5-Bromoindole-2-carboxylic acid

Base Information

• Chemical Name: 5-Bromoindole-2-carboxylic acid
• CAS No.: 7254-19-5
• Molecular Formula: C9H6BrNO2
• Molecular Weight: 240.056
• Hs Code.: 29339980
• European Community (EC) Number: 805-759-9
• NSC Number: 73384
• DSSTox Substance ID: DTXSID60291139
• Nikkaji Number: J377.426K
• Wikidata: Q72457361
• ChEMBL ID: CHEMBL22435
• Mol file: 7254-19-5.mol

Synonyms:5-Bromoindole-2-carboxylic acid;7254-19-5;5-Bromo-1H-indole-2-carboxylic acid;1H-Indolecarboxylic acid, 5-bromo-;MFCD00022705;5-bromo-2-indolecarboxylic acid;NSC73384;1H-Indole-2-carboxylic acid, 5-bromo-;Oprea1_523989;CHEMBL22435;SCHEMBL378196;5-bromo indole carboxylic acid;DTXSID60291139;BCP26712;5-Bromo-1H-indole-2-carboxylicacid;AM1164;BBL022460;NSC-73384;STK504240;AKOS000158641;AC-8797;CS-W007593;GA-0937;HY-W007593;SB13265;5-Bromo-1H-indole-2-carboxylic acid #;SY035588;B3836;BB 0248942;FT-0601303;EN300-30450;B-8660;A837559;Z285234024

Chemical Property of 5-Bromoindole-2-carboxylic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 287-288 °C
• Refractive Index: 1.749
• Boiling Point: 470.932 °C at 760 mmHg
• PKA: 4.25±0.30(Predicted)
• Flash Point: 238.611 °C
• PSA: 53.09000
• Density: 1.828 g/cm³
• LogP: 2.62860
• Storage Temp.: −20°C
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 238.95819
• Heavy Atom Count: 13
• Complexity: 222

Purity/Quality:

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

5-Bromoindole-2-carboxylic Acid ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C1Br)C=C(N2)C(=O)O
• Uses: 5-Bromoindole-2-carboxylic acid,Reactant involved in studies of biologically active molecules including:Discovery of indole inhibitors of MMP-13 for treatment of arthritic diseases1;Synthesis of indolyl ethanones as indoleamine 2,3-dioxygenase inhibitors2 ;cis-Diaminocyclohexane derivatives prepared for use as factor Xa inhibitors3 ;Synthesis of tubulin polymerization inhibitors and cancer cell growth inhibitors4 ;Preparation of dual PPARγ/δ agonists5;Synthesis of chemical probes to examine the role of hFPRL1 receptor . Reactant involved in studies of biologically active molecules including:Discovery of indole inhibitors of MMP-13 for treatment of arthritic diseasesSynthesis of indolyl ethanones as indoleamine 2,3-dioxygenase inhibitorscis-Diaminocyclohexane derivatives prepared for use as factor Xa inhibitorsSynthesis of tubulin polymerization inhibitors and cancer cell growth inhibitorsPreparation of dual PPARγ/δ agonistsSynthesis of chemical probes to examine the role of hFPRL1 receptor in inflammation

Technology Process of 5-Bromoindole-2-carboxylic acid

There total 7 articles about 5-Bromoindole-2-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: 95.0%

ethyl 5-bromoindolecarboxylate (16732-70-0) → 5-bromo-2-indolecarboxylic acid (7254-19-5)

Guidance literature:

With sodium hydroxide; at 110 ℃; for 0.0333333h; Microwave irradiation;

DOI:10.1021/jm900016t

Reference yield: 90.0%

→ 5-bromo-2-indolecarboxylic acid (7254-19-5)

Guidance literature:

With sodium hydroxide; In methanol; at 20 ℃;

Reference yield:

4-bromo-2-iodoaniline (66416-72-6) + 2-oxo-propionic acid (127-17-3) → 5-bromo-2-indolecarboxylic acid (7254-19-5)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; palladium diacetate; In N,N-dimethyl-formamide; at 105 ℃; for 4h;

DOI:10.1016/j.bmcl.2003.09.022

upstream raw materials:

(5-bromo-2-nitro-phenyl)-pyruvic acid

4-bromo-2-iodoaniline

2-oxo-propionic acid

ethyl 5-bromoindolecarboxylate

Downstream raw materials:

5-bromo-1H-indole

5-Bromo-1H-indole-2-carboxylic acid ((1S)-carbamoyl-2-phenyl-ethyl)-amide

(5-bromo-1H-indol-2-yl)methanol

5-bromo-1H-indole-2-carbaldehyde

Refernces

• 1、 -. "Cathepsin K inhibitor and application thereof". Paragraph 0219; 0220; 0221; 0276; 0277; 0278. . Retrieved 2017/08/28.
• 2、 Jiang, Xiaojian,Zhang, Feng,Yang, Junjie,Yu, Pei,Yi, Peng,Sun, Yewei,Wang, Yuqiang. "Synthesis of 3,3-Dihalo-2-oxindoles from 2-Substituted Indoles via Halogenation–Decarboxylation/Desulfonamidation–Oxidation Process". supporting information. p. 3938 - 3942. Retrieved 2016/12/30.