2-(5-bromo-1H-indol-3-yl)acetamide

Base Information

• Chemical Name: 2-(5-bromo-1H-indol-3-yl)acetamide
• CAS No.: 196081-79-5
• Molecular Formula: C10H9BrN2O
• Molecular Weight: 253.098
• Hs Code.: 2933990090
• NSC Number: 88146
• DSSTox Substance ID: DTXSID10293264
• Wikidata: Q82031936
• Mol file: 196081-79-5.mol

Synonyms:2-(5-bromo-1H-indol-3-yl)acetamide;196081-79-5;5-BROMOINDOLE-3-ACETAMIDE;1H-Indole-3-acetamide,5-bromo-;NSC88146;SCHEMBL1396045;DTXSID10293264;MFCD00022752;NSC-88146;AKOS015898356;5-bromoindole-3-acetamide, AldrichCPR;2-(5-bromo-1H-indol-3-yl)-acetamide;AS-10438;BP-13341;CS-0136358;FT-0643832;B-8500;1,2-CYCLOHEXANEDICARBOXYLICACIDDIGLYCIDYLESTER

Chemical Property of 2-(5-bromo-1H-indol-3-yl)acetamide

Chemical Property:

• Vapor Pressure: 8.18E-11mmHg at 25°C
• Melting Point: 290?°C (dec.)
• Refractive Index: 1.711
• Boiling Point: 517.5 °C at 760 mmHg
• Flash Point: 266.8 °C
• PSA: 58.88000
• Density: 1.668 g/cm³
• LogP: 2.65850
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 251.98983
• Heavy Atom Count: 14
• Complexity: 234

Purity/Quality:

98%min ^*data from raw suppliers

5-Bromoindole-3-acetamide ^*data from reagent suppliers

Safty Information:

• Statements: 36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C1Br)C(=CN2)CC(=O)N
• Uses: 5-Bromoindole-3-acetamide can be used for discovery and optimization of small-mol. ligands for CBP/p300 bromodomains. Amino derivatives of indole as potent inhibitors of isoprenylcysteine carboxyl methyltransferase.

Technology Process of 2-(5-bromo-1H-indol-3-yl)acetamide

There total 3 articles about 2-(5-bromo-1H-indol-3-yl)acetamide 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: 89.0%

(5-bromo-1H-indol-3-yl)-acetonitrile (774-14-1) → 2-(5-bromo-1H-indol-3-yl)acetamide (196081-79-5)

Guidance literature:

With potassium hydroxide; In tert-butyl alcohol; for 3h; Reflux;

DOI:10.1021/jm1002843

Reference yield:

(5-bromo-1H-indol-3-yl)-acetic acid (40432-84-6) → 2-(5-bromo-1H-indol-3-yl)acetamide (196081-79-5)

Guidance literature:

(5-bromo-1H-indol-3-yl)-acetic acid; With 1,1'-carbonyldiimidazole; In tetrahydrofuran;

With ammonia; In methanol; Further stages.;

DOI:10.1016/j.bmcl.2008.02.058

Reference yield:

5-bromo-1H-indole-3-carboxaldehyde (877-03-2) → 2-(5-bromo-1H-indol-3-yl)acetamide (196081-79-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: formamide; sodium tetrahydroborate / methanol / 0.5 h

1.2: 2.5 h / 100 °C

2.1: potassium hydroxide / tert-butyl alcohol / 3 h / Reflux

With sodium tetrahydroborate; formamide; potassium hydroxide; In methanol; tert-butyl alcohol;

upstream raw materials:

(5-bromo-1H-indol-3-yl)-acetonitrile

(5-bromo-1H-indol-3-yl)-acetic acid

5-bromo-1H-indole-3-carboxaldehyde

Refernces

• 1、 Go, Mei-Lin,Leow, Jo Lene,Gorla, Suresh Kumar,Schüller, Andreas Peter,Wang, Mei,Casey, Patrick J.. "Amino derivatives of indole as potent inhibitors of isoprenylcysteine carboxyl methyltransferase". experimental part. p. 6838 - 6850. Retrieved 2010/11/18.
• 2、 Levy, Daniel E.,Wang, Dan-Xiong,Lu, Qing,Chen, Zheng,Perumattam, John,Xu, Yong-jin,Liclican, Albert,Higaki, Jeffrey,Dong, Hanmin,Laney, Maureen,Mavunkel, Babu,Dugar, Sundeep. "Aryl-indolyl maleimides as inhibitors of CaMKIIδ. Part 1: SAR of the aryl region". . p. 2390 - 2394. Retrieved 2008/09/21.