3-Bromo-2-methylbenzoic acid

Bezeichnung:3-Bromo-2-methylbenzoic acid

CAS-Nr76006-33-2

Englisch Name:3-Bromo-2-methylbenzoic acid

CBNumberCB4400044

SummenformelC8H7BrO2

Molgewicht215.04

MOL-Datei76006-33-2.mol

3-Bromo-2-methylbenzoic acid physikalisch-chemischer Eigenschaften

Schmelzpunkt	152-156 °C (lit.)
Siedepunkt	316.1±30.0 °C(Predicted)
Dichte	1.599±0.06 g/cm3(Predicted)
storage temp.	Sealed in dry,Room Temperature
Löslichkeit	Soluble in chloroform, methanol
Aggregatzustand	Powder
pka	3.56±0.10(Predicted)
Farbe	White to orange or brown
Sensitive	Light Sensitive/Air Sensitive
InChI	InChI=1S/C8H7BrO2/c1-5-6(8(10)11)3-2-4-7(5)9/h2-4H,1H3,(H,10,11)
InChIKey	BJGKVCKGUBYULR-UHFFFAOYSA-N
SMILES	C(O)(=O)C1=CC=CC(Br)=C1C
CAS Datenbank	76006-33-2(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38
S-Sätze:	26-36/37/39-37/39
WGK Germany	3
HazardClass	IRRITANT
HS Code	29163990
Speicherklasse	11 - Combustible Solids

Gefahreninformationscode (GHS)

3-Bromo-2-methylbenzoic acid 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
White to orange or brown powder
Verwenden
3-Bromo-2-methylbenzoic acid may be used to synthesize 4-(bromoacetyl)isoindolin-1-one and isocoumarins.
Verwenden
3-Bromo-2-methylbenzoic Acid is a disubstituted benzoic acid used in the preparation of various biologically active compounds such as α-2 adrenoceptor agonists, Smoothened receptor anatogonists and HIV-1 entry inhibitors.
Synthese

124-38-9

69321-60-4

76006-33-2

Example 27 Synthesis of 3-bromo-2-methylbenzoic acid: tert-butyl lithium (t-BuLi, 1.5 M pentane solution, 17 mL) was slowly added to an anhydrous solution of 1,3-dibromo-2-methylbenzene (6.57 g) in anhydrous tetrahydrofuran (THF, 100 mL) under argon gas protection and the reaction temperature was kept at -80 °C. After the dropwise addition was completed, the reaction mixture was stirred between -76 and -78 °C for 2 hours. Subsequently, the mixture was further cooled below -80 °C, dry ice (solid carbon dioxide) was added and the mixture was allowed to warm up naturally to room temperature. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure, 5% aqueous sodium hydroxide (NaOH) solution (40 mL) was added to the residue, and the aqueous phase was washed with dichloromethane (CH2Cl2, 10 mL x 2). The aqueous phase was acidified with concentrated hydrochloric acid (HCl) to pH=1 and then extracted with ethyl acetate (EtOAc, 100 mL x 2). The organic phases were combined and dried with anhydrous sodium sulfate (Na2SO4). After concentration under reduced pressure, the residue was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate = 8:1 to 1:1) to afford 3.58 g of the target product, 3-bromo-2-methylbenzoic acid, in 63.4% yield. The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3): δ2.73 (s, 3H), 7.15 (t, J=8.0 Hz, 1H), 7.77 (dd, J=8.0 Hz, J=1.2 Hz, 1H), 7.94 (dd, J=8.0 Hz, J=1.2 Hz, 1H).
Einzelnachweise
[1] Patent: US2009/203657, 2009, A1. Location in patent: Page/Page column 49-50
[2] Patent: US2009/203677, 2009, A1. Location in patent: Page/Page column 52; 53
[3] Patent: US2009/197871, 2009, A1. Location in patent: Page/Page column 52
[4] Patent: WO2009/100169, 2009, A1. Location in patent: Page/Page column 129-130

3-Bromo-2-methylbenzoic acid Upstream-Materialien And Downstream Produkte

3-Bromo-2-methylbenzoic acid Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

76006-33-2, 3-Bromo-2-methylbenzoic acid Verwandte Suche:

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