Product Name

  • Name

    1,3,3-Trimethyl-2-(formylmethylene)indoline

  • EINECS 201-565-8
  • CAS No. 84-83-3
  • Article Data16
  • CAS DataBase
  • Density 1.102 g/cm3
  • Solubility
  • Melting Point 112-116 ºC
  • Formula C13H15NO
  • Boiling Point 301.4 ºC at 760 mmHg
  • Molecular Weight 201.268
  • Flash Point 107.2 ºC
  • Transport Information
  • Appearance
  • Safety 26-36
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 84-83-3 (1,3,3-Trimethyl-2-(formylmethylene)indoline)
  • Hazard Symbols IrritantXi
  • Synonyms 1,3,3-Trimethyl-2-methyleneindoline-w-aldehyde;1,3,3-Trimethyl-D2,a-indolineacetaldehyde;2-(1,3,3-Trimethylindolin-2-ylidene)acetaldehyde;2-(2,3-Dihydro-1,3,3-trimethyl-1H-indol-2-ylidene)acetaldehyde;2-(Formylmethylene)-1,3,3-trimethylindoline;2-(Formylmethylene)-2,3-dihydro-1,3,3-trimethylindole;Fischer's aldehyde;NSC68048;(1,3-Dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)acetaldehyde;(1,3,3-Trimethylindolin-2-ylidene)acetaldehyde;D2,a-Indolinacetaldehyde, 1,3,3-trimethyl- (6CI);D2,a-Indolineacetaldehyde, 1,3,3-trimethyl- (7CI,8CI);Acetaldehyde,(1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)- (9CI);1,3,3-Trimethyl-2-(formylmethylene)-2,3-dihydroindole;
  • PSA 20.31000
  • LogP 2.56180

Synthetic 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%

1,3,3-Trimethyl-2-(formylmethylene)indoline Chemical Properties

Chemistry informtion about Fischer's Aldehyde (CAS NO.84-83-3) is:
IUPAC Name: (2E)-2-(1,3,3-trimethylindol-2-ylidene)acetaldehyde
Synonyms: 2-(Formylmethylene)-1,3,3-Trimethylindoline ; 2-Methylene-1,3,3-Trimethylindoline Acetaldehyde ; 2-(1,3,3-Trimethylindolin-2-Ylidene)Acetaldehyde ; 1,3,3-Trimethyl-2-(Formylmethylene)Indoline ; (1,3,3-Trimethyl-1,3-Dihydro-2h-Indol-2-Ylidene)Acetaldehyde ; (1,3,3-Trimethyl-1,3-Dihydro-Indol-2-Ylidene)-Acetaldehyde ; 1,3-Dihydro-1,3,3-Trimethyl-2h-Indol-2-Ylidene Acetaldehyde ; Fischer's Aldehyde
Product Categories: Intermediates of Dyes and Pigments ; Building Blocks ; Heterocyclic Building Blocks ; Indoles 
MF: C13H15NO
MW: 201.26
EINECS: 201-565-8 
Melting Point: 112-116 °C(lit.)
Density: 1.102 g/cm3
Flash Point: 107.2 °C
Boiling Point: 301.4 °C at 760 mmHg
Vapour Pressure: 0.00105 mmHg at 25°C
Enthalpy of Vaporization: 54.16 kJ/mol
Following is the molecular structure of Fischer's Aldehyde (CAS NO.84-83-3) is:

1,3,3-Trimethyl-2-(formylmethylene)indoline Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rat LD50 oral > 215mg/kg (215mg/kg) behavioral: somnolence (general depressed activity) lungs, thorax, or respiration: chronic pulmonary edema lungs, thorax, or respiration: dyspnea National Technical Information Service. Vol. OTS0535466,

1,3,3-Trimethyl-2-(formylmethylene)indoline Safety Profile

A poison by ingestion. When heated to decomposition it emits toxic vapors of NOx
Hazard Codes:
IrritantXi
Risk Statements:
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements:
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing.
WGK Germany: 3
RTECS: AB2812500

1,3,3-Trimethyl-2-(formylmethylene)indoline Specification

First Aid Measures about Fischer's Aldehyde (CAS NO.84-83-3) is:
Ingestion: Seek medical assistance.
Inhalation: Move victim to fresh air. Apply artificial respiration if victim is not breathing. Do not use mouth-to-mouth method if victim ingested or inhaled the substance; induce artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. Administer oxygen if breathing is difficult.
Skin: Remove and isolate contaminated clothing and shoes. Immediately flush with running water for at least 20 minutes. For minor skin contact, avoid spreading material on unaffected skin.
Eyes: Immediately flush with running water for at least 20 minutes.

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