3-CHLORO-4-METHOXYBENZYLAMINE HYDROCHLORIDE Chemical Properties

Melting point:

250-255 °C (lit.)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

soluble in Methanol

form 

Solid

color 

White to Almost white

InChI

InChI=1S/C8H10ClNO.ClH/c1-11-8-3-2-6(5-10)4-7(8)9;/h2-4H,5,10H2,1H3;1H

InChIKey

IKWWOZCEHOYKAO-UHFFFAOYSA-N

SMILES

NCC1=CC=C(OC)C(Cl)=C1.[H]Cl

CAS DataBase Reference

41965-95-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

T

Risk Statements 

25-37/38-41

Safety Statements 

26-36/37-45-39

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

Hazard Note 

Toxic

HazardClass 

IRRITANT

HazardClass 

6.1

HS Code 

2922290090

MSDS

• Language:English Provider:SigmaAldrich

3-CHLORO-4-METHOXYBENZYLAMINE HYDROCHLORIDE Usage And Synthesis

Uses

3-Chloro-4-methoxybenzylamine hydrochloride can be used to synthesize avanafil; it is an intermediate side chain in the synthesis of avanafil.

Chemical Properties

White powder solid

Synthesis

General procedure for the synthesis of 3-chloro-4-methoxybenzylamine hydrochloride from 4-methoxybenzylamine: acetic acid (100 ml) was slowly added to 4-methoxybenzylamine (100 g) at 25-30 °C. Subsequently, additional acetic acid (750 ml) was added to the reaction mixture. Sulfonyl chloride (87.84 ml) was slowly added dropwise to the reaction mixture at 20-25 °C and stirred continuously for 6 h at the same temperature. After completion of the reaction, methyl tert-butyl ether (850 ml) was added to the reaction mixture at 25-30 °C. The reaction mixture was cooled to 15-20°C and stirring was continued at this temperature for 1 hour. The precipitated solid product was filtered, washed with methyl tert-butyl ether and dried to give 3-chloro-4-methoxybenzylamine hydrochloride. Yield: 118 g.

References

[1] Synthesis, 2003, # 3, p. 403 - 407
[2] Synthetic Communications, 2000, vol. 30, # 14, p. 2609 - 2612
[3] Tetrahedron, 2003, vol. 59, # 35, p. 6991 - 7009
[4] Organic letters, 2001, vol. 3, # 25, p. 4063 - 4066
[5] Patent: WO2015/1567, 2015, A1. Location in patent: Page/Page column 21

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