Product Name

  • Name

    2-Methylindene

  • EINECS
  • CAS No. 2177-47-1
  • Article Data54
  • CAS DataBase
  • Density 1.003 g/cm3
  • Solubility
  • Melting Point 80°C
  • Formula C10H10
  • Boiling Point 205.567 °C at 760 mmHg
  • Molecular Weight 130.189
  • Flash Point 70.76 °C
  • Transport Information
  • Appearance transparent to yellow liquid
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 2177-47-1 (2-Methylindene)
  • Hazard Symbols
  • Synonyms 2-Methylindene;2-Methyl-1H-indene;Indene,2-methyl- (7CI,8CI);
  • PSA 0.00000
  • LogP 2.64600

Synthetic route

2,3-dihydro-2-methyl-1H-inden-1-one
17496-14-9

2,3-dihydro-2-methyl-1H-inden-1-one

2-Methylindene
2177-47-1

2-Methylindene

Conditions
ConditionsYield
With toluene-4-sulfonic acid; 2,2-Dimethyl-1,3-propanediol In toluene for 24h; Reflux;92%
With oxalic acid
Multi-step reaction with 2 steps
1: NaBH4 / tetrahydrofuran; methanol / 4 h / 25 °C
2: p-toluenesulfonic acid*H2O / benzene / 1 h / Heating
View Scheme
2-methylene-2,3-dihydro-1H-indene
68846-65-1

2-methylene-2,3-dihydro-1H-indene

2-Methylindene
2177-47-1

2-Methylindene

Conditions
ConditionsYield
With hydrogen bromide In acetonitrile for 1h; Heating;90%
2-bromoindene
10485-09-3

2-bromoindene

[3-(dimethylamino)propyl]dimethyl aluminium(III)

[3-(dimethylamino)propyl]dimethyl aluminium(III)

A

2-Methylindene
2177-47-1

2-Methylindene

B

1,2-dimethylindene
70063-93-3

1,2-dimethylindene

C

1-indene
95-13-6

1-indene

Conditions
ConditionsYield
With tetrakis(triphenylphosphine)palladium dichloride In benzene at 80℃; for 2h; Yields of byproduct given;A 88%
B n/a
C n/a
2-Trimethylsilanylmethyl-indan-2-ol
105991-56-8

2-Trimethylsilanylmethyl-indan-2-ol

2-Methylindene
2177-47-1

2-Methylindene

Conditions
ConditionsYield
With potassium hydride In tetrahydrofuran Ambient temperature;86%
1,1-dibromo-3-(2-bromophenyl)-2-methylpropene
507261-02-1

1,1-dibromo-3-(2-bromophenyl)-2-methylpropene

2-Methylindene
2177-47-1

2-Methylindene

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane at -90℃; for 0.5h;85%
Stage #1: 1,1-dibromo-3-(2-bromophenyl)-2-methylpropene With n-butyllithium In tetrahydrofuran; hexane at -90℃; for 0.5h;
Stage #2: With methanol; ammonium chloride In tetrahydrofuran; hexane
85%
1-allyl-2-(chloromethyl)benzene
89121-39-1

1-allyl-2-(chloromethyl)benzene

A

2-Methylindene
2177-47-1

2-Methylindene

B

2-methylene-2,3-dihydro-1H-indene
68846-65-1

2-methylene-2,3-dihydro-1H-indene

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); triethylamine In acetonitrile for 1h; Heating;A 1%
B 82%
With tetrakis(triphenylphosphine) palladium(0); triethylamine In acetonitrile for 1h; Product distribution; Heating; other o-alkenyl- and o-alkynylbenzyl halides, other time, other reagents;A 1%
B 82%
1-allyl-2-(bromomethyl)benzene
120906-16-3

1-allyl-2-(bromomethyl)benzene

A

2-Methylindene
2177-47-1

2-Methylindene

B

2-methylene-2,3-dihydro-1H-indene
68846-65-1

2-methylene-2,3-dihydro-1H-indene

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); triethylamine In acetonitrile for 0.5h; Heating;A 1%
B 82%
2-hydroxy-2-methylindan
33223-84-6

2-hydroxy-2-methylindan

2-Methylindene
2177-47-1

2-Methylindene

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene for 4h; Dehydration; Heating;69%
With phosphoric acid at 150℃;37%
With phosphorus pentoxide; benzene
1-allyl-2-(iodomethyl)benzene
120906-17-4

1-allyl-2-(iodomethyl)benzene

A

2-Methylindene
2177-47-1

2-Methylindene

B

2-methylene-2,3-dihydro-1H-indene
68846-65-1

2-methylene-2,3-dihydro-1H-indene

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); triethylamine In acetonitrile for 0.5h; Heating;A 18%
B 64%
Methanesulfonic acid 2-allyl-benzyl ester

Methanesulfonic acid 2-allyl-benzyl ester

A

2-Methylindene
2177-47-1

2-Methylindene

B

2-methylene-2,3-dihydro-1H-indene
68846-65-1

2-methylene-2,3-dihydro-1H-indene

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); triethylamine In acetonitrile for 1h; Heating;A 1%
B 60%
C16H18O2S

C16H18O2S

methylmagnesium bromide
75-16-1

methylmagnesium bromide

2-Methylindene
2177-47-1

2-Methylindene

Conditions
ConditionsYield
With bis(triphenylphosphine)nickel(II) diiodide; tricyclohexylphosphine In tetrahydrofuran at 70℃; Kumada Cross-Coupling; Inert atmosphere; chemoselective reaction;57%
1-[(2-13C)ethynyl]-2-(prop-1-yn-1-yl)benzene

1-[(2-13C)ethynyl]-2-(prop-1-yn-1-yl)benzene

2-Methylindene
2177-47-1

2-Methylindene

Conditions
ConditionsYield
With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]gold bis(trifluoromethanesulfonyl)imidate; water In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; Schlenk technique;53%
2,3-dihydro-2-methyl-1H-inden-1-one
17496-14-9

2,3-dihydro-2-methyl-1H-inden-1-one

2-hydroxy-2-methylindan
33223-84-6

2-hydroxy-2-methylindan

water
7732-18-5

water

2-Methylindene
2177-47-1

2-Methylindene

Conditions
ConditionsYield
With MeMgBr; toluene-4-sulfonic acid; hydroquinone In toluene48%
1-ethynyl-2-(prop-1-yn-1-yl)benzene
849799-68-4

1-ethynyl-2-(prop-1-yn-1-yl)benzene

2-Methylindene
2177-47-1

2-Methylindene

Conditions
ConditionsYield
With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]gold bis(trifluoromethanesulfonyl)imidate; water In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; Schlenk technique;42%
sulfuric acid
7664-93-9

sulfuric acid

2-indanone
615-13-4

2-indanone

methyl iodide
74-88-4

methyl iodide

2-Methylindene
2177-47-1

2-Methylindene

Conditions
ConditionsYield
With magnesium In diethyl ether; dichloromethane; water; toluene30%
Carbonic acid 2-allyl-benzyl ester methyl ester

Carbonic acid 2-allyl-benzyl ester methyl ester

A

2-Methylindene
2177-47-1

2-Methylindene

B

2-methylene-2,3-dihydro-1H-indene
68846-65-1

2-methylene-2,3-dihydro-1H-indene

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); triethylamine In acetonitrile for 120h; Heating;A 23%
B 26%
butyl magnesium bromide
693-04-9

butyl magnesium bromide

3-trifluoromethanesulfonyloxy-2-methyl-1H-indene

3-trifluoromethanesulfonyloxy-2-methyl-1H-indene

A

2-Methylindene
2177-47-1

2-Methylindene

B

3-butyl-2-methyl-1H-indene
229031-59-8

3-butyl-2-methyl-1H-indene

Conditions
ConditionsYield
1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In tetrahydrofuran; toluene at 55℃; for 2h;A n/a
B 24%
3-trifluoromethanesulfonyloxy-2-methyl-1H-indene

3-trifluoromethanesulfonyloxy-2-methyl-1H-indene

A

2-Methylindene
2177-47-1

2-Methylindene

B

3-butyl-2-methyl-1H-indene
229031-59-8

3-butyl-2-methyl-1H-indene

Conditions
ConditionsYield
With butyl magnesium bromide; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In tetrahydrofuran; toluene at 55℃; for 2h;A n/a
B 24%
naphthalene-2-sulfonate
120-18-3

naphthalene-2-sulfonate

2-hydroxy-2-methylindan
33223-84-6

2-hydroxy-2-methylindan

2-Methylindene
2177-47-1

2-Methylindene

Conditions
ConditionsYield
at 140℃;
at 140℃;
2-Methylindene
2177-47-1

2-Methylindene

Conditions
ConditionsYield
at 350 - 650℃; Pyrolysis;
2-Methylindene
2177-47-1

2-Methylindene

Conditions
ConditionsYield
at 350 - 600℃; Pyrolysis;
2-methylindane
824-63-5

2-methylindane

2-Methylindene
2177-47-1

2-Methylindene

Conditions
ConditionsYield
With sodium acetate; acetic acid (electrolysis);
syn-9-Acetoxy-9-methylbicyclo <4.2.1> nona-2.4.7-trien

syn-9-Acetoxy-9-methylbicyclo <4.2.1> nona-2.4.7-trien

2-Methylindene
2177-47-1

2-Methylindene

Conditions
ConditionsYield
at 200℃;
tetralin
119-64-2

tetralin

decane
124-18-5

decane

A

styrene
292638-84-7

styrene

B

naphthalene
91-20-3

naphthalene

C

1,2-Dihydronaphthalene
447-53-0

1,2-Dihydronaphthalene

D

2-Methylindene
2177-47-1

2-Methylindene

E

3-Methylindene
767-60-2

3-Methylindene

F

1-indene
95-13-6

1-indene

Conditions
ConditionsYield
at 730℃; Product distribution; Mechanism; other temperature;A 4.4 % Chromat.
B 14 % Chromat.
C 35.7 % Chromat.
D 1.2 % Chromat.
E 4.3 % Chromat.
F 7.1 % Chromat.
INDANE
496-11-7

INDANE

A

naphthalene
91-20-3

naphthalene

B

1,2-Dihydronaphthalene
447-53-0

1,2-Dihydronaphthalene

C

2-Methylindene
2177-47-1

2-Methylindene

D

3-Methylindene
767-60-2

3-Methylindene

E

toluene
108-88-3

toluene

F

1-indene
95-13-6

1-indene

Conditions
ConditionsYield
at 800℃; Product distribution; Mechanism;A 2.5 % Chromat.
B 1.1 % Chromat.
C 2.6 % Chromat.
D 5.7 % Chromat.
E 4.7 % Chromat.
F 77.2 % Chromat.
1-methylene-2-phenylcyclopropane
29817-09-2, 22664-13-7

1-methylene-2-phenylcyclopropane

A

1-phenylmethylenecyclopropane
7555-67-1

1-phenylmethylenecyclopropane

B

2-Methylindene
2177-47-1

2-Methylindene

C

2-methylene-2,3-dihydro-1H-indene
68846-65-1

2-methylene-2,3-dihydro-1H-indene

Conditions
ConditionsYield
In gas at 150.7 - 280.8℃; Kinetics; Thermodynamic data; also further temperatures in the presence of O2; Ea, ΔH(excit.), ΔS(excit.);
1-Methylinden
767-59-9

1-Methylinden

2-Methylindene
2177-47-1

2-Methylindene

Conditions
ConditionsYield
In cyclohexane at 25℃; Quantum yield; Irradiation;
In hexane Quantum yield; Ambient temperature; Irradiation;
1-Methylinden
767-59-9

1-Methylinden

A

2-Methylindene
2177-47-1

2-Methylindene

B

3-Methylindene
767-60-2

3-Methylindene

Conditions
ConditionsYield
at 42℃; for 0.0166667h; Irradiation;
at 42℃; Product distribution; Irradiation; effect of excitation wavelength; various reaction times;
1-Methylinden
767-59-9

1-Methylinden

A

2-Methylindene
2177-47-1

2-Methylindene

B

3-Methylindene
767-60-2

3-Methylindene

C

1-indene
95-13-6

1-indene

Conditions
ConditionsYield
at 42℃; for 0.0166667h; Product distribution; Irradiation; initial sample temperatures from -15 deg C to 25 deg C; also with varying pressures of n-butane;
3-Methylindene
767-60-2

3-Methylindene

A

2-Methylindene
2177-47-1

2-Methylindene

B

1-Methylinden
767-59-9

1-Methylinden

Conditions
ConditionsYield
at 42℃; for 0.0166667h; Irradiation;
at 42℃; Product distribution; Irradiation; effect of excitation wavelength; various reaction times;
2-Methylindene
2177-47-1

2-Methylindene

(2-methylindenyl)lithium
56423-64-4

(2-methylindenyl)lithium

Conditions
ConditionsYield
With n-butyllithium In hexane at 20℃; for 5h;98.4%
With n-butyllithium In hexane85%
1-iodo-butane
542-69-8

1-iodo-butane

2-Methylindene
2177-47-1

2-Methylindene

1-Butyl-2-methyl-1H-indene

1-Butyl-2-methyl-1H-indene

Conditions
ConditionsYield
Stage #1: 2-Methylindene With n-butyllithium In tetrahydrofuran; hexane at 20℃; for 3h; Inert atmosphere; Cooling with ice;
Stage #2: 1-iodo-butane In tetrahydrofuran; hexane for 2h; Cooling with ice;
97%
2-Methylindene
2177-47-1

2-Methylindene

1-tert-butoxy-6-iodohexane
81060-09-5

1-tert-butoxy-6-iodohexane

3-(6-tert-butoxyhexyl)-2-methyl-1H-indene

3-(6-tert-butoxyhexyl)-2-methyl-1H-indene

Conditions
ConditionsYield
With tetra-(n-butyl)ammonium iodide; potassium hydroxide In toluene at 25℃; for 24h;97%
2-Methylindene
2177-47-1

2-Methylindene

2-methylindane
824-63-5

2-methylindane

Conditions
ConditionsYield
With hydrogen; platinum(IV) oxide In tetrahydrofuran under 1034.3 - 1551.4 Torr;95%
With C7H14N3(1+)*Cl(1-); sodium triethylborohydride; cobalt(II) chloride In tetrahydrofuran at 60℃; under 37503.8 Torr; for 16h; Autoclave;95%
With hydrogen; palladium on activated charcoal In hexane for 5h; Catalytic hydrogenation;91%
2-Methylindene
2177-47-1

2-Methylindene

2,2'-dimethyl-1,1'-biindenyl
110452-27-2

2,2'-dimethyl-1,1'-biindenyl

Conditions
ConditionsYield
With n-butyllithium; copper dichloride 1.) ether, -30 deg C, 30 min, 2.) ether, -30 deg C, 30 min;95%
diiodomethane
75-11-6

diiodomethane

2-Methylindene
2177-47-1

2-Methylindene

5-Methyl-2,3-benzobicyclo<3.1.0>hex-2-en
78926-56-4

5-Methyl-2,3-benzobicyclo<3.1.0>hex-2-en

Conditions
ConditionsYield
Stage #1: diiodomethane With diethylzinc; trifluoroacetic acid In hexane; dichloromethane for 0.333333h; cooling;
Stage #2: 2-Methylindene In hexane; dichloromethane at 20℃; for 3h;
94%
2-Methylindene
2177-47-1

2-Methylindene

chloro-diphenylphosphine
1079-66-9

chloro-diphenylphosphine

3-(diphenylphosphino)-2-methylindene
718638-63-2

3-(diphenylphosphino)-2-methylindene

Conditions
ConditionsYield
Stage #1: 2-Methylindene With n-butyllithium In diethyl ether at -78 - 20℃;
Stage #2: chloro-diphenylphosphine In diethyl ether at -78 - 20℃;
94%
2-Methylindene
2177-47-1

2-Methylindene

7-(bromomethyl)-2-methyl-1H-indene
1126942-56-0

7-(bromomethyl)-2-methyl-1H-indene

2-methyl-1-[(2-methyl-1H-inden-7-yl)methyl]-1H-indene
1126942-68-4

2-methyl-1-[(2-methyl-1H-inden-7-yl)methyl]-1H-indene

Conditions
ConditionsYield
Stage #1: 2-Methylindene With n-butyllithium In diethyl ether; hexane at 0 - 20℃; for 2h;
Stage #2: 7-(bromomethyl)-2-methyl-1H-indene In tetrahydrofuran; diethyl ether; hexane at -80 - 20℃; for 12h;
92%
bromobenzene
108-86-1

bromobenzene

2-Methylindene
2177-47-1

2-Methylindene

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

4,4,5,5-tetramethyl-2-(2-methyl-1-phenyl-2,3-dihydro-1H-inden-2-yl)-1,3,2-dioxaborolane

4,4,5,5-tetramethyl-2-(2-methyl-1-phenyl-2,3-dihydro-1H-inden-2-yl)-1,3,2-dioxaborolane

Conditions
ConditionsYield
Stage #1: bis(pinacol)diborane With potassium ethoxide In N,N-dimethyl acetamide at 20℃; for 1h; Inert atmosphere; Sealed tube;
Stage #2: bromobenzene; 2-Methylindene With (1,2-dimethoxyethane)dichloronickel(II) In N,N-dimethyl acetamide at 0 - 20℃; for 24h; Inert atmosphere; Sealed tube;
91%
2-Methylindene
2177-47-1

2-Methylindene

chloro(dimethyl)(2-methyl-1H-inden-7-yl)silane
1126942-58-2

chloro(dimethyl)(2-methyl-1H-inden-7-yl)silane

dimethyl(2-methyl-1H-inden-1-yl)(2-methyl-1H-inden-7-yl)silane
1126942-86-6

dimethyl(2-methyl-1H-inden-1-yl)(2-methyl-1H-inden-7-yl)silane

Conditions
ConditionsYield
Stage #1: 2-Methylindene With n-butyllithium In diethyl ether; hexane at 0 - 20℃; for 12h;
Stage #2: With copper(l) cyanide In diethyl ether; hexane at -50 - -30℃; for 1h;
Stage #3: chloro(dimethyl)(2-methyl-1H-inden-7-yl)silane In diethyl ether; hexane at -80 - 20℃; for 12h;
88%
1-methyl-1H-imidazole
616-47-7

1-methyl-1H-imidazole

2-Methylindene
2177-47-1

2-Methylindene

ammonium chloride

ammonium chloride

dimethylsilicon dichloride
75-78-5

dimethylsilicon dichloride

bis(2-methyl-1-indenyl)-dimethylsilane
143232-13-7

bis(2-methyl-1-indenyl)-dimethylsilane

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; toluene87%
2-Methylindene
2177-47-1

2-Methylindene

cyclohexa-2,5-dien-1-yltriethylgermane

cyclohexa-2,5-dien-1-yltriethylgermane

triethyl(2-methyl-2,3-dihydro-1H-inden-2-yl)germane

triethyl(2-methyl-2,3-dihydro-1H-inden-2-yl)germane

Conditions
ConditionsYield
With tris(pentafluorophenyl)borate at 20℃; for 3h; Glovebox;87%
2-Methylindene
2177-47-1

2-Methylindene

2-bromoindene
10485-09-3

2-bromoindene

dimethylsilicon dichloride
75-78-5

dimethylsilicon dichloride

C21H22Si

C21H22Si

Conditions
ConditionsYield
Stage #1: 2-bromoindene With iodine; magnesium In tetrahydrofuran at 80℃; for 3h; Inert atmosphere;
Stage #2: dimethylsilicon dichloride In tetrahydrofuran; hexane at -78℃; for 18h;
Stage #3: 2-Methylindene With 1,3-dimethyl-2-imidazolidinone; n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 5h; Inert atmosphere;
87%
dimethylmonochlorosilane
1066-35-9

dimethylmonochlorosilane

2-Methylindene
2177-47-1

2-Methylindene

3-dimethylsilyl-2-methylindene

3-dimethylsilyl-2-methylindene

Conditions
ConditionsYield
Stage #1: 2-Methylindene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Metallation;
Stage #2: dimethylmonochlorosilane In tetrahydrofuran; hexane at 20℃; for 12h; silylation; Further stages.;
86%
2-Methylindene
2177-47-1

2-Methylindene

2-methylindene oxide
3199-85-7

2-methylindene oxide

Conditions
ConditionsYield
With dihydrogen peroxide; Ru(2,2':6',2''-terpyridine)(2,6-pyridinedicarboxylate) In tert-Amyl alcohol at 20℃; for 12h; Conversion of starting material;86%
With dihydrogen peroxide; ruthenium(2,2',6':2''-terpyridine)(2,6-pyridinedicarboxylate) In tert-Amyl alcohol at 20℃; for 12h;86 % Chromat.
2-Methylindene
2177-47-1

2-Methylindene

chloro(1,3-dimethyl-1H-inden-2-yl)dimethylsilane

chloro(1,3-dimethyl-1H-inden-2-yl)dimethylsilane

(1,3-dimethyl-1H-inden-2-yl)(2-methyl-1H-inden-1-yl)dimethylsilane

(1,3-dimethyl-1H-inden-2-yl)(2-methyl-1H-inden-1-yl)dimethylsilane

Conditions
ConditionsYield
Stage #1: 2-Methylindene With n-butyllithium In diethyl ether; hexane at 20℃; Inert atmosphere;
Stage #2: chloro(1,3-dimethyl-1H-inden-2-yl)dimethylsilane In diethyl ether; hexane at -80 - 20℃; Inert atmosphere;
86%
ethyl bromide
74-96-4

ethyl bromide

2-Methylindene
2177-47-1

2-Methylindene

3-ethyl-2-methyl-1H-indene
51293-55-1

3-ethyl-2-methyl-1H-indene

Conditions
ConditionsYield
Stage #1: 2-Methylindene With n-butyllithium In diethyl ether; hexane at 0℃;
Stage #2: ethyl bromide In diethyl ether at 20℃;
85%
2-Methylindene
2177-47-1

2-Methylindene

dimethylsilicon dichloride
75-78-5

dimethylsilicon dichloride

bis(2-methyl-1-indenyl)-dimethylsilane
143232-13-7

bis(2-methyl-1-indenyl)-dimethylsilane

Conditions
ConditionsYield
Stage #1: 2-Methylindene With n-butyllithium In tetrahydrofuran; toluene at 20 - 80℃; for 1h;
Stage #2: dimethylsilicon dichloride In tetrahydrofuran; toluene at 20 - 60℃;
84%
Stage #1: 2-Methylindene With n-butyllithium In tetrahydrofuran; toluene at 80℃; for 1h;
Stage #2: dimethylsilicon dichloride In tetrahydrofuran; toluene at 40 - 60℃;
84%
With n-butyllithium 1) n-hexane, THF, reflux, 1 h , 2) r. t., 15 h; Multistep reaction;
With n-butyllithium In tetrahydrofuran; hexane; water
With n-butyllithium In tetrahydrofuran; water; toluene8.16 g (84%)
2-Methylindene
2177-47-1

2-Methylindene

2-methyl-2,3-dihydro-1H-inden-2-amine
312753-94-9

2-methyl-2,3-dihydro-1H-inden-2-amine

Conditions
ConditionsYield
With benzene-1,3-dicarbonitrile; 1,2,4-triphenylbenzene; ammonia In water; acetonitrile at 20℃; Irradiation;83%
Stage #1: 2-Methylindene With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]}; O-(2,4-dinitrophenyl)hydroxylamine In 2,2,2-trifluoroethanol at 0 - 5℃; for 5h;
Stage #2: With palladium on activated charcoal; hydrogen In 2,2,2-trifluoroethanol at 25℃; for 15h;
60%
Multi-step reaction with 2 steps
1: bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]}; O-(2,4-dinitrophenyl)hydroxylamine / 2,2,2-trifluoroethanol / 2.5 h / 0 - 5 °C / Inert atmosphere
2: palladium 10% on activated carbon; hydrogen / methanol / 15 h / 760.05 Torr
View Scheme
2-Methylindene
2177-47-1

2-Methylindene

Diethyl carbonate
105-58-8

Diethyl carbonate

ethyl 2-methyl-1H-indene-3-carboxylate

ethyl 2-methyl-1H-indene-3-carboxylate

Conditions
ConditionsYield
Stage #1: 2-Methylindene With sodium hydride In tetrahydrofuran at 0 - 20℃; for 0.5h;
Stage #2: Diethyl carbonate In tetrahydrofuran for 7h; Reflux;
83%
2-Methylindene
2177-47-1

2-Methylindene

methoxybenzene
100-66-3

methoxybenzene

(1RS,2RS)-1-(4-methoxyphenyl)-2-methyl-2,3-dihydro-1H-indene

(1RS,2RS)-1-(4-methoxyphenyl)-2-methyl-2,3-dihydro-1H-indene

Conditions
ConditionsYield
With toluene-4-sulfonic acid In chloroform-d1 at 20℃; for 5h; Friedel-Crafts Alkylation; Inert atmosphere; stereoselective reaction;83%
diethylchlorophosphine
686-69-1

diethylchlorophosphine

2-Methylindene
2177-47-1

2-Methylindene

tributyltin chloride
1461-22-9

tributyltin chloride

1-diethylphosphanyl-1-tributylstannyl-2-methylindene
247027-70-9

1-diethylphosphanyl-1-tributylstannyl-2-methylindene

Conditions
ConditionsYield
With n-BuLi In diethyl ether; hexane byproducts: LiCl; (anaerobic conds.); addn. of n-BuLi in hexane at 0°C to 2-methylindene in Et2O, stirring (room temp., 1 h), addn. of ClPEt2 at 0°C, stirring (r.t., ca. 1 h), addn. of n-BuLi at 0°C, stirring (1 h), addn. of Bu3SnCl, stirring (1.5 h); removal of volatiles (vac.), addn. of hexane, filtration, removal of solvent;80%
2,2'-bis-(bromomethyl)-1,1'-biphenyl
38274-14-5

2,2'-bis-(bromomethyl)-1,1'-biphenyl

2-Methylindene
2177-47-1

2-Methylindene

2,2'-bis(2-methylinden-3-ylmethyl) biphenyl

2,2'-bis(2-methylinden-3-ylmethyl) biphenyl

Conditions
ConditionsYield
Stage #1: 2-Methylindene With n-butyllithium In tetrahydrofuran at 0 - 20℃; for 3h; Inert atmosphere;
Stage #2: 2,2'-bis-(bromomethyl)-1,1'-biphenyl In tetrahydrofuran at -40 - 20℃; Inert atmosphere; Schlenk technique;
75%

2-Methylindene Chemical Properties

Molecular Structure of 2-Methylindene (CAS No.2177-47-1):
 
Molecular Formula: C10H10 
Molecular Weight: 130.1864
CAS No: 2177-47-1
Index of Refraction: 1.572
Molar Refractivity: 42.73 cm3
Molar Volume: 129.8 cm3
Surface Tension: 35.3 dyne/cm
Density: 1.002 g/cm3
Flash Point: 70.8 °C
Enthalpy of Vaporization: 42.38 kJ/mol
Boiling Point: 205.6 °C at 760 mmHg
Vapour Pressure: 0.356 mmHg at 25°C
InChI: InChI=1/C10H10/c1-8-6-9-4-2-3-5-10(9)7-8/h2-6H,7H2,1H3
InChIKey: YSAXEHWHSLANOM-UHFFFAOYAW
Std. InChI: InChI=1S/C10H10/c1-8-6-9-4-2-3-5-10(9)7-8/h2-6H,7H2,1H3
Std. InChIKey: YSAXEHWHSLANOM-UHFFFAOYSA-N
IUPAC Name: 2-Methyl-1H-indene 
Product Categories: Indanone Indene;Arenes;Building Blocks;Organic Building Blocks

2-Methylindene Safety Profile

WGK Germany: 3

2-Methylindene Specification

   2-Methylindene (CAS No.2177-47-1), its synonyms are 1H-indene, 2-methyl- ; 2-Methyl-1H-indene .

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