4-Nitrocinnamaldehyde

Base Information

• Chemical Name: 4-Nitrocinnamaldehyde
• CAS No.: 49678-08-2
• Deprecated CAS: 1619932-86-3
• Molecular Formula: C9H7NO3
• Molecular Weight: 177.159
• Hs Code.: 2913000090
• European Community (EC) Number: 217-076-8,626-477-0
• NSC Number: 1318
• UNII: 48R8LAM7YX
• Nikkaji Number: J48.407E,J533.507H
• Wikidata: Q27259167
• Mol file: 49678-08-2.mol

Synonyms:4-nitrocinnamaldehyde;4-nitrocinnamaldehyde, (E)-isomer;p-nitrocinnamaldehyde

Chemical Property of 4-Nitrocinnamaldehyde

Chemical Property:

• Melting Point: 140-143oC(lit.)
• Boiling Point: 311.6±17.0 °C(Predicted)
• PSA: 62.89000
• Density: 1.269±0.06 g/cm3(Predicted)
• LogP: 2.33010
• Storage Temp.: 0-6°C
• Solubility.: very faint turbidity in hot EtOH
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 177.042593085
• Heavy Atom Count: 13
• Complexity: 211

Purity/Quality:

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

(E)-4-Nitrocinnamaldehyde >98.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=CC=C1C=CC=O)[N+](=O)[O-]
• Isomeric SMILES: C1=CC(=CC=C1/C=C/C=O)[N+](=O)[O-]
• Uses: 4-Nitrocinnamaldehyde has been used in the preparation of 2, 2′-[(E)-3-(4-nitrophenyl) prop-2-ene-1,1-diyl] bis(3-hydroxy-5, 5-dimethylcyclohex-2-en-1-one).

Technology Process of 4-Nitrocinnamaldehyde

There total 44 articles about 4-Nitrocinnamaldehyde 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%

(E)-4-nitrocinnamyl alcohol (35271-56-8) → 3-(4-nitrophenyl)-propenal (49678-08-2)

Guidance literature:

With Iron(III) nitrate nonahydrate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen; sodium chloride; In 1,2-dichloro-ethane; at 20 ℃; for 2h;

DOI:10.1021/ol402434x

Reference yield: 99.0%

p-nitrobenzene iodide (636-98-6) + (E)-3-(tri-n-butylstannyl)-2-propenal (81925-30-6,149538-53-4,219726-39-3) → 3-(4-nitrophenyl)-propenal (49678-08-2)

Guidance literature:

With Pd-NHC star polymer P₃; In d₇-N,N-dimethylformamide; at 20 ℃; for 19h;

DOI:10.1021/acs.orglett.5b02388

Reference yield: 98.0%

(E)-N-methoxy-N-methyl-3-(4-nitrophenyl)acrylamide (253122-46-2) → 3-(4-nitrophenyl)-propenal (49678-08-2)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; at -70 ℃; for 0.333333h;

DOI:10.1080/00397919908085894

upstream raw materials:

4-nitrobenzaldehdye

acetaldehyde

2,4,4,6-tetramethyl-5,6-dihydro-4H-1,3-oxazine

(triphenylphosphoranylidene)acetaldehyde

Downstream raw materials:

4-[2]quinolyl-N-(4-nitro-trans-cinnamyliden)-aniline

(E)-3-(4-nitrophenyl)prop-2-ene-1,1-diyl diacetate

2-(4-nitrophenyl)quinoline

N-((E)-4-nitro-trans-cinnamylidene)-p-phenetidine

Refernces

• 1、 Kaide, Sho,Watanabe, Hiroyuki,Iikuni, Shimpei,Hasegawa, Masato,Itoh, Kyoko,Ono, Masahiro. "Chalcone Analogue as New Candidate for Selective Detection of α-Synuclein Pathology". . p. 16 - 26. Retrieved 2022/01/03.
• 2、 Buijs, Ned,Campagna, Roberto,Emanuelli, Monica,Gao, Yongzhi,Innocenti, Paolo,Jespers, Willem,Martin, Nathaniel I.,Parsons, Richard B.,Sartini, Davide,Van Haren, Matthijs J.,Van Westen, Gerard J. P.,Zhang, Yurui,Gutiérrez-De-Terán, Hugo. "Potent Inhibition of Nicotinamide N-Methyltransferase by Alkene-Linked Bisubstrate Mimics Bearing Electron Deficient Aromatics". . p. 12938 - 12963. Retrieved 2021/09/11.