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5-Acetylindole

  • Name 5-Acetylindole
  • EINECSN/A
  • CAS No. 53330-94-2
  • Density1.193 g/cm3
  • PSA32.86000
  • LogP2.37050
  • SolubilityN/A
  • Melting Point95-96 °C
  • FormulaC10H9NO
  • Boiling Point333.9 °C at 760 mmHg
  • Molecular Weight159.188
  • Flash Point163.7 °C
  • Transport InformationN/A
  • AppearanceN/A
  • Safety26-36/37/39
  • Risk Codes36/37/38
  • Molecular Structure
    Molecular Structure of 53330-94-2 (5-Acetylindole)
  • Hazard SymbolsIrritantXi
  • SynonymsIrritantXi
  • Article Data20

5-Acetylindole Synthetic route

936840-08-3

1-(4-amino-3-ethynylphenyl)ethanone

53330-94-2

1-(1H-indol-5-yl)ethanone

Conditions
ConditionsYield
With P(p-C6H4F)3; chloro(1,5-cyclooctadiene)rhodium(I) dimer In N,N-dimethyl-formamide at 85℃; for 2h;93%
16078-34-5

5-Acetyl-2,3-dihydro-1H-indole

53330-94-2

1-(1H-indol-5-yl)ethanone

Conditions
ConditionsYield
With acetone for 70h; Irradiation;90%
With rhodium(III) chloride hydrate; C13H19N4(1+)*Br(1-) In toluene at 110℃; for 24h; Schlenk technique; Inert atmosphere;85%
With oxygen; 1-(2,2-diphenyl-2λ4,3λ4-[1,3,2]diazaborolo[4,5,1-ij]quinolin-1(2H)-yl)-3-phenylpropan-1-one In 1-methyl-pyrrolidin-2-one at 20℃; for 5h; Irradiation; Green chemistry;74%
With chloranil; xylene
With chloranil
1670-81-1

1H-Indole-5-carboxylic acid

917-54-4

methyllithium

53330-94-2

1-(1H-indol-5-yl)ethanone

Conditions
ConditionsYield
In tetrahydrofuran at 0℃; for 12h; Inert atmosphere;87.97%
In tetrahydrofuran at 0 - 20℃;80%
In tetrahydrofuran; diethyl ether at 0 - 20℃; Inert atmosphere;72.9%
626234-82-0

5-acetylindole-3-carboxylic acid

53330-94-2

1-(1H-indol-5-yl)ethanone

Conditions
ConditionsYield
With quinoline; 5-acetylindole-3-carboxylic acid cupric(II) salt at 155℃; for 2h;86%
889108-48-9

5-ethynyl-1H-indole

53330-94-2

1-(1H-indol-5-yl)ethanone

Conditions
ConditionsYield
With 4-cyanobenzaldehyde oxime; bis-[(trifluoroacetoxy)iodo]benzene In methanol; water at 20℃;84%
10075-50-0

5-bromo-1H-indole

127-19-5

N,N-dimethyl acetamide

53330-94-2

1-(1H-indol-5-yl)ethanone

Conditions
ConditionsYield
With tert.-butyl lithium; potassium hydride Yield given. Multistep reaction;
120-72-9

indole

75-36-5

acetyl chloride

68-12-2, 33513-42-7

N,N-dimethyl-formamide

A

53330-94-2

1-(1H-indol-5-yl)ethanone

B

81223-73-6

1-(1H-indol-6-yl)ethan-1-one

Conditions
ConditionsYield
Yield given. Multistep reaction. Yields of byproduct given;
1027340-50-6

C11H14SiNCH3CO

53330-94-2

1-(1H-indol-5-yl)ethanone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate / methanol / 25 °C
2: 93 percent / tris(4-fluorophenyl)phosphine / [Rh(COD)Cl]2 / dimethylformamide / 2 h / 85 °C
View Scheme
99-92-3

4-Aminoacetophenone

53330-94-2

1-(1H-indol-5-yl)ethanone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: benzyltrimethylammonium iodine dichloride; CaCO3 / CH2Cl2; methanol / 25 °C
2: CuI; diethylamine / PdCl2(PPh3)2 / 25 °C
3: potassium carbonate / methanol / 25 °C
4: 93 percent / tris(4-fluorophenyl)phosphine / [Rh(COD)Cl]2 / dimethylformamide / 2 h / 85 °C
View Scheme
97776-06-2

4-acetyl-2-iodoaniline

53330-94-2

1-(1H-indol-5-yl)ethanone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: CuI; diethylamine / PdCl2(PPh3)2 / 25 °C
2: potassium carbonate / methanol / 25 °C
3: 93 percent / tris(4-fluorophenyl)phosphine / [Rh(COD)Cl]2 / dimethylformamide / 2 h / 85 °C
View Scheme

5-Acetylindole Standards and Recommendations

DOT Classification:  3; Label: Flammable Liquid

5-Acetylindole Specification

The 5-Acetylindole, with the CAS registry number 53330-94-2, has the IUPAC name 1-(1H-indol-5-yl)ethanone. Its classification code is Drug / Therapeutic Agent and its product categories are Acetylgroup; Indoles and Derivatives. However, this chemical should be kept cool and dry. What's more, it finds its use on dry powder fire extinguishing agent, foam, sand, carbon dioxide and water spray.

Other characteristics of the 5-Acetylindole can be summarised as followings: (1)ACD/LogP: 1.59; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.59; (4)ACD/LogD (pH 7.4): 1.59; (5)ACD/BCF (pH 5.5): 9.5; (6)ACD/BCF (pH 7.4): 9.5; (7)ACD/KOC (pH 5.5): 174.37; (8)ACD/KOC (pH 7.4): 174.37; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 22 Å2; (13)Index of Refraction: 1.648; (14)Molar Refractivity: 48.55 cm3; (15)Molar Volume: 133.4 cm3; (16)Polarizability: 19.24×10-24cm3; (17)Surface Tension: 50.6 dyne/cm; (18)Density: 1.193 g/cm3; (19)Flash Point: 163.7 °C; (20)Enthalpy of Vaporization: 57.68 kJ/mol; (21)Boiling Point: 333.9 °C at 760 mmHg; (22)Vapour Pressure: 0.000132 mmHg at 25°C.

When you are using this chemical, please be cautious about it as the following: This chemical is irritating / toxic to eyes, respiratory system and skin. You should wear suitable protective clothing if you use it. In case of contacting with eyes, rinse immediately with plenty of water and seek medical advice. As it's flammable, keep it away from the sources of ignition.

You can still convert the following datas into molecular structure:
1.SMILES: O=C(c1cc2c(cc1)ncc2)C
2.InChI: InChI=1/C10H9NO/c1-7(12)8-2-3-10-9(6-8)4-5-11-10/h2-6,11H,1H3
3.InChIKey: GOFIUEUUROFVMA-UHFFFAOYAP

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 450mg/kg (450mg/kg)   European Journal of Medicinal Chemistry--Chimie Therapeutique. Vol. 9, Pg. 453, 1974.

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