5-Bromo-8-naphtholactam

Base Information

• Chemical Name: 5-Bromo-8-naphtholactam
• CAS No.: 24856-00-6
• Molecular Formula: C11H6BrNO
• Molecular Weight: 248.079
• European Community (EC) Number: 413-480-5
• DSSTox Substance ID: DTXSID201306358
• Mol file: 24856-00-6.mol

Synonyms:24856-00-6;5-bromo-8-naphtholactam;6-bromobenzo[cd]indol-2(1H)-one;6-bromo-benzo[cd]indol-2(1h)-one;6-bromo-1H-benzo[cd]indol-2-one;6-bromobenz[cd]indol-2(1H)-one;EC 413-480-5;CBMicro_016418;6-bromobenz(cd)indol-2one;6-bromobenz(cd)indol-2-one;SCHEMBL7118963;DTXSID201306358;6-bromo-benz[cd]indol-2(1H)-one;CCG-5454;BIM-0016449.P001;CS-0435648;E87856;A936057;9-bromo-2-azatricyclo[6.3.1.0?,??]dodeca-1(12),4,6,8,10-pentaen-3-one

Chemical Property of 5-Bromo-8-naphtholactam

Chemical Property:

• Melting Point: 255-256 °C
• Boiling Point: 284.8±19.0 °C(Predicted)
• PKA: 12.57±0.20(Predicted)
• PSA: 32.86000
• Density: 1.727±0.06 g/cm3(Predicted)
• LogP: 2.88160
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 246.96328
• Heavy Atom Count: 14
• Complexity: 268

Purity/Quality:

99.9% ^*data from raw suppliers

Safty Information:

• Hazard Codes: Xn,N
• Statements: 22-43-50/53
• Safety Statements: 22-24-37-60-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=CC3=C2C(=C1)C(=O)N3)Br

Technology Process of 5-Bromo-8-naphtholactam

There total 8 articles about 5-Bromo-8-naphtholactam 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%

1,8-naphtholactam (130-00-7) → 6-bromo-benzo[cd]indol-2(1H)-one (24856-00-6)

Guidance literature:

With bromine; In chloroform; at 0 - 20 ℃; for 24h;

Reference yield: 56.0%

pyridine-2-carboxylic acid (4-bromo-naphthalen-1-yl)amide + benzene-1,3,5-triyl triformate → 6-bromo-benzo[cd]indol-2(1H)-one (24856-00-6)

Guidance literature:

With triethylamine; silver carbonate; cobalt(II) chloride; Trimethylacetic acid; In 1,4-dioxane; at 130 ℃; for 20h; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.orglett.9b02037

Reference yield:

4-Bromo-1-naphthylamine (2298-07-9) → 6-bromo-benzo[cd]indol-2(1H)-one (24856-00-6)

Guidance literature:

Multi-step reaction with 2 steps

1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere

2: triethylamine; cobalt(II) chloride; silver carbonate; Trimethylacetic acid / 1,4-dioxane / 20 h / 130 °C / Inert atmosphere; Sealed tube

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; silver carbonate; cobalt(II) chloride; Trimethylacetic acid; In 1,4-dioxane; dichloromethane;

DOI:10.1021/acs.orglett.9b02037

upstream raw materials:

1,8-naphtholactam

5-bromo-8-nitro-[1]naphthoic acid

1-naphthalenecarboxylic acid

5-bromo-1-naphthalenecarboxylic acid

Downstream raw materials:

6-hydroxybenzo[cd]indol-2(1H)-one

Refernces

• 1、 -. "ADVANTAGEOUS THERAPIES FOR DISORDERS MEDIATED BY IKAROS OR AIOLOS". Page/Page column 149; 161-162. . Retrieved 2022/02/15.
• 2、 -. "PROTEIN TYROSINE PHOSPHATASE DEGRADERS AND METHODS OF USE THEREOF". Page/Page column 203. . Retrieved 2021/06/26.