3-Bromo-2-methylbenzoic acid Chemical Properties

Melting point:

152-156 °C (lit.)

Boiling point:

316.1±30.0 °C(Predicted)

Density 

1.599±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Soluble in chloroform, methanol

pka

3.56±0.10(Predicted)

form 

Powder

color 

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 DataBase Reference

76006-33-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39-37/39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29163990

MSDS

• Language:English Provider:SigmaAldrich

3-Bromo-2-methylbenzoic acid Usage And Synthesis

Chemical Properties

White to orange or brown powder

Uses

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.

Uses

3-Bromo-2-methylbenzoic acid may be used to synthesize 4-(bromoacetyl)isoindolin-1-one and isocoumarins.

Synthesis

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).

References

[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

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