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84-83-3 Usage

Uses

Different sources of media describe the Uses of 84-83-3 differently. You can refer to the following data:
1. Reactant for preparation of:? ;Cyanine dyes1? ;Photopolymer holographic recording materials2
2. 2-(1,3,3-Trimethylindolin-2-ylidene)acetaldehyde may be used in the preparation of 1,3,3-trimethyl-2-anilino-vinyl-3-H-indolium salts, which are mainly used as hemicyanine dyes in textile industry.

General Description

2-(1,3,3-Trimethylindolin-2-ylidene)acetaldehyde is an a,?-unsaturated aldehyde.

Check Digit Verification of cas no

The CAS Registry Mumber 84-83-3 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 4 respectively; the second part has 2 digits, 8 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 84-83:
(4*8)+(3*4)+(2*8)+(1*3)=63
63 % 10 = 3
So 84-83-3 is a valid CAS Registry Number.
InChI:InChI=1/C13H15NO/c1-13(2)10-6-4-5-7-11(10)14(3)12(13)8-9-15/h4-9H,1-3H3/b12-8-

84-83-3 Well-known Company Product Price

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  • Aldrich

  • (550817)  2-(1,3,3-Trimethylindolin-2-ylidene)acetaldehyde  97%

  • 84-83-3

  • 550817-25G

  • 3,638.70CNY

  • Detail

84-83-3SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-(1,3,3-Trimethylindolin-2-ylidene)acetaldehyde

1.2 Other means of identification

Product number -
Other names 1,3,3-Trimethyl-2-(formylmethylene)indoline

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:84-83-3 SDS

84-83-3Synthetic route

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

1,3,3-Trimethyl-2-methyleneindoline

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

1,3,3-trimethyl-2-formylmethyleneindoline
84-83-3

1,3,3-trimethyl-2-formylmethyleneindoline

Conditions
ConditionsYield
Stage #1: N,N-dimethyl-formamide With trichlorophosphate at 0℃; for 2h;
Stage #2: 1,3,3-Trimethyl-2-methyleneindoline In N,N-dimethyl-formamide at 0 - 60℃;
76.4%
Stage #1: N,N-dimethyl-formamide With trichlorophosphate Inert atmosphere;
Stage #2: 1,3,3-Trimethyl-2-methyleneindoline In N,N-dimethyl-formamide at 50℃; for 0.75h; Inert atmosphere;
60%
With trichlorophosphate anschliessendes Hydrolysieren;
With trichlorophosphate at 10 - 20℃; for 10h;8.1 g
1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

Vilsmeier reagent
3724-43-4, 149409-22-3

Vilsmeier reagent

1,3,3-trimethyl-2-formylmethyleneindoline
84-83-3

1,3,3-trimethyl-2-formylmethyleneindoline

Conditions
ConditionsYield
Stage #1: 1,3,3-Trimethyl-2-methyleneindoline; Vilsmeier reagent In dichloromethane at 20℃; Inert atmosphere;
Stage #2: With potassium carbonate In tetrahydrofuran; water at 20℃; for 12h;
43%
With sodium hydroxide In dichloromethane; water for 1.75h; Cooling with ice;
1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

N-methyl-N-phenylformamide
93-61-8

N-methyl-N-phenylformamide

1,3,3-trimethyl-2-formylmethyleneindoline
84-83-3

1,3,3-trimethyl-2-formylmethyleneindoline

Conditions
ConditionsYield
With 1,2-dichloro-benzene; trichlorophosphate anschliessendes Hydrolysieren;
With phosgene; benzene anschliessendes Hydrolysieren;
With 1,2-dichloro-benzene; trichlorophosphate anschliessendes Hydrolysieren;
1,3,3-trimethylspiro[indoline-2,3'-[3H]naphtho[2,1-b]pyran]
1592-43-4

1,3,3-trimethylspiro[indoline-2,3'-[3H]naphtho[2,1-b]pyran]

A

1,3,3-trimethyl-1,3-dihydro-2H-indol-2-one
20200-86-6

1,3,3-trimethyl-1,3-dihydro-2H-indol-2-one

B

1,3,3-trimethyl-2-formylmethyleneindoline
84-83-3

1,3,3-trimethyl-2-formylmethyleneindoline

Conditions
ConditionsYield
In acetonitrile at 13℃; Product distribution; Irradiation; photodecomposition and singlet oxygen production during photosensitization;
2,3,3-trimethylindoleniune
1640-39-7

2,3,3-trimethylindoleniune

1,3,3-trimethyl-2-formylmethyleneindoline
84-83-3

1,3,3-trimethyl-2-formylmethyleneindoline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetonitrile / Reflux; Inert atmosphere
2: trichlorophosphate / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1: acetonitrile / 24 h / 85 °C / Inert atmosphere
2: sodium hydroxide / diethyl ether / 0.5 h
3: sodium hydroxide / dichloromethane; water / 1.75 h / Cooling with ice
View Scheme
Multi-step reaction with 3 steps
1: acetonitrile / 12 h / Reflux
2: sodium hydroxide / water / 2 h / 50 °C
3: trichlorophosphate / 10 h / 10 - 20 °C
View Scheme
1,2,3,3-tetramethyl-3H-indolium iodide
5418-63-3

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

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

1,3,3-trimethyl-2-formylmethyleneindoline
84-83-3

1,3,3-trimethyl-2-formylmethyleneindoline

Conditions
ConditionsYield
Stage #1: 1,2,3,3-tetramethyl-3H-indolium iodide; N,N-dimethyl-formamide With trichlorophosphate Vilsmeier-Haack Formylation; Inert atmosphere;
Stage #2: With sodium hydroxide Vilsmeier-Haack Formylation;
1,1′,3,3,3′,3′-hexamethylindotricarbocyanine iodide
19764-96-6

1,1′,3,3,3′,3′-hexamethylindotricarbocyanine iodide

A

1,3,3-trimethyl-1,3-dihydro-2H-indol-2-one
20200-86-6

1,3,3-trimethyl-1,3-dihydro-2H-indol-2-one

B

1,3,3-trimethyl-2-formylmethyleneindoline
84-83-3

1,3,3-trimethyl-2-formylmethyleneindoline

Conditions
ConditionsYield
With sodium 3-(4-methyl-1-naphthyl)propionate endoperoxide In acetonitrile at 34℃;A 71.7 %Chromat.
B 10.3 %Chromat.
1,1′,3,3,3′,3′-hexamethylindotricarbocyanine iodide
19764-96-6

1,1′,3,3,3′,3′-hexamethylindotricarbocyanine iodide

A

1,3,3-trimethyl-1,3-dihydro-2H-indol-2-one
20200-86-6

1,3,3-trimethyl-1,3-dihydro-2H-indol-2-one

B

1,3,3-trimethyl-2-formylmethyleneindoline
84-83-3

1,3,3-trimethyl-2-formylmethyleneindoline

C

C18H20NO(1+)

C18H20NO(1+)

D

C16H18NO(1+)

C16H18NO(1+)

Conditions
ConditionsYield
With water In acetonitrile at 22℃; Irradiation;A 56.6 %Chromat.
B 11.5 %Chromat.
C n/a
D n/a
1,2,3,3-tetramethyl-3H-indolium iodide
5418-63-3

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

1,3,3-trimethyl-2-formylmethyleneindoline
84-83-3

1,3,3-trimethyl-2-formylmethyleneindoline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / diethyl ether / 0.5 h
2: sodium hydroxide / dichloromethane; water / 1.75 h / Cooling with ice
View Scheme
phenylhydrazine
100-63-0

phenylhydrazine

1,3,3-trimethyl-2-formylmethyleneindoline
84-83-3

1,3,3-trimethyl-2-formylmethyleneindoline

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: acetic acid / 10 h / 90 °C
2: acetonitrile / 12 h / Reflux
3: sodium hydroxide / water / 2 h / 50 °C
4: trichlorophosphate / 10 h / 10 - 20 °C
View Scheme
3-methyl-butan-2-one
563-80-4

3-methyl-butan-2-one

1,3,3-trimethyl-2-formylmethyleneindoline
84-83-3

1,3,3-trimethyl-2-formylmethyleneindoline

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: acetic acid / 10 h / 90 °C
2: acetonitrile / 12 h / Reflux
3: sodium hydroxide / water / 2 h / 50 °C
4: trichlorophosphate / 10 h / 10 - 20 °C
View Scheme
1,2,3,3-tetramethyl-3H-indol-1-ium iodide
46149-03-5

1,2,3,3-tetramethyl-3H-indol-1-ium iodide

1,3,3-trimethyl-2-formylmethyleneindoline
84-83-3

1,3,3-trimethyl-2-formylmethyleneindoline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / water / 2 h / 50 °C
2: trichlorophosphate / 10 h / 10 - 20 °C
View Scheme
IR-797 chloride

IR-797 chloride

A

1,3,3-trimethyl-1,3-dihydro-2H-indol-2-one
20200-86-6

1,3,3-trimethyl-1,3-dihydro-2H-indol-2-one

B

1,3,3-trimethyl-2-formylmethyleneindoline
84-83-3

1,3,3-trimethyl-2-formylmethyleneindoline

C

C25H28NO3(1+)*Cl(1-)

C25H28NO3(1+)*Cl(1-)

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 0.25 h / 70 °C / Inert atmosphere; Microwave irradiation; Sealed tube
2.1: oxygen / dimethyl sulfoxide; aq. phosphate buffer / pH 7.4 / Irradiation; Inert atmosphere
2.2: 1 h / 37 °C / Irradiation; Inert atmosphere
View Scheme
IR797-acac

IR797-acac

A

1,3,3-trimethyl-1,3-dihydro-2H-indol-2-one
20200-86-6

1,3,3-trimethyl-1,3-dihydro-2H-indol-2-one

B

1,3,3-trimethyl-2-formylmethyleneindoline
84-83-3

1,3,3-trimethyl-2-formylmethyleneindoline

C

C25H28NO3(1+)*Cl(1-)

C25H28NO3(1+)*Cl(1-)

Conditions
ConditionsYield
Stage #1: IR797-acac With oxygen In aq. phosphate buffer; dimethyl sulfoxide pH=7.4; Irradiation; Inert atmosphere;
Stage #2: In aq. phosphate buffer; dimethyl sulfoxide at 37℃; for 1h; Irradiation; Inert atmosphere;
1,3,3-trimethyl-2-formylmethyleneindoline
84-83-3

1,3,3-trimethyl-2-formylmethyleneindoline

2-methyl-4-tert-butylbenzothiopyrylium perchlorate

2-methyl-4-tert-butylbenzothiopyrylium perchlorate

1,1,3-trimethyl-2-<3-(4-tert-butylbenzothiopyran-2-ylidene)-1-propen-1-yl>-3H-indolium perchlorate

1,1,3-trimethyl-2-<3-(4-tert-butylbenzothiopyran-2-ylidene)-1-propen-1-yl>-3H-indolium perchlorate

Conditions
ConditionsYield
In acetic anhydride at 100℃; for 0.166667h;98%
1,3,3-trimethyl-2-formylmethyleneindoline
84-83-3

1,3,3-trimethyl-2-formylmethyleneindoline

isocyanatophosphoryl difluoride
1495-54-1

isocyanatophosphoryl difluoride

N-[2-(1,3,3-trimethyl-1,3-dihydro-2H-indol-2-yl-idene)ethylidene]phosphorodifluoridamide

N-[2-(1,3,3-trimethyl-1,3-dihydro-2H-indol-2-yl-idene)ethylidene]phosphorodifluoridamide

Conditions
ConditionsYield
In dichloromethane at 20℃; for 2h;96%
1,3,3-trimethyl-2-formylmethyleneindoline
84-83-3

1,3,3-trimethyl-2-formylmethyleneindoline

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

(4-{[(E)-2-(1,3,3-trimethyl-3H-2-indoliumyl)-1-ethenyl]amino}phenyl)-(E)-2-(1,3,3-trimethyl-3H-2-indoliumyl)-1-ethen-1-amine bis(hydrogen sulfate)

(4-{[(E)-2-(1,3,3-trimethyl-3H-2-indoliumyl)-1-ethenyl]amino}phenyl)-(E)-2-(1,3,3-trimethyl-3H-2-indoliumyl)-1-ethen-1-amine bis(hydrogen sulfate)

Conditions
ConditionsYield
With sulfuric acid at 20℃; for 24h;95%
1,3,3-trimethyl-2-formylmethyleneindoline
84-83-3

1,3,3-trimethyl-2-formylmethyleneindoline

C22H22N(1+)*ClO4(1-)

C22H22N(1+)*ClO4(1-)

1-Methyl-2,4-diphenyl-8-<2-(1,3,3-trimethylindolin-2-ylidene)vinyl>-5,6,7,8-tetrahydroquinolinium Perchlorate

1-Methyl-2,4-diphenyl-8-<2-(1,3,3-trimethylindolin-2-ylidene)vinyl>-5,6,7,8-tetrahydroquinolinium Perchlorate

Conditions
ConditionsYield
In isopropyl alcohol; acetonitrile Heating;95%
1,3,3-trimethyl-2-formylmethyleneindoline
84-83-3

1,3,3-trimethyl-2-formylmethyleneindoline

2,4-Diphenyl-5,6-dihydrocyclopenta pyrylium perchlorate
21016-30-8

2,4-Diphenyl-5,6-dihydrocyclopenta pyrylium perchlorate

1,3,3-Trimethyl-2-<2-(2,4-diphenyl-5,6-dihydrocyclopentapyran-7-yl)-vinyl>-3H-indolium Perchlorate

1,3,3-Trimethyl-2-<2-(2,4-diphenyl-5,6-dihydrocyclopentapyran-7-yl)-vinyl>-3H-indolium Perchlorate

Conditions
ConditionsYield
In isopropyl alcohol; acetonitrile Heating;95%
1,3,3-trimethyl-2-formylmethyleneindoline
84-83-3

1,3,3-trimethyl-2-formylmethyleneindoline

2-(1,3,3-trimethyl-2,3-dihydro-1H-indol-2-yl)ethanol

2-(1,3,3-trimethyl-2,3-dihydro-1H-indol-2-yl)ethanol

Conditions
ConditionsYield
With chlorine[2-(4,5-dihydro-1H-imidazol-2-yl)-6-methoxypyridine](pentamethylcyclopentadienyl)iridium(III) chloride; sodium formate In water at 80℃; for 0.5h; Schlenk technique; chemoselective reaction;95%
1,3,3-trimethyl-2-formylmethyleneindoline
84-83-3

1,3,3-trimethyl-2-formylmethyleneindoline

2,2-difluoro-4-methyl-5-oxo-(5H)-(2,3,4,6,7,8-hexahydroquinolyzine)[9,10,1-g,h]chromeno[4,3-d]-1,3,2-(2H)-dioxaborine
1262110-39-3

2,2-difluoro-4-methyl-5-oxo-(5H)-(2,3,4,6,7,8-hexahydroquinolyzine)[9,10,1-g,h]chromeno[4,3-d]-1,3,2-(2H)-dioxaborine

2,2-difluoro-4-[3-(1,3,3-trimethylindolin-2-ylidene)-1-propenyl]-5-oxo-(5H)-(2,3,4,6,7,8-hexahydroquinolyzine)[9,10,1-g,h]chromeno[4,3-d]1,3,2-(2H)-dioxaborine
1262110-48-4

2,2-difluoro-4-[3-(1,3,3-trimethylindolin-2-ylidene)-1-propenyl]-5-oxo-(5H)-(2,3,4,6,7,8-hexahydroquinolyzine)[9,10,1-g,h]chromeno[4,3-d]1,3,2-(2H)-dioxaborine

Conditions
ConditionsYield
With acetic anhydride; triethylamine for 0.0833333h;94%
1,3,3-trimethyl-2-formylmethyleneindoline
84-83-3

1,3,3-trimethyl-2-formylmethyleneindoline

C27H36N2(2+)*2ClO4(1-)

C27H36N2(2+)*2ClO4(1-)

C53H62N4(2+)*2ClO4(1-)

C53H62N4(2+)*2ClO4(1-)

Conditions
ConditionsYield
With acetic anhydride for 0.0666667h; Heating;92%
1,3,3-trimethyl-2-formylmethyleneindoline
84-83-3

1,3,3-trimethyl-2-formylmethyleneindoline

m-phenylenediamine
108-45-2

m-phenylenediamine

(3-{[(E)-2-(1,3,3-trimethyl-3H-2-indoliumyl)-1-ethenyl]amino}phenyl)-(E)-2-(1,3,3-trimethyl-3H-2-indoliumyl)-1-ethen-1-amine bis(hydrogen sulfate)

(3-{[(E)-2-(1,3,3-trimethyl-3H-2-indoliumyl)-1-ethenyl]amino}phenyl)-(E)-2-(1,3,3-trimethyl-3H-2-indoliumyl)-1-ethen-1-amine bis(hydrogen sulfate)

Conditions
ConditionsYield
With sulfuric acid at 20℃; for 24h;92%
1,3,3-trimethyl-2-formylmethyleneindoline
84-83-3

1,3,3-trimethyl-2-formylmethyleneindoline

2-Methyl-4-phenyl-1-benzo-1-thiopyrylium perchlorate
55181-01-6

2-Methyl-4-phenyl-1-benzo-1-thiopyrylium perchlorate

1,3,3-Trimethyl-2-<3-(4-phenylbenzothiopyran-2-ylidene)propen-1-yl>-3H-indolium Perchlorate

1,3,3-Trimethyl-2-<3-(4-phenylbenzothiopyran-2-ylidene)propen-1-yl>-3H-indolium Perchlorate

Conditions
ConditionsYield
In acetic anhydride; acetic acid for 0.0333333h; heating;90%
1,3,3-trimethyl-2-formylmethyleneindoline
84-83-3

1,3,3-trimethyl-2-formylmethyleneindoline

3-methylpyrido<3,2,1-j,k>carbazolium perchlorate

3-methylpyrido<3,2,1-j,k>carbazolium perchlorate

3-<3-(1,3,3-trimethylindolinylidene-2)propenyl>pyrido<3,2,1-j,k>carbazolium perchlorate

3-<3-(1,3,3-trimethylindolinylidene-2)propenyl>pyrido<3,2,1-j,k>carbazolium perchlorate

Conditions
ConditionsYield
In acetic anhydride for 0.5h; Heating;90%
1,3,3-trimethyl-2-formylmethyleneindoline
84-83-3

1,3,3-trimethyl-2-formylmethyleneindoline

1,5-diaminonaphthalene
2243-62-1

1,5-diaminonaphthalene

(5-{[(E)-2-(1,3,3-trimethyl-3H-2-indoliumyl)-1-ethenyl]amino}-1-naphthyl)-(E)-2-(1,3,3-trimethyl-2,3-dihydro-1H-2-indolyl)-1-ethen-1-amine bis(hydrogen sulfate)

(5-{[(E)-2-(1,3,3-trimethyl-3H-2-indoliumyl)-1-ethenyl]amino}-1-naphthyl)-(E)-2-(1,3,3-trimethyl-2,3-dihydro-1H-2-indolyl)-1-ethen-1-amine bis(hydrogen sulfate)

Conditions
ConditionsYield
With sulfuric acid at 20℃; for 24h;90%
1,3,3-trimethyl-2-formylmethyleneindoline
84-83-3

1,3,3-trimethyl-2-formylmethyleneindoline

2,2'-thiodianiline
5873-51-8

2,2'-thiodianiline

C38H40N4S(2+)*2HO4S(1-)

C38H40N4S(2+)*2HO4S(1-)

Conditions
ConditionsYield
With sulfuric acid at 20℃; for 24h;90%
1,3,3-trimethyl-2-formylmethyleneindoline
84-83-3

1,3,3-trimethyl-2-formylmethyleneindoline

1-butyl-6-hydroxy-4-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile
39108-47-9

1-butyl-6-hydroxy-4-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile

C24H27N3O2

C24H27N3O2

Conditions
ConditionsYield
With acetic anhydride; ammonium chloride; acetic acid at 105℃; for 6h;90%
1,3,3-trimethyl-2-formylmethyleneindoline
84-83-3

1,3,3-trimethyl-2-formylmethyleneindoline

C24H26NO3

C24H26NO3

3H-indolium-2-[2-[9-(2-carboxyphenyl)-6-(diethylamino)-2,3-dihydro-1H-xanthen-4-yl]ethenyl]-1,3,3-trimethylperchlorate

3H-indolium-2-[2-[9-(2-carboxyphenyl)-6-(diethylamino)-2,3-dihydro-1H-xanthen-4-yl]ethenyl]-1,3,3-trimethylperchlorate

Conditions
ConditionsYield
In acetic anhydride at 50℃; for 2.5h; Knoevenagel Condensation;89.4%
1,3,3-trimethyl-2-formylmethyleneindoline
84-83-3

1,3,3-trimethyl-2-formylmethyleneindoline

2,2',3,3,3',3'-hexamethyl-1,1'-tetramethylenedi<2(3H)-indolium> diiodide
52535-51-0

2,2',3,3,3',3'-hexamethyl-1,1'-tetramethylenedi<2(3H)-indolium> diiodide

2,2'-di<3-(1,3,3-trimethyl-2(3H)-indolylidene)-1-propenyl>-3,3,3',3'-tetramethyl-1,1'-tetramethylenedi(3H-indolium) diiodide

2,2'-di<3-(1,3,3-trimethyl-2(3H)-indolylidene)-1-propenyl>-3,3,3',3'-tetramethyl-1,1'-tetramethylenedi(3H-indolium) diiodide

Conditions
ConditionsYield
With acetic anhydride for 0.0833333h; Heating;87%
1,3,3-trimethyl-2-formylmethyleneindoline
84-83-3

1,3,3-trimethyl-2-formylmethyleneindoline

4-Methyl-1-(2-oxo-2-phenyl-ethyl)-quinolinium; perchlorate

4-Methyl-1-(2-oxo-2-phenyl-ethyl)-quinolinium; perchlorate

1-{(E)-1-Benzoyl-3-[1,3,3-trimethyl-1,3-dihydro-indol-(2Z)-ylidene]-propenyl}-4-{(E)-3-[1,3,3-trimethyl-1,3-dihydro-indol-(2Z)-ylidene]-propenyl}-quinolinium; perchlorate

1-{(E)-1-Benzoyl-3-[1,3,3-trimethyl-1,3-dihydro-indol-(2Z)-ylidene]-propenyl}-4-{(E)-3-[1,3,3-trimethyl-1,3-dihydro-indol-(2Z)-ylidene]-propenyl}-quinolinium; perchlorate

Conditions
ConditionsYield
In acetic anhydride Heating;86%
1,3,3-trimethyl-2-formylmethyleneindoline
84-83-3

1,3,3-trimethyl-2-formylmethyleneindoline

2,3,4,9-Tetrahydrofuro<2,3-b>quinoline-3,4-dione
74120-99-3

2,3,4,9-Tetrahydrofuro<2,3-b>quinoline-3,4-dione

C24H20N2O3

C24H20N2O3

Conditions
ConditionsYield
With sodium hydroxide In ethanol for 6h; Reagent/catalyst; Solvent; Reflux;86%
1,3,3-trimethyl-2-formylmethyleneindoline
84-83-3

1,3,3-trimethyl-2-formylmethyleneindoline

2-(1H-inden-2(3H)-ylidene)malononitrile
2510-00-1

2-(1H-inden-2(3H)-ylidene)malononitrile

2-((1E,3E)-1,3-bis((E)-2-(1,3,3-trimethylindolin-2-ylidene)ethylidene)-1H-inden-2(3H)-ylidene)malononitrile
1612140-22-3

2-((1E,3E)-1,3-bis((E)-2-(1,3,3-trimethylindolin-2-ylidene)ethylidene)-1H-inden-2(3H)-ylidene)malononitrile

Conditions
ConditionsYield
With acetic anhydride for 0.5h; Reflux;85.7%
1,2,3,3,5,6,7,7-octamethyl-3,7-dihydropyrrolo[2,3-f]indolediium di(4-methyl-1-benzenesulfonate)

1,2,3,3,5,6,7,7-octamethyl-3,7-dihydropyrrolo[2,3-f]indolediium di(4-methyl-1-benzenesulfonate)

1,3,3-trimethyl-2-formylmethyleneindoline
84-83-3

1,3,3-trimethyl-2-formylmethyleneindoline

2-[3-[1,3,3,5,7,7-hexamethyl-6-[3-(1,3,3-trimethyl-3H-indolium-2-yl)-2-propenylidene]-1,2,3,5,6,7-hexahydropyrrolo[2,3-f]indol-2-yliden]-1-propenyl]-1,3,3-trimethyl-3H-indolium di(4-toluenesulfonate)

2-[3-[1,3,3,5,7,7-hexamethyl-6-[3-(1,3,3-trimethyl-3H-indolium-2-yl)-2-propenylidene]-1,2,3,5,6,7-hexahydropyrrolo[2,3-f]indol-2-yliden]-1-propenyl]-1,3,3-trimethyl-3H-indolium di(4-toluenesulfonate)

Conditions
ConditionsYield
With acetic anhydride for 1h; Reflux;85%
1,3,3-trimethyl-2-formylmethyleneindoline
84-83-3

1,3,3-trimethyl-2-formylmethyleneindoline

1,2-dimethylquinolinium hexafluorophosphate

1,2-dimethylquinolinium hexafluorophosphate

1-methyl-2-(3-(1,3,3-trimethylindolin-2-ylidene)prop-1-enyl)quinolin-1-ium hexafluorophosphate

1-methyl-2-(3-(1,3,3-trimethylindolin-2-ylidene)prop-1-enyl)quinolin-1-ium hexafluorophosphate

Conditions
ConditionsYield
In acetic anhydride at 80℃; for 1h;85%
1,3,3-trimethyl-2-formylmethyleneindoline
84-83-3

1,3,3-trimethyl-2-formylmethyleneindoline

4-Methyl-1-(1-naphthylmethyl)quinolinium perchlorate

4-Methyl-1-(1-naphthylmethyl)quinolinium perchlorate

1-(1-Naphthylmethyl)-4-<3-(1,3,3-trimethyl-2-indolinylidene)-1-propenyl>quinolinium perchlorate

1-(1-Naphthylmethyl)-4-<3-(1,3,3-trimethyl-2-indolinylidene)-1-propenyl>quinolinium perchlorate

Conditions
ConditionsYield
In acetic anhydride Condensation; Heating;83%
With acetic anhydride Heating;83%
1,3,3-trimethyl-2-formylmethyleneindoline
84-83-3

1,3,3-trimethyl-2-formylmethyleneindoline

2-methyl-4,6-diphenylpyrilium tetrafluoroborate

2-methyl-4,6-diphenylpyrilium tetrafluoroborate

BAS00127538

BAS00127538

Conditions
ConditionsYield
With acetic anhydride; acetic acid for 5h; Heating;82%
1,3,3-trimethyl-2-formylmethyleneindoline
84-83-3

1,3,3-trimethyl-2-formylmethyleneindoline

4-methyl-1-(2-oxochromen-3-ylcarbonylmethyl)pyridinium bromide

4-methyl-1-(2-oxochromen-3-ylcarbonylmethyl)pyridinium bromide

1-<1-(2-oxochromen-3-yl)-3-(1,3,3-trimethylindolin-2-ylidene)-1-propenyl>-4-<3-(1,3,3-trimethylindolin-2-ylidene)-1-propenyl>pyridinium bromide

1-<1-(2-oxochromen-3-yl)-3-(1,3,3-trimethylindolin-2-ylidene)-1-propenyl>-4-<3-(1,3,3-trimethylindolin-2-ylidene)-1-propenyl>pyridinium bromide

Conditions
ConditionsYield
With acetic anhydride Heating;82%
1,3,3-trimethyl-2-formylmethyleneindoline
84-83-3

1,3,3-trimethyl-2-formylmethyleneindoline

benzoic acid hydrazide
613-94-5

benzoic acid hydrazide

C20H21N3O
389610-87-1

C20H21N3O

Conditions
ConditionsYield
In ethanol for 1h; Heating / reflux;82%
1,3,3-trimethyl-2-formylmethyleneindoline
84-83-3

1,3,3-trimethyl-2-formylmethyleneindoline

2-methyl-6,7-dichlorothiazolo[4,5-b]quinoxaline
443795-60-6

2-methyl-6,7-dichlorothiazolo[4,5-b]quinoxaline

2-[3-(1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)-1-propenyl]-6,7-dichlorothiazolo[4,5-b]quinoxaline

2-[3-(1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)-1-propenyl]-6,7-dichlorothiazolo[4,5-b]quinoxaline

Conditions
ConditionsYield
With piperidine In ethanol for 8h; Knovenagel condensation; Heating;81%
1,3,3-trimethyl-2-formylmethyleneindoline
84-83-3

1,3,3-trimethyl-2-formylmethyleneindoline

C24H26NO4(1+)*ClO4(1-)

C24H26NO4(1+)*ClO4(1-)

C37H39N2O4(1+)*ClO4(1-)

C37H39N2O4(1+)*ClO4(1-)

Conditions
ConditionsYield
With acetic anhydride at 50℃; for 0.5h;81%
1,3,3-trimethyl-2-formylmethyleneindoline
84-83-3

1,3,3-trimethyl-2-formylmethyleneindoline

2,4-bis-(4-methoxy-phenyl)-6-methyl-pyrylium; perchlorate

2,4-bis-(4-methoxy-phenyl)-6-methyl-pyrylium; perchlorate

1,3,3-Trimethyl-2-<3-<4,6-di(4-methoxyphenyl)pyranylidene-2>-1-propenyl>-3H-indoline Perchlorate

1,3,3-Trimethyl-2-<3-<4,6-di(4-methoxyphenyl)pyranylidene-2>-1-propenyl>-3H-indoline Perchlorate

Conditions
ConditionsYield
With acetic anhydride80%
1,3,3-trimethyl-2-formylmethyleneindoline
84-83-3

1,3,3-trimethyl-2-formylmethyleneindoline

4-methyl-1-(2-oxochromen-3-ylcarbonylmethyl)quinolinium bromide

4-methyl-1-(2-oxochromen-3-ylcarbonylmethyl)quinolinium bromide

4-[3-(1,3,3-trimethylindolin-2-ylidene)-1-propenyl]-1-[1-(2-oxochromen-3-yl)-3-(1,3,3-trimethylindolin-2-ylidene)-1-propenyl]quinolinium bromide

4-[3-(1,3,3-trimethylindolin-2-ylidene)-1-propenyl]-1-[1-(2-oxochromen-3-yl)-3-(1,3,3-trimethylindolin-2-ylidene)-1-propenyl]quinolinium bromide

Conditions
ConditionsYield
In acetic anhydride Condensation; Heating;80%
1,3,3-trimethyl-2-formylmethyleneindoline
84-83-3

1,3,3-trimethyl-2-formylmethyleneindoline

5-hydroxycarbonyl-1,2,3,3-tetramethylindoleninium iodide

5-hydroxycarbonyl-1,2,3,3-tetramethylindoleninium iodide

C26H29N2O2(1+)*I(1-)

C26H29N2O2(1+)*I(1-)

Conditions
ConditionsYield
With acetic anhydride at 145℃; for 24h; Inert atmosphere;80%
With acetic anhydride at 20℃; for 2.5h;61%

84-83-3Relevant articles and documents

Synthesis and characterization of a novel indoline based nonlinear optical chromophore with excellent electro-optic activity and high thermal stability by modifying the π-conjugated bridges

Hu, Chaolei,Chen, Zhuo,Xiao, Hongyan,Zhen, Zhen,Liu, Xinhou,Bo, Shuhui

, p. 5111 - 5118 (2017)

Two novel second order nonlinear optical (NLO) chromophores based on indoline donors and tricyanofuran (TCF) acceptors linked together via modified polyene π-conjugation bridges have been synthesized in good overall yields and systematically characterized. Thermal stability, optical property and electro-optic property were measured to investigate the effects of the introduced rigid benzene derivative steric hindrance group on the bridge. Besides, density functional theory (DFT) was used to calculate the HOMO-LUMO energy gaps and first-order hyperpolarizability (β) of these chromophores. After introducing the benzene derivative steric hindrance group into the bridge, chromophore CLH-2 showed very good thermal stability with a decomposition temperature of 250 °C, which was 83 °C higher than chromophore CLH-1 without the isolation group on the bridge. In electro-optic activity, the introduction of rigid steric hindrance groups can effectively reduce dipole-dipole interactions to translate the relatively small β values into bulk high EO activities. By doping chromophores CLH-1 and CLH-2 with a high loading of 45 wt% in APC, EO coefficients (r33) of up to 63 and 102 pm V-1 at 1310 nm can be achieved, respectively. The r33 value of the new chromophore CLH-2 was about 1.6 times that of chromophore CLH-1. The high r33 value, good thermal stability and high yield suggest the promising applications of the new chromophore in nonlinear optical areas.

Development and applications of a near-infrared dye-benzylguanine conjugate to specifically label SNAP-tagged proteins

Song, Xinbo,Bian, Hui,Wang, Chao,Hu, Mingyu,Li, Ning,Xiao, Yi

, p. 8091 - 8101 (2017/10/13)

Near-infrared (NIR) fluorescent probes are advantageous over visible ones, for they can avoid the interference from the short-wavelength background emission in biological systems. However, there are a very limited number of NIR probes that can specifically label target proteins in living cells. In this work, a series of long-wavelength dyes (N-NIR, S-NIR, and K-NIR) analogous to the novel Changsha NIR family are synthesized conveniently through a new approach that is different from the previously reported one. These three dyes have similar conjugation structures but exhibit tunable photophysical properties. N-NIR and S-NIR have large extinction coefficients over 100000, and high fluorescence quantum yields. Although NIR absorption and emission of K-NIR are inferior to the former two, it emits in a much longer wavelength region. And all the three dyes can easily pass through the cell membranes to obtain the high-resolution NIR fluorescence images. Furthermore, N-NIR is chosen as the NIR fluorophore to develop a protein-labeling reagent PYBG-D, since it demonstrates the highest fluorescence quantum yield of up to 0.4 (in methanol). PYBG-D is efficiently synthesized through Sonogashira coupling between bromo-substituted N-NIR and alkyne-substituted benzylguanine (PYBG). The conjugate PYBG-D proves to be a specific and efficient label for O6-alkylguanine-DNA alkyltransferase (SNAP-tag) that fused to target proteins in living cells, which contributes to high resolution NIR fluorescence images under a laser confocal microscope.

INDOLE-BASED COMPOUND, COLORANT COMPOSITION COMPRISING THE SAME AND RESIN COMPOSITION COMPRISING THE SAME

-

Paragraph 0166; 0174-0176, (2016/11/17)

Disclosed in the present invention are a novel indole-based compound, a colorant composition comprising the same, and a resin composition comprising the same. Provided in an embodiment of the present invention is the compound represented by chemical formula 1. According to an embodiment of the present invention, the compound can be acted as a dye, and can be used as a material of a color filter. Specifically, the resin composition comprising the compound has a high color reproduction rate, high luminance, a high contrast ratio, etc.(AA) Comparative example 1(BB) Example 1(CC) Example 2(DD) Example 3(EE) Example 4(FF) Example 5(GG) Example 7(HH) Example 8(II) Example 9(JJ) Example 10COPYRIGHT KIPO 2016

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