Piperonal

Base Information

• Chemical Name: Piperonal
• CAS No.: 120-57-0
• Deprecated CAS: 30024-74-9,659726-32-6,1989611-55-3,659726-32-6
• Molecular Formula: C8H6O3
• Molecular Weight: 150.134
• Hs Code.: 29329300
• European Community (EC) Number: 204-409-7
• NSC Number: 26826
• UNII: KE109YAK00
• DSSTox Substance ID: DTXSID7025924
• Nikkaji Number: J2.919J
• Wikipedia: Piperonal
• Wikidata: Q418985
• RXCUI: 33753
• Metabolomics Workbench ID: 45651
• ChEMBL ID: CHEMBL271663
• Mol file: 120-57-0.mol

Synonyms:3,4-methylenedioxybenzaldehyde;heliotrin;heliotropin;piperonal

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Chemical Property of Piperonal

Chemical Property:

• Appearance/Colour: white crystalline solid
• Vapor Pressure: 1 mm Hg ( 87 °C)
• Melting Point: 35-39 °C(lit
• Refractive Index: 1.614
• Boiling Point: 263.3 °C at 760 mmHg
• Flash Point: 103.6 °C
• PSA: 35.53000
• Density: 1.337 g/cm³
• LogP: 1.22780
• Storage Temp.: Dark Room
• Sensitive.: Air & Light Sensitive
• Solubility.: methanol: 0.1 g/mL, clear
• Water Solubility.: Slightly soluble
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 150.031694049
• Heavy Atom Count: 11
• Complexity: 157

Purity/Quality:

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 38-52/53
• Safety Statements: 61-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Plant Oils and Extracts
• Canonical SMILES: C1OC2=C(O1)C=C(C=C2)C=O
• Uses: Piperonal is an impurity of Tadalafil (T004500). Tadalafil impurity A. In perfumery, in cherry and vanilla flavors, in organic syntheses. Piperonal is used as fragrance and flavoring agent.

Technology Process of Piperonal

There total 203 articles about Piperonal 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: 95.0%

1,3-benzodioxol-5-ylmethyl amine (2620-50-0) → piperonal (120-57-0,30024-74-9) + 1-(benzo[d][1,3]dioxol-5-yl)-N-(benzo[d][1,3]dioxol-5-ylmethyl)methanimine (83471-17-4) + piperonylonitrile (4421-09-4)

Guidance literature:

With sodium hypochlorite; In ethanol; for 0.25h; Ambient temperature;

DOI:10.1080/00397919708007077

Reference yield: 91.0%

isosafrole (120-58-1) → piperonal (120-57-0,30024-74-9) + 3,4-methylenedioxypropiophenone (28281-49-4)

Guidance literature:

With NaY-supported PhI(OAc)2; at 130 ℃; for 0.0833333h; Solvent; Concentration; Temperature; Time; Microwave irradiation;

DOI:10.1021/op060117t

Reference yield: 86.0%

→ piperonal (120-57-0,30024-74-9) + piperonol (495-76-1)

Guidance literature:

upstream raw materials:

Methylenedioxybenzene

5-(chloromethyl)-1,3-benzodioxole

1-allyl-3,4-methylenedioxybenzene

3,4-(methylenedioxy)benzoyl chloride

Downstream raw materials:

1-(benzo[d][1,3]dioxol-6-yl)ethanone

safrole 2',3'-oxide

trans-1-(3,4-methylenedioxyphenyl)-2-phenylethylene

(Z)-3-(3,4-methylenedioxyphenyl)-2-phenylprop-2-enoic acid

Refernces

Preparation of Some Simple Structural Analogs of Khellin

10.1021/jo01091a006

The research encompasses two distinct studies. The first study aims to synthesize simple structural analogs of khellin, a compound with known physiological activity, to further explore its chemistry and potential applications. Key chemicals used in this study include 2,3,4,6-tetramethoxy-3-ethylacetophenone (VI), 2-hydroxy-3,4,6-trimethoxy-5-ethylacetophenone (V), and various reagents such as copper-chromium oxide catalyst, dimethyl sulfate, acetyl chloride, aluminum chloride, and piperonal. The second study investigates the reaction of o-alkenylphenols with peracetic acid to understand the products and mechanisms involved. Key chemicals used in this study include o-allylphenol, o-propenylphenol, peracetic acid, acetic anhydride, and sulfuric acid. The study concludes that the product from o-allylphenol is 2-hydroxymethylcoumaran, not the previously reported epoxide, and that the product from o-propenylphenol is 1-(o-hydroxyphenyl)-2-propanone, formed through a different mechanism than previously thought. This research provides a clearer understanding of the reactions involving o-alkenylphenols and peracetic acid, correcting and expanding upon earlier findings.