5-CHLORO-2-METHOXYBENZALDEHYDE Chemical Properties

Melting point:

75-79℃

Boiling point:

152 °C(Press: 15 Torr)

Density 

1.244±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

solid

Appearance

White to light yellow Solid

Sensitive 

Air Sensitive

InChI

InChI=1S/C8H7ClO2/c1-11-8-3-2-7(9)4-6(8)5-10/h2-5H,1H3

InChIKey

HXTWDGGMXZXOIV-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

7035-09-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22-36-51

Safety Statements 

26

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2913000090

5-CHLORO-2-METHOXYBENZALDEHYDE Usage And Synthesis

Synthesis Reference(s)

Synthetic Communications, 19, p. 799, 1989 DOI: 10.1080/00397918908050996

Synthesis

Step 1: Preparation of 5-chloro-2-methoxybenzaldehyde 5-Chloro-2-hydroxybenzaldehyde (20 g, 128 mmol) was dissolved in N,N-dimethylformamide (DMF, 70 mL) and the solution was cooled to 5-10 °C. Sodium hydride (7.69 g, 192 mmol) was added to the solution in small portions over 20 min. Subsequently, iodomethane (23.8 mL, 384 mmol) was added dropwise while keeping the temperature of the reaction mixture below 15 °C. After addition, the reaction mixture was stirred at room temperature for 2 hours. Upon completion of the reaction, the mixture was poured into pre-cooled saturated ammonium chloride solution (250 mL) and a white precipitate precipitated. The precipitate was collected by filtration and dried under vacuum. The resulting solid was ground with a solvent mixture of pentane and ether (4:1, 100 mL) to afford 18 g (82.58% yield) of the target product, 5-chloro-2-methoxybenzaldehyde, as a white solid.LC-MS analysis showed m/z = 170.1 ([M+H]+).

References

[1] Chemical Communications, 2011, vol. 47, # 9, p. 2679 - 2681
[2] Journal of Medicinal Chemistry, 2013, vol. 56, # 12, p. 5019 - 5032
[3] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 12, p. 2768 - 2776
[4] Patent: WO2014/151472, 2014, A1. Location in patent: Paragraph 00392-00393
[5] Patent: WO2016/40315, 2016, A1. Location in patent: Paragraph 00435; 00436

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