1914-02-9

Basic information

• Product Name: 3,3-diMethyl-2,3-dihydro-1H-indole
• Synonyms: 3,3-diMethyl-2,3-dihydro-1H-indole;2,3-Dihydro-3,3-dimethyl-1H-indole
• CAS NO: 1914-02-9
• Molecular Formula: C₁₀H₁₃N
• Molecular Weight: 147.21692
• Mol File: 1914-02-9.mol
• Article Data: 23

Chemical Properties

• Melting Point: 34 °C
• Boiling Point: 60 °C(Press: 2 Torr)
• Appearance: /
• Density: 0.962±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C(protect from light)
• PKA: 5.28±0.40(Predicted)
• CAS DataBase Reference: 3,3-diMethyl-2,3-dihydro-1H-indole(CAS DataBase Reference)
• NIST Chemistry Reference: 3,3-diMethyl-2,3-dihydro-1H-indole(1914-02-9)
• EPA Substance Registry System: 3,3-diMethyl-2,3-dihydro-1H-indole(1914-02-9)

Safety Data

• Hazardous Substances Data: 1914-02-9(Hazardous Substances Data)

Usage

General Description

3,3-Dimethyl-2,3-dihydro-1H-indole is a chemical compound belonging to the group of indoles, which are heterocyclic aromatic organic compounds. This particular compound contains additional methyl groups, making it a derivative of indole. Its chemical formula is C11H13N. Due to its complex structure, this indole compound is likely to have distinct properties and potentially find applications in diverse fields such as pharmaceuticals, dyes, or agrochemicals. Its physical characteristics and specific uses would be determined by the way the indole and methyl groups react with other substances.

Synthetic route

3,3-dimethyloxindole (19155-24-9) → 3,3-dimethylindoline (1914-02-9)

Conditions	Yield
With sodium bis(2-methoxyethoxy)aluminium dihydride In toluene at 75℃; for 0.75h;	95%
Stage #1: 3,3-dimethyloxindole With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 4h; Heating / reflux; Stage #2: With water In tetrahydrofuran	89%
Stage #1: 3,3-dimethyloxindole With lithium aluminium tetrahydride In tetrahydrofuran at 60℃; for 1h; Inert atmosphere; Stage #2: With water In tetrahydrofuran at 0℃;	88%

1-(3,3-dimethylindolin-1-yl)ethan-1-one (16078-32-3) → 3,3-dimethylindoline (1914-02-9)

Conditions	Yield
Stage #1: 1-(3,3-dimethylindolin-1-yl)ethan-1-one With hydrogenchloride In methanol at 50℃; for 16h; Stage #2: With water pH=8;	94%
With hydrogenchloride Heating; Yield given;

3,3-dimethylindolenine (1504-14-9) → 3,3-dimethylindoline (1914-02-9)

Conditions	Yield
With sodium tetrahydroborate; water; sodium hydroxide In n-heptane at 10℃; for 3h; pH=~ 13;	85%
With copper oxide-chromium oxide at 150 - 170℃; under 25742.8 Torr; Hydrogenation;

1-azido-2-tert-butylbenzene (20442-98-2) → 3,3-dimethylindoline (1914-02-9)

Conditions	Yield
With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]} In toluene at 120℃; for 16h; Inert atmosphere;	75%
With tetrabutylammonium tricarbonylnitrosylferrate In 1,2-dichloro-ethane; N,N-dimethyl-formamide at 120℃; for 1h; Catalytic behavior; Solvent; Temperature; Reagent/catalyst; Microwave irradiation; Inert atmosphere;

2-bromo-β,β-dimethylbenzeneethanamine (71095-49-3) + potassium selenocyanate (3425-46-5) → 3,3-dimethylindoline (1914-02-9) + 3,4-dihydro-4,4-dimethyl-2H-1,2-benzoselenazine

Conditions	Yield
With copper(l) iodide; triethylamine In N,N-dimethyl-formamide at 20℃; for 24h;	A n/a B 68%

2-iodo-N-(2-methylallyl)aniline (73396-94-8) → 3,3-dimethylindoline (1914-02-9)

Conditions	Yield
With tetrabutyl-ammonium chloride; sodium formate; triethylamine; palladium diacetate In N,N-dimethyl-formamide at 80℃; for 24h;	65%

(2-Bromo-phenyl)-(2-methyl-allyl)-amine (207122-91-6) → 3,3-dimethylindoline (1914-02-9)

Conditions	Yield
With palladium diacetate; sodium hydrogencarbonate In N,N-dimethyl-formamide at 90℃;	65%

3,3-dimethyl-2,3-dihydroindol-2-thione (19155-25-0) → 3,3-dimethylindoline (1914-02-9)

Conditions	Yield
With nickel In methanol for 1h; Heating;	60%

1-Benzyl-3,3-dimethylindoline-2-thione (116916-38-2) → 3,3-dimethylindoline (1914-02-9) + 1-Benzyl-3,3-dimethylindoline (19501-85-0)

Conditions	Yield
With nickel In tetrahydrofuran; toluene for 1h; Heating;	A 60% B 6%
With nickel In methanol for 1h; Heating;	A 60% B 6%

isobutyraldehyde (78-84-2) + phenylhydrazine (100-63-0) → 3,3-dimethylindoline (1914-02-9)

Conditions	Yield
In acetic acid at 80℃;	50%

2-methyl-2-(2-nitrophenyl)proponic acid ethyl ester → 3,3-dimethylindoline (1914-02-9) + 2-<(1-Hydroxy-2-methyl)-2-propyl>-aniline

Conditions	Yield
With lithium borohydride In toluene 1.) 100 deg C, 4 h, 2.) r.t., overnight;	A 15% B 28%

C20H22BF3N6Ni → 3,3-dimethylindoline (1914-02-9)

Conditions	Yield
With tetrabutylammoniun azide In acetonitrile at 20℃; for 15h; Inert atmosphere;	20%

2,3-dihydro-1,3,3-trimethylindole (105278-05-5) → 3,3-dimethylindoline (1914-02-9)

Conditions	Yield
With ammonium iodide; hydrogen iodide at 215 - 230℃;

(+-)-6,6,12,12,18,18-hexamethyl-(5ar,11ac,17at)-5a,6,11a,12,17a,18-hexahydro-<1,3,5>triazino<1,2-a;3,4-a';5,6-a''>triindole → 3,3-dimethylindoline (1914-02-9)

Conditions	Yield
With copper oxide-chromium oxide at 150 - 170℃; under 25742.8 Torr; Hydrogenation;

1,4-dioxane (123-91-1) + 3,3-dimethyloxindole (19155-24-9) + diethyl ether (60-29-7) + lithium alanate → 3,3-dimethylindoline (1914-02-9)

Conditions	Yield
unter Stickstoff;

3,3-dimethyloxindole (19155-24-9) + pentan-1-ol (71-41-0) + sodium → 3,3-dimethylindoline (1914-02-9)

trimer(ic) 3.3-dimethyl-indolenine → 3,3-dimethylindoline (1914-02-9)

Conditions	Yield
With pentan-1-ol; sodium

2-bromoaniline (615-36-1) → 3,3-dimethylindoline (1914-02-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 85 percent / K2CO3 / dimethylformamide / Ambient temperature 2: 65 percent / Pd(OAc)2, NaHCO3 / dimethylformamide / 90 °C View Scheme

Acetanilid (103-84-4) + N-phenyl-N'-acetyl-urea → 3,3-dimethylindoline (1914-02-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: 99 percent / NaOH, tetrabutylammonium bromide / toluene / 2.25 h / 75 °C 2: AlCl3 / chlorobenzene / 110 - 115 °C 3: 6N HCl / Heating View Scheme

N-(2-methylprop-2-ene-1-yl)-N-phenylacetamide (102860-03-7) → 3,3-dimethylindoline (1914-02-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: AlCl3 / chlorobenzene / 110 - 115 °C 2: 6N HCl / Heating View Scheme
Multi-step reaction with 2 steps 1.1: aluminum (III) chloride / chlorobenzene / 115 - 120 °C / Inert atmosphere 2.1: hydrogenchloride / methanol / 16 h / 50 °C 2.2: pH 8 View Scheme

1-Benzyl-3,3-dimethylindoline (19501-85-0) → 3,3-dimethylindoline (1914-02-9)

Conditions	Yield
With carbonochloridic acid 1-chloro-ethyl ester; sodium iodide In acetone

1-acetyl-3,3-dimethylindolin-2-one (72934-84-0) → 3,3-dimethylindoline (1914-02-9)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: hydrogenchloride / water / 1 h / Reflux 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 60 °C / Inert atmosphere 2.2: 0 °C View Scheme

1-azido-2-tert-butyl-4-methoxybenzene (1373751-83-7) + 1-azido-2-tert-butylbenzene (20442-98-2) → 3,3-dimethylindoline (1914-02-9) + 3,3-dimethyl-5-methoxy-indoline (87234-77-3)

Conditions	Yield
With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]} In toluene at 120℃; for 3h; Inert atmosphere;

2-(1,1-dimethylethyl)-benzenamine (6310-21-0) → 3,3-dimethylindoline (1914-02-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 2-Methyl-2-nitropropane; trimethylsilylazide / acetonitrile / 20 °C / Inert atmosphere 2: bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]} / toluene / 16 h / 120 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: 2-Methyl-2-nitropropane; trimethylsilylazide / acetonitrile / 20 °C / Inert atmosphere 2: bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]} / toluene / 3 h / 120 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: tert.-butylnitrite; trimethylsilylazide / acetonitrile / 1 h / 0 - 20 °C 2: tetrabutylammonium tricarbonylnitrosylferrate / N,N-dimethyl-formamide; 1,2-dichloro-ethane / 1 h / 120 °C / Microwave irradiation; Inert atmosphere View Scheme

Acetanilid (103-84-4) → 3,3-dimethylindoline (1914-02-9)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: potassium carbonate; sodium hydroxide; tetrabutylammomium bromide / toluene / 75 °C 2.1: aluminum (III) chloride / chlorobenzene / 115 - 120 °C / Inert atmosphere 3.1: hydrogenchloride / methanol / 16 h / 50 °C 3.2: pH 8 View Scheme

N-acetyloxindole (21905-78-2) → 3,3-dimethylindoline (1914-02-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: lithium hexamethyldisilazane / Inert atmosphere 2: lithium aluminium tetrahydride / tetrahydrofuran / Inert atmosphere View Scheme

2-methyl-2-phenylpropionitrile (1195-98-8) → 3,3-dimethylindoline (1914-02-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: dmap; triethylamine / dichloromethane / 24 h / 20 °C / Inert atmosphere 2: copper diacetate / N,N-dimethyl-formamide / 170 °C / Inert atmosphere; Schlenk technique 3: sodium hydroxide / ethanol; water / 4 h / 100 °C / Inert atmosphere View Scheme

N-(2-methyl-2-phenylpropyl)picolinamide → 3,3-dimethylindoline (1914-02-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: copper diacetate / N,N-dimethyl-formamide / 170 °C / Inert atmosphere; Schlenk technique 2: sodium hydroxide / ethanol; water / 4 h / 100 °C / Inert atmosphere View Scheme

(3,3-dimethylindolin-1-yl)(pyridin-2-yl)methanone (1352819-13-6) → 3,3-dimethylindoline (1914-02-9)

Conditions	Yield
With sodium hydroxide In ethanol; water at 100℃; for 4h; Inert atmosphere;	24 mg

3,3-dimethylindoline (1914-02-9) + acetyl chloride (75-36-5) → 1-(3,3-dimethylindolin-1-yl)ethan-1-one (16078-32-3)

Conditions	Yield
With sodium hydrogencarbonate In dichloromethane at 0 - 20℃;	97.1%
With sodium hydrogencarbonate In dichloromethane at 0℃; for 2h;	97.1%

3,3-dimethylindoline (1914-02-9) + ortho-nitrofluorobenzene (1493-27-2) → 3,3-dimethyl-1-(2-nitrophenyl)indoline (917898-58-9)

Conditions	Yield
at 175℃; for 8h;	95%
In neat (no solvent) at 175℃; Inert atmosphere; Microwave irradiation;

1-Methyl-4-piperidone (1445-73-4) + 3,3-dimethylindoline (1914-02-9) → 3,3-dimethyl-1-(1-methyl-4-piperidinyl)-2,3-dihydro-1H-indole (882669-59-2)

Conditions	Yield
Stage #1: 1-Methyl-4-piperidone; 3,3-dimethylindoline In acetic acid for 0.0833333h; Stage #2: With sodium tris(acetoxy)borohydride In acetic acid for 0.5h;	94%

3,3-dimethylindoline (1914-02-9) + 3-phenyl-(2R,3R)-oxiran-2-ylmethanol (98819-68-2) → (2S,3S)-3-(3,3-dimethyl-2,3-dihydro-1H-indol-1-yl)-3-phenyl-propane-1,2-diol (866210-90-4)

Conditions	Yield
at 110℃; for 5h;	93%

3,3-dimethylindoline (1914-02-9) + (2R,3R)-3-(3-fluorophenyl)-2-(hydroxymethyl)oxirane (693220-50-7) → (2S,3S)-3-(3,3-dimethyl-2,3-dihydro-1H-indol-1-yl)-3-(3-fluorophenyl)propane-1,2-diol (866210-86-8)

Conditions	Yield
at 110℃; for 5h;	85%

3,3-dimethylindoline (1914-02-9) + (2R,3R)-3-(3,5-difluorophenyl)glycidol (866209-32-7) → (2S,3S)-3-(3,5-difluorophenyl)-3-(3,3-dimethyl-2,3-dihydro-1H-indol-1-yl)propane-1,2-diol (866210-88-0)

Conditions	Yield
at 110℃; for 5h;	84%

3,3-dimethylindoline (1914-02-9) → 3,3-dimethyl-indoline; hydrochloride

Conditions	Yield
With hydrogenchloride In n-heptane; Isopropyl acetate; isopropyl alcohol for 2h;	75.5%

3,3-dimethylindoline (1914-02-9) + ethyl 7-chlorothiazolo[5,4-d]pyrimidine-2-carboxylate → ethyl 7-(3,3-dimethylindolin-1-yl)thiazolo[5,4-d]pyrimidine-2-carboxylate

Conditions	Yield
In isopropyl alcohol at 70℃; for 4h; Sealed tube;	74%

3,3-dimethylindoline (1914-02-9) + 2-fluoro-3-nitropyridine (1480-87-1) → 3,3-dimethyl-1-(3-nitropyridin-2-yl)indoline (870072-64-3)

Conditions	Yield
at 200℃; for 0.166667h; microwave;	60.4%
In neat (no solvent) at 175℃; Inert atmosphere; Microwave irradiation;

3,3-dimethylindoline (1914-02-9) + 6-[4-(2-oxo-2,3-dihydroimidazo[4,5-b]pyridin-1-yl)-piperidin-1-yl]-pyrimidine-4-carboxylic acid (1159009-67-2) → 1-{1-[6-(3,3-dimethyl-2,3-dihydroindole-1-carbonyl)-pyrimidin-4-yl]piperidin-4-yl}-1,3-dihydro-imidazo[4,5-b]pyridin-2-one (1159007-29-0)

Conditions	Yield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine In N,N-dimethyl-formamide at 20℃;	57%

2,6-Dichloropyrimidine (3934-20-1) + 3,3-dimethylindoline (1914-02-9) → C14H14ClN3

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 75℃; for 2.5h;	57%

3,3-dimethylindoline (1914-02-9) + ethyl [4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate (1260543-99-4) → 2-[2-(3,3-dimethyl-2,3-dihydro-1H-indol-1-yl)-2-oxoethyl]-6-(morpholin-4-yl)pyrimidin-4(3H)-one (1260585-05-4)

Conditions	Yield
Stage #1: ethyl [4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate With sodium hydroxide In tetrahydrofuran at 20℃; for 48h; Stage #2: 3,3-dimethylindoline With pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 16h;	54%

3,3-dimethylindoline (1914-02-9) + sodium salt of (4-methoxy-6-chloropyrimidin-2-yl)acetic acid → 2-(4-chloro-6-methoxypyrimidin-2-yl)-1-(3,3-dimethyl-2,3-dihydroindol-1-yl)ethanone (1384070-87-4)

Conditions	Yield
With pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 20h;	41%

2-furanoic acid (88-14-2) + 3,3-dimethylindoline (1914-02-9) + i-propyl isocyanide (598-45-8) → C19H22N2O3

Conditions	Yield
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 20℃; for 48h; Ugi Condensation; diastereoselective reaction;	35%

3,3-dimethylindoline (1914-02-9) + 2-butyl-4-chloro-1-((5'-chloro-2'-cyano-[1,1'-biphenyl]-4- yl)methyl)-1H-imidazole-5-carboxylic acid + trifluoroacetic acid (76-05-1) → 2-butyl-4-chloro-1-((2'-cyano-5'-(3,3-dimethylindolin-l-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylic acid

Conditions

Yield

Stage #1: 3,3-dimethylindoline; 2-butyl-4-chloro-1-((5'-chloro-2'-cyano-[1,1'-biphenyl]-4- yl)methyl)-1H-imidazole-5-carboxylic acid With chloro(2-dicyclohexylphosphino-2’,6’-diisopropoxy-1,1’-biphenyl)[2-(2’-amino-1,1‘-biphenyl)]palladium(II) 2nd generation; sodium t-butanolate In tetrahydrofuran at 65℃; for 18h; Inert atmosphere; Sealed tube; Stage #2: trifluoroacetic acid In water; acetonitrile

29.4%

3,3-dimethylindoline (1914-02-9) → 3,3-dimethyl-2,3-dihydro-1H-indole-6-sulfonic acid (1316066-02-0)

Conditions	Yield
With sulfuric acid; sulfur trioxide at 20 - 135℃; for 1.75h;	28%

3,3-dimethylindoline (1914-02-9) + 4-(piperidin-1-ylmethyl)benzoyl chloride (768320-30-5) → (3,3-dimethylindolin-1-yl)(4-(piperidin-1-ylmethyl)phenyl)methanone

Conditions	Yield
With triethylamine In dichloromethane at 20℃; Schotten-Baumann Reaction; Inert atmosphere;	24%

3,3-dimethylindoline (1914-02-9) + 3-chloro-2-nitropyridine (54231-32-2) → 3,3-dimethyl-1-(3-nitropyridin-2-yl)indoline (870072-64-3)

Conditions	Yield
at 220℃; for 0.25h; Microwave irradiation;	18%

Upstream product

• 19155-24-9 3,3-dimethyloxindole 
• 73396-94-8 2-iodo-N-(2-methylallyl)aniline 
• 1504-14-9 3,3-dimethylindolenine 
• 1449325-34-1 1-(tert-butyl)-3,3-dimethylindoline 
• 62171-59-9 1-(tert-butyl)-2-iodobenzene 
• 78-84-2 isobutyraldehyde 
• 100-63-0 phenylhydrazine 
• 6310-21-0 2-(1,1-dimethylethyl)-benzenamine 
• 20442-98-2 1-azido-2-tert-butylbenzene 
• 107-06-2 1,2-dichloro-ethane 
• 632324-67-5 tert-butyl 3,3-dimethyl-2-oxo-2,3-dihydroindole-1-carboxylate 
• 1352819-13-6 (3,3-dimethylindolin-1-yl)(pyridin-2-yl)methanone 
• 1195-98-8 2-methyl-2-phenylpropionitrile 
• 21905-78-2 N-acetyloxindole 

Downstream Products

• 917898-58-9 3,3-dimethyl-1-(2-nitrophenyl)indoline 
• 53388-86-6 5-bromo-3,3-dimethylindoline 
• 1613147-59-3 (R)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-5-(3,3-dimethyl-2,3-dihydro-1H-indol-5-yl)pyridin-2-amine 
• 16078-33-4 (3,3-dimethylindolin-1-yl)(phenyl)methanone 
• 19501-85-0 1-Benzyl-3,3-dimethylindoline 
• 866210-90-4 (2S,3S)-3-(3,3-dimethyl-2,3-dihydro-1H-indol-1-yl)-3-phenyl-propane-1,2-diol 
• 866210-88-0 (2S,3S)-3-(3,5-difluorophenyl)-3-(3,3-dimethyl-2,3-dihydro-1H-indol-1-yl)propane-1,2-diol 
• 866210-86-8 (2S,3S)-3-(3,3-dimethyl-2,3-dihydro-1H-indol-1-yl)-3-(3-fluorophenyl)propane-1,2-diol 
• 179898-73-8 6-amino-3,3-dimethylindoline 
• 179898-72-7 3,3-dimethyl-6-nitro-2,3-dihydro-1H-indole 

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