6-Nitroindoline

Base Information

• Chemical Name: 6-Nitroindoline
• CAS No.: 19727-83-4
• Molecular Formula: C8H8N2O2
• Molecular Weight: 164.164
• Hs Code.: 29339900
• European Community (EC) Number: 243-257-6
• NSC Number: 80658
• DSSTox Substance ID: DTXSID90173393
• Nikkaji Number: J41.078K
• Wikidata: Q72494876
• ChEMBL ID: CHEMBL167986
• Mol file: 19727-83-4.mol

Synonyms:6-Nitroindoline;19727-83-4;6-nitro-2,3-dihydro-1H-indole;1H-Indole, 2,3-dihydro-6-nitro-;INDOLINE, 6-NITRO-;2,3-dihydro-6-nitro-(1h)-indole;MFCD00005710;CCRIS 3302;EINECS 243-257-6;NSC 80658;BRN 0156434;2,3-dihydro-6-nitro-1h-indole;4-20-00-02904 (Beilstein Handbook Reference);6-nitro-indoline;6-Nitroindoline, 97%;6-Nitro-2,3-dihydroindole;Oprea1_099066;SCHEMBL427407;CHEMBL167986;WLN: T56 BMT&J HNW;DTXSID90173393;AM821;CS-M1314;NSC80658;NSC-80658;STK387031;AKOS001302667;AC-5398;SB35109;CS-11318;LS-83470;SY015733;6-Nitro-2,3-dihydroindole, NSC 80658;A4315;FT-0600839;N0403;EN300-25980;N-3416;Z220346774

Chemical Property of 6-Nitroindoline

Chemical Property:

• Appearance/Colour: orange crystalline powder or red crystals
• Vapor Pressure: 0.000762mmHg at 25°C
• Melting Point: 67-69 °C(lit.)
• Refractive Index: 1.608
• Boiling Point: 306.6 °C at 760 mmHg
• PKA: 3.39±0.20(Predicted)
• Flash Point: 139.3 °C
• PSA: 57.85000
• Density: 1.298 g/cm³
• LogP: 2.22400
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 164.058577502
• Heavy Atom Count: 12
• Complexity: 190

Purity/Quality:

99% ^*data from raw suppliers

6-Nitroindoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CNC2=C1C=CC(=C2)[N+](=O)[O-]
• Uses: ? ;Reactant for preparation of 2-[(2,3-Dihydro-1H-indol-1-yl)methyl]melatonin analogs as novel MT2-selective melatonin receptor antagonists1? ;Reactant for synthesis of isoindigo and azaisoindigo glycosides as anticancer agents2? ;Reactant for preparation of arylfurancarboxamides with Nav1.8 voltage-gated Na channel blocking/analgesic activities3? ;Reactant for preparation of bicyclic benzamides as 5-HT1 receptor agonists4? ;Reactant for preparation of antiarrhythmic benzopyrans5? ;Reactant for preparation of 5-HT2C/2B receptor antagonists6 Reactant for preparation of 2-[(2,3-Dihydro-1H-indol-1-yl)methyl]melatonin analogs as novel MT2-selective melatonin receptor antagonistsReactant for synthesis of isoindigo and azaisoindigo glycosides as anticancer agentsReactant for preparation of arylfurancarboxamides with Nav1.8 voltage-gated Na channel blocking/analgesic activitiesReactant for preparation of bicyclic benzamides as 5-HT1 receptor agonistsReactant for preparation of antiarrhythmic benzopyransReactant for preparation of 5-HT2C/2B receptor antagonists

Technology Process of 6-Nitroindoline

There total 4 articles about 6-Nitroindoline 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: 95.0%

1-indoline (496-15-1) → 6-nitroindoline (19727-83-4)

Guidance literature:

With sulfuric acid; potassium nitrate; at 20 ℃; for 1.25h;

DOI:10.1016/j.tet.2004.05.067

Reference yield:

6-nitroindole (4769-96-4) → 6-nitroindoline (19727-83-4)

Guidance literature:

With trimethylamine-borane;

DOI:10.1016/S0960-894X(02)00655-8

Reference yield:

1-indoline (496-15-1) + sulfuric acid (7664-93-9) + nitric acid (7697-37-2,78989-43-2) → 6-nitroindoline (19727-83-4)

Guidance literature:

upstream raw materials:

1-indoline

sulfuric acid

nitric acid

6-nitroindole

Downstream raw materials:

C₂₉H₂₆N₂O₇

C₂₉H₂₆N₂O₇

methyl 3-methoxy-4-<(6-nitro-2,3-dihydroindol-1-yl)methyl>benzoate

1-(1-methyl-piperidin-4-yl)-1H-indol-6-ylamine

Refernces

• 1、 Xie, Guilin,Zhao, Yuhan,Cai, Changqun,Deng, Guo-Jun,Gong, Hang. "Palladium-Catalyzed Direct and Specific C-7 Acylation of Indolines with 1,2-Diketones". supporting information. p. 410 - 415. Retrieved 2021/01/26.
• 2、 Prasad, Bagineni,Jamroskovic, Jan,Bhowmik, Sudipta,Kumar, Rajendra,Romell, Tajanena,Sabouri, Nasim,Chorell, Erik. "Flexible Versus Rigid G-Quadruplex DNA Ligands: Synthesis of Two Series of Bis-indole Derivatives and Comparison of Their Interactions with G-Quadruplex DNA". supporting information. p. 7926 - 7938. Retrieved 2018/06/15.