5-Acetylindole supplier | CasNO.53330-94-2

Name
5-Acetylindole
EINECS
CAS No. 53330-94-2
Article Data20
CAS DataBase
Density 1.193 g/cm³
Solubility
Melting Point 95-96 °C
Formula C₁₀H₉NO
Boiling Point 333.9 °C at 760 mmHg
Molecular Weight 159.188
Flash Point 163.7 °C
Transport Information
Appearance
Safety 26-36/37/39
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Ketone,indol-5-yl methyl (6CI);1-(1H-Indol-5-yl)ethanone;
PSA 32.86000
LogP 2.37050

Synthetic route

: 936840-08-3
1-(4-amino-3-ethynylphenyl)ethanone

: 53330-94-2
1-(1H-indol-5-yl)ethanone

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
Yield given. Multistep reaction. Yields of byproduct given;

...Expand

: 1027340-50-6
C11H14SiNCH3CO

: 53330-94-2
1-(1H-indol-5-yl)ethanone

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

: 14618-45-2
2,2,2-trifluoro-1-(1H-indol-3-yl)ethanone

: 53330-94-2
1-(1H-indol-5-yl)ethanone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 62 percent / AlCl3 / nitromethane / 4 h / 20 °C 2: 98 percent / aq. KOH / Heating 3: 86 percent / quinoline; 5-acetylindole-3-carboxylic acid cupric(II) salt / 2 h / 155 °C View Scheme

: 626234-71-7
5-acetyl-3-trifluoroacetylindole

: 53330-94-2
1-(1H-indol-5-yl)ethanone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 98 percent / aq. KOH / Heating 2: 86 percent / quinoline; 5-acetylindole-3-carboxylic acid cupric(II) salt / 2 h / 155 °C View Scheme

: 16078-30-1
1-Acetyl-2,3-dihydro-1H-indole

: 53330-94-2
1-(1H-indol-5-yl)ethanone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 12 percent / acetone / 24 h / Irradiation 2: 90 percent / acetone / 70 h / Irradiation View Scheme
Multi-step reaction with 3 steps 1: AlCl3 2: H3O(1+) 3: chloranile View Scheme
Multi-step reaction with 3 steps 1: aluminium chloride; carbon disulfide 2: hydrochloric acid; water 3: tetrachloro-<1,4>benzoquinone; xylene View Scheme

: 496-15-1
1-indoline

: 53330-94-2
1-(1H-indol-5-yl)ethanone

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 2: AlCl3 3: H3O(1+) 4: chloranile View Scheme

: 16078-35-6
1-(1-acetylindolin-5-yl)ethanone

: 53330-94-2
1-(1H-indol-5-yl)ethanone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: H3O(1+) 2: chloranile View Scheme
Multi-step reaction with 2 steps 1: hydrochloric acid; water 2: tetrachloro-<1,4>benzoquinone; xylene View Scheme

: C14H17NO

: 53330-94-2
1-(1H-indol-5-yl)ethanone

Conditions

Conditions	Yield
With hydrogenchloride at 20℃;

: 10075-50-0
5-bromo-1H-indole

: 53330-94-2
1-(1H-indol-5-yl)ethanone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: potassium hydride / tetrahydrofuran; mineral oil / 0.25 h / 0 °C 1.2: 0.33 h / -78 °C 2.1: tetrahydrofuran; mineral oil; pentane / -78 - 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / acetonitrile / 6 h / 50 °C 1.2: 3 h / 20 °C 2.1: bis-[(trifluoroacetoxy)iodo]benzene; 4-cyanobenzaldehyde oxime / methanol; water / 20 °C View Scheme

: C8H5LiN(1-)*K(1+)

: 78191-00-1
N-Methoxy-N-methylacetamide

: 53330-94-2
1-(1H-indol-5-yl)ethanone

Conditions

Conditions	Yield
In tetrahydrofuran; mineral oil; pentane at -78 - 20℃;

: 1056442-76-2
N-methoxy-N-methyl-1H-indole-5-carboxamide

: 75-16-1
methylmagnesium bromide

: 53330-94-2
1-(1H-indol-5-yl)ethanone

Conditions

Conditions	Yield
In tetrahydrofuran; toluene at 20 - 50℃; for 1h;	323 mg

: 1670-81-1
1H-Indole-5-carboxylic acid

: 53330-94-2
1-(1H-indol-5-yl)ethanone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 4 h / 20 °C 2: tetrahydrofuran; toluene / 1 h / 20 - 50 °C View Scheme

: 53330-94-2
1-(1H-indol-5-yl)ethanone

: 4-methoxy-6-methyl-7,8-dihydro[1,3]dioxolo[4,5-g]isoquinolin-6-ium bromide

: 1-(1H-indol-5-yl)-2-(4-methoxy-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)ethan-1-one

Conditions

Conditions	Yield
Stage #1: 4-methoxy-6-methyl-7,8-dihydro[1,3]dioxolo[4,5-g]isoquinolin-6-ium bromide With potassium hydroxide In methanol at 25℃; for 0.0333333h; Stage #2: 1-(1H-indol-5-yl)ethanone In methanol at 25℃; chemoselective reaction;	90%

: 53330-94-2
1-(1H-indol-5-yl)ethanone

: 74-88-4
methyl iodide

: 61640-20-8
1-(1-methyl-1H-indol-5-yl)ethan-1-one

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran at 0℃; for 1h;	89.71%

: 53330-94-2
1-(1H-indol-5-yl)ethanone

: 2-propylbutyl p-toluenesulfonate

: 5-acetyl-1-(2-propylbutyl)indole

Conditions

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide for 1h; Ambient temperature;	88%

: 53330-94-2
1-(1H-indol-5-yl)ethanone

: 95-92-1
oxalic acid diethyl ester

: ethyl 4-(1H-indol-5-yl)-2,4-dioxobutanoate

Conditions

Conditions	Yield
In ethanol for 3h; Inert atmosphere; Reflux;	83%

: 53330-94-2
1-(1H-indol-5-yl)ethanone

: 24424-99-5
di-tert-butyl dicarbonate

: 848357-27-7
5-acetylindole-1-carboxylic acid tert-butyl ester

Conditions

Conditions	Yield
dmap In tetrahydrofuran at 0℃; for 1.08333h;	81%
Stage #1: 1-(1H-indol-5-yl)ethanone With sodium hydride In tetrahydrofuran for 0.25h; Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran at 20℃; for 1h;	79.9%
Stage #1: 1-(1H-indol-5-yl)ethanone With sodium hydrogencarbonate In tetrahydrofuran at 0℃; for 0.5h; Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran at 20℃; for 0.333333h;	61.7%

: 53330-94-2
1-(1H-indol-5-yl)ethanone

: 100-39-0
benzyl bromide

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

Conditions

Conditions	Yield
With tetra-(n-butyl)ammonium iodide; potassium hydroxide In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	78%

: 53330-94-2
1-(1H-indol-5-yl)ethanone

: 616-38-6
carbonic acid dimethyl ester

: methyl 5-(3-methoxy-3-oxopropanoyl)-1H-indole-1-carboxylate

Conditions

Conditions	Yield
With sodium hydride In mineral oil Reflux;	78%

: 53330-94-2
1-(1H-indol-5-yl)ethanone

: 98-59-9
p-toluenesulfonyl chloride

: 1-[1-(toluene-4-sulfonyl)-1H-indol-5-yl]ethanone

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 2h; Inert atmosphere;	68%

: 110-52-1
1,4-dibromo-butane

: 53330-94-2
1-(1H-indol-5-yl)ethanone

: 1340592-90-6
1-[1-(4-bromobutyl)indol-5-yl]-ethanone

Conditions

Conditions	Yield
Stage #1: 1-(1H-indol-5-yl)ethanone With tetra-(n-butyl)ammonium iodide; potassium hydroxide In N,N-dimethyl-formamide at 20℃; for 0.75h; Stage #2: 1,4-dibromo-butane In N,N-dimethyl-formamide at 0 - 20℃; for 1.25h;	67%

: 53330-94-2
1-(1H-indol-5-yl)ethanone

: 824-79-3
sodium 4-methylbenzenesulfinate

: 1-(3-(p-tolylthio)-1H-indol-5-yl)ethanone

Conditions

Conditions	Yield
With iodine; triphenylphosphine In water Reflux; Inert atmosphere; Schlenk technique; Green chemistry;	60%

: 53330-94-2
1-(1H-indol-5-yl)ethanone

: 901113-92-6
ethyl 3-[4-(2-chloroethoxy)-phenyl]-2-ethoxy-propionate

: 1433194-93-4
ethyl 3-{4-[2-(5-acetylindol-1-yl)ethoxy]phenyl}-2-ethoxypropionate

Conditions

Conditions	Yield
Stage #1: 1-(1H-indol-5-yl)ethanone With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 1h; Stage #2: ethyl 3-[4-(2-chloroethoxy)-phenyl]-2-ethoxy-propionate In N,N-dimethyl-formamide for 15h; Reflux;	56%

: 53330-94-2
1-(1H-indol-5-yl)ethanone

: sodium difluoromethanesulfinate-d

: 1-(3-((difluoromethyl-d)thio)-1H-indol-5-yl)ethan-1-one

Conditions

Conditions	Yield
With chloro-trimethyl-silane; phosphonic acid diethyl ester In toluene at 85℃; for 3h; Sealed tube;	54%

: 53330-94-2
1-(1H-indol-5-yl)ethanone

: 144453-59-8
5-(1-hydroxyethyl)-1H-indole

Conditions

Conditions	Yield
With sodium tetrahydroborate In ethanol	49%

: 1445-73-4
1-Methyl-4-piperidone

: 53330-94-2
1-(1H-indol-5-yl)ethanone

: 1-[3-(1-Methyl-1,2,3,6-tetrahydro-pyridin-4-yl)-1H-indol-5-yl]-ethanone

Conditions

Conditions	Yield
With sodium methylate In methanol for 48h; Heating;	36%

: 53330-94-2
1-(1H-indol-5-yl)ethanone

: 2315-36-8
2-Chloro-N,N-diethylacetamide

: 33234-47-8
2-chloro-1,1'-indole-3,5-diyl-bis-ethanone

Conditions

Conditions	Yield
With trichlorophosphate at 65℃; for 2h;	35%

: 53330-94-2
1-(1H-indol-5-yl)ethanone

: 616-38-6
carbonic acid dimethyl ester

: methyl 3-(1H-indol-5-yl)-3-oxopropanoate

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran; mineral oil	27%

: 53330-94-2
1-(1H-indol-5-yl)ethanone

: 97-51-8
5-Nitrosalicylaldehyde

: 74-88-4
methyl iodide

: 73154-25-3
1-(1',3',3'-trimethyl-6-nitro-1',3'-dihydro-spiro[chromene-2,2'-indol]-5'-yl)-ethanone

Conditions

Conditions	Yield
(i) MeOH, (ii) NaOH, (iii) /BRN= 512565/, EtOH; Multistep reaction;

...Expand

: 53330-94-2
1-(1H-indol-5-yl)ethanone

: 17028-61-4
5-nitro-o-vanilline

: 74-88-4
methyl iodide

: 73154-26-4
1-(8-methoxy-1',3',3'-trimethyl-6-nitro-1',3'-dihydro-spiro[chromene-2,2'-indol]-5'-yl)-ethanone

Conditions

Conditions	Yield
(i) MeOH, (ii) NaOH, (iii) /BRN= 613271/, EtOH; Multistep reaction;

...Expand

: 2460-59-5
3,5-dinitrosalicylaldehyde

: 53330-94-2
1-(1H-indol-5-yl)ethanone

: 74-88-4
methyl iodide

: 73154-28-6
1-(1',3',3'-trimethyl-6,8-dinitro-1',3'-dihydro-spiro[chromene-2,2'-indol]-5'-yl)-ethanone

Conditions

Conditions	Yield
(i) MeOH, (ii) NaOH, (iii) /BRN= 1121900/, EtOH; Multistep reaction;

...Expand

: 53330-94-2
1-(1H-indol-5-yl)ethanone

: 16789-84-7
3-bromo-5-nitrosalicylaldehyde

: 74-88-4
methyl iodide

: 73154-27-5
1-(8-bromo-1',3',3'-trimethyl-6-nitro-1',3'-dihydro-spiro[chromene-2,2'-indol]-5'-yl)-ethanone

Conditions

Conditions	Yield
(i) MeOH, (ii) NaOH, (iii) /BRN= 1213613/, EtOH; Multistep reaction;

...Expand

: 53330-94-2
1-(1H-indol-5-yl)ethanone

: 867-13-0
diethoxyphosphoryl-acetic acid ethyl ester

: 146327-25-5
ethyl (E)-(indol-5-yl)-2-butenoate

Conditions

Conditions	Yield
With ethanol; sodium hydride 1.) THF, 0 deg C, 30 min, 2.) THF, b.) RT, 30 min, b.) reflux, 8 h; Yield given. Multistep reaction;

: 53330-94-2
1-(1H-indol-5-yl)ethanone

: 776-74-9
Bromodiphenylmethane

: 146327-27-7
5-acetyl-1-(diphenylmethyl)indole

Conditions

Conditions	Yield
With potassium tert-butylate 1.) DMF, 0 deg C, 30 min, 2.) DMF, a.) 0 deg C, 1 h, b.) RT, 3 h; Yield given. Multistep reaction;

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.

Product Name

5-Acetylindole

Synthetic route

5-Acetylindole Standards and Recommendations

5-Acetylindole Specification

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