METHYL 6-METHOXY-1H-INDOLE-2-CARBOXYLATE Chemical Properties

Melting point:

117-119 °C(lit.)

Boiling point:

370.1±22.0 °C(Predicted)

Density 

1.253±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

15.20±0.30(Predicted)

form 

Powder

color 

White to beige

InChI

InChI=1S/C11H11NO3/c1-14-8-4-3-7-5-10(11(13)15-2)12-9(7)6-8/h3-6,12H,1-2H3

InChIKey

OPUUCOLVBDQWEY-UHFFFAOYSA-N

SMILES

N1C2=C(C=CC(OC)=C2)C=C1C(OC)=O

CAS DataBase Reference

98081-83-5(CAS DataBase Reference)

Safety Information

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29339980

MSDS

• Language:English Provider:SigmaAldrich

METHYL 6-METHOXY-1H-INDOLE-2-CARBOXYLATE Usage And Synthesis

Chemical Properties

Pale pink crystals

Uses

Methyl 6-methoxy-2-indolecarboxylate is suitable for use in the production of dyes by Escherichia coli expressing naphthalene dioxygenase (NDO) and toluene dioxygenase (TDO). It is also suitable for use in the production of dyes by Escherichia coli expressing multicomponent phenol hydroxylase (mPH) from Pseudomonas sp. strains KL33 and KL28.

Synthesis

General procedure for the synthesis of methyl 6-methoxy-1H-indole-2-carboxylate from compound (CAS: 98081-75-5): compound 10 (3 g, 13.9 mmol) was dissolved in xylene (42 mL) under refluxing conditions and slowly added dropwise to a preheated to refluxing solution of xylene (55 mL), the dropwise process lasted for 20 minutes. After the dropwise addition was completed, the reaction mixture was continued to be stirred at reflux for 6 hours. Upon completion of the reaction, the mixture was cooled to room temperature and subsequently concentrated under reduced pressure to remove the solvent. By recrystallization from benzene, compound 11a (1.97 g, 75% yield) was obtained as a white solid. Thin layer chromatography (TLC) analysis showed an Rf value of 0.40 (unfolding agent was hexane/ethyl acetate = 2:1).1H NMR (400 MHz, CDCl3) δ 8.82 (broad single peak, 1H), 7.56 (double peaks, 1H, J = 9.2 Hz), 7.36 (single peak, 1H), 7.16 (single peak, 1H), 6.83 (multiple peaks, 2H), and 3.93 (single peak, 3H), 3.86 (single peak, 3H).13C NMR (100 MHz, CDCl3) δ 162.4, 158.9, 138.0, 126.0, 123.4, 121.8, 112.3, 109.2, 93.6, 55.4, 51.8.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 6, p. 1740 - 1742
[2] Journal of Organic Chemistry, 2009, vol. 74, # 17, p. 6442 - 6451
[3] Inorganic Chemistry, 2017, vol. 56, # 8, p. 4253 - 4257
[4] Chemical Communications, 2010, vol. 46, # 37, p. 6926 - 6928
[5] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 10, p. 3057 - 3061

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