1,3,3-Trimethyl-2-methyleneindoline

Base Information

• Chemical Name: 1,3,3-Trimethyl-2-methyleneindoline
• CAS No.: 118-12-7
• Molecular Formula: C12H15N
• Molecular Weight: 173.258
• Hs Code.: 29339990
• European Community (EC) Number: 204-235-1
• NSC Number: 66176
• DSSTox Substance ID: DTXSID8051596
• Nikkaji Number: J131.403C
• Wikidata: Q72514138
• Mol file: 118-12-7.mol

Synonyms:1,3,3-Trimethyl-2-methyleneindoline;118-12-7;Fischer's base;Fischer base;2-Methylene-1,3,3-trimethylindoline;1H-Indole, 2,3-dihydro-1,3,3-trimethyl-2-methylene-;Fischer's methylene base;NSC 66176;1,3,3-trimethyl-2-methylideneindole;Fischers Base;CCRIS 6608;Indoline, 1,3,3-trimethyl-2-methylene-;Indoline, 2-methylene-1,3,3-trimethyl-;EINECS 204-235-1;BRN 0131162;1,3,3-trimethyl-2-methyleneindole;1,3-Dihydro-1,3,3-trimethyl-2-methyleneindoline;5-20-07-00141 (Beilstein Handbook Reference);1,3,3-trimethyl-2-methylidene-2,3-dihydro-1H-indole;Fischer''''s base;1,3,3-trimethyl-2-methylene-indoline;Indoline,3,3-trimethyl-;Fischer''''s methylene base;SCHEMBL918366;SCHEMBL8397425;DTXSID8051596;AMY3795;1,3-Trimethyl-2-methyleneindoline;2-Methylene-1,3-trimethylindoline;1,3,3-trimetil-2-metilenoindolina;2-metileno-1,3,3-trimetilindolina;NSC66176;MFCD00005813;NSC-66176;STK802332;1 3 3-Trimethyl-2-methyleneindoline;2-methylene 1,3,3-trimethylindoline;2-Methylene-1 3 3-trimethylindoline;AKOS000119124;1,3,3-trimethyl-2-methylidene-indole;Indolina, 1,3,3-trimetil-2-metilen-;LS-14079;LS-83461;1,3,3-Trimethyl-2-methyleneindoline, 95%;1,3,3-Trimethyl-2-methyleneindoline, 97%;12-Dihydro-133-trimethyl-2-methyleneindole;FT-0613040;T0879;WLN: T56 BNY DHJ B1 CU1 D1 D1;1,3,3-trimetil-2-metileno-2,3-dihidroindol;EN300-16764;1,2-dihidro-1,3,3-trimetil-2-metilenoindole;E78126;T-6680;1 3 3-Trimethyl-2-methylene-2 3-dihydroindole;1,3-dihidro-1,3,3-trimetil-2-metilenoindolina;2 3-Dihydro-1 3 3-trimethyl-2-methyleneindole;2,3-dihidro-1, 3,3--trimetil-2-metilenoindol;1 3-Dihydro-1 3 3-trimethyl-2-methyleneindoline;A803883;Indoline133-trimethyl-2-methylene-(6CI7CI8CI);1H-indol, 2,3-dihidro-1,3,3-trimetil-2-metilen-;J-013592;Z56769766;F0001-0295;Indoline, 1,3,3-trimethyl-2-methylene- (6CI,7CI,8CI);1,3,3-Trimethyl-2-methyleneindoline, liquid, for paper chromatography, >=96.0%

Chemical Property of 1,3,3-Trimethyl-2-methyleneindoline

Chemical Property:

• Appearance/Colour: clear red liquid
• Vapor Pressure: 0.0249mmHg at 25°C
• Melting Point: -8 °C
• Refractive Index: n20/D 1.577(lit.)
• Boiling Point: 248 °C at 760 mmHg
• PKA: 2.19±0.40(Predicted)
• Flash Point: 101.7 °C
• PSA: 3.24000
• Density: 1 g/cm³
• LogP: 2.99270
• Storage Temp.: Store below +30°C.
• Solubility.: negligible
• Water Solubility.: negligible
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 173.120449483
• Heavy Atom Count: 13
• Complexity: 229

Purity/Quality:

97% ^*data from raw suppliers

1,3,3-Trimethyl-2-methyleneindoline >96.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,N
• Hazard Codes: Xn,N
• Statements: 22-38-50/53
• Safety Statements: 28-60-61-57-37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C(=C)N(C2=CC=CC=C21)C)C
• General Description: 1,3,3-Trimethyl-2-methyleneindoline (Fischer base) is a versatile intermediate in organic synthesis, particularly for introducing ethynyl groups into aryl and heteroaryl compounds via its acyl derivatives. It reacts with acylating agents and phosphorus oxychloride to form indolenium salts, which, upon treatment with aqueous alkali, yield monosubstituted acetylenes and 1,3,3-trimethyl-2-oxindole. This method is effective for aromatic and heterocyclic systems but unsuitable for alkylacetylenes due to resinification. The Fischer base thus serves as a key building block for synthesizing acetylenes, which are valuable in producing dyes and thermochromic materials.

Technology Process of 1,3,3-Trimethyl-2-methyleneindoline

There total 37 articles about 1,3,3-Trimethyl-2-methyleneindoline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

2-(1,3,3-tri-methylindolin-2-ylidene)acetonitrile (5114-82-9) → 1,3,3-Trimethyl-2-methyleneindoline (118-12-7)

Guidance literature:

With hydrogenchloride; for 6h; Heating;

DOI:10.1007/BF00473933

Reference yield: 100.0%

spiro-1,3,3-trimethylindoline<2:3'>-3',4'-dihydroisoxazole (144598-21-0) → 1,3,3-Trimethyl-2-methyleneindoline (118-12-7)

Guidance literature:

With hydrogenchloride; for 6h; Heating;

DOI:10.1007/BF00473933

Reference yield: 100.0%

1,3,3-trimethyl-2-methyleneacetamidoindoline (301673-89-2) → 1,3,3-Trimethyl-2-methyleneindoline (118-12-7)

Guidance literature:

With hydrogenchloride; for 6h; Heating;

DOI:10.1007/BF00473933

upstream raw materials:

indole

methyl iodide

2-methyl-1H-indole

methanol

Downstream raw materials:

<1,3,3-Trimethyl-indolinyliden-(2)>-<4,6-dichlor-1,3,5-triazinyl-(2)>-methan

[4-(1,3,3-trimethyl-indolin-2-ylidene)-but-2-enylidene]-malononitrile

2-acetylmethylene-1,3,3-trimethylindoline

Bis-<1.3.3-trimethyl-indolinyliden-(2)-methyl>-keton

Refernces

ACETYLENIC FRAGMENTATION OF ACYL DERIVATIVES OF THE FISCHER BASE

10.1007/BF00475641

The research investigates a method for synthesizing aryl- and heteroarylacetylenes using acyl derivatives of the Fischer base. The study aims to develop a convenient and efficient route for introducing an ethynyl group into organic compounds. The key chemicals used include 1,3,3-trimethyl-2-methylene-indoline (the Fischer base), various acylating agents (such as p-nitrobenzoyl chloride), phosphorus oxychloride, and aqueous alkali (e.g., NaOH or KOH). The method involves heating acyl derivatives of the Fischer base with phosphorus oxychloride to form indolenium salts, which are then treated with aqueous alkali to yield monosubstituted acetylenes and 1,3,3-trimethyl-2-oxindole. The researchers synthesized a series of aryl- and heteroarylacetylenes and demonstrated the versatility of the method by using various acyl groups from aliphatic, aromatic, and heterocyclic acids. The study concludes that this method is effective for synthesizing aryl- and heteroarylacetylenes, but not for alkylacetylenes, which tend to undergo resinification under the reaction conditions. The findings provide a valuable synthetic route for preparing acetylenes, which are important in the synthesis of various organic compounds, including dyes and thermochromic materials.

Mild acylation of fischer indole with 5-aryl-2,3-dihydrofuran-2,3-diones

10.1134/S107042800906027X

The research investigates the reaction of 5-aryl-2,3-dihydrofuran-2,3-diones with Fischer indole. The study found that when 5-aryl-2,3-dihydrofuran-2,3-diones (Ia and Ib) were reacted with 1,3,3-trimethyl-2-methylidene-2,3-dihydro-1H-indole (II) at a 1:1 molar ratio in boiling anhydrous benzene for 1–2 minutes, the products (2Z)-1-aryl-3-hydroxy-5-(1,3,3-trimethyl-2,3-dihydro-1H-indol-2-ylidene)pent-2-ene-1,4-diones (IIIa and IIIb) were obtained in good yields of 89% and 87%, respectively. The spectral parameters of compounds IIIa and IIIb indicated that they exist in DMSO-d6 solution as mixtures of enol and diketone tautomers A and B at a ratio of approximately 5:1. The transformation is believed to involve acylation of the exocyclic methylene group in indole II by the carbonyl group in position 2 of 5-aryl-2,3-dihydrofuran-2,3-dione Ia or Ib, followed by opening of the furan ring at the O1–C2 bond.