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933-67-5 Usage

Uses

7-Methylindole is a reactant in the synthesis of α-amino amides that are found in a variety of biological-active compounds.

Chemical Properties

white to slightly beige shiny flakes

Synthesis Reference(s)

Tetrahedron Letters, 30, p. 2129, 1989 DOI: 10.1016/S0040-4039(01)93730-X

Check Digit Verification of cas no

The CAS Registry Mumber 933-67-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 9,3 and 3 respectively; the second part has 2 digits, 6 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 933-67:
(5*9)+(4*3)+(3*3)+(2*6)+(1*7)=85
85 % 10 = 5
So 933-67-5 is a valid CAS Registry Number.
InChI:InChI=1/C9H9N/c1-7-3-2-4-8-5-6-10-9(7)8/h2-6,10H,1H3

933-67-5 Well-known Company Product Price

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  • Detail
  • Alfa Aesar

  • (L17521)  7-Methylindole, 98%   

  • 933-67-5

  • 1g

  • 655.0CNY

  • Detail
  • Alfa Aesar

  • (L17521)  7-Methylindole, 98%   

  • 933-67-5

  • 5g

  • 2602.0CNY

  • Detail
  • Aldrich

  • (M51490)  7-Methylindole  97%

  • 933-67-5

  • M51490-1G

  • 700.83CNY

  • Detail
  • Aldrich

  • (M51490)  7-Methylindole  97%

  • 933-67-5

  • M51490-5G

  • 2,102.49CNY

  • Detail

933-67-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 7-Methylindole

1.2 Other means of identification

Product number -
Other names 7-methyl-indole

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:933-67-5 SDS

933-67-5Synthetic route

2,3-dihydro-7-methylindole
65673-86-1

2,3-dihydro-7-methylindole

7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

Conditions
ConditionsYield
With 6C44H32N6O4Ru(2+)*12Hf(2+)*8O(2-)*14HO(1-)*6C16H22ClCoN5O6(1-) In 2,2,2-trifluoroethanol; acetonitrile at 20℃; for 12h; Catalytic behavior; Reagent/catalyst; Inert atmosphere; Irradiation;99%
With H8O20P8Pt2(4-)*4C34H72N(1+) In methanol Inert atmosphere; Irradiation;97%
With tris(bipyridine)ruthenium(II) dichloride hexahydrate; chloropyridinecobaloxime(III) In ethanol at 30℃; for 24h; Inert atmosphere; Schlenk technique; Irradiation;89%
7-methyl-1-pivaloylindole

7-methyl-1-pivaloylindole

7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

Conditions
ConditionsYield
With lithium diisopropyl amide In tetrahydrofuran; hexane at 40 - 45℃; for 40h;93%
With n-butyllithium; diisopropylamine In tetrahydrofuran; hexanes at -78 - 45℃; for 40h; Inert atmosphere;93%
7-methyl-1-tosylindoline

7-methyl-1-tosylindoline

7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

Conditions
ConditionsYield
Stage #1: 7-methyl-1-tosylindoline In tetrahydrofuran at -78℃; for 2h;
Stage #2: With oxygen In tetrahydrofuran at 20℃;
84%
6-methyl-2-vinylaniline
210536-43-9

6-methyl-2-vinylaniline

7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

Conditions
ConditionsYield
With p-benzoquinone; lithium chloride; dichloro bis(acetonitrile) palladium(II) In tetrahydrofuran for 10h; Heating;82%
triethanolamine hydrochloride
637-39-8

triethanolamine hydrochloride

o-toluidine
95-53-4

o-toluidine

7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

Conditions
ConditionsYield
With triphenylphosphine; tin(ll) chloride; ruthenium trichloride In 1,4-dioxane; water at 180℃; for 20h; Cyclization;80%
With tin(ll) chloride; ruthenium trichloride; triphenylphosphine In 1,4-dioxane; water at 180℃; for 20h;80%
C9H8N2O4
1428257-94-6

C9H8N2O4

7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

Conditions
ConditionsYield
With indium; acetic acid In benzene at 80℃; for 5h; Inert atmosphere;76%
7-methyl-1-(phenylsulfonyl)-1H-indole
130103-44-5

7-methyl-1-(phenylsulfonyl)-1H-indole

7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

Conditions
ConditionsYield
With potassium hydroxide In methanol; 1,2-dimethoxyethane for 24h; Heating;75%
7-methyl-2-trimethylsilanyl-indole-1-carboxylic acid diethylamide
548775-76-4

7-methyl-2-trimethylsilanyl-indole-1-carboxylic acid diethylamide

7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

Conditions
ConditionsYield
With potassium hydroxide In ethanol for 12h; Heating;75%
1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

vinyl magnesium bromide
1826-67-1

vinyl magnesium bromide

7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

Conditions
ConditionsYield
In tetrahydrofuran at -45 - -40℃; Cyclization; Bartoli reaction;71%
In tetrahydrofuran at -40℃; for 0.333333h;67%
In tetrahydrofuran at -40℃; for 1h; Inert atmosphere;34%
1-(2-amino-3-methylphenyl)-2-chloroethan-1-one
109532-22-1

1-(2-amino-3-methylphenyl)-2-chloroethan-1-one

7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

Conditions
ConditionsYield
With sodium tetrahydroborate In 1,4-dioxane; water for 2h; Heating;71%
2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

2-methylphenylhydrazine
529-27-1

2-methylphenylhydrazine

7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

Conditions
ConditionsYield
With phosphorus pentachloride; zinc(II) chloride for 0.0666667h; microwave irradiation;71%
1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

vinyl magnesium bromide
1826-67-1

vinyl magnesium bromide

A

7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

B

acetaldehyde
75-07-0

acetaldehyde

C

2,2'-dimethylazobenzene
584-90-7

2,2'-dimethylazobenzene

D

o-toluidine
95-53-4

o-toluidine

E

N,N'-Di-o-tolyl-diazene N-oxide
956-31-0, 51284-68-5, 116723-89-8

N,N'-Di-o-tolyl-diazene N-oxide

Conditions
ConditionsYield
In tetrahydrofuran at -40℃; for 0.333333h; other nitroarenes and vinyl Grignard reagents;A 67%
B n/a
C n/a
D 5%
E n/a
(E)-1-(3-methyl-2-nitrostyryl)pyrrolidine

(E)-1-(3-methyl-2-nitrostyryl)pyrrolidine

7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

Conditions
ConditionsYield
Stage #1: (E)-1-(3-methyl-2-nitrostyryl)pyrrolidine With iron(III) chloride; pyrographite In methanol for 0.166667h; Heating;
Stage #2: With hydrazine hydrate In methanol for 3h; Heating; Further stages.;
67%
triethanolamine
102-71-6

triethanolamine

o-toluidine
95-53-4

o-toluidine

7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

Conditions
ConditionsYield
With tin(ll) chloride; ruthenium trichloride; triphenylphosphine In 1,4-dioxane at 180℃; for 20h;66%
2-(2-tolylamino)ethan-1-ol
136-80-1

2-(2-tolylamino)ethan-1-ol

7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

Conditions
ConditionsYield
With o-toluidine In acetonitrile64.3%
(2,6-Dimethyl-phenyl)-[2-(phenyl-hydrazono)-prop-(Z)-ylidene]-amine

(2,6-Dimethyl-phenyl)-[2-(phenyl-hydrazono)-prop-(Z)-ylidene]-amine

A

7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

B

2,5-dimethylquinoxaline
26941-20-8

2,5-dimethylquinoxaline

C

{(R)-4-[1-Cyano-meth-(Z)-ylidene]-2,2-dimethyl-thietan-3-yl}-carbamic acid benzyl ester

{(R)-4-[1-Cyano-meth-(Z)-ylidene]-2,2-dimethyl-thietan-3-yl}-carbamic acid benzyl ester

D

2,8-dimethylquinoxaline
81576-25-2

2,8-dimethylquinoxaline

Conditions
ConditionsYield
at 650℃; under 0.01 Torr;A 62%
B 7%
C n/a
D 11%
(2,6-Dimethyl-phenyl)-[2-(phenyl-hydrazono)-prop-(Z)-ylidene]-amine

(2,6-Dimethyl-phenyl)-[2-(phenyl-hydrazono)-prop-(Z)-ylidene]-amine

A

7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

B

2,7-dimethyl-1H-indole
5621-13-6

2,7-dimethyl-1H-indole

C

2,5-dimethylquinoxaline
26941-20-8

2,5-dimethylquinoxaline

D

2,8-dimethylquinoxaline
81576-25-2

2,8-dimethylquinoxaline

Conditions
ConditionsYield
at 650℃; under 0.01 Torr;A 62%
B 3%
C 7%
D 11%
7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

methyl p-toluene sulfonate
80-48-8

methyl p-toluene sulfonate

7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

Conditions
ConditionsYield
With nickel(II) iodide; 4,4'-dimethyl-2,2'-bipyridines; tetra-(n-butyl)ammonium iodide; magnesium chloride; zinc In N,N-dimethyl acetamide at 20℃; for 12h; Inert atmosphere; Schlenk technique; Sealed tube;60%
1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

vinylmagnesium chloride
3536-96-7

vinylmagnesium chloride

7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

Conditions
ConditionsYield
In tetrahydrofuran at -45 - -40℃; Cyclization; Bartoli reaction;58%
7-methyl-1H-indole-2,3-dione
1127-59-9

7-methyl-1H-indole-2,3-dione

7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

Conditions
ConditionsYield
With dimethylsulfide borane complex In tetrahydrofuran BH3*THF or LAH;55%
2-[(Z)-2,6-Dimethyl-phenylimino]-propionaldehyde O-methyl-oxime

2-[(Z)-2,6-Dimethyl-phenylimino]-propionaldehyde O-methyl-oxime

A

7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

B

2,7-dimethyl-1H-indole
5621-13-6

2,7-dimethyl-1H-indole

C

2,5-dimethylquinoxaline
26941-20-8

2,5-dimethylquinoxaline

D

2,8-dimethylquinoxaline
81576-25-2

2,8-dimethylquinoxaline

Conditions
ConditionsYield
at 650℃; under 0.01 Torr;A 55%
B 5%
C 4%
D 17%
2,6-dimethylnitrobenzene
81-20-9

2,6-dimethylnitrobenzene

N,N-dimethyl-formamide dimethyl acetal
4637-24-5

N,N-dimethyl-formamide dimethyl acetal

7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

Conditions
ConditionsYield
Stage #1: 2,6-dimethylnitrobenzene; N,N-dimethyl-formamide dimethyl acetal With pyrrolidine In 1,4-dioxane at 102℃; for 22h; Leimgruber-Batcho Indole Synthesis; Reflux; Inert atmosphere;
Stage #2: With hydrazine hydrate In 1,4-dioxane at 45℃; for 1h; Leimgruber-Batcho Indole Synthesis;
53%
7-methyl-1H-indole-5-carboxylic acid
180624-00-4

7-methyl-1H-indole-5-carboxylic acid

7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

Conditions
ConditionsYield
With copper(I) oxide In quinoline at 230℃; for 4h; Decarboxylation;50%
1,1-dimethylethyl (3S,4S)-3,4-dihydroxy-4-(7-methyl-1H-indol-3-yl)-1-piperidinecarboxylate

1,1-dimethylethyl (3S,4S)-3,4-dihydroxy-4-(7-methyl-1H-indol-3-yl)-1-piperidinecarboxylate

A

7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

B

1-dimethylethyl (3R)-3-hydroxy-4-(7-methyl-1H-indol-3-yl)-3,6-dihydro-1(2H)-pyridinecarboxylate
1143455-52-0

1-dimethylethyl (3R)-3-hydroxy-4-(7-methyl-1H-indol-3-yl)-3,6-dihydro-1(2H)-pyridinecarboxylate

Conditions
ConditionsYield
With potassium hydroxide In methanol at 70℃;A 48%
B 36%
(2,6-Dimethyl-phenyl)-[2-(phenyl-hydrazono)-eth-(Z)-ylidene]-amine

(2,6-Dimethyl-phenyl)-[2-(phenyl-hydrazono)-eth-(Z)-ylidene]-amine

A

7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

B

5-methylquinoxaline
13708-12-8

5-methylquinoxaline

Conditions
ConditionsYield
at 650℃; under 0.01 Torr;A 32%
B 40%
at 650℃; under 0.01 Torr; Product distribution; Mechanism; also 15N labelled;
ethylene glycol
107-21-1

ethylene glycol

o-toluidine
95-53-4

o-toluidine

A

7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

B

2-(2-tolylamino)ethan-1-ol
136-80-1

2-(2-tolylamino)ethan-1-ol

C

1,2-bis[(2-methylphenyl)amino]ethane
94-92-8

1,2-bis[(2-methylphenyl)amino]ethane

D

1,4-di-o-tolyl-piperazine
3367-47-3

1,4-di-o-tolyl-piperazine

Conditions
ConditionsYield
With palladium on activated charcoal; zinc(II) oxide In water at 150℃; for 24h; Sealed tube;A 20%
B 28%
C n/a
D n/a
3-acetoxy-1-acetyl-7-methyl-indole

3-acetoxy-1-acetyl-7-methyl-indole

7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

Conditions
ConditionsYield
With calcium hydroxide; kieselguhr; water; nickel at 30 - 40℃; under 132391 Torr; Hydrogenation;
7,7'-Dimethyl-2,3-dihydro-1H,1'H-[2,3']biindolyl

7,7'-Dimethyl-2,3-dihydro-1H,1'H-[2,3']biindolyl

7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

Conditions
ConditionsYield
at 225 - 240℃; Vakuum;
2,6-dimethylphenyl isonitrile
119072-54-7, 2769-71-3

2,6-dimethylphenyl isonitrile

7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

Conditions
ConditionsYield
With n-butyllithium; diisopropylamine Yield given. Multistep reaction;
Ru(H)2(1,2-bis(dimethylphosphino)ethane)2 In benzene-d6 at 140℃; for 25h; in a sealed tube;98 % Spectr.
7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

methyl iodide
74-88-4

methyl iodide

1,7-dimethyl-1H-indole
5621-16-9

1,7-dimethyl-1H-indole

Conditions
ConditionsYield
Stage #1: 7-methyl-1H-indole With sodium hydride In DMF (N,N-dimethyl-formamide) at 20℃; for 0.25h;
Stage #2: methyl iodide In DMF (N,N-dimethyl-formamide) at 30℃; for 1h;
100%
With sodium hydroxide In dimethyl sulfoxide at 20℃;99%
Stage #1: 7-methyl-1H-indole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; Inert atmosphere;
Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; Inert atmosphere;
97%
7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

2,3-dihydro-7-methylindole
65673-86-1

2,3-dihydro-7-methylindole

Conditions
ConditionsYield
Stage #1: 7-methyl-1H-indole With sodium cyanoborohydride; acetic acid In N,N-dimethyl-formamide at 20℃; for 2h;
Stage #2: With water; sodium hydroxide In N,N-dimethyl-formamide
99%
With tetrahydroxydiboron; palladium on activated carbon In 2,2,2-trifluoroethanol; water at 40℃; for 24h; Schlenk technique;99%
With sodium cyanoborohydride In acetic acid; ethyl acetate94%
7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

1,1,1-trifluoroacetophenone
434-45-7

1,1,1-trifluoroacetophenone

(R)-2,2,2-trifluoro-1-(7-methyl-1H-indol-3-yl)-1-phenylethanol
1160936-85-5

(R)-2,2,2-trifluoro-1-(7-methyl-1H-indol-3-yl)-1-phenylethanol

Conditions
ConditionsYield
With (S)-3,3'-bis(2,4,6-tri-iso-propylphenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate In dichloromethane at 25℃; for 48h; optical yield given as %ee; enantioselective reaction;99%
7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

hydroxy-(7-methyl-1H-indol-3-yl)-acetic acid ethyl ester

hydroxy-(7-methyl-1H-indol-3-yl)-acetic acid ethyl ester

Conditions
ConditionsYield
With cupreidine 9-O-(4-(perfluoro-n-octyl)benzyl) ether In 1,1,1,3,3-pentafluorobutane; toluene at 20℃; for 1h; Friedel-Crafts alkylation; Inert atmosphere; optical yield given as %ee; enantioselective reaction;99%
Stage #1: 7-methyl-1H-indole With C43H64N4O4; scandium tris(trifluoromethanesulfonate); ortho-chlorobenzoic acid In dichloromethane at 30℃; for 1h; Inert atmosphere;
Stage #2: glyoxylic acid ethyl ester In dichloromethane at -20℃; for 12h; Friedel Crafts alkylation; Inert atmosphere; optical yield given as %ee; enantioselective reaction;
90%
7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

methyl 4-phenyl-2-oxo-3-butenoate
107969-78-8, 6395-86-4

methyl 4-phenyl-2-oxo-3-butenoate

4-(7-methylindol-3-yl)-2-oxo-4-phenylbutyric acid methyl ester

4-(7-methylindol-3-yl)-2-oxo-4-phenylbutyric acid methyl ester

Conditions
ConditionsYield
With C35H48N4O4; samarium(III) trifluoromethanesulfonate In dichloromethane at -20℃; for 27h; asymmetric Friedel-Crafts alkylation; Inert atmosphere; optical yield given as %ee;99%
7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

ethyl-3,3,3-trifluoropyruvate
13081-18-0

ethyl-3,3,3-trifluoropyruvate

3,3,3-trifluoro-2-hydroxy-2-(7-methyl-1H-indol-3-yl)-propionic acid ethyl ester
1262999-81-4

3,3,3-trifluoro-2-hydroxy-2-(7-methyl-1H-indol-3-yl)-propionic acid ethyl ester

Conditions
ConditionsYield
Stage #1: 7-methyl-1H-indole With C33H52N4O4; zinc trifluoromethanesulfonate In dichloromethane at 35℃; for 0.5h;
Stage #2: ethyl-3,3,3-trifluoropyruvate In dichloromethane at 0℃; for 0.5h; Friedel Crafts alkylation; optical yield given as %ee; enantioselective reaction;
99%
With (3aR,11aR,14aS,16bS)-2,2,13,13-tetra-isopropyl-3a,11a,14a,16b-tetrahydro-bis(1,3-dioxolano[4',5':3,4]pyrrolo)[1,2-a:1',2'-a]naphtho[1,2-d:8,7-d']diimidazole; copper(II) bis(trifluoromethanesulfonate) at 0℃; for 1h; Friedel-Crafts Alkylation; Inert atmosphere; Schlenk technique; stereoselective reaction;97.6%
7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

ethyl-3,3,3-trifluoropyruvate
13081-18-0

ethyl-3,3,3-trifluoropyruvate

3,3,3-trifluoro-2-hydroxy-2-(7-methyl-1H-indol-3-yl)-propionic acid ethyl ester
1179934-54-3

3,3,3-trifluoro-2-hydroxy-2-(7-methyl-1H-indol-3-yl)-propionic acid ethyl ester

Conditions
ConditionsYield
In 1,1,1,3,3-pentafluorobutane at 20℃; for 0.5h; Inert atmosphere;99%
With triethylamine In dichloromethane at 0℃; Friedel Crafts alkylation;
With copper(II) bis(trifluoromethanesulfonate) In chloroform at 25℃; for 16h; Friedel-Crafts Alkylation; Inert atmosphere; Schlenk technique;
7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

hydroxy-(7-methyl-1H-indol-3-yl)-acetic acid ethyl ester

hydroxy-(7-methyl-1H-indol-3-yl)-acetic acid ethyl ester

Conditions
ConditionsYield
With cupreine 9-O-(4-(perfluoro-n-octyl)benzyl) ether In 1,1,1,3,3-pentafluorobutane; toluene at 20℃; for 1h; Friedel-Crafts alkylation; Inert atmosphere; optical yield given as %ee; enantioselective reaction;99%
7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

dimethyl 2-(2,2,2-trifluoroethylidene)malonate
170564-83-7

dimethyl 2-(2,2,2-trifluoroethylidene)malonate

dimethyl (R)-2-(2,2,2-trifluoro-1-(7-methyl-1H-indol-3-yl)ethyl)malonate
1275518-06-3

dimethyl (R)-2-(2,2,2-trifluoro-1-(7-methyl-1H-indol-3-yl)ethyl)malonate

Conditions
ConditionsYield
Stage #1: dimethyl 2-(2,2,2-trifluoroethylidene)malonate With copper(II) bis(trifluoromethanesulfonate); 2,2-bis[(4S)-4-isopropyloxazolin-2-yl]propane In diethyl ether at 20℃; for 0.333333h; Inert atmosphere;
Stage #2: 7-methyl-1H-indole In diethyl ether at -35℃; for 10h; Friedel-Crafts alkylation; Inert atmosphere; optical yield given as %ee; enantioselective reaction;
99%
7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

chloromethyl methyl ether
107-30-2

chloromethyl methyl ether

1-methoxymethyl-7-methylindole
1322763-47-2

1-methoxymethyl-7-methylindole

Conditions
ConditionsYield
Stage #1: 7-methyl-1H-indole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.5h; Inert atmosphere;
Stage #2: chloromethyl methyl ether In N,N-dimethyl-formamide; mineral oil for 1h; Inert atmosphere;
99%
7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

diethyl benzalmalonate
5292-53-5

diethyl benzalmalonate

(S)-ethyl 2-ethoxycarbonyl-3-[3-(7-methylindolyl)]-3-phenylpropanoate
668463-75-0

(S)-ethyl 2-ethoxycarbonyl-3-[3-(7-methylindolyl)]-3-phenylpropanoate

Conditions
ConditionsYield
Stage #1: diethyl benzalmalonate With 1,1-bis[(S)-4-benzyloxazolin-2-yl]-2,2-diphenylethene; copper(II) bis(trifluoromethanesulfonate) In ethanol at 20℃; for 0.5h; Friedel-Crafts alkylation; Inert atmosphere;
Stage #2: 7-methyl-1H-indole In ethanol at 20℃; for 24h; Friedel-Crafts alkylation; Inert atmosphere; optical yield given as %ee; enantioselective reaction;
99%
7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

C11H10N2O4
1436859-42-5

C11H10N2O4

5-methoxy-1-methyl-3-(7-methyl-1H-indol-3-yl)-3-(nitromethyl)indolin-2-one

5-methoxy-1-methyl-3-(7-methyl-1H-indol-3-yl)-3-(nitromethyl)indolin-2-one

Conditions
ConditionsYield
With 1,1,1,3',3',3'-hexafluoro-propanol; 6-bromo-2-(((((4S,5S)-4,5-diphenyl-1-tosyl-4,5-dihydro-1H-imidazol-2-yl)methyl)((S)-1-phenylethyl)amino)methyl)-4-nitrophenol; copper(I) triflate In toluene at 20℃; for 7h; Friedel-Crafts Alkylation; Inert atmosphere; enantioselective reaction;99%
7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

C11H10N2O3
1436859-40-3

C11H10N2O3

1,5-dimethyl-3-(7-methyl-1H-indol-3-yl)-3-(nitromethyl)indolin-2-one

1,5-dimethyl-3-(7-methyl-1H-indol-3-yl)-3-(nitromethyl)indolin-2-one

Conditions
ConditionsYield
With 1,1,1,3',3',3'-hexafluoro-propanol; 6-bromo-2-(((((4S,5S)-4,5-diphenyl-1-tosyl-4,5-dihydro-1H-imidazol-2-yl)methyl)((S)-1-phenylethyl)amino)methyl)-4-nitrophenol; copper(I) triflate In toluene at 20℃; for 1h; Friedel-Crafts Alkylation; Inert atmosphere; enantioselective reaction;99%
7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

ethyl 5-methyl-2-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-3-carboxylate
1533443-74-1

ethyl 5-methyl-2-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-3-carboxylate

ethyl (R)-5-methyl-3-(7-methyl-1H-indol-3-yl)-2-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-3-carboxylate
1533444-40-4

ethyl (R)-5-methyl-3-(7-methyl-1H-indol-3-yl)-2-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-3-carboxylate

Conditions
ConditionsYield
With C38H33O4P In toluene at -78℃; for 5h; enantioselective reaction;99%
pyrrolidine
123-75-1

pyrrolidine

7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

4-cyanobenzaldehyde
105-07-7

4-cyanobenzaldehyde

4-((7-methyl-1H-indol-3-yl)(pyrrolidin-1-yl)methyl)benzonitrile
1634687-10-7

4-((7-methyl-1H-indol-3-yl)(pyrrolidin-1-yl)methyl)benzonitrile

Conditions
ConditionsYield
In methanol at 30℃; for 72h;99%
7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

celastrol
34157-83-0

celastrol

(2R,4aS,6aS,12bR,14aS,14bR)-10,11-dihydroxy-2,4a,6a,9,12b,14a-hexamethyl-8-(7-methyl-1H-indol-3-yl)-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylic acid

(2R,4aS,6aS,12bR,14aS,14bR)-10,11-dihydroxy-2,4a,6a,9,12b,14a-hexamethyl-8-(7-methyl-1H-indol-3-yl)-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylic acid

Conditions
ConditionsYield
With aluminium(III) chloride hexahydrate In dichloromethane at 20℃; for 3h; Friedel-Crafts Alkylation; Sealed tube;99%
With scandium tris(trifluoromethanesulfonate) In dichloromethane at 20℃; for 24h; Friedel-Crafts Alkylation;
7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

7-methyl-3-(2-nitro-1-phenylethyl)-1H-indole
1455513-15-1

7-methyl-3-(2-nitro-1-phenylethyl)-1H-indole

Conditions
ConditionsYield
With 2,6-bis(2,2-dimethylpropionylamino)benzoic acid In chloroform at 40℃; for 24h; Friedel-Crafts Alkylation;99%
7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

ammonium thiocyanate
1147550-11-5

ammonium thiocyanate

7-methyl-3-thiocyanato-1H-indole
1112908-23-2

7-methyl-3-thiocyanato-1H-indole

Conditions
ConditionsYield
With oxygen In tetrahydrofuran at 25℃; under 750.075 Torr; for 7h; Irradiation;99%
With copper(II) choride dihydrate; oxygen In ethanol at 20℃; for 24h; Irradiation;93%
With TiO2/MoS2 In acetonitrile at 20℃; for 16h; Irradiation;90%
7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

dibenz[b,f][1,4]oxazepine
257-07-8

dibenz[b,f][1,4]oxazepine

2-(2-(bis(7-methyl-1H-indol-3-yl)methyl)phenoxy)aniline

2-(2-(bis(7-methyl-1H-indol-3-yl)methyl)phenoxy)aniline

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 20℃; for 3h; Friedel-Crafts Alkylation;99%
7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

methyl 5-methylbenzo[d]isothiazole-3-carboxylate 1,1-dioxide

methyl 5-methylbenzo[d]isothiazole-3-carboxylate 1,1-dioxide

(S)-3-methoxycarbonyl-3-(7-methyl-3-indolyl)-5-methyl-2,3-dihydrobenzo[d]isothiazole-1,1-dioxide

(S)-3-methoxycarbonyl-3-(7-methyl-3-indolyl)-5-methyl-2,3-dihydrobenzo[d]isothiazole-1,1-dioxide

Conditions
ConditionsYield
With (R)-2,6-bis(naphthalen-2-yl)-4-oxo-3,5-dioxa-4λ5-phosphacyclohepta[2,1-a;3,4-a']dinapthalen-4-ol In 1,2-dichloro-ethane at 20℃; for 16h; enantioselective reaction;99%
7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

methyl benzo[d]isothiazole-3-carboxylate 1,1-dioxide

methyl benzo[d]isothiazole-3-carboxylate 1,1-dioxide

(S)-3-methoxycarbonyl-3-(7-methyl-3-indolyl)-2,3-dihydrobenzo[d]isothiazole-1,1-dioxide

(S)-3-methoxycarbonyl-3-(7-methyl-3-indolyl)-2,3-dihydrobenzo[d]isothiazole-1,1-dioxide

Conditions
ConditionsYield
With (R)-2,6-bis(naphthalen-2-yl)-4-oxo-3,5-dioxa-4λ5-phosphacyclohepta[2,1-a;3,4-a']dinapthalen-4-ol In 1,2-dichloro-ethane at 20℃; for 16h; enantioselective reaction;99%
7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

diphenyl diselenide
1666-13-3

diphenyl diselenide

7-methyl-3-(phenylselanyl)-1H-indole

7-methyl-3-(phenylselanyl)-1H-indole

Conditions
ConditionsYield
With oxygen In tetrahydrofuran at 20℃; under 760.051 Torr; Irradiation;99%
With iridium(III) bis[2-(4,6-difluorophenyl)pyridinato]picolinate In acetonitrile at 25℃; Irradiation; Green chemistry;90%
With iridium(III) bis[2-(4,6-difluorophenyl)pyridinato]picolinate In acetonitrile at 20℃; Irradiation; Green chemistry;90%
With 3-chloro-benzenecarboperoxoic acid; sodium bromide In acetonitrile at 20℃; for 24h; regioselective reaction;61%
7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

2-nitrohydroquinone
16090-33-8

2-nitrohydroquinone

C15H10N2O4

C15H10N2O4

Conditions
ConditionsYield
With cerium(III) chloride; silver(l) oxide In 1,2-dichloro-ethane at 20℃; Darkness;99%
7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

ethyl 3,3,3-trifluoro-2-iminopropionate
213908-78-2

ethyl 3,3,3-trifluoro-2-iminopropionate

ethyl (S)-2-amino-3,3,3-trifluoro-2-(7-methyl-1H-indol-3-yl)propanoate
1014691-30-5

ethyl (S)-2-amino-3,3,3-trifluoro-2-(7-methyl-1H-indol-3-yl)propanoate

Conditions
ConditionsYield
With (S)-3-(anthracen-9-yl)-1,1'-binaphthyl-2,2'-diyl hydrogen phosphate In chloroform at -60℃; for 1h; Inert atmosphere; enantioselective reaction;99%
7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

N-(4-bromobenzylidene)-4-methylbenzenesulfonamide
36176-90-6

N-(4-bromobenzylidene)-4-methylbenzenesulfonamide

(S)-N-((4-bromophenyl)(7-methyl-1H-indol-3-yl)methyl)-4-methylbenzenesulfonamide

(S)-N-((4-bromophenyl)(7-methyl-1H-indol-3-yl)methyl)-4-methylbenzenesulfonamide

Conditions
ConditionsYield
With (Rp)-4,12-di(4-(3',5'-bis(trifluoromethyl))-phenyl-3-yl)-[2.2]paracyclophane-hydrogenphosphate In toluene at -20℃; for 12h; Molecular sieve; enantioselective reaction;99%
7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

tert-butyl (1,3-dioxo-2-phenyl-2,3-dihydroisoquinolin-4(1H)-ylidene)carbamate

tert-butyl (1,3-dioxo-2-phenyl-2,3-dihydroisoquinolin-4(1H)-ylidene)carbamate

(S)-tert-butyl (4-(7-methyl-1H-indol-3-yl)-1,3-dioxo-2-phenyl-1,2,3,4-tetrahydroisoquinolin-4-yl)carbamate

(S)-tert-butyl (4-(7-methyl-1H-indol-3-yl)-1,3-dioxo-2-phenyl-1,2,3,4-tetrahydroisoquinolin-4-yl)carbamate

Conditions
ConditionsYield
With (11aR)-3,7-di-9-anthracenyl-10,11,12,13-tetrahydro-5-hydroxy-5-oxide diindeno[7,1de:10,70-fg][1,3,2] dioxaphosphocin In toluene at 60℃; for 3h; enantioselective reaction;99%
7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

C17H14N2O3

C17H14N2O3

benzyl (R)-(1-methyl-3-(7-methyl-1H-indol-3-yl)-2-oxoindolin-3-yl)carbamate

benzyl (R)-(1-methyl-3-(7-methyl-1H-indol-3-yl)-2-oxoindolin-3-yl)carbamate

Conditions
ConditionsYield
With C55H51F3N4O3PdS In toluene at 40℃; Inert atmosphere; Alkaline conditions; enantioselective reaction;99%
7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

9-phenyl-fluoren-9-ol
25603-67-2

9-phenyl-fluoren-9-ol

7-methyl-3-(9-phenyl-9H-fluoren-9-yl)-1H-indole

7-methyl-3-(9-phenyl-9H-fluoren-9-yl)-1H-indole

Conditions
ConditionsYield
With scandium tris(trifluoromethanesulfonate) In dichloromethane at 60℃; for 4h; Sealed tube;99%
7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

2-((trifluoromethyl)sulfonyl)benzo[d]thiazole

2-((trifluoromethyl)sulfonyl)benzo[d]thiazole

7-methyl-3-((trifluoromethyl)sulfinyl)-1H-indole

7-methyl-3-((trifluoromethyl)sulfinyl)-1H-indole

Conditions
ConditionsYield
With Diphenylphosphinic chloride In acetonitrile at 60℃; for 1h; Schlenk technique; Inert atmosphere;99%

933-67-5Relevant articles and documents

Intermolecular Nucleophilic Addition Reaction of a C-7 Anion from N -[Bis(dimethylamino)phosphoryl]indole to Electrophiles/Arynes: Synthesis of 7-Substituted Indoles

Kaur, Amarjit,Kaur, Babaldeep,Kaur, Manjot,Sharma, Esha,Singh, Kamal Nain,Singh, Paramjit

, p. 84 - 87 (2022/01/04)

A novel approach to the C-7 substitution of N-[bis(dimethylamino)phosphoryl]indole by nucleophilic addition of the corresponding C-7 carbanion to electrophiles or arynes is described. The directing group can be easily removed, providing a simple route to the synthesis of 7-functionalized indoles.

Covalent Organic Frameworks toward Diverse Photocatalytic Aerobic Oxidations

Liu, Shuyang,Tian, Miao,Bu, Xiubin,Tian, Hua,Yang, Xiaobo

supporting information, p. 7738 - 7744 (2021/05/07)

Photoactive two-dimensional covalent organic frameworks (2D-COFs) have become promising heterogenous photocatalysts in visible-light-driven organic transformations. Herein, a visible-light-driven selective aerobic oxidation of various small organic molecules by using 2D-COFs as the photocatalyst was developed. In this protocol, due to the remarkable photocatalytic capability of hydrazone-based 2D-COF-1 on molecular oxygen activation, a wide range of amides, quinolones, heterocyclic compounds, and sulfoxides were obtained with high efficiency and excellent functional group tolerance under very mild reaction conditions. Furthermore, benefiting from the inherent advantage of heterogenous photocatalysis, prominent sustainability and easy photocatalyst recyclability, a drug molecule (modafinil) and an oxidized mustard gas simulant (2-chloroethyl ethyl sulfoxide) were selectively and easily obtained in scale-up reactions. Mechanistic investigations were conducted using radical quenching experiments and in situ ESR spectroscopy, all corroborating the proposed role of 2D-COF-1 in photocatalytic cycle.

Efficient acceptorless photo-dehydrogenation of alcohols and: N -heterocycles with binuclear platinum(ii) diphosphite complexes

Zhong, Jian-Ji,To, Wai-Pong,Liu, Yungen,Lu, Wei,Che, Chi-Ming

, p. 4883 - 4889 (2019/05/16)

Although photoredox catalysis employing Ru(ii) and Ir(iii) complexes as photocatalysts has emerged as a versatile tool for oxidative C-H functionalization under mild conditions, the need for additional reagents acting as electron donor/scavenger for completing the catalytic cycle undermines the practicability of this approach. Herein we demonstrate that photo-induced oxidative C-H functionalization can be catalysed with high product yields under oxygen-free and acceptorless conditions via inner-sphere atom abstraction by binuclear platinum(ii) diphosphite complexes. Both alcohols (51 examples), particularly the aliphatic ones, and saturated N-heterocycles (24 examples) can be efficiently dehydrogenated under light irradiation at room temperature. Regeneration of the photocatalyst by means of reductive elimination of dihydrogen from the in situ formed platinum(iii)-hydride species represents an alternative paradigm to the current approach in photoredox catalysis.

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