2-Nitrobenzaldehyd

Bezeichnung:2-Nitrobenzaldehyd

CAS-Nr552-89-6

Englisch Name:2-Nitrobenzaldehyde

CBNumberCB8414184

SummenformelC7H5NO3

Molgewicht151.12

MOL-Datei552-89-6.mol

Synonyma

2-Nitrobenzaldehyd

2-Nitrobenzaldehyd physikalisch-chemischer Eigenschaften

Schmelzpunkt	42-44 °C(lit.)
Siedepunkt	153 °C23 mm Hg(lit.)
Dichte	1,284 g/cm³
Dampfdichte	5.2 (vs air)
Brechungsindex	1.5800 (estimate)
Flammpunkt	>230 °F
storage temp.	Store below +30°C.
Löslichkeit	Chloroform (Slightly), Ethyl Acetate (Slightly)
Aggregatzustand	Crystalline Powder, Needles and/or Chunks
Farbe	Yellow
Wasserlöslichkeit	Insoluble in water.
Sensitive	Air Sensitive
Merck	14,6586
BRN	742624
LogP	1.74 at 25℃
CAS Datenbank	552-89-6(CAS DataBase Reference)
NIST chemische Informationen	Benzaldehyde, 2-nitro-(552-89-6)
EPA chemische Informationen	Benzaldehyde, 2-nitro- (552-89-6)

Sicherheit

Kennzeichnung gefährlicher	Xn,Xi
R-Sätze:	22-36/37/38-68
S-Sätze:	26-24/25-36/37/39-36
WGK Germany	2
RTECS-Nr.	CU7300000
F	8
Selbstentzündungstemperatur	200 °C (Lit.)
Hazard Note	Irritant
TSCA	Yes
HS Code	29130000

Gefahreninformationscode (GHS)

2-Nitrobenzaldehyde Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R68:Irreversibler Schaden möglich.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S24/25:Berührung mit den Augen und der Haut vermeiden.
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Chemische Eigenschaften
yellow or bright yellow needle-like crystals. It can volatilize with water vapor and has the fragrance of benzaldehyde. Soluble in ethanol, ether, benzene, slightly soluble in water, flash point>110℃, reacts violently with pyrrole.
Verwenden
2-Nitrobenzaldehyde is a benzaldhyde with a nitro group substituted in the ortho position. 2-Nitrobenzaldehyde is used in the preparation of dyes and colorants such as Indigo carmine. 2-Nitrobenzaldehyde gas been shown to be a useful photoremovable protecting group as well as in the preparation of more effective ones such as o-Nitrophenylethylene glycol.
Definition
ChEBI: 2-nitrobenzaldehyde is benzaldehyde substituted at the ortho-position with a nitro group. It is a C-nitro compound and a member of benzaldehydes.
Application
2-Nitrobenzaldehyde can react with chitosan to form 2-nitrobenzyl-chitosan, which is soluble in trifluoroacetic acid and can also be electrospun into nanofiber matrices. On photolysis, the nitrobenzyl group is cleaved to form neat chitosan nanofiber matrices. The same principle has been applied for the preparation of gelatin nanofiber matrices. The condensation of o-NBA with 2-aminobenzothiazole forms o-nitrobenzylidene 2-aminobenzothiazole, a Schiff′s base that can react with metal ions to form complexes.
synthetische
2-Nitrobenzaldehyde is synthesized from 2-Nitrotoluene by nitration and oxidation.
Synthesis of 2-Nitrobenzaldehyde from 2-Nitrotoluene
Synthesis Reference(s)
Synthetic Communications, 19, p. 3385, 1989 DOI: 10.1080/00397918908052745
Allgemeine Beschreibung
The 2-Nitrobenzyl group of 2-nitrobenzaldehyde is photolabile that can be cleaved when exposed to UV-light.
Synthese
50 g (0.24 mol) of 2-nitrophenylpyruvic acid of melting point 115° C are introduced into 500 ml of aqueous sodium carbonate until a clear solution is obtained. After the addition of 350 ml of toluene, the mixture is cooled to 0° C, and 40 g of solid potassium permanganate is then added in portions at 0°- 3° C. After one hour at 0°- 3° C, 95 ml of 50% strength sulphuric acid are added dropwise. The temperature is not allowed to rise above 30° C. The reaction mixture is filtered, and the toluene phase is separated from the filtrate. The filter residue is washed with toluene, and the combined toluene phases are extracted with 15% strength sodium carbonate solution and with water. The toluene phase is then dried with sodium sulfate and concentrated in a vacuo. The remaining residue consists of 19.7 g (54.7% of theory) of 2-nitrobenzaldehyde, which crystallizes on cooling.
läuterung methode
Crystallise the aldehyde from toluene (2-2.5mL/g) by addition of 7mL pet ether (b 40-60o) for 1mL of solution. It can also be distilled under reduced pressures. [Beilstein 7 IV 584.]

2-Nitrobenzaldehyde Upstream-Materialien And Downstream Produkte

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