| Identification | Back Directory | [Name]
BIS(2,4-DIMETHOXYBENZYL)AMINE | [CAS]
20781-23-1 | [Synonyms]
Einecs 244-037-2
Bis(2,4-dimethoxybenzyl)
Bis(2,4-dimethoxybenyl)amine
BIS(2,4-DIMETHOXYBENZYL)AMINE
Bis(2,4-dimenthoxybenzyl)amine
2,2',4,4'TETRAMETHOXYDIBENZYLAMINE
bis[(2,4-diMethoxyphenyl)Methyl]aMine
Benzenemethanamine, N-(2,4-dimethoxyphenyl)methyl-2,4-dimethoxy-
1-(2,4-DIMETHOXYPHENYL)-N-[(2,4-DIMETHOXYPHENYL)METHYL]METHANAMINE | [EINECS(EC#)]
244-037-2 | [Molecular Formula]
C18H23NO4 | [MDL Number]
MFCD00040480 | [MOL File]
20781-23-1.mol | [Molecular Weight]
317.38 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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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