4-Methoxycinnamaldehyde

Base Information

• Chemical Name: 4-Methoxycinnamaldehyde
• CAS No.: 24680-50-0
• Deprecated CAS: 1619932-83-0
• Molecular Formula: C₁₀H₁₀O₂
• Molecular Weight: 162.188
• Hs Code.: 29124990
• European Community (EC) Number: 217-807-0,679-263-4
• NSC Number: 134287,26454
• UNII: 54098389BL
• DSSTox Substance ID: DTXSID1044308
• Nikkaji Number: J185.780K,J199.786F
• Wikipedia: 4-Methoxycinnamaldehyde
• Wikidata: Q15410215
• Metabolomics Workbench ID: 45650
• ChEMBL ID: CHEMBL452173
• Mol file: 24680-50-0.mol

Synonyms:4-methoxy-cinnamaldehyde;4-methoxycinnamaldehyde

Chemical Property of 4-Methoxycinnamaldehyde

Chemical Property:

• Melting Point: 55-60 °C(lit.)
• Refractive Index: 1.6000 (estimate)
• Boiling Point: 145 °C7 mm Hg(lit.)
• Flash Point: 146.5°C
• PSA: 26.30000
• Density: 1.068g/cm³
• LogP: 1.90730
• Storage Temp.: 2-8°C
• Sensitive.: Air Sensitive
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: Insoluble in water.
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 162.068079557
• Heavy Atom Count: 12
• Complexity: 155

Purity/Quality:

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

trans-p-Methoxycinnamaldehyde ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)C=CC=O
• Isomeric SMILES: COC1=CC=C(C=C1)/C=C/C=O
• Uses: trans-p-Methoxycinnamaldehyde is used in the food industry as a flavor and fragrance agent. It also acts as a nematicidal agent in certain organisms. trans-4-Methoxycinnamaldehyde is used as an intermediate in chemical research.

Technology Process of 4-Methoxycinnamaldehyde

There total 135 articles about 4-Methoxycinnamaldehyde 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: 93.0%

Estragole (140-67-0) → 4-methoxy-trans-cinnamaldehyde (24680-50-0,71277-11-7,1963-36-6)

Guidance literature:

With water; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium dichloride; In 1,2-dichloro-ethane; at 50 ℃; for 2h; stereoselective reaction;

DOI:10.1021/ol1030316

Reference yield: 91.0%

(E)-p-methoxy-cinnamyl alcohol (53484-50-7) → 4-methoxy-trans-cinnamaldehyde (24680-50-0,71277-11-7,1963-36-6)

Guidance literature:

With manganese(IV) oxide; In dichloromethane; at 20 ℃; for 4h; Inert atmosphere;

DOI:10.1021/acs.orglett.0c00901

Reference yield: 86.0%

3-(4-methoxyphenyl)propional (20401-88-1) → 4-methoxy-trans-cinnamaldehyde (24680-50-0,71277-11-7,1963-36-6)

Guidance literature:

With manganese(IV) oxide; benzyl-methyl-amine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; at 20 ℃; for 6h;

DOI:10.1002/adsc.201300919

upstream raw materials:

(E)-p-methoxy-cinnamyl alcohol

3-isobutoxy-1-(4-methoxy-phenyl)-propenone

4-methoxy-benzaldehyde

acetaldehyde

Downstream raw materials:

4-(4-methoxy-trans-cinnamylidene)-5-methyl-2-phenyl-2,4-dihydro-pyrazol-3-one

e-N,N-dimethyl-3-(p-methoxyphenyl)-2-propylideniminium perchlorate

(3E,7E)-6-hydroxy-8-(4-methoxyphenyl)-3-methyl-1,3,7-octatriene

(2E,4E)-5-(4-methoxyphenyl)penta-2,4-dienal

Refernces

• 1、 Zhao, Jiangui,Zheng, Xueli,Tao, Shaokun,Zhu, Yuxin,Yi, Jiwei,Tang, Songbai,Li, Ruixiang,Chen, Hua,Fu, Haiyan,Yuan, Maolin. "Selective Rhodium-Catalyzed Hydroformylation of Terminal Arylalkynes and Conjugated Enynes to (Poly)enals Enabled by a π-Acceptor Biphosphoramidite Ligand". supporting information. p. 6067 - 6072. Retrieved 2021/08/16.
• 2、 Zhu, Quan,Luo, Yunsong,Guo, Yongyan,Zhang, Yushun,Tao, Yunhai. "Saegusa Oxidation of Enol Ethers at Extremely Low Pd-Catalyst Loadings under Ligand-free and Aqueous Conditions: Insight into the Pd(II)/Cu(II)-Catalyst System". . p. 5463 - 5476. Retrieved 2021/05/05.