-ensaeure;1-propenylacetate;E-3-Pentensaeure;pent-3t-enoic acid;beta.gamma-Pentensaeure;trans-Pent-3-ensaeure;NoName_1679;C5:1, n-2 trans;beta-Aethyliden-propionsaeure;SCHEMBL34656;(E)-CH3CH=CHCH2COOH;beta-Butylen-alpha-carbonsaeure;trans-beta,gamma-penteneoic acid;CHEBI:38368;CHEBI:38370;DTXSID20902436;UIUWNILCHFBLEQ-NSCUHMNNSA-N;LMFA01030006;MFCD00063291;AKOS000183095;C5:1, n-2;HY-W088501;CS-0129103;P1072;EN300-186781;J-009854;Q27117626;3-Pentenoic acid, is mainly present in the trans-form (>=90% GC), >=95.0% (sum of isomers, GC)

Chemical Property of 3-Pentenoic acid

Chemical Property:

• Vapor Pressure: 0.219mmHg at 25°C
• Melting Point: 1.5°C
• Refractive Index: n20/D 1.435
• Boiling Point: 192°C at 760 mmHg
• PKA: 4.51(at 25℃)
• Flash Point: 89.5°C
• PSA: 37.30000
• Density: 1.008g/cm³
• LogP: 1.03720
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• XLogP3: 0.8
• 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

(E)-Pent-3-enoicAcid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=CCC(=O)O
• Isomeric SMILES: C/C=C/CC(=O)O
• Uses: (E)-Pent-3-enoic Acid is a useful reagent as both a hydride and alkyl source in catalytic regioselective reductive olefin hydroalkylation.

Technology Process of 3-Pentenoic acid

There total 36 articles about 3-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: 99.5%

3-Pentenenitrile (16529-66-1) → (E)-3-pentenoic acid (1617-32-9)

Guidance literature:

With potassium phosphate buffer; at 30 ℃; for 12h; Rhodococcus sp. AJ₂₇₀ cells;

DOI:10.1039/a607977f

Reference yield: 92.0%

methyl (E)-pent-3-enoate (818-58-6) → (E)-3-pentenoic acid (1617-32-9)

Guidance literature:

With sodium hydroxide; In methanol; at 20 ℃; for 1.33333h;

DOI:10.1021/acs.orglett.0c02714

Reference yield: 90.0%

(E)-4-iodobut-3-en-1-oic acid (190203-25-9) + zinc methyl bromide (18815-74-2) → (E)-3-pentenoic acid (1617-32-9)

Guidance literature:

With dichloro bis(acetonitrile) palladium(II); In N,N-dimethyl-formamide; at 50 ℃; for 12h;

DOI:10.1016/S0040-4020(03)00616-1

upstream raw materials:

1,3-butadiene-1-carboxylic acid

malonic acid

propionaldehyde

trans-but-2-enyl chloride

Downstream raw materials:

5-methyl-5H-furan-2-one

dihydro-4-acetoxy-5-methyl-2(3H)-furanone

cis-dihydro-4-acetoxy-5-methyl-2(3H)-furanone

2-methyl-1,1-diphenylpropene

Refernces

• 1、 Galatsis, Paul,Manwell, Jeffrey J.,Millan, Scott D.. "Stereochemical consequences in the deprotonation of enoates". . p. 5261 - 5264. Retrieved 1996.
• 2、 Beckwith, Athelstan L. J.,Bowry, Vincent W.. "Kinetics and Regioselectivity of Ring Opening of Substituted Cyclopropylmethyl Radicals". . p. 2681 - 2688. Retrieved 1989.
• 3、 Hoshino, Yoshihiko,Iwabuchi, Yoshiharu,Kuriyama, Yuse,Sasano, Yusuke,Uesugi, Shun-ichiro,Yamaichi, Aoto. "Highly Regioselective 5-endo-tet Cyclization of 3,4-Epoxy Amines into 3-Hydroxypyrrolidines Catalyzed by La(OTf)3". supporting information. p. 1961 - 1965. Retrieved 2021/01/04.
• 4、 -. "Method for synthesizing (9Z, 12E)-9,12-tetradecadien-1-ol acetate". Paragraph 0011; 0026-0028. . Retrieved 2020/06/16.