4-Nitrobenzaldehyde

Base Information

• Chemical Name: 4-Nitrobenzaldehyde
• CAS No.: 555-16-8
• Molecular Formula: C7H5NO3
• Molecular Weight: 153.137
• Hs Code.: 2913.00
• European Community (EC) Number: 209-084-5
• NSC Number: 6103
• UNII: NX859P8MB0
• DSSTox Substance ID: DTXSID5022061
• Nikkaji Number: J1.618G
• Wikipedia: 4-Nitrobenzaldehyde
• Wikidata: Q2816679
• Metabolomics Workbench ID: 64858
• ChEMBL ID: CHEMBL164236
• Mol file: 555-16-8.mol

Synonyms:4-nitrobenzaldehyde;4-nitrobenzaldehyde, 1-(13)C-labeled;4-nitrobenzaldehyde, aldehyde-(18)O-labeled;4-nitrobenzaldehyde, ion(1-);4-nitrobenzaldehyde, ion(1-), potassium salt;para-nitrobenzaldehyde

Chemical Property of 4-Nitrobenzaldehyde

Chemical Property:

• Appearance/Colour: Yellow to brown crystalline powder
• Vapor Pressure: 0.00118mmHg at 25°C
• Melting Point: 103-106 °C(lit.)
• Refractive Index: 1.617
• Boiling Point: 299.6 °C at 760 mmHg
• Flash Point: 155.2 °C
• PSA: 62.89000
• Density: 1.338 g/cm³
• LogP: 1.93050
• Storage Temp.: Store below +30°C.
• Sensitive.: Air Sensitive
• Solubility.: 2.34g/l
• Water Solubility.: Soluble in water, ethanol, benzene, glacial acetic acid. Slightly soluble in ether.
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 151.026943022
• Heavy Atom Count: 11
• Complexity: 156

Purity/Quality:

99% ^*data from raw suppliers

4-Nitrobenzaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36-43-52/53-36/37/38-68
• Safety Statements: 26-36/37-61-24/25-36/37/39-36

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Aromatics (Nitrogen)
• Canonical SMILES: C1=CC(=CC=C1C=O)[N+](=O)[O-]
• Uses: 4-Nitrobenzaldehyde is a benzaldehyde with a nitro group in the para position. It is used as a reagent in decarboxylative aldol reactions that are catalyzed by lipases and proteases in organic co-solvent mixtures. 4-Nitrobenzaldehyde was used in the preparation of homoallylic alcohols. It was also used to develop and evaluate a series of tripeptide organocatalysts.

Technology Process of 4-Nitrobenzaldehyde

There total 605 articles about 4-Nitrobenzaldehyde 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: 91.0%

4-nitrobenzyl chloride (619-73-8) + diethylazodicarboxylate (1972-28-7,218603-74-8) → diethyl hydrazodicarboxylate (4114-28-7) + 4-nitrobenzaldehdye (555-16-8)

Guidance literature:

With zinc dibromide; In toluene; for 1.5h; Reflux;

DOI:10.1016/j.tetlet.2009.01.080

Reference yield: 51.0%

4-nitrobenzyl chloride (619-73-8) → formaldehyd (50-00-0,30525-89-4,61233-19-0) + 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + 4-nitrobenzaldehdye (555-16-8)

Guidance literature:

With Amberlite IRA-120; urea-hydrogen peroxide; 1-n-butyl-3-methylimidazolim bromide; at 70 ℃; for 0.583333h;

DOI:10.1246/cl.2008.496

Reference yield: 43.0%

4-nitrobenzyl chloride (619-73-8) → 4-nitrobenzaldehdye (555-16-8) + 4-nitrobenzyl chloride (100-14-1)

Guidance literature:

With 2-chloro-1,3-dimethylimidazolinium chloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at 20 ℃;

DOI:10.1021/jo990211q

upstream raw materials:

5-methoxy-2-(4-nitro-phenyl)-[1,3]dioxane

pyridine

N-(4-nitrobenzylidene)-1-phenylmethanamine

4-nitrobenzyl chloride

Downstream raw materials:

(E)-2-methyl-3-(4-nitrophenyl)acrylic acid

α-ethyl-p-nitrocinnamic acid

1,1'-(4-nitro-phenylmethanediyl)-bis-piperidine

acetaldehyde

Refernces

• 1、 Hosahalli,Byadagi,Nandibewoor,Chimatadar. "Kinetics and mechanism of ruthenium(III) catalyzed oxidation of chloromphenicol - An antibiotic drug by diperiodatocuprate(III) in aqueous alkaline medium". . p. 65 - 74. Retrieved 2012.
• 2、 Ding, Peigang,Wang, Jinhui,Cheng, Junye,Zhao, Yufen,Ye, Yong. "Three N-stabilized rhodamine-based fluorescent probes for Al3+ via Al3+-promoted hydrolysis of Schiff bases". . p. 342 - 348. Retrieved 2015.
• 3、 Zhou, Chunmei,Chen, Hong,Yan, Yibo,Jia, Xinli,Liu, Chang-Jun,Yang, Yanhui. "Argon plasma reduced Pt nanocatalysts supported on carbon nanotube for aqueous phase benzyl alcohol oxidation". . p. 104 - 108. Retrieved 2013.
• 4、 Pires, Jose Ricardo,Stachissini, Antonia Sonia,Amaral, Luciano Do. "SECONDARY α-DEUTERIUM ISOTOPE EFFECT ON THE HYDRATION OF THE p-NITROBENZALDEHYDE". . p. 192 - 195. Retrieved 1994.
• 5、 Inui,Murata. "Photochemical generation of acetonitrile oxide via the C-N bond cleavage of 3-methyl-2-(4-nitrophenyl)-2H-azirine". . p. 1036 - 1037. Retrieved 2001.
• 6、 Kornblum,Weaver. "". . p. 1213. Retrieved 1958.
• 7、 Zvezdina,Golyanskaya,Andreeva,Popova,Medyantseva,Dorofeenko. "Reactions of heterocyclic cations with nitrogen-containing nucleophiles. 10. Synthesis of 3,5,7-triaryl-1,2-oxazepinium perchlorates by the reaction of 2,4,6-triarylpyrylium salts with nitrones and substituted hydroxylamines". . p. 340 - 343. Retrieved 1982.
• 8、 Nelson, Peter N.,Robertson, Tahjna I.. "A DFT and experimental study of the spectroscopic and hydrolytic degradation behaviour of some benzylideneanilines". . . Retrieved 2021/10/12.
• 9、 Azeez, Sadaf,Kandasamy, Jeyakumar,Sabiah, Shahulhameed,Sureshbabu, Popuri. "Controlled reduction of activated primary and secondary amides into aldehydes with diisobutylaluminum hydride". supporting information. p. 2048 - 2053. Retrieved 2022/03/31.