Tert-butyl 7-formylindoline-1-carboxylate

Base Information

• Chemical Name: Tert-butyl 7-formylindoline-1-carboxylate
• CAS No.: 174539-67-4
• Molecular Formula: C₁₄H₁₇NO₃
• Molecular Weight: 247.294
• Hs Code.: 2933990090
• European Community (EC) Number: 625-136-3
• DSSTox Substance ID: DTXSID00363223
• Wikidata: Q82146818
• Mol file: 174539-67-4.mol

Synonyms:174539-67-4;tert-butyl 7-formylindoline-1-carboxylate;N-Boc-indoline-7-carboxaldehyde;1-Boc-2,3-dihydro-7-indolecarbaldehyde;tert-butyl 7-formyl-2,3-dihydroindole-1-carboxylate;TERT-BUTYL 7-FORMYL-2,3-DIHYDRO-1H-INDOLE-1-CARBOXYLATE;tert-butyl 7-formyl-1-indolinecarboxylate;Oprea1_876995;SCHEMBL3127248;DTXSID00363223;AMY36699;ZGA53967;methyl-4-methoxyindole-2-carboxylate;MFCD02187200;AKOS005099124;N-Boc-indoline-7-carboxaldehyde, 97%;tert-butyl7-formylindoline-1-carboxylate;AC-27793;A3858;FT-0655066;EN300-106013;6R-0040;Q-102583;1-BOC-2 pound not3-DIHYDRO-7-INDOLECARBALDEHYDE;Tert-butyl 7-formyl-2,3-dihydro-indole-1-carboxylate;Z1397933452

Chemical Property of Tert-butyl 7-formylindoline-1-carboxylate

Chemical Property:

• Vapor Pressure: 1.69E-05mmHg at 25°C
• Melting Point: 86-90 °C
• Refractive Index: 1.575
• Boiling Point: 364.4 °C at 760 mmHg
• Flash Point: 174.2 °C
• PSA: 46.61000
• Density: 1.186 g/cm³
• LogP: 2.86170
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 247.12084340
• Heavy Atom Count: 18
• Complexity: 334

Purity/Quality:

98%,99%, ^*data from raw suppliers

N-Boc-indoline-7-carboxaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCC2=C1C(=CC=C2)C=O
• Uses: Useful bi-functional starter in indoline chemistry and natural product chemistry

Technology Process of Tert-butyl 7-formylindoline-1-carboxylate

There total 2 articles about Tert-butyl 7-formylindoline-1-carboxylate 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: 69.0%

1-(tert-butoxycarbonyl)indoline (143262-10-6) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → C22H24N2O3 + 1-(tert-butoxycarbonyl)-7-indolinecarboxaldehyde (174539-67-4)

Guidance literature:

1-(tert-butoxycarbonyl)indoline; With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; In diethyl ether; cyclohexane; at -70 ℃; Inert atmosphere;

N,N-dimethyl-formamide; In diethyl ether; cyclohexane; at -78 ℃; for 0.5h; Inert atmosphere;

With ammonium chloride; In diethyl ether; cyclohexane; at -50 ℃; Temperature; Inert atmosphere;

DOI:10.15227/orgsyn.073.0085

Reference yield:

1-indoline (496-15-1) + di-tert-butyl dicarbonate (24424-99-5) → C22H24N2O3 + 1-(tert-butoxycarbonyl)-7-indolinecarboxaldehyde (174539-67-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tetrahydrofuran / 3.5 h / 20 °C

2.1: N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium / diethyl ether; cyclohexane / -70 °C / Inert atmosphere

2.2: 0.5 h / -78 °C / Inert atmosphere

2.3: -50 °C / Inert atmosphere

With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; In tetrahydrofuran; diethyl ether; cyclohexane;

DOI:10.15227/orgsyn.073.0085

Reference yield: 95.0%

1-(tert-butoxycarbonyl)-7-indolinecarboxaldehyde (174539-67-4) → indoline-7-carboxyaldehyde (143262-21-9)

Guidance literature:

1-(tert-butoxycarbonyl)-7-indolinecarboxaldehyde; With hydrogenchloride; at 20 ℃; for 0.25h;

With ammonia; In water; at 20 ℃;

DOI:10.15227/orgsyn.073.0085

upstream raw materials:

1-(tert-butoxycarbonyl)indoline

N,N-dimethyl-formamide

1-indoline

di-tert-butyl dicarbonate

Downstream raw materials:

indoline-7-carboxyaldehyde

Refernces