1,3-DIACETOXYINDOLE Chemical Properties

Melting point:

80 °C

Boiling point:

345.3±15.0 °C(Predicted)

Density 

1.21±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,2-8°C

solubility 

Chloroform, Ethyl Acetate, Methanol

form 

Solid

color 

Light Brown

InChI

InChI=1S/C12H11NO3/c1-8(14)13-7-12(16-9(2)15)10-5-3-4-6-11(10)13/h3-7H,1-2H3

InChIKey

DNVFBLDIZKYQPL-UHFFFAOYSA-N

SMILES

C(=O)(N1C2=C(C=CC=C2)C(OC(C)=O)=C1)C

CAS DataBase Reference

16800-67-2(CAS DataBase Reference)

Safety Information

Safety Statements 

24/25

WGK Germany 

3

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich

1,3-DIACETOXYINDOLE Usage And Synthesis

Chemical Properties

Light Brown Solid

Uses

An indole derivative

Uses

1,3-Diacetoxyindole is a useful synthetic intermediate.

Synthesis

Synthesis of 2-[(carboxymethyl)amino]benzoic acid (Intermediate-32): to a 500 mL two-necked RB flask equipped with a magnetic stirrer, o-aminobenzoic acid (20 g, 145 mmol) was added dropwise to a stirred solution of K2CO3 (83 g, 602 mmol) in water (140 mL), followed by chloroacetic acid (13.7 g, 145 mmol) dropwise under N2 atmosphere at room temperature for about 30 min. , 145 mmol) for about 30 minutes at room temperature under N2 atmosphere. The reaction material was then heated at 90??C for 16 hours. After the reaction material was cooled to room temperature, the pH of the reaction material was adjusted to 4-5 using citric acid. the solids were then filtered and dried in a vacuum oven at 70??C for 12 hours to produce Intermediate-32 (23 g) as a light brown solid.

Synthesis of N,O-1,3-diacetylindole (Intermediate-33): To a 500 mL two-necked RB flask equipped with a magnetic stirrer, acetic anhydride (110 mL, 1200 mmol) was slowly added to a stirred solution of triethylamine (170 mL, 1242 mmol) and Intermediate-32 (23 g, 117 mmol) at 0 ??C under an N2 atmosphere. 1200 mmol). The reaction material was stirred at room temperature for 5 hours and further heated at 80??C for 16 hours. The reaction material was then cooled to 0??C and extracted with ethyl acetate (4 x 150 mL). The organic layer was washed with brine solution, dried over Na2SO4 and concentrated. The crude material was purified by silica gel column elution with hexane:EtOAc to yield Intermediate-33 (5.5 g) as a brown solid.

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