1,5,6,7-TETRAHYDRO-4H-INDOL-4-ONE Chemical Properties

Melting point:

188-190 °C (lit.)

Boiling point:

311℃

Density 

1.216

Flash point:

150℃

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

form 

powder to crystal

pka

15.91±0.20(Predicted)

color 

White to Light yellow to Light orange

InChI

InChI=1S/C8H9NO/c10-8-3-1-2-7-6(8)4-5-9-7/h4-5,9H,1-3H2

InChIKey

KASJZXHXXNEULX-UHFFFAOYSA-N

SMILES

N1C2=C(C(=O)CCC2)C=C1

CAS DataBase Reference

13754-86-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

HS Code 

2914390090

MSDS

• Language:English Provider:SigmaAldrich

1,5,6,7-TETRAHYDRO-4H-INDOL-4-ONE Usage And Synthesis

Uses

• ;Reactant in synthesis of psammopemmin A as antitumor agent1• ;Reactant in synthesis of a 1,3,4,5-tetrahydrobenzindole β-ketoesters and tricyclic tetrahydrobenzindoles via C-H insertion reactions2• ;Reactant in preparation of tricyclic indole and dihydroindole derivatives as inhibitors of guanylate cyclase3• ;Reactant in preparation of condensed pyrroloindoles via Pd-catalyzed intramolecular C-H bond functionalization of (halobenzyl)pyrroles4• ;Reactant in enantioselective preparation of arylalkenyl indoles via asymmetric C-H insertion of rhodium carbenoids foll

Uses

1,5,6,7-Tetrahydro-4H-indol-4-one, is a versatile building block used for the synthesis of more complex pharmaceutical compounds. It can be used for the preparation of Psammopemmin A.

General Description

Iodination of 1,5,6,7-tetrahydro-4H-indol-4-one using 1-chloromethyl--4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetra-fluoroborate) yields α-iodo derivative as the main product.

Synthesis

The general procedure for the synthesis of 1,5,6,7-tetrahydro-4H-indol-4-one from 6,7-dihydro-4(5H)-benzofuranone is as follows: 6,7-dihydro-4(5H)-benzofuranone (0.10 g, 0.73 mmol) was dissolved in 20% aqueous ethanol (ca. 2 mL) along with the corresponding amine (3 equiv.) in an airtight tube at 150°C, respectively, and was Heating for 12 h or 36 h, respectively. Upon completion of the reaction, the reaction mixture was poured into water (10 mL) and the resulting aqueous solution was extracted with dichloromethane (3 x 10 mL). The organic extracts were combined, dried with anhydrous magnesium sulfate and concentrated to give a brown residue. This residue was purified by silica gel column chromatography with a solvent mixture of ethyl acetate/petroleum ether as eluent.

References

[1] Heterocycles, 1984, vol. 22, # 10, p. 2313 - 2316
[2] Tetrahedron Letters, 2012, vol. 53, # 33, p. 4276 - 4279
[3] Bulletin of the Korean Chemical Society, 2012, vol. 33, # 1, p. 341 - 343

1,5,6,7-TETRAHYDRO-4H-INDOL-4-ONE(13754-86-4)Related Product Information

• 1,2,3,9-TETRAHYDRO-4H-9-METHYL-CARBAZOLE-4-ONE
• 1,2,3,9-Tetrahydro-4(H)-carbazol-4-one
• 1,5,6,7-TETRAHYDRO-4H-INDOL-4-ONE
• 1,5,6,7-TETRAHYDRO-2-METHYL-4H-INDOL-4-ONE
• 3-Ethyl-2-methyl-6-(4-morpholinylmethyl)-1,5,6,7-tetrahydro-4H-indol-4-one
• 1-(4-METHOXYPHENYL)-2-PHENYL-1,5,6,7-TETRAHYDRO-4H-INDOL-4-ONE
• 3-ethyl-2-methyl-4,5,6,7-tetrahydroindol-4-one
• 2,6,6-trimethyl-4,5,6,7-tetrahydro-1H-indol-4-one
• 1-(3-METHOXYPHENYL)-2,6,6-TRIMETHYL-1,5,6,7-TETRAHYDRO-4H-INDOL-4-ONE
• 1-(4-METHYLPHENYL)-2-PHENYL-1,5,6,7-TETRAHYDRO-4H-INDOL-4-ONE
• 1-(3-CHLOROPHENYL)-2-PHENYL-1,5,6,7-TETRAHYDRO-4H-INDOL-4-ONE
• 1-(4-CHLOROPHENYL)-2-PHENYL-1,5,6,7-TETRAHYDRO-4H-INDOL-4-ONE
• 2-METHYL-1,2,3,9-TETRAHYDRO-CARBAZOL-4-ONE
• 2-(4-BROMOPHENYL)-1-(4-CHLOROPHENYL)-6,6-DIMETHYL-5,6,7-TRIHYDROINDOL-4-ONE
• 1,2-DIPHENYL-1,5,6,7-TETRAHYDRO-4H-INDOL-4-ONE
• 5-[(DIMETHYLAMINO)METHYLENE]-1-(4-METHYLPHENYL)-2-PHENYL-1,5,6,7-TETRAHYDRO-4H-INDOL-4-ONE
• 2-(4-FLUORO-3-METHYLPHENYL)-6,6-DIMETHYL-5,6,7-TRIHYDROINDOL-4-ONE
• 1-(3,5-BIS(TRIFLUOROMETHYL)PHENYL)-2-(4-BROMOPHENYL)-6,6-DIMETHYL-5,6,7-TRIHYDROINDOL-4-ONE