1,6-Dibrom-2-naphthol

Bezeichnung:1,6-Dibrom-2-naphthol

CAS-Nr16239-18-2

Englisch Name:1,6-Dibromo-2-naphthol

CBNumberCB7194023

SummenformelC10H6Br2O

Molgewicht301.96

MOL-Datei16239-18-2.mol

Synonyma

1,6-Dibrom-2-naphthol

1,6-Dibrom-2-naphthol physikalisch-chemischer Eigenschaften

Schmelzpunkt	105-107 °C(lit.)
Siedepunkt	368.5±22.0 °C(Predicted)
Dichte	1.7523 (rough estimate)
Brechungsindex	1.5560 (estimate)
storage temp.	Sealed in dry,Room Temperature
pka	6.94±0.50(Predicted)
Aggregatzustand	Powder
Farbe	Pink to purple or light brown
CAS Datenbank	16239-18-2(CAS DataBase Reference)
EPA chemische Informationen	1,6-Dibromo-2-naphthol (16239-18-2)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38
S-Sätze:	26-37/39-24/25
WGK Germany	3
RTECS-Nr.	QL3500000
HS Code	29081990

Gefahreninformationscode (GHS)

1,6-Dibromo-2-naphthol 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.
S24/25:Berührung mit den Augen und der Haut vermeiden.
Chemische Eigenschaften
Pink to purple or light brown powder
Synthese

15231-91-1

16239-18-2

General procedure for the synthesis of 1,6-dibromo-2-naphthol from 6-bromo-2-naphthol: 6-bromo-2-naphthol (500 mg, 2.242 mmol, 1.0 eq.) was reacted with N-bromosuccinimide (NBS, 558.7 mg, 3.319 mmol, 1.4 eq.) in acetone (4.4 mL) and 1 N HCl (22 μL) in a mixed solution of acetone (4.4 mL) and 1 N HCl (22 μL) at room temperature with stirring for 15 min. Upon completion of the reaction, ethyl acetate was added for extraction and the organic phase was washed three times with 1 N HCl to remove unreacted NBS and by-products. Subsequently, the organic phase was dried with anhydrous magnesium sulfate, the desiccant was removed by filtration, and the filtrate was concentrated under reduced pressure on a rotary evaporator to afford the target product 1,6-dibromo-2-naphthol in quantitative yield (677 mg). The product characterization data were as follows: molecular formula C10H6Br2O; molecular weight 300/302/304; 1H NMR (CDCl3, δ): 7.90 (d, J = 1.8 Hz, 1H), 7.87 (d, J = 8.8 Hz, 1H), 7.61 (d, J = 8.8 Hz, 1H), 7.59 (dd, J = 2.1 Hz, J = 9.1 Hz, 1H), 7.24 (d, J = 8.8 Hz, 1H); 13C NMR (CDCl3, δ): 177.5, 151.0, 131.0, 130.6, 130.1, 128.4, 128.3, 127.2, 118.0, 106.1; IR (cm-1): 3443, 1688, 1617, 1586 1382, 1209, 1183, 1130.
Einzelnachweise
[1] Patent: US2010/204234, 2010, A1. Location in patent: Page/Page column 15
[2] RSC Advances, 2018, vol. 8, # 32, p. 17806 - 17812
[3] Synthetic Communications, 1996, vol. 26, # 13, p. 2597 - 2601
[4] Chemical Communications, 2018, vol. 54, # 39, p. 4935 - 4938

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