5-Nitrovanillin

Bezeichnung:5-Nitrovanillin

CAS-Nr6635-20-7

Englisch Name:5-Nitrovanillin

CBNumberCB0281908

SummenformelC8H7NO5

Molgewicht197.14

MOL-Datei6635-20-7.mol

Synonyma

5-Nitrovanillin

5-Nitrovanillin physikalisch-chemischer Eigenschaften

Schmelzpunkt	172-175 °C (lit.)
Siedepunkt	334.23°C (rough estimate)
Dichte	1.5023 (rough estimate)
Dampfdruck	0.001Pa at 25℃
Brechungsindex	1.5700 (estimate)
Flammpunkt	97℃
storage temp.	Inert atmosphere,2-8°C
Löslichkeit	2.1g/L in organic solvents at 20 ℃
Aggregatzustand	powder to crystal
pka	4.97±0.38(Predicted)
Farbe	Yellow to Brown to Dark green
Wasserlöslichkeit	700mg/L at 23℃
Sensitive	Air Sensitive
BRN	1973746
InChI	1S/C8H7NO5/c1-14-7-3-5(4-10)2-6(8(7)11)9(12)13/h2-4,11H,1H3
InChIKey	ZEHYRTJBFMZHCY-UHFFFAOYSA-N
SMILES	[H]C(=O)c1cc(OC)c(O)c(c1)[N+]([O-])=O
LogP	0.301 at 23℃
CAS Datenbank	6635-20-7(CAS DataBase Reference)
EPA chemische Informationen	5-Nitrovanillin (6635-20-7)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38
S-Sätze:	26-36-24/25
WGK Germany	3
HS Code	29130000
Speicherklasse	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2

Gefahreninformationscode (GHS)

5-Nitrovanillin Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S24/25:Berührung mit den Augen und der Haut vermeiden.
Chemische Eigenschaften
yellow-green fine crystalline powder
Verwenden
5-Nitrovanillin is a reagent used in the synthesis of feruloyl and caffeoyl which have antitumor properties.
Definition
ChEBI: A member of the class of benzaldehydes that is vanillin in which the hydrogen ortho- to the hydroxy group is substituted by a nitro group.
Flammability and Explosibility
Non flammable
Synthese

121-33-5

6635-20-7

The general procedure for the synthesis of 5-nitrovanillin from vanillin was as follows: vanillin (94 mg, 1 mmol) was dissolved in 3 mL of glacial acetic acid in a 50 mL test tube. Solid Y(NO3)3-6H2O (383 mg, 1 mmol) was then added and the reaction mixture was shaken continuously for 10 min at room temperature. The reaction process was monitored by thin layer chromatography (TLC) in petroleum ether with 10% ethyl acetate. Upon completion of the reaction, 30 mL of ice-cold water was added to the reaction mixture and allowed to stand for 15 min. The solid product formed was collected by filtration and washed with cold water. The solid product obtained was used directly for analysis without further purification. The experimental methods for synthesizing compounds 2a-2e are detailed in Supporting Information.
läuterung methode
It forms yellow plates from AcOH and needles from EtOH [Slotta & Szyszke Chem Ber 68 184 1935]. With diazomethane, 5-nitro-3,4-dimethoxyacetophenone is formed [Brady & Manjunath J Chem Soc 125 1067 1924]. The methyl ether crystallises from EtOAc or AcOH, m 88o, 90-91o, and the phenylhydrazone has m 108-110o (from aqueous EtOH). [Finger & Schott J Prakt Chem [2] 115 288 1927.] The oxime has m 216o (from EtOH or AcOH), and the oxime acetate has m 147o (from aqueous EtOH) [Vogel Monatsh Chem 20 384 1899, Brady & Dunn J Chem Soc 107 1861 1915]. [Beilstein 8 III 2064.]
Einzelnachweise
[1] Journal of Physical Organic Chemistry, 2000, vol. 13, # 9, p. 511 - 517
[2] Journal of Medicinal Chemistry, 2010, vol. 53, # 8, p. 3396 - 3411
[3] Tetrahedron Letters, 2006, vol. 47, # 15, p. 2507 - 2509
[4] Synthetic Communications, 2008, vol. 38, # 11, p. 1745 - 1752
[5] Tetrahedron, 1992, vol. 48, # 10, p. 1895 - 1910

5-Nitrovanillin Upstream-Materialien And Downstream Produkte

5-Nitrovanillin Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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