BIS(2,4-DIMETHOXYBENZYL)AMINE Chemical Properties

Boiling point:

443.5±40.0 °C(Predicted)

Density 

1.102±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

7.90±0.20(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C18H23NO4/c1-20-15-7-5-13(17(9-15)22-3)11-19-12-14-6-8-16(21-2)10-18(14)23-4/h5-10,19H,11-12H2,1-4H3

InChIKey

IZWMZVDEYOKQCG-UHFFFAOYSA-N

SMILES

C1(CNCC2=CC=C(OC)C=C2OC)=CC=C(OC)C=C1OC

Safety Information

HS Code 

2922290090

BIS(2,4-DIMETHOXYBENZYL)AMINE Usage And Synthesis

Uses

Bis(2,4-Dimethoxybenzyl)amine is used in the preparation of TLR8 agonists.

Synthesis

At room temperature, 2,4-dimethoxybenzaldehyde (Sigma Aldrich; 1.1 g, 6.61 mmol) was dissolved in 20 mL of tetrahydrofuran (THF). To this solution 2,4-dimethoxybenzylamine (Sigma Aldrich; 1.5 mL, 9.98 mmol) was added dropwise, followed by sodium triacetoxyborohydride (Sigma Aldrich; 17 g; 80.4 mmol). The reaction mixture gradually became turbid and the reaction was stirred overnight at room temperature. Upon completion of the reaction, the reaction mixture was diluted with saturated sodium bicarbonate (NaHCO3) solution and subsequently extracted with ethyl acetate (EtOAc). The organic phases were combined, dried with anhydrous magnesium sulfate (MgSO4), filtered and concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography (using a 40 g ISCO column with an elution gradient of 0 to 100% ethyl acetate/hexane) to afford bis(2,4-dimethoxybenzyl)amine (2.08 g, 6.55 mmol, 99% yield, 96% purity).

References

[1] Patent: WO2017/147410, 2017, A1. Location in patent: Page/Page column 1832
[2] Tetrahedron Letters, 2010, vol. 51, # 28, p. 3645 - 3648
[3] Chemische Berichte, 1968, vol. 101, # 10, p. 3623 - 3641
[4] Patent: US2013/131050, 2013, A1. Location in patent: Paragraph 0570; 0571
[5] Patent: WO2018/97945, 2018, A1. Location in patent: Paragraph 0395

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