Malonaldehyde

Base Information

• Chemical Name: Malonaldehyde
• CAS No.: 542-78-9
• Molecular Formula: C3H4 O2
• Molecular Weight: 72.0636
• Hs Code.: 2912190090
• ICSC Number: 1632
• UNII: 4Y8F71G49Q
• DSSTox Substance ID: DTXSID90202556
• Nikkaji Number: J1.601B
• Wikipedia: Malondialdehyde
• Wikidata: Q418661
• NCI Thesaurus Code: C94711
• RXCUI: 1657018
• Metabolomics Workbench ID: 38821
• ChEMBL ID: CHEMBL446036
• Mol file: 542-78-9.mol

Synonyms:Malonaldehyde;Malondialdehyde;Malondialdehyde, Sodium;Malonylaldehyde;Malonyldialdehyde;Propanedial;Sodium Malondialdehyde

Chemical Property of Malonaldehyde

Chemical Property:

• Vapor Pressure: 26mmHg at 25°C
• Melting Point: 72-74°
• Refractive Index: 1.366
• Boiling Point: 108.3°Cat760mmHg
• PKA: 5(at 25℃)
• Flash Point: 28.9°C
• PSA: 34.14000
• Density: 0.991g/cm³
• LogP: -0.22570
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 72.021129366
• Heavy Atom Count: 5
• Complexity: 34.2

Purity/Quality:

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

MALONALDEHYDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Aldehydes
• Canonical SMILES: C(C=O)C=O
• Inhalation Risk: A harmful concentration of airborne particles can be reached quickly.
• Uses: Propanedial, exists in horseradish hairy root taht has shown strong antioxidant capacity under arsenic stress which indicates possible use of Armoracia rusticana plants for phytoremediation.

Technology Process of Malonaldehyde

There total 44 articles about Malonaldehyde 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: 99.0%

1,3-bis(trimethylsiloxy)propane (17887-80-8) → Malondialdehyde (542-78-9)

Guidance literature:

With chromium(VI) oxide; HZSM-5 zeolite; for 0.025h; microwave irradiation;

DOI:10.1080/10426500490463853

Reference yield: 41.0%

PGH2 methyl ester (63942-75-6) → Malondialdehyde (542-78-9) + (5Z,8E,10E,12S)-12-hydroxy-5,8,10-heptadecatrienoic acid methyl ester (79171-56-5)

Guidance literature:

With tris(triphenylphosphine)ruthenium(II) chloride; In dichloromethane; at 19 ℃; for 4h;

DOI:10.1021/jo00283a023

Reference yield: 39.0%

(1R*,4R*,5S*)-5-phenyl-2,3-dioxabicyclo<2.2.1>heptane (113331-81-0,113331-84-3,114738-36-2) → styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + Malondialdehyde (542-78-9) + (3RS,4SR)-3-hydroxy-4-phenyl-1-cyclopentanone (113331-87-6) + (3SR,4SR)-4,5-epoxy-3-phenyl-1-pentanal (113331-88-7,120708-35-2,120708-36-3) + (1R*,3R*,4S*)-4-phenylcyclopentane-1,3-diol (113331-85-4,114817-51-5,114817-54-8,114817-56-0,120708-38-5) + (2ξ,4RS,6SR)-6-phenyltetrahydropyran-2,4-diol (113331-86-5,113428-36-7,113428-37-8,113428-41-4,119238-85-6)

Guidance literature:

With iron(II) sulfate; In water; acetonitrile; at 0 ℃; for 0.5h; Product distribution; Mechanism;

DOI:10.1039/c39870000722

upstream raw materials:

malondialdehyde bis(diethyl acetal)

3-dimethylaminoacrolein

cyclopropanol

1,3-epiperoxycyclopentane

Downstream raw materials:

β-aminoacrolein

3-aminoacrylaldehyde

malonaldehyde bis-(2,4-dinitro-phenylhydrazone)

NH-pyrazole

Refernces

• 1、 Chowdhury, Pramit K.,Haider, Mintu,Choudhury, Prabir K.,Kraus, George A.,Desai, Meera J.,Armstrong, Daniel W.,Casey, Thomas A.,Rasmussen, Mark A.,Petrich, Jacob W.. "Generation of Fluorescent Adducts of Malondialdehyde and Amino Acids: Toward an Understanding of Lipofuscin". . p. 21 - 25. Retrieved 2004.
• 2、 Scherz. "On the formation of malondialydehyde during irradiation of glycerin". . p. 420 - 421. Retrieved 1968.
• 3、 Pleskushkina,Nikolaevskii,Filippenko. "Antiradical and antioxidant activity of phenylhydrazones of aromatic aldehydes". . p. 792 - 795. Retrieved 2001.
• 4、 Bond, A. M.,Deprez, P. P.,Jones, R. D.,Wallace, G. G.,Briggs, M. H.. "Polarographic Method for the Determination of Propanedial (Malonaldehyde)". . p. 2211 - 2213. Retrieved 1980.
• 5、 Scherz,Stehlik. "". . p. 1143. Retrieved 1968.
• 6、 Shao, Xusheng,Hua,Xiaoyong,Xinglei,Zewen,Zhong,Qian, Xuhong. "Divalent and oxabridged neonicotinoids constructed by dialdehydes and nitromethylene analogues of imidacloprid: Design, synthesis, crystal structure, and insecticidal activities". . p. 2696 - 2702. Retrieved 2010.
• 7、 Crawford et al.. "". . p. 182,183. Retrieved 1966.
• 8、 Seto, Hiroshi,Seto, Takako,Nagakura, Koichi,Koike, Hiroshi. "Reaction of Malonaldehyde with Adenosine. Formation of a Novel Adduct Containing a Dioxazatricycloundecene Residue in the Base-pairing Region". . p. 435 - 438. Retrieved 1993.
• 9、 Kadoya, Akinori,Miyake, Hiromi,Ohyashiki, Takao. "Contribution of lipid dynamics on the inhibition of bovine brain synaptosomal Na+-K+-ATPase activity induced by 4-hydroxy-2-nonenal". . p. 787 - 793. Retrieved 2003.
• 10、 -. "Preparation method of 3-thiophenecarboxaldehyde". Page/Page column 6-8. . Retrieved 2018/06/15.