METHYL 5-BROMOSALICYLATE Chemical Properties

Melting point:

61-65 °C (lit.)

Boiling point:

266.6±20.0 °C(Predicted)

Density 

1.627±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

9.19±0.18(Predicted)

form 

Solid

color 

White to pale brown

InChI

InChI=1S/C8H7BrO3/c1-12-8(11)6-4-5(9)2-3-7(6)10/h2-4,10H,1H3

InChIKey

FJYDBKPPGRZSOZ-UHFFFAOYSA-N

SMILES

C(OC)(=O)C1=CC(Br)=CC=C1O

CAS DataBase Reference

4068-76-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2918290090

MSDS

• Language:English Provider:SigmaAldrich

METHYL 5-BROMOSALICYLATE Usage And Synthesis

Uses

Methyl 5-bromosalicylate was used as starting reagent in the synthesis of immobilization precursor of photoswitchable piperidine base.

Synthesis

General procedure for the synthesis of methyl 5-bromosalicylate from methanol and 5-bromosalicylic acid: Step a) Synthesis of methyl 5-bromosalicylate: thionyl chloride (440 g, 3.7 mol) was slowly added to a solution of toluene (2 L) containing 5-bromosalicylic acid (200 g, 0.92 mol) at 0 °C and the reaction was stirred. The reaction mixture was then heated to 70 °C and refluxed for 40 hours. Upon completion of the reaction, the excess solvent was removed by distillation. Ethyl acetate (2 L) was added to the crude product for dissolution, and the organic layer was washed sequentially with 10% cold aqueous sodium bicarbonate (2 x 1 L) and brine, and then dried. Finally, the solvent was removed by vacuum to afford methyl 5-bromosalicylate as a low melting point solid (190 g, 89% yield). TLC conditions: petroleum ether/ethyl acetate (7:3), Rf value: 0.6.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 10, p. 2621 - 2625
[2] Journal of Materials Chemistry, 1996, vol. 6, # 8, p. 1297 - 1307
[3] Organic Letters, 2014, vol. 16, # 19, p. 5140 - 5143
[4] Patent: WO2005/12280, 2005, A1. Location in patent: Page/Page column 46-47
[5] Patent: WO2005/11685, 2005, A1. Location in patent: Page/Page column 41

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