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Cas Database |
| Name |
1,3,3-Trimethyl-2-(formylmethylene)indoline |
EINECS | 201-565-8 |
| CAS No. | 84-83-3 | Density | 1.102 g/cm3 |
| PSA | 20.31000 | LogP | 2.56180 |
| Solubility | N/A | 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 | N/A | Appearance | N/A |
| Safety | 26-36 | Risk Codes | 36/37/38 |
| Molecular Structure |
|
Hazard Symbols |
 Xi
|
| 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; |
Article Data | 16 |
1,3,3-Trimethyl-2-(formylmethylene)indoline Synthetic route
- 118-12-7
1,3,3-Trimethyl-2-methyleneindoline
- 68-12-2, 33513-42-7
N,N-dimethyl-formamide
- 84-83-3
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 |
- 118-12-7
1,3,3-Trimethyl-2-methyleneindoline
- 3724-43-4, 149409-22-3
Vilsmeier reagent
- 84-83-3
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; |
- 118-12-7
1,3,3-Trimethyl-2-methyleneindoline
- 93-61-8
N-methyl-N-phenylformamide
- 84-83-3
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; |
- 1592-43-4
1,3,3-trimethylspiro[indoline-2,3'-[3H]naphtho[2,1-b]pyran]
A
- 20200-86-6
1,3,3-trimethyl-1,3-dihydro-2H-indol-2-one
B
- 84-83-3
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 |
- 5418-63-3
1,2,3,3-tetramethyl-3H-indolium iodide
- 68-12-2, 33513-42-7
N,N-dimethyl-formamide
- 84-83-3
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; |
- 19764-96-6
1,1′,3,3,3′,3′-hexamethylindotricarbocyanine iodide
A
- 20200-86-6
1,3,3-trimethyl-1,3-dihydro-2H-indol-2-one
B
- 84-83-3
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. |
- 19764-96-6
1,1′,3,3,3′,3′-hexamethylindotricarbocyanine iodide
A
- 20200-86-6
1,3,3-trimethyl-1,3-dihydro-2H-indol-2-one
B
- 84-83-3
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 |
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:
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
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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