Indoline-5-carboxylic acid

Base Information

• Chemical Name: Indoline-5-carboxylic acid
• CAS No.: 15861-30-0
• Molecular Formula: C9H9NO2
• Molecular Weight: 163.17
• Hs Code.: 29349990
• DSSTox Substance ID: DTXSID00429272
• Wikidata: Q72483080
• Mol file: 15861-30-0.mol

Synonyms:indoline-5-carboxylic acid;15861-30-0;2,3-dihydro-1H-indole-5-carboxylic Acid;1H-Indole-5-carboxylic acid, 2,3-dihydro-;indoline-5-carboxylicacid;1H-INDOLE-5-CARBOXYLIC ACID,2,3-DIHYDRO-,;SCHEMBL2638095;DTXSID00429272;DZTLKUKANGQSRN-UHFFFAOYSA-N;HMS1773A12;MFCD07371642;AKOS001200253;CS-W019001;SB33958;Indoline-5-carboxylic acid, AldrichCPR;AC-27801;BS-13605;BB 0262347;FT-0688922;EN300-23678;A21420;Q-102597;Z164676906

Chemical Property of Indoline-5-carboxylic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.611
• Boiling Point: 369.037 °C at 760 mmHg
• Flash Point: 176.987 °C
• PSA: 49.33000
• Density: 1.284 g/cm³
• LogP: 1.49080
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 163.063328530
• Heavy Atom Count: 12
• Complexity: 193

Purity/Quality:

NLT 98% ^*data from raw suppliers

Indoline-5-carboxylicacid ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CNC2=C1C=C(C=C2)C(=O)O

Technology Process of Indoline-5-carboxylic acid

There total 4 articles about Indoline-5-carboxylic acid 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:

2,3-dihydro-1H-indole-5-carboxylic acid methyl ester (141452-01-9) → 2,3-dihydro-1H-indole-5-formic acid (15861-30-0)

Guidance literature:

With sodium hydroxide; In methanol; at 85 ℃; for 1h;

DOI:10.1021/jm0602413

Reference yield:

5-methoxycarbonylindole (1011-65-0) → 2,3-dihydro-1H-indole-5-formic acid (15861-30-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / sodium cyanoborohydride; acetic acid / 20 °C

2: aq. NaOH / methanol / 1 h / 85 °C

With sodium hydroxide; sodium cyanoborohydride; acetic acid; In methanol;

DOI:10.1021/jm0602413

Reference yield:

1H-Indole-5-carboxylic acid (1670-81-1,142396-03-0) → 2,3-dihydro-1H-indole-5-formic acid (15861-30-0)

Guidance literature:

With sodium cyanoborohydride; acetic acid; for 0.333333h;

DOI:10.1055/s-2001-14661

upstream raw materials:

1H-Indole-5-carboxylic acid

2,3-dihydro-1H-indole-5-carboxylic acid methyl ester

5-methoxycarbonylindole

Downstream raw materials:

1-acetylindoline-5-carboxylic acid

5-Chlorocarbonyl-2,3-dihydro-indole-1-carboxylic acid benzyl ester

(S)-2-[(1-Benzyloxycarbonyl-2,3-dihydro-1H-indole-5-carbonyl)-amino]-hexanedioic acid dimethyl ester

(S)-2-[(1-Benzyloxycarbonyl-2,3-dihydro-1H-indole-5-carbonyl)-amino]-pentanedioic acid diethyl ester

Refernces

• 1、 Wishka, Donn G.,Walker, Daniel P.,Yates, Karen M.,Reitz, Steven C.,Jia, Shaojuan,Myers, Jason K.,Olson, Kirk L.,Jacobsen, E. Jon,Wolfe, Mark L.,Groppi, Vincent E.,Hanchar, Alexander J.,Thornburgh, Bruce A.,Cortes-Burgos, Luz A.,Wong, Erik H. F.,Staton, Brian A.,Raub, Thomas J.,Higdon, Nicole R.,Wall, Theron M.,Hurst, Raymond S.,Walters, Rodney R.,Hoffmann, William E.,Hajos, Mihaly,Franklin, Stanley,Carey, Galen,Gold, Lisa H.,Cook, Karen K.,Sands, Steven B.,Zhao, Sabrina X.,Soglia, John R.,Kalgutkar, Amit S.,Arneric, Stephen P.,Rogers, Bruce N.. "Discovery of N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]furo[2,3-c]pyridine-5- carboxamide, an agonist of the α7 nicotinic acetylcholine receptor, for the potential treatment of cognitive deficits in schizophrenia: Synthesis and structure-activity relationship". . p. 4425 - 4436. Retrieved 2007/10/03.