Benz[cd]indol-2(1H)-one

Base Information

• Chemical Name: Benz[cd]indol-2(1H)-one
• CAS No.: 130-00-7
• Molecular Formula: C11H7NO
• Molecular Weight: 169.183
• Hs Code.: 29337900
• European Community (EC) Number: 204-973-4
• NSC Number: 25094
• DSSTox Substance ID: DTXSID5059610
• Nikkaji Number: J10.019F
• Wikipedia: Naphtholactam
• Wikidata: Q27451626
• ChEMBL ID: CHEMBL217045
• Mol file: 130-00-7.mol

Synonyms:benz(cd)indol-2(1H)-one;naphtholactam

Chemical Property of Benz[cd]indol-2(1H)-one

Chemical Property:

• Appearance/Colour: light yellow powder
• Vapor Pressure: 0.0521mmHg at 25°C
• Melting Point: 173-178 °C(lit.)
• Refractive Index: 1.723
• Boiling Point: 234.7 °C at 760 mmHg
• PKA: 13.27±0.20(Predicted)
• Flash Point: 128.9 °C
• PSA: 32.86000
• Density: 1.327 g/cm³
• LogP: 2.11910
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: methanol: soluble25mg/mL, clear to slightly hazy, yellow to brow
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 169.052763847
• Heavy Atom Count: 13
• Complexity: 238

Purity/Quality:

99% ^*data from raw suppliers

Benzo[cd]indol-2(1H)-one >97.0%(HPLC)(N) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C3C(=C1)C(=O)NC3=CC=C2
• Uses: ? ;Reactant in photo-Fries rearrangement1? ;Reactant in preparation of potential antitumor agents2? ;Reactant in synthesis of inhibitors of thymidylate synthase3 Benz[cd]indol-2(1H)-one was used in the synthesis of 2-oxo-1,2-dihydrobenzo[cd]indole-6-sulfonamide analog, novel Mycobacterium protein tyrosine phosphatase B (mPTPB) inhibitor.

Technology Process of Benz[cd]indol-2(1H)-one

There total 50 articles about Benz[cd]indol-2(1H)-one 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: 94.0%

1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl 4-methylbenzenesulfonate (5551-72-4) → 1,8-naphtholactam (130-00-7)

Guidance literature:

1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl 4-methylbenzenesulfonate; With sodium hydroxide; In ethanol; water; for 3h; Reflux;

With hydrogenchloride; In water; at 75 ℃;

In ethanol; water; for 3h; Reflux;

Reference yield: 94.0%

N-hydroxy-1,8-naphthalenedicarboximide (7797-81-1) → 1,8-naphtholactam (130-00-7)

Guidance literature:

With sodium hydroxide; In ethanol; water; for 3h; Reflux;

DOI:10.3109/14756366.2014.895718

Reference yield: 91.0%

1,8-Naphthalic anhydride (81-84-5) → 1,8-naphtholactam (130-00-7)

Guidance literature:

1,8-Naphthalic anhydride; With hydroxylamine hydrochloride; In pyridine; for 1h; Heating;

With p-toluenesulfonyl chloride; In pyridine; for 1h; Further stages.; Heating;

DOI:10.1021/jo0260488

upstream raw materials:

1,8-Naphthalimide

ethanol

8-amino-[1]naphthoic acid

8-bromonaphthalene-1-carboxylic acid

Downstream raw materials:

2-(4-methyl-1-piperazinyl)benz[cd]indole dihydrochloride

1-hydroxymethylbenzindol-2(1H)-one (HMBI)

N-<3-(4-phenyl-1,2,3,6-tetrahydropyridyl)propyl>benzindol-2-(1H)-one

Benzo[cd]indol-2-yl-phenethyl-amine; hydrochloride

Refernces

• 1、 Nie, Jing,Dong, Dan-Dan,Zhang, Yan,Wang, Tai-Yi,Liu, Wei,Yi, Shou-Zhi. "Synthesis and biological evaluation of a benz[cd]indol-2(1H)-one derivatives". . p. 7329 - 7336. Retrieved 2014.
• 2、 Eaborn et al.. "-". . p. 171,172. Retrieved 1967.
• 3、 Rule,Brown. "-". . p. 137. Retrieved 1934.
• 4、 Xue, Xiaoqian,Zhang, Yan,Liu, Zhaoxuan,Song, Ming,Xing, Yanli,Xiang, Qiuping,Wang, Zhen,Tu, Zhengchao,Zhou, Yulai,Ding, Ke,Xu, Yong. "Discovery of Benzo[cd]indol-2(1H)-ones as Potent and Specific BET Bromodomain Inhibitors: Structure-Based Virtual Screening, Optimization, and Biological Evaluation". . p. 1565 - 1579. Retrieved 2016.
• 5、 -. "Preparation method of aristolochia debilis alkaloid and intermediate thereof". Paragraph 0057-0061. . Retrieved 2021/01/29.