Hexa-2,4-dienedial

Base Information

• Chemical Name: Hexa-2,4-dienedial
• CAS No.: 18409-46-6
• Molecular Formula: C6H6 O2
• Molecular Weight: 110.112
• European Community (EC) Number: 221-833-8
• DSSTox Substance ID: DTXSID20878889
• Nikkaji Number: J555.804B,J555.883B,J557.985F,J262.358G
• Wikidata: Q76293944
• Metabolomics Workbench ID: 3410
• Mol file: 18409-46-6.mol

Synonyms:muconaldehyde

Chemical Property of Hexa-2,4-dienedial

Chemical Property:

• Vapor Pressure: 0.0577mmHg at 25°C
• Boiling Point: 232.8°Cat760mmHg
• Flash Point: 84.8°C
• PSA: 34.14000
• Density: 1.006g/cm³
• LogP: 0.49660
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 110.036779430
• Heavy Atom Count: 8
• Complexity: 107

Purity/Quality:

99% ^*data from raw suppliers

(2E,4E)-2,4-Hexadienedial ^*data from reagent suppliers

Safty Information:

• Pictogram(s): A poison.
• Hazard Codes: A poison.

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(=CC=O)C=CC=O
• Isomeric SMILES: C(=C/C=O)\C=C\C=O
• Uses: (2E,4E)-2,4-Hexadienedial is a cytotoxic metabolite of benzene in mouse liver by alcohol dehydrogenase ADH1 and aldehyde reductase AKR1A4;Also, it is an intermediate used in the synthesis of (2E,4E,6Z)-2,4,6-Nonatrienal (N649575), which is a natural aroma compound found in variety of foods such as oats and black tea.

Technology Process of Hexa-2,4-dienedial

There total 22 articles about Hexa-2,4-dienedial 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: 100.0%

hexa-2t,4ξ-dienedial → (E,E)-muconaldehyde (18409-46-6)

Guidance literature:

With iodine; In dichloromethane;

DOI:10.1039/c39930001220

Reference yield: 68.0%

(E)-6-hydroxyhex-2-enal (1403231-79-7) → (E,E)-muconaldehyde (18409-46-6)

Guidance literature:

With (S)-diphenylprolinol; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dimethyl sulfoxide; acetonitrile; at 20 ℃; for 12h; stereoselective reaction;

DOI:10.1039/c5cc10093c

Reference yield: 65.0%

benzoyl chloride (98-88-4) + (E)-3-(tri-n-butylstannyl)-2-propenal (81925-30-6,149538-53-4,219726-39-3) → (E,E)-muconaldehyde (18409-46-6) + (E)-4-oxo-4-phenylbut-2-enal (127921-80-6)

Guidance literature:

tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; at 100 ℃; for 2h;

DOI:10.1021/jo00094a032

upstream raw materials:

1,1,6,6-tetraethoxy-hexa-2,4-diene

cis,cis-2,4-hexadienedial

cis,trans-hexa-2,4-dienedial

benzoyl chloride

Downstream raw materials:

hexanedial

(2E,4E)-2,4-hexadienedioic acid

buta-1,3-diene

acetylene

Refernces

• 1、 Sutaria, Saurin R.,Nantz, Michael H.. "A Convenient Preparation of Muconaldehyde Using a One-Pot Acid-to-Aldehyde Reduction Protocol". . p. 488 - 492. Retrieved 2021.
• 2、 Adger, Brian J.,Barrett, Collette,Brennan, Joseph,McGuigan, Peter,McKervey, M. Anthony,Tarbit, Brian. "Oxidation of Furans with Dimethyldioxirane. Interception of Malealdehyde and Related Aldehydes via Wittig Reactions". . p. 1220 - 1222. Retrieved 1993.
• 3、 Chen, Xiaobei,Zhang, Yinan,Wan, Huixin,Wang, Wei,Zhang, Shilei. "Stereoselective organocatalytic oxidation of alcohols to enals: A homologation method to prepare polyenes". supporting information. p. 3532 - 3535. Retrieved 2016/03/04.
• 4、 Klotz, Bjoern,Volkamer, Rainer,Hurley, Michael D.,Andersen, Mads P. Sulbaek,Nielsen, Ole John,Barnes, Ian,Imamura, Takashi,Wirtz, Klaus,Becker, Karl-Heinz,Platt, Ulrich,Wallington, Timothy J.,Washida, Nobuaki. "OH-initiated oxidation of benzene part II. Influence of elevated NOx concentrations". . p. 4399 - 4411. Retrieved 2007/10/03.