6-Nitroveratraldehyde

Base Information

• Chemical Name: 6-Nitroveratraldehyde
• CAS No.: 20357-25-9
• Molecular Formula: C9H9NO5
• Molecular Weight: 211.174
• Hs Code.: 29130000
• European Community (EC) Number: 243-762-1
• NSC Number: 65590
• UNII: 3V2SVJ99E2
• DSSTox Substance ID: DTXSID30174268
• Nikkaji Number: J261.068J
• Wikidata: Q27187519
• ChEMBL ID: CHEMBL1332518
• Mol file: 20357-25-9.mol

Synonyms:4,5-dimethoxy-2-nitrobenzaldehyde

Chemical Property of 6-Nitroveratraldehyde

Chemical Property:

• Appearance/Colour: yellow fluffy powder
• Vapor Pressure: 2.59E-06mmHg at 25°C
• Melting Point: 133.2-134.5 °C
• Refractive Index: 1.571
• Boiling Point: 390.8 °C at 760 mmHg
• Flash Point: 194.3 °C
• PSA: 81.35000
• Density: 1.312 g/cm³
• LogP: 1.94770
• Storage Temp.: 2-8°C
• Sensitive.: Air & Light Sensitive
• Solubility.: DMSO: 22 mg/mL
• Water Solubility.: Insoluble in water. Soluble to 25 mM in ethanol with gentle warming and to 100 mM in DMSO.
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 211.04807239
• Heavy Atom Count: 15
• Complexity: 239

Purity/Quality:

99% ^*data from raw suppliers

DMNB ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Aromatics (Nitrogen)
• Canonical SMILES: COC1=C(C=C(C(=C1)C=O)[N+](=O)[O-])OC
• Uses: 6-Nitroveratraldehyde has been used in the preparation of no-carrier-added 6-18F-fluoro-L-dopa, fundamental tracer for cerebral positron emission tomography studies of dopaminergic system in humans and o-nitroaryl-bis(5-methylfur-2-yl)methanes, versatile synthons for the synthesis of nitrogen-containing heterocycles. DMNB is also an enzyme involved in the non-homologous end-joining (NHEJ) pathway of double-stranded DNA break (DSB) repair. It is also used for synthesizing analogs of alpha-asarone.

Technology Process of 6-Nitroveratraldehyde

There total 28 articles about 6-Nitroveratraldehyde 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: 96.0%

6-nitroveratryl alcohol (1016-58-6) → 6-nitroveratraldehyde (20357-25-9)

Guidance literature:

With macroporous polystyrene-supported IBX amide; In acetonitrile; at 20 ℃; for 4h;

DOI:10.1016/j.tetlet.2007.03.089

Reference yield:

N-(4,5-dimethoxy-2-nitrobenzyloxy)-1,1,1-trifluoromethanesulfonamide → 6-nitroveratraldehyde (20357-25-9)

Guidance literature:

In aq. phosphate buffer; [D₃]acetonitrile; pH=7; Photolysis; Sealed tube;

DOI:10.1016/j.jphotochem.2019.112033

Reference yield:

N-(4,5-dimethoxy-2-nitrobenzyloxy)methanesulfonamide → 6-nitroveratraldehyde (20357-25-9)

Guidance literature:

In aq. phosphate buffer; [D₃]acetonitrile; pH=7; Photolysis; Sealed tube;

DOI:10.1016/j.jphotochem.2019.112033

upstream raw materials:

6-nitrovanillin

4-allyl-1,2-dimethoxy-5-nitrobenzene

3,4-dimethoxy-benzaldehyde

6-nitroveratryl alcohol

Downstream raw materials:

4-(4.5-Dimethoxy-2-nitro-benzyliden)-3-methyl-1-phenyl-2-pyrazolin-5-on

4-(4,5-dimethoxy-2-nitrophenyl)-2,6-dimethyl-3,5-dicarbethoxy-1,4-dihydropyridine

4-(4,5-dimethoxy-2-nitro-benzylidene)-2-phenyl-4H-oxazol-5-one

4-((Z)-4,5-dimethoxy-2-nitro-benzylidene)-2-phenyl-4H-oxazol-5-one

Refernces

• 1、 Chen, Zhijun,Sun, Wen,Butt, Hans-Jürgen,Wu, Si. "Upconverting-nanoparticle-assisted photochemistry induced by low-intensity near-infrared light: How low can we go?". . p. 9165 - 9170. Retrieved 2015.
• 2、 Iioka, Ryoya,Yorozu, Kohei,Sakai, Yoko,Kawai, Rika,Hatae, Noriyuki,Takashima, Katsuki,Tanabe, Genzoh,Wasada, Hiroaki,Yoshimatsu, Mitsuhiro. "Synthesis of Azepino[1,2-a]indole-10-amines via [6+1] Annulation of Ynenitriles with Reformatsky Reagent". . p. 1553 - 1558. Retrieved 2021/02/26.
• 3、 Altevogt, Luca,Baro, Angelika,Bilitewski, Ursula,Freund, Marcel,Laschat, Sabine,Lin, Yulin,Rudolf, Richard,Seubert, Philipp. "Buchwald-Hartwig versus Microwave-Assisted Amination of Chloroquinolines: En Route to the Pyoverdin Chromophore". supporting information. p. 1177 - 1181. Retrieved 2020/07/20.