2,5-Dimethoxybenzylamine Chemical Properties

Boiling point:

95 °C/0.2 mmHg (lit.)

Density 

1.11 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.548(lit.)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

9.12±0.10(Predicted)

form 

clear liquid

color 

Colorless to Light orange to Yellow

InChI

1S/C9H13NO2/c1-11-8-3-4-9(12-2)7(5-8)6-10/h3-5H,6,10H2,1-2H3

InChIKey

UWMCHDDHXMFKMA-UHFFFAOYSA-N

SMILES

COc1ccc(OC)c(CN)c1

CAS DataBase Reference

3275-95-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

C

Risk Statements 

34

Safety Statements 

26-27-36/37/39-45

RIDADR 

UN 2735 8/PG 3

WGK Germany 

3

RTECS 

DP4430000

HazardClass 

IRRITANT

PackingGroup 

III

HS Code 

29222990

Storage Class

8A - Combustible corrosive hazardous materials

Hazard Classifications

Skin Corr. 1B

MSDS

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2,5-Dimethoxybenzylamine Usage And Synthesis

Chemical Properties

Colorless to light yellow liqui

Uses

2,5-Dimethoxybenzylamine reacts with ethyl bromoacetate to yield N-(2,5-dimethoxy)benzylglycine ethyl ester.

Uses

2,5-Dimethoxybenzylamine is used in the preparation of pyrrolo[2,3-b]pyrazine-7-carboxamide derivatives as JAK and SYK inhibitors for the treatment of autoimmune and inflammatory diseases.

Synthesis

Hexamethylenetetramine (urotropine) (2.1 g, 15.0 mmol) was dissolved in 60 mL of chloroform and heated to reflux; 2,5-dimethoxybenzyl bromide (2.97 g, 12.9 mmol) was dissolved in 60 mL of chloroform, then dripped into urotropine within 30 min, refluxed for 3 h, stored at 4 ?? overnight, and a white solid precipitated. After filtration, 2.33 g of white solid was obtained. The above solid was dissolved in the mixture [V (methanol): V (concentrated hydrochloric acid): V (water) = 42:12:10], heated to reflux for 3 d. Concentration was performed by adding 10 mL of water, adding 6 mol/L sodium hydroxide aqueous solution (about 40 mL) to adjust the pH to neutral, and then extracted with ether (50 mL??3), washed with saturated brine, and then concentrated by drying with anhydrous potassium carbonate to obtain 0.96 g of crude amine. The product was 0.96 g of crude amine, yield 44.5%.

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