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

(5Z)-5-(1,3-benzodioxol-5-ylmethylene)-2-thioxo-1,3-thiazolidin-4-one

5-(1,3-benzodioxol-5-ylmethylidene)-2-thioxo-1,3-thiazolidin-4-one

Refernces

• 1、 Guram, Anil S.,Bei, Xiaohong,Turner, Howard W.. "Productive utilization of chlorobenzene: Palladium-catalyzed selective oxidation of alcohols". . p. 2485 - 2487. Retrieved 2003.
• 2、 Morey, Jeronimo,Dzielenziak, Adam,Saa, Jose Manuel. "CHEMOSELECTIVE OXIDATION OF BENZYLIC ALCOHOLS BY FREMY'S SALT". . p. 263 - 264. Retrieved 1985.
• 3、 Lei,Denecker,Jegasothy,Sherrington,Slater,Sutherland. "A facile route to a polymer-supported IBX reagent". . p. 1635 - 1637. Retrieved 2003.
• 4、 Luo, Yin,Zhou, Yang,Song, Yanhua,Chen, Guo,Wang, Yu-Xiang,Tian, Ye,Fan, Wei-Wei,Yang, Yu-Shun,Cheng, Tao,Zhu, Hai-Liang. "Optimization of substituted cinnamic acyl sulfonamide derivatives as tubulin polymerization inhibitors with anticancer activity". . p. 3634 - 3638. Retrieved 2018.
• 5、 Yu, Pan,Xia, Chao-Jie,Li, Dong-Dong,Ni, Jun-Jun,Zhao, Lin-Guo,Ding, Gang,Wang, Zhen-Zhong,Xiao, Wei. "Design, synthesis, and anti-inflammatory activity of caffeoyl salicylate analogs as NO production inhibitors". . p. 25 - 33. Retrieved 2018.
• 6、 Wang, Fang,Wang, Xue,Zhang, Min-Xia,Yang, Yong-Hua,Zhu, Hai-Liang. "Synthesis, biological evaluation and molecular modeling of 1H-benzo[d]imidazole derivatives as novel anti-tubulin polymerization agents". . p. 74425 - 74437. Retrieved 2015.
• 7、 Zhang, Bingyu,Lv, Chao,Li, Weibo,Cui, Zhiming,Chen, Dongdong,Cao, Fangjun,Miao, Fang,Zhou, Le. "Ethyl cinnamate derivatives as promising high-efficient acaricides against Psoroptes cuniculi: Synthesis, bioactivity and structure-activity relationship". . p. 255 - 262. Retrieved 2015.
• 8、 Bj?rsvik, Hans-Rene?,Liguori, Lucia,Minisci, Francesco. "High selectivity in the oxidation of mandelic acid derivatives and in 0-methylation of protocatechualdehyde: New processes for synthesis of vanillin, iso-vanillin, and heliotropin". . p. 534 - 543. Retrieved 2000.
• 9、 Kimura, Yoshikazu,Warashina, Takuya. "Convenient preparation of dichloromethyl alkyl ethers". . p. 4598 - 4599. Retrieved 2017.
• 10、 El-Hendawy, A. M.,Al-Kubaisi, A. H.,Shoair, A. F.. "Complexes of some Platinum Group Metals with Hydrazone Ligands and their Catalytic Oxidative Properties". . p. 1291 - 1302. Retrieved 1995.