METHYL 3-CHLORO-4-HYDROXYBENZOATE Chemical Properties

Melting point:

108-110°C

Boiling point:

284.9±20.0 °C(Predicted)

Density 

1.354±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

6.89±0.18(Predicted)

Appearance

White to off-white Solid

BRN 

2641291

InChI

InChI=1S/C8H7ClO3/c1-12-8(11)5-2-3-7(10)6(9)4-5/h2-4,10H,1H3

InChIKey

ZSBIMTDWIGWJPW-UHFFFAOYSA-N

SMILES

C(OC)(=O)C1=CC=C(O)C(Cl)=C1

CAS DataBase Reference

3964-57-6(CAS DataBase Reference)

Safety Information

Safety Statements 

22-24/25

MSDS

• Language:English Provider:ALFA

METHYL 3-CHLORO-4-HYDROXYBENZOATE Usage And Synthesis

Uses

Methyl 3-Chloro-4-hydroxybenzoate is a reagent in the preparation of alkylidene hydrazides as human glucagon receptor antagonists for the treatment of hyperglycemia and diabetes.

Synthesis

1. Sulfuric acid (3 mL, 56.3 mmol) was added to a solution of 3-chloro-4-hydroxybenzoic acid (1.0 g, 5.8 mmol) in methanol (30 mL). 2. The reaction mixture was stirred at 60 °C for 12 hours. 3. Upon completion of the reaction, the mixture was cooled to room temperature and the methanol was removed under vacuum. 4. The residue was partitioned between saturated sodium bicarbonate solution and ethyl acetate (3 x 30 mL). 5. The organic layer was separated, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum to afford methyl 3-chloro-4-hydroxybenzoate (0.9 g, 83% yield) as a white solid. 6. The product was characterized by ESI-MS and NMR: ESI-MS m/z calculated 186.5, measured 187.5 (M + 1)+; retention time: 1.17 min (3 min run). ,2.2H, 1H), 7.06 (d, J = 8.8 Hz, 1H) and 3.90 (s, 3H).

References

[1] Journal of Medicinal Chemistry, 1987, vol. 30, # 10, p. 1887 - 1891
[2] Patent: WO2012/125613, 2012, A1. Location in patent: Page/Page column 145
[3] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2015, vol. 54B, # 7, p. 902 - 907
[4] Chemische Berichte, 1897, vol. 30, p. 1477
[5] Patent: US2009/298894, 2009, A1. Location in patent: Page/Page column 63

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