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

Base Information

• Chemical Name: 1,3,3-Trimethyl-2-(formylmethylene)indoline
• CAS No.: 84-83-3
• Molecular Formula: C13H15NO
• Molecular Weight: 201.268
• Hs Code.: 2933990090
• European Community (EC) Number: 201-565-8
• Nikkaji Number: J36.859H
• ChEMBL ID: CHEMBL1610155
• Mol file: 84-83-3.mol

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;

Chemical Property of 1,3,3-Trimethyl-2-(formylmethylene)indoline

Chemical Property:

• Vapor Pressure: 0.00105mmHg at 25°C
• Melting Point: 112-116 ºC
• Refractive Index: 1.6
• Boiling Point: 301.4 ºC at 760 mmHg
• PKA: 0.82±0.40(Predicted)
• Flash Point: 107.2 ºC
• PSA: 20.31000
• Density: 1.102 g/cm³
• LogP: 2.56180
• Storage Temp.: 2-8°C
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 201.115364102
• Heavy Atom Count: 15
• Complexity: 293

Purity/Quality:

99% ^*data from raw suppliers

2-(1,3,3-Trimethylindolin-2-ylidene)acetaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C2=CC=CC=C2N(C1=CC=O)C)C
• Isomeric SMILES: CC\1(C2=CC=CC=C2N(/C1=C\C=O)C)C
• Uses: Reactant for preparation of:? ;Cyanine dyes1? ;Photopolymer holographic recording materials2 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.

Technology Process of 1,3,3-Trimethyl-2-(formylmethylene)indoline

There total 18 articles about 1,3,3-Trimethyl-2-(formylmethylene)indoline 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: 81.0%

1,3,3-Trimethyl-2-methyleneindoline (118-12-7) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → (2E)-(1,3,3-trimethyl-1,3-dihydro-2H-indol-2-ylidene)acetaldehyde (84-83-3,85654-15-5)

Guidance literature:

With trichlorophosphate;

DOI:10.1016/S0040-4020(01)96787-0

Reference yield: 76.4%

1,3,3-Trimethyl-2-methyleneindoline (118-12-7) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 1,3,3-trimethyl-2-formylmethyleneindoline (84-83-3)

Guidance literature:

N,N-dimethyl-formamide; With trichlorophosphate; at 0 ℃; for 2h;

1,3,3-Trimethyl-2-methyleneindoline; In N,N-dimethyl-formamide; at 0 - 60 ℃;

DOI:10.1039/c7tc00735c

Reference yield: 43.0%

1,3,3-Trimethyl-2-methyleneindoline (118-12-7) + Vilsmeier reagent (3724-43-4,149409-22-3) → 1,3,3-trimethyl-2-formylmethyleneindoline (84-83-3)

Guidance literature:

1,3,3-Trimethyl-2-methyleneindoline; Vilsmeier reagent; In dichloromethane; at 20 ℃; Inert atmosphere;

With potassium carbonate; In tetrahydrofuran; water; at 20 ℃; for 12h;

DOI:10.1021/jacs.7b10639

upstream raw materials:

1,3,3-Trimethyl-2-methyleneindoline

N,N-dimethyl-formamide

N-methyl-N-phenylformamide

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

Downstream raw materials:

1,1′,3,3,3′,3′-hexamethylindocarbocyanine chloride

2-<3-(1,3-Dihydro-1,3,3-trimethyl-2H-2-indolylidene)-1-propenyl>-1,3-diphenylbenzimidazolium iodide

p-Triphenylphosphoniobromide benzoylvinyl(1,3,3-trimethyl-2-methyleneindolenyl)

7-phenyl-2-<(4-methyl-6-phenyl-2-pyrimidinylthio)acetyl>-5-<3-(1,3,3-trimethyl-2,3-dihydro-2-indolylidene)-1-propenyl>thiazolo<3,2-a>pyrimidin-3-ylio oxide

Refernces

• 1、 Mitra, Koushambi,Lyons, Charles E.,Hartman, Matthew C. T.. "A Platinum(II) Complex of Heptamethine Cyanine for Photoenhanced Cytotoxicity and Cellular Imaging in Near-IR Light". . p. 10263 - 10267. Retrieved 2018/07/31.
• 2、 Song, Xinbo,Bian, Hui,Wang, Chao,Hu, Mingyu,Li, Ning,Xiao, Yi. "Development and applications of a near-infrared dye-benzylguanine conjugate to specifically label SNAP-tagged proteins". . p. 8091 - 8101. Retrieved 2017/10/13.