2-BROMO-5-HYDROXYBENZALDEHYDE

Bezeichnung:2-BROMO-5-HYDROXYBENZALDEHYDE

CAS-Nr2973-80-0

Englisch Name:2-BROMO-5-HYDROXYBENZALDEHYDE

CBNumberCB1114360

SummenformelC7H5BrO2

Molgewicht201.02

MOL-Datei2973-80-0.mol

2-BROMO-5-HYDROXYBENZALDEHYDE physikalisch-chemischer Eigenschaften

Schmelzpunkt	130-135 °C
Siedepunkt	286.7±20.0 °C(Predicted)
Dichte	1.737±0.06 g/cm3(Predicted)
storage temp.	Inert atmosphere,2-8°C
Löslichkeit	Soluble in chloroform, dichloromethane and ethyl acetate.
Aggregatzustand	Solid
pka	8.67±0.18(Predicted)
Farbe	White to Gray to Brown
InChI	InChI=1S/C7H5BrO2/c8-7-2-1-6(10)3-5(7)4-9/h1-4,10H
InChIKey	SCRQAWQJSSKCFN-UHFFFAOYSA-N
SMILES	C(=O)C1=CC(O)=CC=C1Br
CAS Datenbank	2973-80-0(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi,N,Xn
R-Sätze:	36/37/38-50-22
S-Sätze:	26-36/37/39-61
RIDADR	UN 3077
WGK Germany	3
Hazard Note	Irritant
HazardClass	9
PackingGroup	III
HS Code	2909500090
Speicherklasse	11 - Combustible Solids
Hazard Classifications	Acute Tox. 4 Oral Aquatic Acute 1

Gefahreninformationscode (GHS)

2-BROMO-5-HYDROXYBENZALDEHYDE 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.
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
Chemische Eigenschaften
Pale Grey Solid
Verwenden
2-Bromo-5-hydroxybenzadehyde is a reactant used in the preparation of many pharmaceutical agents: Bcl-XL, PDE4 inhibitors, inhibitors of prostate cancer cell growth and anti-inflamatory agents.
Verwenden
2-Bromo-5-hydroxybenzaldehyde is a useful reactant used in the synthesis of PDE4 inhibitors, BCL-XL and cancel cell growth inhibitors. Also an reactant used in the preparation of many pharmaceutical agents.
Synthese

100-83-4

2973-80-0

General procedure for the synthesis of 2-bromo-5-hydroxybenzaldehyde from m-hydroxybenzaldehyde: 3-hydroxybenzaldehyde (120 g, 0.98 mol) was suspended in 2400 mL of dichloromethane (CH2Cl2) in a 5 L four-necked, round-bottomed flask fitted with an overhead stirrer, a temperature probe, a dosing funnel, and a condenser tube. The mixture was heated to 35-40 °C to completely dissolve the raw material. Bromine (52 mL, 1.0 mol, 1.02 eq.) was added slowly dropwise through the addition funnel, controlling the rate of dropwise acceleration to maintain the reaction temperature between 35-38°C. After dropwise addition, the reaction mixture was stirred at 35 °C overnight. Subsequently, the mixture was slowly cooled to -5-0 °C over a period of 2 h and stirring was continued for 1 h at this temperature. The precipitated solid was collected by filtration through a Brinell funnel and the filter cake was washed with 400 mL of cold 1:1 n-heptane/dichloromethane mixture. The resulting gray solid was dried under vacuum at room temperature (0.2 mmHg). The yield was 124.3 g in 63% yield.
Einzelnachweise
[1] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 8, p. 955 - 959
[2] Patent: US2004/19018, 2004, A1. Location in patent: Page/Page column Sheet 2
[3] Journal of the Iranian Chemical Society, 2011, vol. 8, # 2, p. 531 - 536
[4] Tetrahedron Letters, 2009, vol. 50, # 9, p. 1007 - 1009
[5] Synthetic Communications, 2007, vol. 37, # 4, p. 581 - 585

2-BROMO-5-HYDROXYBENZALDEHYDE Upstream-Materialien And Downstream Produkte

2-BROMO-5-HYDROXYBENZALDEHYDE Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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