5-Chloro-2-methoxybenzoic acid Chemical Properties

Melting point:

98-100 °C (lit.)

Boiling point:

150-152C

Density 

1,259g/cm

refractive index 

1,544-1546

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform, Methanol

form 

Crystalline Powder

pka

3.72±0.10(Predicted)

color 

White to off-white

InChI

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

InChIKey

HULDRQRKKXRXBI-UHFFFAOYSA-N

SMILES

C(O)(=O)C1=CC(Cl)=CC=C1OC

LogP

2.368 (est)

CAS DataBase Reference

3438-16-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39-36

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29189900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

5-Chloro-2-methoxybenzoic acid Usage And Synthesis

Chemical Properties

White to off-white crystalline powder

Uses

5-Chloro-2-methoxybenzoic acid has been used in the synthesis of 5-chloro-2-methoxybenzoates of La(III), Ga(III) and Lu(III).

General Description

Complexes of 4-chloro-2-methoxybenzoic acid anion with Mn²⁺, Co²⁺, Ni²⁺, Cu²⁺ and Zn²⁺ have been investigated.

Synthesis

General procedure for the synthesis of 5-chloro-2-methoxybenzoic acid from methyl 5-chloro-2-methoxybenzoate: to a 1 M aqueous sodium hydroxide solution (60 mL, 0.06 mol) was added a solution of methyl 5-chloro-2-methoxybenzoate (2.0 g, 0.01 mol) [Alfa Aesar] in ethanol (60 mL). The reaction mixture was stirred at room temperature for 4 h. The progress of the reaction was monitored by thin layer chromatography (TLC) until completion of the reaction. Subsequently, the reaction mixture was concentrated under reduced pressure to remove ethanol and the residue was separated by extraction with ethyl acetate. The aqueous phase was cooled in an ice bath and the pH was adjusted with concentrated aqueous hydrochloric acid to 2. After continued stirring in an ice bath for 1 h, the precipitated solid was collected by filtration, washed with water and dried in air to afford 1.4 g (74.9% yield) of the target product, 5-chloro-2-methoxybenzoic acid, as a white solid. Mass spectrum (MS): m/z 185.1 (MH+). 1H NMR (500 MHz, DMSO-d6): δ 3.818 (s, 3H), 7.162 (d, 1H), 7.551 (dd, 1H), 7.607 (d, 1H).

References

[1] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 21, p. 6819 - 6829
[2] Patent: WO2014/165816, 2014, A1. Location in patent: Page/Page column 98-99
[3] Journal of the American Chemical Society, 1988, vol. 110, p. 7178
[4] Patent: US4895860, 1990, A

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