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118-12-7 Usage

Chemical Properties

clear red liquid

Uses

Reactant for:Cycloaddition reactionsPreparation of red photochromic dyesSynthesis of photochromic homopolymers via ring-opening metathesis polymerization

Check Digit Verification of cas no

The CAS Registry Mumber 118-12-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 8 respectively; the second part has 2 digits, 1 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 118-12:
(5*1)+(4*1)+(3*8)+(2*1)+(1*2)=37
37 % 10 = 7
So 118-12-7 is a valid CAS Registry Number.
InChI:InChI=1/C12H15N/c1-9-12(2,3)10-7-5-6-8-11(10)13(9)4/h5-8H,1H2,2-4H3

118-12-7 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
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  • Detail
  • Alfa Aesar

  • (A16741)  1,3,3-Trimethyl-2-methyleneindoline, 95%   

  • 118-12-7

  • 50g

  • 737.0CNY

  • Detail
  • Alfa Aesar

  • (A16741)  1,3,3-Trimethyl-2-methyleneindoline, 95%   

  • 118-12-7

  • 250g

  • 1760.0CNY

  • Detail
  • Aldrich

  • (M46209)  1,3,3-Trimethyl-2-methyleneindoline  97%

  • 118-12-7

  • M46209-5G

  • 300.69CNY

  • Detail
  • Aldrich

  • (M46209)  1,3,3-Trimethyl-2-methyleneindoline  97%

  • 118-12-7

  • M46209-100G

  • 673.92CNY

  • Detail

118-12-7SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 1,3,3-Trimethyl-2-methyleneindoline

1.2 Other means of identification

Product number -
Other names 1,3,3-trimethyl-2-methylideneindole

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:118-12-7 SDS

118-12-7Synthetic route

2-(1,3,3-tri-methylindolin-2-ylidene)acetonitrile
5114-82-9

2-(1,3,3-tri-methylindolin-2-ylidene)acetonitrile

1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

Conditions
ConditionsYield
With hydrogenchloride for 6h; Heating;100%
spiro-1,3,3-trimethylindoline<2:3'>-3',4'-dihydroisoxazole
144598-21-0

spiro-1,3,3-trimethylindoline<2:3'>-3',4'-dihydroisoxazole

1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

Conditions
ConditionsYield
With hydrogenchloride for 6h; Heating;100%
1,3,3-trimethyl-2-methyleneacetamidoindoline
301673-89-2

1,3,3-trimethyl-2-methyleneacetamidoindoline

1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

Conditions
ConditionsYield
With hydrogenchloride for 6h; Heating;100%
2,3,3-trimethylindoleniune
1640-39-7

2,3,3-trimethylindoleniune

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

Conditions
ConditionsYield
at 180 - 220℃; under 22502.3 - 37503.8 Torr; Inert atmosphere; Sealed tube; Autoclave;97.8%
1,2,3,3-tetramethyl-3H-indolium iodide
5418-63-3

1,2,3,3-tetramethyl-3H-indolium iodide

1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

Conditions
ConditionsYield
With sodium hydroxide In diethyl ether; water for 0.5h;71%
With potassium hydroxide at 20℃; for 1h;55%
With potassium hydroxide Ambient temperature;
(S)-1-phenyl-1-propanol
613-87-6

(S)-1-phenyl-1-propanol

1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

Conditions
ConditionsYield
10%
indole
120-72-9

indole

methyl iodide
74-88-4

methyl iodide

1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

Conditions
ConditionsYield
With methanol; sodium carbonate at 130℃;
2-methyl-1H-indole
95-20-5

2-methyl-1H-indole

methanol
67-56-1

methanol

1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

Conditions
ConditionsYield
With hydrogenchloride at 160℃;
2-methyl-1H-indole
95-20-5

2-methyl-1H-indole

methyl iodide
74-88-4

methyl iodide

1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

1-methylindole
603-76-9

1-methylindole

methyl iodide
74-88-4

methyl iodide

1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

Conditions
ConditionsYield
With potassium hydroxide at 40℃;
With methanol at 100℃;
3-Methylindole
83-34-1

3-Methylindole

methyl iodide
74-88-4

methyl iodide

1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

Conditions
ConditionsYield
With methanol at 130℃;
2,3-dimethylindole
91-55-4

2,3-dimethylindole

methyl iodide
74-88-4

methyl iodide

1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

Conditions
ConditionsYield
at 100℃;
With methanol at 100℃;
2,3,3-trimethylindoleniune
1640-39-7

2,3,3-trimethylindoleniune

methyl iodide
74-88-4

methyl iodide

1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

1,2,3-trimethylindole
1971-46-6

1,2,3-trimethylindole

methyl iodide
74-88-4

methyl iodide

1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

Conditions
ConditionsYield
at 100℃;
2-tert-butylindole
1805-65-8

2-tert-butylindole

methyl iodide
74-88-4

methyl iodide

1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

Conditions
ConditionsYield
at 110℃;
3-methyl-butan-2-one-(methyl-phenyl-hydrazone)
15754-36-6

3-methyl-butan-2-one-(methyl-phenyl-hydrazone)

1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

Conditions
ConditionsYield
With ethanol; zinc(II) chloride Zersetzen der erhaltenen Zinkverbindung mit Kalilauge;
2,3,3-trimethylindoleniune
1640-39-7

2,3,3-trimethylindoleniune

Trimethylsilylmethyl trifluoromethanesulfonate
64035-64-9

Trimethylsilylmethyl trifluoromethanesulfonate

1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

Conditions
ConditionsYield
Yield given. Multistep reaction;
2,3,3-trimethylindoleniune
1640-39-7

2,3,3-trimethylindoleniune

Trimethylsilylmethyl trifluoromethanesulfonate
64035-64-9

Trimethylsilylmethyl trifluoromethanesulfonate

dimethyl cis-but-2-ene-1,4-dioate
624-48-6

dimethyl cis-but-2-ene-1,4-dioate

A

1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

(1S,2R,9aS)-9,9,9a-Trimethyl-2,3,9,9a-tetrahydro-1H-pyrrolo[1,2-a]indole-1,2-dicarboxylic acid dimethyl ester

(1S,2R,9aS)-9,9,9a-Trimethyl-2,3,9,9a-tetrahydro-1H-pyrrolo[1,2-a]indole-1,2-dicarboxylic acid dimethyl ester

(1R,2S,9aS)-9,9,9a-Trimethyl-2,3,9,9a-tetrahydro-1H-pyrrolo[1,2-a]indole-1,2-dicarboxylic acid dimethyl ester

(1R,2S,9aS)-9,9,9a-Trimethyl-2,3,9,9a-tetrahydro-1H-pyrrolo[1,2-a]indole-1,2-dicarboxylic acid dimethyl ester

Conditions
ConditionsYield
Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;
2,3,3-trimethylindoleniune
1640-39-7

2,3,3-trimethylindoleniune

Trimethylsilylmethyl trifluoromethanesulfonate
64035-64-9

Trimethylsilylmethyl trifluoromethanesulfonate

dimethyl acetylenedicarboxylate
762-42-5

dimethyl acetylenedicarboxylate

A

1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

B

dimethyl 9,9a-dihydro-9,9,9a-trimethyl-3H-pyrrolo<1,2a>indole-1,2-dicarboxylate
114676-05-0

dimethyl 9,9a-dihydro-9,9,9a-trimethyl-3H-pyrrolo<1,2a>indole-1,2-dicarboxylate

Conditions
ConditionsYield
Yield given. Multistep reaction;
1,3-Bis(1,3,3-trimethyl-2-indolinyl)-2-phospha-trimethinium-tetrafluoroborat

1,3-Bis(1,3,3-trimethyl-2-indolinyl)-2-phospha-trimethinium-tetrafluoroborat

A

1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

B

1,2,3,3-tetramethylindoline
13034-76-9

1,2,3,3-tetramethylindoline

C

1,2,3,3-tetramethyl-3H-indolium tetrafluoroborate
21654-46-6

1,2,3,3-tetramethyl-3H-indolium tetrafluoroborate

Conditions
ConditionsYield
With water Product distribution; hydrolysis/protonation, also in chloroform (some weeks);
2-acetylmethylene-1,3,3-trimethylindoline
74145-97-4

2-acetylmethylene-1,3,3-trimethylindoline

concentrated acids

concentrated acids

1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

methyl iodide
74-88-4

methyl iodide

N-methyl-indole

N-methyl-indole

1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

Conditions
ConditionsYield
With methanol at 130℃;
methylene chloride
74-87-3

methylene chloride

lithium 2,3,3-trimethylindolenide
115590-27-7

lithium 2,3,3-trimethylindolenide

A

1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

B

C-methylated product

C-methylated product

Conditions
ConditionsYield
In tetrahydrofuran at 19℃; for 1h; Product distribution; further solvent;
1,2,3,3-tetramethyl-3H-indolium iodide
5418-63-3

1,2,3,3-tetramethyl-3H-indolium iodide

A

1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

B

1,3,3-trimethyl-2-dideuteriomethyleneindoline

1,3,3-trimethyl-2-dideuteriomethyleneindoline

C

C12H14(2)HN

C12H14(2)HN

Conditions
ConditionsYield
With potassium deuteroxide; water-d2 at 20℃; Title compound not separated from byproducts.;A 32 % Spectr.
B 50 % Spectr.
C 18 % Spectr.
(2E)-(1,3,3-trimethyl-1,3-dihydro-2H-indol-2-ylidene)acetaldehyde
84-83-3, 85654-15-5

(2E)-(1,3,3-trimethyl-1,3-dihydro-2H-indol-2-ylidene)acetaldehyde

A

1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

B

zinc dust

zinc dust

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 67 percent / hydroxylamine hydrochloride, pyridine / ethanol / 3 h / Heating
2: 100 percent / HCl / 6 h / Heating
View Scheme
1,3,3-trimethyl-2-methyleneiminohydroxindoline
144598-22-1

1,3,3-trimethyl-2-methyleneiminohydroxindoline

A

1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

B

zinc dust

zinc dust

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: ammonia / 70 °C
2: 100 percent / HCl / 6 h / Heating
View Scheme
3,3-dimethyl-butan-2-one-phenylhydrazone
39263-43-9

3,3-dimethyl-butan-2-one-phenylhydrazone

1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: zinc chloride / 190 °C
2: 110 °C
View Scheme
2,3,3-trimethylindoleniune
1640-39-7

2,3,3-trimethylindoleniune

1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1,2-dichloro-ethane / 5 h / 20 °C / Reflux
2: sodium hydroxide / water; acetone
View Scheme
Multi-step reaction with 2 steps
1: dichloromethane / 4 h / Reflux
2: sodium hydroxide / water
View Scheme
Multi-step reaction with 2 steps
1: diethyl ether; hexane
2: sodium hydroxide / diethyl ether
View Scheme
1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

1,2,3,3-tetramethylindoline
13034-76-9

1,2,3,3-tetramethylindoline

Conditions
ConditionsYield
With [P(H)t-Bu2][B(C6F5)4]; 1,3-diisopropylimidazol-2-ylidene-9-borabicyclo[3.3.1]nonane; hydrogen In chlorobenzene at 100℃; under 77525.2 Torr; for 4h; Time; Temperature; Reagent/catalyst; Glovebox;100%
With 2C2H3O2(1-)*Pd(2+)*3Na(1+)*C18H12O9PS3(3-); hydrogen; glycerol at 100℃; under 2250.23 Torr; for 2h; Schlenk technique;96%
With [1,3-diisopropylimidazol-2-ylidene-9-borabicyclo[3.3.1]nonane][tetrakis (pentafluorophenyl)borate]; hydrogen In chlorobenzene at 20℃; under 77525.2 Torr; for 4h; Solvent; Inert atmosphere;94%
1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

2-[(E)-2-(4-Dimethylamino-phenyl)-vinyl]-1,3,3-trimethyl-3H-indolium; dihydrogen phosphate

2-[(E)-2-(4-Dimethylamino-phenyl)-vinyl]-1,3,3-trimethyl-3H-indolium; dihydrogen phosphate

Conditions
ConditionsYield
With phosphoric acid In water; isopropyl alcohol for 6h; Heating;100%
1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

2-hydroxy-5-t-butylisophthalaldehyde
84501-28-0

2-hydroxy-5-t-butylisophthalaldehyde

6-(tert-butyl)-1′,3′,3′-trimethylspiro[chromene-2,2′-indoline]-8-carbaldehyde
1370284-34-6

6-(tert-butyl)-1′,3′,3′-trimethylspiro[chromene-2,2′-indoline]-8-carbaldehyde

Conditions
ConditionsYield
In ethanol Reflux;99%
In ethanol at 85℃; for 12h;80%
1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

2,3-dihydroxybenzaldehyde
24677-78-9

2,3-dihydroxybenzaldehyde

spiro[2H-1-benzopyran-2,2’-(8-hydroxy-1’,3’,3’-trimethylindoline)]
23022-12-0

spiro[2H-1-benzopyran-2,2’-(8-hydroxy-1’,3’,3’-trimethylindoline)]

Conditions
ConditionsYield
In neat (no solvent) for 0.166667h; Microwave irradiation; Green chemistry;99%
1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

C4H7F3N(1+)*BF4(1-)

C4H7F3N(1+)*BF4(1-)

1,1-difluoro-3-(1,3,3-trimethylindolin-2-ylidene)propan-2-one

1,1-difluoro-3-(1,3,3-trimethylindolin-2-ylidene)propan-2-one

Conditions
ConditionsYield
In acetonitrile at 20℃; for 0.5h; Inert atmosphere; Schlenk technique;99%
1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

5-(ethoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione
15568-86-2

5-(ethoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione

2,2-Dimethyl-5-{2-[1,3,3-trimethyl-1,3-dihydro-indol-(2E)-ylidene]-ethylidene}-[1,3]dioxane-4,6-dione

2,2-Dimethyl-5-{2-[1,3,3-trimethyl-1,3-dihydro-indol-(2E)-ylidene]-ethylidene}-[1,3]dioxane-4,6-dione

Conditions
ConditionsYield
In toluene 1.) 60 deg C, 20 min, 2.) r.t., 2 h;98%
1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

4-methoxy-aniline
104-94-9

4-methoxy-aniline

2,3-Dihydro-1,3,3-trimethylindol-2-ylidenmethanaza(4'-methoxybenzol)
40842-68-0

2,3-Dihydro-1,3,3-trimethylindol-2-ylidenmethanaza(4'-methoxybenzol)

Conditions
ConditionsYield
With carbon dioxide; sodium nitrite In water at 35 - 40℃; under 37503 Torr; for 3h;98%
N-(2-iodo-phenyl)-4-methyl-N-(3-phenyl-propynoyl)-benzenesulfonamide
845958-95-4

N-(2-iodo-phenyl)-4-methyl-N-(3-phenyl-propynoyl)-benzenesulfonamide

1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

phenylacetylene
536-74-3

phenylacetylene

(E)-3-((2Z,4Z)-1,3-diphenyl-4-(1,3,3-trimethylindolin-2-ylidene)but-2-en-1-ylidene)-1-tosylindolin-2-one

(E)-3-((2Z,4Z)-1,3-diphenyl-4-(1,3,3-trimethylindolin-2-ylidene)but-2-en-1-ylidene)-1-tosylindolin-2-one

Conditions
ConditionsYield
Stage #1: N-(2-iodo-phenyl)-4-methyl-N-(3-phenyl-propynoyl)-benzenesulfonamide; phenylacetylene With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 16h; Inert atmosphere;
Stage #2: 1,3,3-Trimethyl-2-methyleneindoline With N-ethyl-N,N-diisopropylamine In tetrahydrofuran; ethanol at 80℃; for 48h; Inert atmosphere; Sealed tube; diastereoselective reaction;
98%
1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

o-carboxybenzaldehyde
119-67-5

o-carboxybenzaldehyde

3-[(1,3,3-trimethylindolin-2-ylidene)methyl]isobenzofuran-1(3H)-one
84548-42-5

3-[(1,3,3-trimethylindolin-2-ylidene)methyl]isobenzofuran-1(3H)-one

Conditions
ConditionsYield
for 0.0833333h; Microwave irradiation; Green chemistry;98%
1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

salicylaldehyde
90-02-8

salicylaldehyde

1',3',3'-trimethylspiro(2H-1-benzopyran-2,2'-indoline)
1485-92-3

1',3',3'-trimethylspiro(2H-1-benzopyran-2,2'-indoline)

Conditions
ConditionsYield
In ethanol for 5h; Reflux;97%
In neat (no solvent) for 0.166667h; Microwave irradiation; Green chemistry;93%
In isopropyl alcohol Inert atmosphere; Reflux;90%
1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

Methanesulfonyl azide
624-90-8, 1516-70-7

Methanesulfonyl azide

2,3-Dihydro-1,3,3-trimethyl-2-<(methylsulfonyl)imino>-1H-indol
143268-71-7

2,3-Dihydro-1,3,3-trimethyl-2-<(methylsulfonyl)imino>-1H-indol

Conditions
ConditionsYield
In toluene 1) 0 to 5 deg C, 1 h, 2) 20 deg C, 1 h;97%
In (2)H8-toluene at 0℃;
1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

1,3-Bis(trifluoromethylsulfonyl)-5-nitro-2,4,6-trichlorobenzene
111222-84-5

1,3-Bis(trifluoromethylsulfonyl)-5-nitro-2,4,6-trichlorobenzene

1,3,3-Trimethyl-2-<2',6'-bis(trifluoromethylsulfonyl)-3',5'-dichloro-4'-nitrophenylmethylene>-2H-indole
115848-44-7

1,3,3-Trimethyl-2-<2',6'-bis(trifluoromethylsulfonyl)-3',5'-dichloro-4'-nitrophenylmethylene>-2H-indole

Conditions
ConditionsYield
With triethylamine In acetonitrile; benzene at 20℃; for 15h;97%
1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

sodium 1,3,3-trimethyl-2-methyleneindoline-5-sulfonate
128814-41-5

sodium 1,3,3-trimethyl-2-methyleneindoline-5-sulfonate

Conditions
ConditionsYield
With sulfuric acid; sulfur trioxide; sodium carbonate97%
1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

5-formyl-2-hydroxybenzaldehyde
3328-70-9

5-formyl-2-hydroxybenzaldehyde

6-formyl-1',3',3'-trimethylspiro<2H-1-benzopyran-2,2'-<1H>-indole>
20200-69-5

6-formyl-1',3',3'-trimethylspiro<2H-1-benzopyran-2,2'-<1H>-indole>

Conditions
ConditionsYield
In ethanol Addition; Heating;97%
In ethanol for 14.5h;80%
In ethanol Heating;75%
In ethanol for 5h; Heating;
1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

2,5-Dihydroxybenzaldehyde
1194-98-5

2,5-Dihydroxybenzaldehyde

6-hydroxy spiropyran
23001-29-8

6-hydroxy spiropyran

Conditions
ConditionsYield
In neat (no solvent) for 0.166667h; Microwave irradiation; Green chemistry;97%
In ethanol Addition; Heating;90%
In ethanol for 2h; Inert atmosphere; Reflux;84.8%
1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

5-sulfonic acid 1,3,3-trimethyl-2-methyleneindoline

5-sulfonic acid 1,3,3-trimethyl-2-methyleneindoline

Conditions
ConditionsYield
With sulfuric acid at 0 - 5℃; for 5h;97%
1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

Hexafluoroacetone
684-16-2

Hexafluoroacetone

1,3,3-trimethyl-2-<2-hydroxy-2-(trifluoromethyl)-3,3,3-trifluoropropylidene>indoline
127870-87-5, 127870-89-7

1,3,3-trimethyl-2-<2-hydroxy-2-(trifluoromethyl)-3,3,3-trifluoropropylidene>indoline

Conditions
ConditionsYield
In hexane at 0℃; Product distribution; other perfluorinated carbonyl compounds;96%
In hexane at 0℃;96%
1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

4,4'-dihydroxybenzophenone-3-carboxaldehyde
219560-21-1

4,4'-dihydroxybenzophenone-3-carboxaldehyde

C26H23NO3

C26H23NO3

Conditions
ConditionsYield
In methanol at 50℃;96%
1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

bis<(1,3,3-trimethyl-2-indolinylidene)methyl>phosphinous chloride
76372-77-5

bis<(1,3,3-trimethyl-2-indolinylidene)methyl>phosphinous chloride

Conditions
ConditionsYield
With triethylamine; phosphorus trichloride In chloroform; benzene for 6h; Heating;94.7%
1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

phosphonic acid diethyl ester
762-04-9

phosphonic acid diethyl ester

2-diethoxyphosphonyl-1,2,3,3-tetramethylindoline
109350-75-6

2-diethoxyphosphonyl-1,2,3,3-tetramethylindoline

Conditions
ConditionsYield
for 48h; Ambient temperature;94%
5,5'-thiobis(3-nitrosalicylaldehyde)
381732-60-1

5,5'-thiobis(3-nitrosalicylaldehyde)

1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

C38H34N4O6S

C38H34N4O6S

Conditions
ConditionsYield
94%
1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

5-mesyl-2-phenyl-4-tosyloxazole

5-mesyl-2-phenyl-4-tosyloxazole

4-[(4-methylphenyl)sulfonyl]-5-[(1,3,3-trimethylindolin-2-ylidene)methyl]-2-phenyl-1,3-oxazole

4-[(4-methylphenyl)sulfonyl]-5-[(1,3,3-trimethylindolin-2-ylidene)methyl]-2-phenyl-1,3-oxazole

Conditions
ConditionsYield
In ethanol for 5h; Reflux;94%
1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

1,2,3,3-tetramethyl-3H-indolium tetrafluoroborate
21654-46-6

1,2,3,3-tetramethyl-3H-indolium tetrafluoroborate

Conditions
ConditionsYield
With tetrafluoroboric acid In ethanol 1) 10 min, 20 deg C, 2) 15 min, ice-cooled;93%
1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

C7H10N2O4
219774-63-7

C7H10N2O4

2,2',3,3'-tetrahydro-1,3,3,5'-tetramethyl-4'-methoxycarbonyl-1'-(methoxycarbonylamino)spiro[1H-indole-2,2'-pyrrole]

2,2',3,3'-tetrahydro-1,3,3,5'-tetramethyl-4'-methoxycarbonyl-1'-(methoxycarbonylamino)spiro[1H-indole-2,2'-pyrrole]

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 2h;93%
1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

3,3'-[naphthalene-1,5-diylidi(E)diazene-2,1-diyl]bis(4,4'-diethylamino-6-hydroxy benzaldehyde)
1449790-53-7

3,3'-[naphthalene-1,5-diylidi(E)diazene-2,1-diyl]bis(4,4'-diethylamino-6-hydroxy benzaldehyde)

3,3'-[naphthalene-1,5-diylidi(E)diazene-2,1-diyl]bis(4,4'-diethylamino-6-hydroxy benzaldehyde)
1449790-58-2

3,3'-[naphthalene-1,5-diylidi(E)diazene-2,1-diyl]bis(4,4'-diethylamino-6-hydroxy benzaldehyde)

Conditions
ConditionsYield
In chloroform for 2h; Reflux;93%
1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

Dimethyl phosphite
868-85-9

Dimethyl phosphite

2-dimethoxyphosphonyl-1,2,3,3-tetramethylindoline

2-dimethoxyphosphonyl-1,2,3,3-tetramethylindoline

Conditions
ConditionsYield
Ambient temperature;92%

118-12-7Relevant articles and documents

A NEW METHOD OF SYNTHESIS OF CONJUGATED SYSTEMS WITH TRIS(FLUOROMETHINE) CHAIN

Pazenok, S. V.,Kovtyukh, I. P.,Yagupolskii, L. M.

, p. 4595 - 4598 (1991)

The interaction of compounds having the active methylene group with perflouroallyliodide leads to the formation of conjugated systems with the tris(fluoromethine) chain.

Crystal and solution structures of photochromic spirobenzothiopyran. First full characterization of the meta-stable colored species

Hirano, Masafumi,Osakada, Kohtaro,Nohira, Hiroyuki,Miyashita, Akira

, p. 533 - 540 (2002)

Full elucidation for stable, colorless, and meta-stable colored structures of a new spirobenzothiopyran has been achieved both in the solid state and in a solution. 1′,3′,3′-Trimethyl-6-nitrospiro[(2H)-1-benzothiopyran-2, 2′-indoline] with an ester group as a substituent at the 8-position of 1-sp shows photochromism. The blue-green colored species resulted from UV irradiation (365 nm) in one minute and spontaneously bleaches within one minute in acetone and methanol at 27 °C. UV exposure (365 nm) of 1-sp in methanol for 3 h at room temperature results in the growth of deep blue needlelike single crystals of the open form of spirobenzothiopyran, photomerocyanine 1-pmc, whose structures in the solid state and in solution were obtained unambiguously. The X-ray structural analysis of 1-pmc revealed the molecular structure of the zwitterionic photomerocyanine with s-trans,s-trans conformation. 1-pmc is soluble to polar solvents and thermally returns to 1-sp. In the DMSO solution, 1-pmc is found to return slowly to 1-sp (1-pmc gave only 18% of 1-sp for 30 min at 22 °C). The detailed NMR studies in DMSO-d6 including COSY and NOE techniques as well as isotope labeling of the compound showed the structure with s-trans,s-cis conformation in a solution.

Structures of Lithium Salts of 2,3,3-Trimethylindolenine and Its 5-Methoxy Derivative in Solution and the Solid State

Jackman, L. M.,Scarmoutzos, L. M.,Smith, B. D.,Williard, Paul G.

, p. 6058 - 6063 (1988)

An X-ray crystal structure of lithium 2,3,3-trimethylindolenide etherate shows it to be a disolvated dimer having a η3-azaallyl-type structure.The structures of the salt in several solvents have been established by studies of 13C chemical shifts, 6Li, 15N spin-spin splitting, 7Li quadrupole splitting constants, and apparent degrees of aggregation determined by vapor pressure barometry.It is the η3-azaallyl dimer disolvate in diethyl ether, a tetrasolvated dimer in dioxolane, a mixture of monomer splitting constants of 230, 156, 180 - 190 (0.27 - 0.75 M), and 217 kHz, respectively.In diethyl ether with 4 equiv of hexamethylphosphoric triamide, the salt is a mixture of monomeric and triple ion species.Lithium 5-methoxy-2,3,3-trimethylindolenide forms similar species except that, in tetrahydrofuran, the tendency for dimer formation is enhanced, which leads to a higher proportion of C- to N-methylation in its reaction with methyl chloride in that solvent.

-

Bernauer et al.

, p. 717,723 (1960)

-

Method for preparing indoline

-

Paragraph 0016; 0018; 0019; 0021; 0024, (2021/01/12)

The invention relates to a method for preparing indoline. The metho is characterized by comprising the following steps of: a, performing condensation and cyclization on phenylhydrazine hydrochloride or substituted phenylhydrazine hydrochloride and a methyl ketone compound in a solvent under a non-catalytic condition to generate C2-methylindole or a derivative thereof, and conducting cooling, salting-out, suction filtration and desolventizing successively; b, subjecting the condensation ring-closing product C2-methylindole or the derivative thereof to reacting with chloromethane under the conditions of pressurization, solvent presence and catalysis to generate corresponding quaternary ammonium salt or quaternary ammonium salt containing substituent groups; and c, dissolving the salt generated in the step b in water, then carrying out alkaline hydrolysis in a solvent and alkali liquor, and successively performing layering, desolvation and distillation to obtain a product, namely 1,3,3-trimethyl-2-methyleneindoline or a derivative thereof. The whole technological process is simple, the amount of three wastes is small, the cost is low, the yield is high, and the method is a green technology suitable for industrial amplification and outstanding in economic benefit.

Method for preparing indoline polymethin dye via one-pot method

-

Paragraph 0075; 0077; 0094; 0095; 0097, (2019/01/14)

The invention discloses a method for preparing an indoline polymethin dye via a one-pot method. The method comprises the following steps of: carrying out condensation and ring closing on phenylhydrazine or para-substituted phenylhydrazine hydrochloride and methyl isopropyl ketone in an alcohol solvent under the catalysis of sulfuric acid so as to generate 2,3,3-trimethylindole or a derivative thereof, adding alkali to carry out neutralization, and carrying out filtration to remove salt; adding an appropriate acid-binding agent in the filtrate, dropwise adding dimethyl sulfate to generate 1,3,3-trimethyl-2--methylene indoline or a derivative thereof; and directly adding 1-phenyl-3-methyl-4-formyl-5-pyrazolone, and carrying out acid catalysis and condensation to generate a target dye. The method has the advantages of being easy to operate, high in yield, low in cost and less in wastewater.

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