4-Oxopentanal

Base Information

• Chemical Name: 4-Oxopentanal
• CAS No.: 626-96-0
• Molecular Formula: C5H8O2
• Molecular Weight: 100.117
• UNII: BL58BK264G
• DSSTox Substance ID: DTXSID60211655
• Nikkaji Number: J6.865I
• Wikidata: Q26841304
• Mol file: 626-96-0.mol

Synonyms:4-oxopentanal

Chemical Property of 4-Oxopentanal

Chemical Property:

• Vapor Pressure: 1.48mmHg at 25°C
• Refractive Index: 1.4257
• Boiling Point: 170.3°Cat760mmHg
• Flash Point: 57.7°C
• PSA: 34.14000
• Density: 0.948g/cm³
• LogP: 0.55450
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 100.052429494
• Heavy Atom Count: 7
• Complexity: 76.1

Purity/Quality:

99%, ^*data from raw suppliers

4-Oxopentanal ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)CCC=O
• Uses: 4-Oxopentanal is an intermediate used to prepare enantiopure sulfinimines. It is also used in the synthesis of 2-pyridinone derivatives as HIV-1-specific reverse transcriptase inhibitors.

Technology Process of 4-Oxopentanal

There total 98 articles about 4-Oxopentanal 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: 91.0%

1,4-Pentanediol (626-95-9) → 4-oxopentanal (626-96-0) + 5-methyl-dihydro-furan-2-one (108-29-2)

Guidance literature:

With 1-methyl-1H-imidazole; [2,2]bipyridinyl; tetrakis(acetonitrile)copper(I) trifluoromethanesulfonate; 9-azabicyclo<3.3.1>nonane-N-oxyl; In acetonitrile; at 22 ℃; for 2h;

DOI:10.1021/jacs.5b01036

Reference yield: 82.0%

1,3-epiperoxycyclopentane (279-35-6) → cyclopent-2-enone (930-30-3) + 4-oxopentanal (626-96-0) + rac-3-hydroxycyclopentanone (26831-63-0)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; Rate constant; Product distribution; Et₃N, Dabco, Dabco+AcOH in C₆D₆; Me₄NOAc in CD₃Cl;

DOI:10.1021/ja00376a042

Reference yield: 76.0%

2,5-dihydro-4-(1-methylethyl)-5-oxo-2-(3-oxobutyl)-oxazol-5-one (152343-03-8) → 4-oxopentanal (626-96-0) + 3-methyl-2-ketobutanoic acid (759-05-7)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; Ambient temperature;

DOI:10.1016/S0040-4039(00)79260-4

upstream raw materials:

2-methylfuran

5-Hexen-2-one

5,5-diethoxylpentan-2-one

2,6-dimethyl-hepta-1,5-diene

Downstream raw materials:

2-methyl-1H-pyrrole

levulinic acid

curcumin

(Z)-undec-5-en-2-one

Refernces

• 1、 Averina,Budynina,Ivanova,Grishin, Yu. K.,Gerdov,Kuznetsova,Zefirov. "Three-component reactions of tetranitromethane with olefins". . p. 162 - 173. Retrieved 2004.
• 2、 Miyakoshi, Tetsuo. "A Convenient Synthesis of 4-Oxoalkanals". . p. 766 - 768. Retrieved 1986.
• 3、 Ledneczki, István,Tapolcsányi, Pál,Gábor, Eszter,Visegrády, András,Vass, Márton,éles, János,Holm, Patrik,Horváth, Anita,Pocsai, Anikó,Mahó, Sándor,Greiner, István,Krámos, Balázs,Béni, Zoltán,Kóti, János,Káncz, Anna E.,Thán, Márta,Kolok, Sándor,Laszy, Judit,Balázs, Ottilia,Bugovits, Gyula,Nagy, József,Vastag, Mónika,Szájli, ágota,Bozó, éva,Lévay, Gy?rgy,Lendvai, Balázs,Némethy, Zsolt. "Discovery of novel positive allosteric modulators of the α7 nicotinic acetylcholine receptor: Scaffold hopping approach". . . Retrieved 2021/02/06.
• 4、 Schnell, Simon D.,Linden, Anthony,Gademann, Karl. "Synthesis of Two Key Fragments of the Complex Polyhalogenated Marine Meroterpenoid Azamerone". supporting information. p. 1144 - 1147. Retrieved 2019/05/16.