1,3,3-Trimethyl-2-methyleneindoline
N,N-dimethyl-formamide
1,3,3-trimethyl-2-formylmethyleneindoline
Conditions | Yield |
---|---|
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
Vilsmeier reagent
1,3,3-trimethyl-2-formylmethyleneindoline
Conditions | Yield |
---|---|
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
N-methyl-N-phenylformamide
1,3,3-trimethyl-2-formylmethyleneindoline
Conditions | Yield |
---|---|
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]
A
1,3,3-trimethyl-1,3-dihydro-2H-indol-2-one
B
1,3,3-trimethyl-2-formylmethyleneindoline
Conditions | Yield |
---|---|
In acetonitrile at 13℃; Product distribution; Irradiation; photodecomposition and singlet oxygen production during photosensitization; |
Conditions | Yield |
---|---|
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
N,N-dimethyl-formamide
1,3,3-trimethyl-2-formylmethyleneindoline
Conditions | Yield |
---|---|
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
A
1,3,3-trimethyl-1,3-dihydro-2H-indol-2-one
B
1,3,3-trimethyl-2-formylmethyleneindoline
Conditions | Yield |
---|---|
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
A
1,3,3-trimethyl-1,3-dihydro-2H-indol-2-one
B
1,3,3-trimethyl-2-formylmethyleneindoline
Conditions | Yield |
---|---|
With water In acetonitrile at 22℃; Irradiation; | A 56.6 %Chromat. B 11.5 %Chromat. C n/a D n/a |
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
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
1,3,3-trimethyl-2-formylmethyleneindoline
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium hydroxide / water / 2 h / 50 °C 2: trichlorophosphate / 10 h / 10 - 20 °C View Scheme |
A
1,3,3-trimethyl-1,3-dihydro-2H-indol-2-one
B
1,3,3-trimethyl-2-formylmethyleneindoline
Conditions | Yield |
---|---|
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 |
A
1,3,3-trimethyl-1,3-dihydro-2H-indol-2-one
B
1,3,3-trimethyl-2-formylmethyleneindoline
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
In acetic anhydride at 100℃; for 0.166667h; | 98% |
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 2h; | 96% |
Conditions | Yield |
---|---|
With sulfuric acid at 20℃; for 24h; | 95% |
1,3,3-trimethyl-2-formylmethyleneindoline
Conditions | Yield |
---|---|
In isopropyl alcohol; acetonitrile Heating; | 95% |
1,3,3-trimethyl-2-formylmethyleneindoline
2,4-Diphenyl-5,6-dihydrocyclopenta pyrylium perchlorate
Conditions | Yield |
---|---|
In isopropyl alcohol; acetonitrile Heating; | 95% |
1,3,3-trimethyl-2-formylmethyleneindoline
Conditions | Yield |
---|---|
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
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
Conditions | Yield |
---|---|
With acetic anhydride; triethylamine for 0.0833333h; | 94% |
Conditions | Yield |
---|---|
With acetic anhydride for 0.0666667h; Heating; | 92% |
Conditions | Yield |
---|---|
With sulfuric acid at 20℃; for 24h; | 92% |
1,3,3-trimethyl-2-formylmethyleneindoline
2-Methyl-4-phenyl-1-benzo-1-thiopyrylium perchlorate
Conditions | Yield |
---|---|
In acetic anhydride; acetic acid for 0.0333333h; heating; | 90% |
1,3,3-trimethyl-2-formylmethyleneindoline
Conditions | Yield |
---|---|
In acetic anhydride for 0.5h; Heating; | 90% |
Conditions | Yield |
---|---|
With sulfuric acid at 20℃; for 24h; | 90% |
Conditions | Yield |
---|---|
With sulfuric acid at 20℃; for 24h; | 90% |
1,3,3-trimethyl-2-formylmethyleneindoline
1-butyl-6-hydroxy-4-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile
Conditions | Yield |
---|---|
With acetic anhydride; ammonium chloride; acetic acid at 105℃; for 6h; | 90% |
1,3,3-trimethyl-2-formylmethyleneindoline
Conditions | Yield |
---|---|
In acetic anhydride at 50℃; for 2.5h; Knoevenagel Condensation; | 89.4% |
1,3,3-trimethyl-2-formylmethyleneindoline
2,2',3,3,3',3'-hexamethyl-1,1'-tetramethylenedi<2(3H)-indolium> diiodide
Conditions | Yield |
---|---|
With acetic anhydride for 0.0833333h; Heating; | 87% |
1,3,3-trimethyl-2-formylmethyleneindoline
Conditions | Yield |
---|---|
In acetic anhydride Heating; | 86% |
1,3,3-trimethyl-2-formylmethyleneindoline
2,3,4,9-Tetrahydrofuro<2,3-b>quinoline-3,4-dione
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol for 6h; Reagent/catalyst; Solvent; Reflux; | 86% |
1,3,3-trimethyl-2-formylmethyleneindoline
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
Conditions | Yield |
---|---|
With acetic anhydride for 0.5h; Reflux; | 85.7% |
1,3,3-trimethyl-2-formylmethyleneindoline
Conditions | Yield |
---|---|
With acetic anhydride for 1h; Reflux; | 85% |
1,3,3-trimethyl-2-formylmethyleneindoline
Conditions | Yield |
---|---|
In acetic anhydride at 80℃; for 1h; | 85% |
1,3,3-trimethyl-2-formylmethyleneindoline
Conditions | Yield |
---|---|
In acetic anhydride Condensation; Heating; | 83% |
With acetic anhydride Heating; | 83% |
1,3,3-trimethyl-2-formylmethyleneindoline
Conditions | Yield |
---|---|
With acetic anhydride; acetic acid for 5h; Heating; | 82% |
1,3,3-trimethyl-2-formylmethyleneindoline
Conditions | Yield |
---|---|
With acetic anhydride Heating; | 82% |
1,3,3-trimethyl-2-formylmethyleneindoline
benzoic acid hydrazide
C20H21N3O
Conditions | Yield |
---|---|
In ethanol for 1h; Heating / reflux; | 82% |
1,3,3-trimethyl-2-formylmethyleneindoline
2-methyl-6,7-dichlorothiazolo[4,5-b]quinoxaline
Conditions | Yield |
---|---|
With piperidine In ethanol for 8h; Knovenagel condensation; Heating; | 81% |
Conditions | Yield |
---|---|
With acetic anhydride at 50℃; for 0.5h; | 81% |
1,3,3-trimethyl-2-formylmethyleneindoline
Conditions | Yield |
---|---|
With acetic anhydride | 80% |
1,3,3-trimethyl-2-formylmethyleneindoline
Conditions | Yield |
---|---|
In acetic anhydride Condensation; Heating; | 80% |
1,3,3-trimethyl-2-formylmethyleneindoline
Conditions | Yield |
---|---|
With acetic anhydride at 145℃; for 24h; Inert atmosphere; | 80% |
With acetic anhydride at 20℃; for 2.5h; | 61% |
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:
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, |
A poison by ingestion. When heated to decomposition it emits toxic vapors of NOx.
Hazard Codes:
Xi
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
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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