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6872-06-6

Basic Information
CAS No.: 6872-06-6
Name: 2-Methylindoline
Molecular Structure:
Molecular Structure of 6872-06-6 (2-Methylindoline)
Formula: C9H11N
Molecular Weight: 133.19
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;
EINECS: 229-971-0
Density: 0.989 g/cm3
Melting Point: -51 °C
Boiling Point: 232.6 °C at 760 mmHg
Flash Point: 93.3 °C
Solubility: negligible
Appearance: clear yellow to brown liquid
Hazard Symbols: HarmfulXn, IrritantXi
Risk Codes: 36/37/38-52/53-22
Safety: 26-36/37/39-60-57
Transport Information:
PSA: 12.03000
LogP: 2.18110
Synthetic route
95-20-5

2-methyl-1H-indole

6872-06-6

2-methyl indoline

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With hydrazine80%
589-09-3

N-allyl-N-phenylamine

6872-06-6

2-methyl indoline

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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%

2-(2-chloro-propyl)-aniline

6872-06-6

2-methyl indoline

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With ammonia; sodium In diethyl ether for 2h; Heating;A n/a
B 245 mg
C 207 mg
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
ConditionsYield
at 190℃; under 220652 Torr; Hydrogenation;
95-20-5

2-methyl-1H-indole

lead electrodes

lead electrodes

6872-06-6

2-methyl indoline

Conditions
ConditionsYield
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

7647-01-0

hydrogenchloride

85440-79-5

1-nitroso-2-methylindoline

tin

tin

6872-06-6

2-methyl indoline

7647-01-0

hydrogenchloride

23876-59-7

2-methyl-1H-indol-3-ylamine

zinc dust

zinc dust

6872-06-6

2-methyl indoline

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

32704-22-6

2-allyl-phenylamine

A

95-20-5

2-methyl-1H-indole

B

6872-06-6

2-methyl indoline

Conditions
ConditionsYield
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
ConditionsYield
With water; β‐cyclodextrin for 1h; Irradiation;
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
ConditionsYield
In benzene for 0.833333h; Irradiation;
589-09-3

N-allyl-N-phenylamine

A

6872-06-6

2-methyl indoline

B

nickel

nickel

Conditions
ConditionsYield
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
ConditionsYield
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

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

6872-06-6

2-methyl indoline

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

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    Molecular Formula C9H11N Molecular Weight 133.19 CAS Registry Number 6872-06-6 EINECS 229-971-0 ISO system SGS inspection Appearance:transparent liquid Storage:Warehouse ventilation, away from open flame, high temperature, and antioxidant

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    2-Methylindoline CAS: 6872-06-6

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    Chemical Name: 2-Methylindoline CAS No.: 6872-06-6 Chemical Structure: Molecular weight: 133.19 Appearance: Transparent to yellow liquid Appearance: Colorless Liquid Storage:Store in cool and dry place, away from sun light. Package: 25kg

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    2-Methylindoline 6872-06-6

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  • 2-Methylindoline

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Chemistry

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

Toxicity Data With Reference

1.    

ipr-mus LD50:360 mg/kg

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

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

A poison by intraperitoneal route. When heated to decomposition it emits toxic vapors of NOx.
Safety Information of 2-Methylindoline (CAS NO.6872-06-6):
Hazard Codes : XiIrritant,XnHarmful 
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

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 .