delta-Valerolactone

Base Information

• Chemical Name: delta-Valerolactone
• CAS No.: 26354-94-9
• Deprecated CAS: 2425576-33-4
• Molecular Formula: C5H8O2
• Molecular Weight: 0
• European Community (EC) Number: 208-807-1
• NSC Number: 65442,6247
• UNII: 14V1X9149L
• DSSTox Substance ID: DTXSID6044438
• Nikkaji Number: J6.398C
• Wikipedia: Delta-Valerolactone
• Wikidata: Q903610
• Metabolomics Workbench ID: 49850
• ChEMBL ID: CHEMBL452383
• Mol file: 26354-94-9.mol

Synonyms:delta-valerolactone;delta-valerothiolactone

Chemical Property of delta-Valerolactone

Chemical Property:

• Boiling Point: 218°Cat760mmHg
• Flash Point: 81°C
• PSA: 26.30000
• Density: 1.065g/cm³
• LogP: 0.71350
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 100.052429494
• Heavy Atom Count: 7
• Complexity: 78.1

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCOC(=O)C1

Technology Process of delta-Valerolactone

There total 224 articles about delta-Valerolactone 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: 50.0%

cyclopentanone (120-92-3) → 3,4,5,6-tetrahydro-2H-pyran-2-one (542-28-9,26354-94-9) + valeric acid (13392-69-3)

Guidance literature:

With 2,3,4,5,6-pentafluoroperoxybenzoic acid; In dichloromethane; 1,2-dichloro-ethane; at 40 ℃; for 6h;

DOI:10.1016/j.mencom.2018.11.027

Reference yield: 30.0%

tetrahydro-2-(benzyloxy)-2H-pyran (1927-62-4) → 3,4,5,6-tetrahydro-2H-pyran-2-one (542-28-9,26354-94-9) + benzyl bromide (100-39-0) + benzaldehyde (100-52-7) + Benzyl 5-bromovalerate (60343-28-4)

Guidance literature:

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In chloroform; Mechanism; Heating; reaction time 15-30 min, other THP ethers;

DOI:10.1080/00397919608003870

Reference yield:

pent-4-enoic acid allyl ester (75265-78-0) → 3,4,5,6-tetrahydro-2H-pyran-2-one (542-28-9,26354-94-9) + 5-methyl-5H-furan-2-one (591-11-7) + 5-methylenedihydrofuran-2-one (10008-73-8) + pent-4-enoic acid (591-80-0)

Guidance literature:

tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N,N,N,N,N-hexamethylphosphoric triamide; benzene-d6; at 140 ℃; for 6h;

upstream raw materials:

glutaric anhydride,

2-(tert-butylperoxy)tetrahydro-2H-pyran

δ-chlorovaleronitrile

5-hydroxypentanal

Downstream raw materials:

3-((Ξ)-benzylidene)-tetrahydro-pyran-2-one

N-β-(3,4-dimethoxyphenyl)ethylvalerolactam

4-(1-pyrrolyl)pentanoic acid

Tetrahydro-2,2-diphenyl-2H-pyran

Refernces

• 1、 Zhulin, V. M.,Khueidzha, I.,Kabotyanskaya, E. B.,Bogdanov, V. S.,Koreshkov, Yu. D.. "EFFECT OF PRESSURE ON THE FREE RADICAL REACTIONS OF 2-ALKOXYTETRAHYDROPYRANS". . p. 638 - 642. Retrieved 1992.
• 2、 Ma, Qingguo,Xing, Wanzhen,Xu, Junhui,Peng, Xinhua. "Baeyer-Villiger oxidation of cyclic ketones with aqueous hydrogen peroxide catalyzed by transition metal oxides". . p. 5 - 8. Retrieved 2014.
• 3、 Yang, Zhiwang,Niu, Lengyuan,Ma, Zhenhong,Ma, Hengchang,Lei, Ziqiang. "Fabrication of highly active Sn/W mixed transition-metal oxides as solid acid catalysts". . p. 269 - 274. Retrieved 2011.
• 4、 Keglevich, András,Szigetvári, áron,Dékány, Miklós,Szántay Jr, Csaba,Keglevich, Péter,Hazai, László. "Synthesis of vinca alkaloid–triphenylphosphine derivatives having potential antitumor effect". . p. 606 - 609. Retrieved 2019.
• 5、 Olszówka, Joanna,Karcz, Robert,Napruszewska, Bogna D.,Duraczyńska, Dorota,Gawe?, Adam,Bahranowski, Krzysztof,Serwicka, Ewa M.. "Baeyer-Villiger oxidation of cyclohexanone with H2O2/acetonitrile over hydrotalcite-like catalysts: Effect of Mg/Al ratio on the ε-caprolactone yield". . p. 196 - 201. Retrieved 2017.
• 6、 Baba,Kameta,Nishiyama,Tsuruya,Masai. "Liquid-phase oxidative lactonization of butane-1,4-diol into γ-butyrolactone with oxygen over palladium supported on K-L zeolite". . p. 255 - 257. Retrieved 1990.
• 7、 Huisgen,Ott. "-". . p. 253,256. Retrieved 1959.
• 8、 Islam, Monirul,Das, Asim K.. "Heteroaromatic N-base ligands in 1,10-phenanthroline- and 2,2′-bipyridyl-assisted chromic acid oxidation of (-)-l-sorbose in aqueous micellar acid media: a kinetic study". . p. 2308 - 2314. Retrieved 2008.
• 9、 Rebek,McCready. "-". . p. 4337. Retrieved 1979.
• 10、 Kondo, Shuji,Ohira, Mari,Kawasoe, Shinya,Kunisada, Hideo,Yuki, Yasuo. "Selective Oxidation of Alcohols and Oxidative Lactonization of Diols with Trichloromelamine". . p. 5003 - 5004. Retrieved 1993.