2,6-DIMETHOXYANILINE Chemical Properties

Melting point:

71-74

Boiling point:

254℃

Density 

1.096

refractive index 

1.4770 (estimate)

Flash point:

116℃

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

powder to crystal

pka

4.48±0.10(Predicted)

color 

White to Gray to Brown

Water Solubility 

Slightly soluble in water.

InChI

InChI=1S/C8H11NO2/c1-10-6-4-3-5-7(11-2)8(6)9/h3-5H,9H2,1-2H3

InChIKey

HQBJSEKQNRSDAZ-UHFFFAOYSA-N

SMILES

C1(N)=C(OC)C=CC=C1OC

CAS DataBase Reference

2734-70-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,T

Risk Statements 

20/21/22-36/37/38-36-33

Safety Statements 

26-36/37/39-36/37-28

RIDADR 

UN2811

Hazard Note 

Toxic/Irritant

TSCA 

N

HazardClass 

6.1

PackingGroup 

III

HS Code 

29214200

2,6-DIMETHOXYANILINE Usage And Synthesis

Chemical Properties

Off-white solid

Uses

2,6-Dimethylaniline degradation by Fenton process has been studied in depth for the purpose of learning more about the reactions involved in the oxidation of 2,6-dimethylaniline under various reaction conditions. Using a previously developed gas chromatographic-mass spectrometric assay, hemoglobin adducts of 2,6-dimethylaniline were detected covalently bound to rat hemoglobin after administration of either 2,6-dimethylaniline or lidocaine.

Synthesis

N-hydroxy-2,6-dimethoxybenzamide (1a) (0.237 g, 1.2 mmol) was used as a raw material and it was mixed with K2CO3 (0.166 g, 1.2 mmol) and DMSO (0.5 mL). Acetic anhydride (1.1 mL, 0.012 mmol) was added to the mixture and the reaction system was heated to 50°C. After stirring the reaction at this temperature for 10 min, the reaction mixture was cooled to 0°C and subsequently treated with 2M HCl (~2 mL). After the mixture was transformed into a clarified solution, it was neutralized by the addition of 2M NaOH (ca. 2 mL) and subsequently extracted with ether (Et2O, 15 mL x 3). The organic layers were combined, dried with anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ether, 1:1) to afford the target product 2,6-dimethoxyaniline (2a) (0.171 g, 93% yield) as a white crystalline solid.

References

[1] Chemical Communications, 2009, # 17, p. 2281 - 2283
[2] Organic and Biomolecular Chemistry, 2016, vol. 14, # 38, p. 9046 - 9054
[3] Tetrahedron Letters, 2015, vol. 56, # 5, p. 710 - 712

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