2-Methylindoline supplier | CasNO.6872-06-6

Name
2-Methylindoline
EINECS 229-971-0
CAS No. 6872-06-6
Article Data89
CAS DataBase
Density 0.989 g/cm³
Solubility negligible
Melting Point -51 °C
Formula C₉H₁₁N
Boiling Point 232.6 °C at 760 mmHg
Molecular Weight 133.193
Flash Point 93.3 °C
Transport Information
Appearance clear yellow to brown liquid
Safety 26-36/37/39-60-57
Risk Codes 36/37/38-52/53-22
Molecular Structure
Hazard Symbols Xn, Xi
Synonyms Indoline,2-methyl- (6CI,7CI,8CI);2,3-Dihydro-2-methyl-1H-indole;2,3-Dihydro-2-methylindole;2-Methyl-1H-indoline;2-Methyl-2,3-dihydro-1H-indole;2-Methyl-2,3-dihydroindole;NSC 65598;a-Methyldihydroindole;
PSA 12.03000
LogP 2.18110

Synthetic route

: 95-20-5
2-methyl-1H-indole

: 6872-06-6
2-methyl indoline

Conditions

Conditions	Yield
With tetrahydroxydiboron; palladium on activated carbon In 2,2,2-trifluoroethanol; water at 40℃; for 24h; Schlenk technique;	99%
With zinc borohydride In diethyl ether for 48h; Ambient temperature;	94%
With formic acid; C29H32ClIrNO; sodium formate In water at 30℃; for 16h; pH=4.5;	92%

: 32704-22-6
2-allyl-phenylamine

: 6872-06-6
2-methyl indoline

Conditions

Conditions	Yield
With C48H66N2O2Zr(2-); trityl tetrakis(pentafluorophenyl)borate In chlorobenzene at 140℃; for 48h; Glovebox; Inert atmosphere;	94%
With C25H37BN4O2Zr(2+) In benzene-d6 at 20℃; for 72h; Reagent/catalyst; Inert atmosphere; stereoselective reaction;	90%
With (pentamethylcyclopentadienyl)2LaCH(TMS)2 In pentane for 24h; Ambient temperature;

: 1534360-76-3
2-(prop-2-yn-1-yl)aniline

: 6872-06-6
2-methyl indoline

Conditions

Conditions	Yield
With C33H63N15Zr3 In toluene at 140℃; for 48h; Glovebox; Inert atmosphere;	93%

: 149312-00-5, 18982-43-9
1ξ-(2-chloro-phenyl)-2-nitro-propene

: 6872-06-6
2-methyl indoline

Conditions

Conditions	Yield
With potassium carbonate; copper(l) chloride In water at 110℃; under 760.051 Torr; for 6h; Reagent/catalyst; Temperature;	92%

: 131880-76-7
1-(2-methyl-2,3-dihydro-indol-1-yl)-ethanone

A: 54813-73-9
1-ethyl-2-methylindoline

B: 6872-06-6
2-methyl indoline

Conditions

Conditions	Yield
With triethyl borane; Triethoxysilane; sodium hydroxide In hexane at 80℃; for 6h; Reagent/catalyst; Solvent; Inert atmosphere; Sealed tube;	A 10% B 90%
With Triethoxysilane; sodium triethylborohydride In hexane at 80℃; for 6h; Schlenk technique; Glovebox; Sealed tube; Inert atmosphere;	A 90% B n/a
With Triethoxysilane; sodium triethylborohydride In hexane at 80℃; for 6h; Inert atmosphere; Schlenk technique; High pressure; Sealed tube;	A 90% B n/a
With sodium triethylborohydride In tetrahydrofuran at 80℃; for 12h; Inert atmosphere; Schlenk technique; Glovebox; Sealed tube;	A n/a B 72%
With sodium triethylborohydride In tetrahydrofuran at 80℃; for 6h; Inert atmosphere; Schlenk technique; High pressure; Sealed tube;	A n/a B 72%

: 15804-71-4
2-bromo-β-methyl-β-nitrostyrene

: 6872-06-6
2-methyl indoline

Conditions

Conditions	Yield
With copper(l) chloride; sodium hydroxide In water at 120℃; under 760.051 Torr; for 4h; Reagent/catalyst; Temperature;	90%

: tert-Butyl-[1-(2-methyl-2,3-dihydro-indol-1-yl)-meth-(E)-ylidene]-amine

: 6872-06-6
2-methyl indoline

Conditions

Conditions	Yield
With hydrazine	80%

: 589-09-3
N-allyl-N-phenylamine

: 6872-06-6
2-methyl indoline

Conditions

Conditions	Yield
Zn(2+) montmorillonite for 0.05h; Cyclization; 3-Aza-Cope rearrangement; microwave irradiation;	80%
Multi-step reaction with 2 steps 1: BF3/Et2O / xylene / 72 h / Heating 2: Cp'2LaCH(TMS)2 (Cp'= η5Me5C5) / pentane / 24 h / Ambient temperature View Scheme

: 2058-74-4
1-methyl-1H-indole-2,3-dione

: 51315-70-9
2-methyl-1-(toluene-4-sulfonyl)-2,3-dihydro-1H-indole

: 6872-06-6
2-methyl indoline

Conditions

Conditions	Yield
Stage #1: 1-methyl-1H-indole-2,3-dione With sodium amalgam In N,N-dimethyl-formamide at 20℃; for 4h; Stage #2: 2-methyl-1-(toluene-4-sulfonyl)-2,3-dihydro-1H-indole In N,N-dimethyl-formamide at 110℃; for 18h;	79%

: 95-20-5
2-methyl-1H-indole

A: 50669-77-7
2-methyloctahydroindole

B: 6872-06-6
2-methyl indoline

Conditions

Conditions	Yield
With hydrogen; platinum on activated charcoal In acetic acid at 100℃; under 45600 Torr; for 2h;	A n/a B 70%
With hydrogen; platinum on activated charcoal In acetic acid at 100℃; under 45600 Torr; for 2h; Product distribution; other catalyst, other solvent, other temperature, other pressure;	A n/a B 70%
With hydrogen; cobalt(II) acetate for 3h;	A 17% B 55%
With hydrogen In decalin at 180℃; under 37503.8 Torr; for 16h; Autoclave;

: 61610-64-8
2-(ortho-bromophenyl)-1-methylethylamine

: 6872-06-6
2-methyl indoline

Conditions

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; palladium 10% on activated carbon; sodium t-butanolate In 1,3,5-trimethyl-benzene at 140℃; for 24h; Inert atmosphere;	70%

: 1-azido-2-n-propylbenzene

: 6872-06-6
2-methyl indoline

Conditions

Conditions	Yield
With C52H62FeN5O4S2(1-)*C8H20N(1+) In N,N-dimethyl-formamide at 115℃; for 24h; Molecular sieve;	57%
With tetrabutylammonium tricarbonylnitrosylferrate In 1,2-dichloro-ethane; N,N-dimethyl-formamide at 120℃; for 1h; Microwave irradiation; Inert atmosphere;

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

: 1-azido-2-n-propylbenzene

A: 1821-39-2
2-propylaniline

B: 6872-06-6
2-methyl indoline

Conditions

Conditions	Yield
With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]} In toluene at 120℃; for 16h; Inert atmosphere;	A 30% B 30%

...Expand

: 2-(2-chloro-propyl)-aniline

: 6872-06-6
2-methyl indoline

Conditions

Conditions	Yield
With water inactive 2-methyl-indoline;

: furan-2,3,5(4H)-trione pyridine (1:1)

: (+/-)-2-methyl-indoline; (1R)-3endo-bromo-2-oxo-(7antiC8)-bornane-8-sulfonate

: 6872-06-6
2-methyl indoline

: 81777-39-1
tert-Butyl-[1-(2-methyl-2,3-dihydro-indol-1-yl)-meth-(E)-ylidene]-amine

: 6872-06-6
2-methyl indoline

Conditions

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide for 3.5h; heating;

: 77435-11-1
ethyl 1-benzyl-2-methyl-1H-indole-3-carboxylate

A: 53855-47-3
ethyl 2-methyl-1H-indole-3-carboxylate

B: 77435-28-0
3-hydroxymethyl-2-methylindoline

C: 6872-06-6
2-methyl indoline

Conditions

Conditions	Yield
With ammonia; sodium In diethyl ether for 2h; Heating;	A n/a B 245 mg C 207 mg

...Expand

: 123-91-1
1,4-dioxane

: 95-20-5
2-methyl-1H-indole

copper oxide-chromium oxide: copper oxide-chromium oxide

: 6872-06-6
2-methyl indoline

Conditions

Conditions	Yield
at 190℃; under 220652 Torr; Hydrogenation;

...Expand

: 95-20-5
2-methyl-1H-indole

lead electrodes: lead electrodes

: 6872-06-6
2-methyl indoline

Conditions

Conditions	Yield
bei der elektrolytischen Reduktion in saurer Loesung;

: 95-20-5
2-methyl-1H-indole

: 7647-01-0
hydrogenchloride

tin: tin

: 6872-06-6
2-methyl indoline

...Expand

: 7647-01-0
hydrogenchloride

: 85440-79-5
1-nitroso-2-methylindoline

tin: tin

: 6872-06-6
2-methyl indoline

...Expand

: 7647-01-0
hydrogenchloride

: 23876-59-7
2-methyl-1H-indol-3-ylamine

zinc dust: zinc dust

: 6872-06-6
2-methyl indoline

...Expand

: 95-20-5
2-methyl-1H-indole

: 10034-85-2
hydrogen iodide

red phosphorus: red phosphorus

A: 1821-39-2
2-propylaniline

B: 6872-06-6
2-methyl indoline

...Expand

: 32704-22-6
2-allyl-phenylamine

A: 95-20-5
2-methyl-1H-indole

B: 6872-06-6
2-methyl indoline

Conditions

Conditions	Yield
In benzene for 0.833333h; Irradiation;
With air In benzene for 0.833333h; Irradiation;
In acetonitrile for 1h; Irradiation;
With 2-(1,3-bis(3'-hexylimidazol-2'-ylidene)phenylene)bis(dimethylamido)iodo zirconium (IV) In (2)H8-toluene at 160℃; for 192h; Inert atmosphere; Sealed tube; Glovebox;

: 32704-22-6
2-allyl-phenylamine

A: 95-20-5
2-methyl-1H-indole

B: 635-46-1
1,2,3,4-tetrahydroisoquinoline

C: 65826-91-7
1-(2-aminophenyl)-2-propanol

D: 6872-06-6
2-methyl indoline

Conditions

Conditions	Yield
With water; β‐cyclodextrin for 1h; Irradiation;

...Expand

: 68267-69-6
N-acetyl-2-allylaniline

A: 32704-22-6
2-allyl-phenylamine

B: 6872-06-6
2-methyl indoline

C: 3-allyl-2-aminoacetophenone

D: 3-allyl-4-aminoacetophenone

Conditions

Conditions	Yield
In benzene for 0.833333h; Irradiation;

...Expand

: 589-09-3
N-allyl-N-phenylamine

A: 6872-06-6
2-methyl indoline

B nickel: nickel

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: ZnCl2 / xylene / 5.5 h / 145 °C 2.1: selenenyl bromide resin; SnCl4 / CH2Cl2 / 0.5 h / -20 °C 2.2: n-Bu3SnH; AIBN / toluene / 2 h / 90 °C View Scheme

: 62-53-3
aniline

5-(4-formyl-3,5-dimethoxyphenoxy)valeric aldehyde linker on a polyethylene glycol resin: 5-(4-formyl-3,5-dimethoxyphenoxy)valeric aldehyde linker on a polyethylene glycol resin

A: 6872-06-6
2-methyl indoline

B nickel: nickel

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: dimethylformamide / 12 h / 20 °C 2.1: ZnCl2 / xylene / 5.5 h / 145 °C 3.1: selenenyl bromide resin; SnCl4 / CH2Cl2 / 0.5 h / -20 °C 3.2: n-Bu3SnH; AIBN / toluene / 2 h / 90 °C View Scheme

...Expand

: tert-Butyl-[1-(2,3-dihydro-indol-1-yl)-meth-(E)-ylidene]-amine

: 6872-06-6
2-methyl indoline

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 92 percent / t-BuLi / tetrahydrofuran / 1.) -20 deg C 2: 80 percent / N2H4 View Scheme

: 17697-12-0
benzeneseleninic anhydride

: 6872-06-6
2-methyl indoline

: 85677-01-6
2-methyl-3-(phenylselanyl)-1H-indole

Conditions

Conditions	Yield
In tetrahydrofuran for 1h;	100%
In tetrahydrofuran at 0℃; for 2h;	96%

: 124-63-0
methanesulfonyl chloride

: 6872-06-6
2-methyl indoline

: 66929-70-2
1H-indole,2,3-dihydro-2-methyl-1-(methylsulfonyl)

Conditions

Conditions	Yield
In pyridine at 20℃; for 20h;	100%
With pyridine at 20℃; for 2h; Inert atmosphere;	30%

2-Methylindoline Chemical Properties

Product Name: 2-Methylindoline (CAS NO.6872-06-6)

MF: C₉H₁₁N
MW: 133.190340 g/mol
Flash Point: 93.3 °C
Melting Point: -51 °C
EINECS: 229-971-0
Water Solubility: negligible
IUPAC Name: 2-methyl-2,3-dihydro-1H-indole
Density: 1.023 g/mL at 25 °C(lit.)
Refractive index: n20/D 1.569(lit.)
Enthalpy of Vaporization: 46.93 kJ/mol
Boiling Point: 232.6 °C at 760 mmHg
Vapour Pressure: 0.0585 mmHg at 25°C
Product Categories: Indoles and derivatives; pharmacetical; Indoline & Oxindole; Heterocyclic Compounds; Building Blocks; Heterocyclic Building Blocks; Indoles

2-Methylindoline Toxicity Data With Reference

ipr-mus LD50:360 mg/kg

FATOAO Farmakologiya i Toksikologiya (Moscow). 29 (1966),721.

2-Methylindoline Consensus Reports

Reported in EPA TSCA Inventory.

2-Methylindoline Safety Profile

A poison by intraperitoneal route. When heated to decomposition it emits toxic vapors of NO_x.
Safety Information of 2-Methylindoline (CAS NO.6872-06-6):
Hazard Codes : Xi Irritant ,Xn Harmful
Risk Statements: 36/37/38-52/53-22
36/37/38: Irritating to eyes, respiratory system and skin
52/53: Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment
22: Harmful if swallowed
Safety Statements: 26-36/37/39-60-57
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36/37/39: Wear suitable protective clothing, gloves and eye/face protection 60: This material and/or its container must be disposed of as hazardous waste
57: Use appropriate container to avoid environmental contamination
WGK Germany: 3
RTECS: NM1926350
Hazard Note : Irritant

2-Methylindoline Specification

2-Methylindoline , its CAS NO. is 6872-06-6, the synonyms are R,S)-2-Methyl-2,3-dihydro-1H-indole ; 1H-Indole, 2,3-dihydro-2-methyl- ; 1H-Indole,2,3-dihydro-2-methyl- ; 2,3-dihydro-2-methyl-1h-indol ; 2,3-Dihydro-2-methyl-1H-indole ; 2-Methyl-2,3-dihydroindole ; 2-methyl-indolin ; alpha-Methyldihydroindole .

Product Name

2-Methylindoline

Synthetic route

2-Methylindoline Chemical Properties

2-Methylindoline Toxicity Data With Reference

2-Methylindoline Consensus Reports

2-Methylindoline Safety Profile

2-Methylindoline Specification

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