N-Benzylhydroxylamine hydrochloride

Bezeichnung:N-Benzylhydroxylamine hydrochloride

CAS-Nr29601-98-7

Englisch Name:N-Benzylhydroxylamine hydrochloride

CBNumberCB0664646

SummenformelC7H10ClNO

Molgewicht159.61

MOL-Datei29601-98-7.mol

N-Benzylhydroxylamine hydrochloride physikalisch-chemischer Eigenschaften

Schmelzpunkt	108-110 °C(lit.)
storage temp.	Inert atmosphere,Room Temperature
Löslichkeit	DMSO (Slightly), Ethyl Acetate (Slightly, Heated), Methanol (Slightly)
Aggregatzustand	powder to crystal
Farbe	White to Light yellow
BRN	507948
InChI	InChI=1S/C7H9NO.ClH/c9-8-6-7-4-2-1-3-5-7;/h1-5,8-9H,6H2;1H
InChIKey	YSNXOQGDHGUKCZ-UHFFFAOYSA-N
SMILES	N(CC1=CC=CC=C1)O.[H]Cl
CAS Datenbank	29601-98-7

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38
S-Sätze:	26-37/39
WGK Germany	3
F	3-10
HS Code	29280000
Speicherklasse	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

Gefahreninformationscode (GHS)

N-Benzylhydroxylamine hydrochloride 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.
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
Chemische Eigenschaften
White crystalline
Verwenden
N-Benzylhydroxylamine hydrochloride may be used in the preparation of a precursor to hitherto unknown aminocyclopentitol derivative, hydroxy functionalised 4-exo-ethoxycarbonyl-3-oxa-2-azabicyclo[3.3.0]octane system.
Allgemeine Beschreibung
N-Benzylhydroxylamine hydrochloride is a N-substituted-hydroxylamine. It participates in the ring opening of (2S,3R)-1,2-epoxy-4-penten-3-ol. Two-step synthesis of N-benzylhydroxylamine starting from dibenzylamine is reported.
Biochem/physiol Actions
N-Benzylhydroxylamine is a potential pharmacological agent in the prevention and progression of acrolein-induced damage to the retinal pigment epithelium.
Synthese

3376-26-9

29601-98-7

The general procedure for the synthesis of N-benzylhydroxylamine hydrochloride from the compound (CAS:3376-26-9) was as follows: in a two-necked round-bottomed flask equipped with a stirrer, a mixture of dibenzylamine (1) (32.8 g, 0.17 mol), Na2WO4-2H2O (0.98 g, 3.33 mmol) and methanol (0.17 L) was cooled to -15 °C. A 30% aqueous solution of H2O2 (57 mL, 0.5 mol) was slowly added dropwise over about 1 h via a pressure equalizing dropping funnel. After the dropwise addition, the reaction mixture was stirred continuously at room temperature for 16 hours. Subsequently, the mixture was transferred to a 3 L beaker and crushed ice (1 kg) was added under vigorous stirring. The white precipitate formed was collected by filtration and washed several times with ice water (1 L) to completely remove the peroxide. The wet crude nitrone was dissolved in 20% aqueous HCl solution (0.33 L) and concentrated under reduced pressure at a water bath temperature of 70 °C. To remove trace water, the mixture was washed with toluene (3 x 33 mL) and subsequently concentrated under vacuum to dryness overnight. Finally, recrystallization was carried out using minimal amounts of hot methanol (30 mL) and ether (115 mL) to give a white crystalline pure product (19.3 g, 71% yield). The 1H and 13C NMR spectra of the product were in agreement with those reported in the literature; ESI-HRMS analysis resulted in a calculated value of 124.07 and a measured value of 124.0750 for C7H9NO(M + H)+.
Einzelnachweise
[1] Synthetic Communications, 2005, vol. 35, # 18, p. 2445 - 2451
[2] Journal of Organic Chemistry, 1983, vol. 48, # 9, p. 1444 - 1448
[3] Synthesis, 2009, # 18, p. 3174 - 3176
[4] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 17, p. 4969 - 4972

N-Benzylhydroxylamine hydrochloride Upstream-Materialien And Downstream Produkte

N-Benzylhydroxylamine hydrochloride Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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