4-Chloro-3-nitrocoumarin

Base Information

• Chemical Name: 4-Chloro-3-nitrocoumarin
• CAS No.: 38464-20-9
• Molecular Formula: C9H4ClNO4
• Molecular Weight: 225.588
• Hs Code.: 2932209090
• European Community (EC) Number: 623-785-7
• DSSTox Substance ID: DTXSID40351003
• Nikkaji Number: J267.292H
• Wikidata: Q82127090
• Metabolomics Workbench ID: 74121
• Mol file: 38464-20-9.mol

Synonyms:4-Chloro-3-nitrocoumarin;38464-20-9;4-chloro-3-nitro-2H-chromen-2-one;4-chloro-3-nitrochromen-2-one;4-Chloro-3-nitro-chromen-2-one;3-Nitro-4-chlorocoumarin;SCHEMBL2017838;DTXSID40351003;4-Chloro-3-nitrocoumarin, 96%;OFLRQEKOAGDHKT-UHFFFAOYSA-N;MFCD00051670;STK728376;AKOS000637771;4-chloro-3-nitro-2H- chromen-2-one;UPCMLD0ENAT5889195:001;AS-61392;C1691;CS-0204833;FT-0618092;EN300-26160;D89448;A824163;BRD-K26343485-001-01-1;Z57066919

Chemical Property of 4-Chloro-3-nitrocoumarin

Chemical Property:

• Vapor Pressure: 9.68E-05mmHg at 25°C
• Melting Point: 160-164 °C(lit.)
• Refractive Index: 1.642
• Boiling Point: 338.7 °C at 760 mmHg
• Flash Point: 158.6 °C
• PSA: 76.03000
• Density: 1.6 g/cm³
• LogP: 2.87780
• Water Solubility.: Insoluble in water.
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 224.9828853
• Heavy Atom Count: 15
• Complexity: 347

Purity/Quality:

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

4-Chloro-3-nitrocoumarin ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=C(C(=O)O2)[N+](=O)[O-])Cl
• Uses: 4-Chloro-3-nitrocoumarin, is used in synthesis and antimicrobial activity of new 4-heteroarylamino coumarin derivatives that contain nitrogen and sulfur as heteroatoms.

Technology Process of 4-Chloro-3-nitrocoumarin

There total 4 articles about 4-Chloro-3-nitrocoumarin 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: 97.0%

4-hydroxy-3-nitrocoumarin (20261-31-8) → 4-chloro-3-nitro-chromen-2-one (38464-20-9)

Guidance literature:

With trichlorophosphate;

DOI:10.1002/jhet.5570330224

Reference yield:

4-hydroxy[1]benzopyran-2-one (1076-38-6,92395-12-5) → 4-chloro-3-nitro-chromen-2-one (38464-20-9)

Guidance literature:

Multi-step reaction with 2 steps

1: nitric acid; acetic acid

2: trichlorophosphate / N,N-dimethyl-formamide / 0.25 h / 10 °C

With nitric acid; acetic acid; trichlorophosphate; In N,N-dimethyl-formamide;

DOI:10.2298/JSC140619085R

Reference yield:

phenol (108-95-2,27073-41-2) → 4-chloro-3-nitro-chromen-2-one (38464-20-9)

Guidance literature:

Multi-step reaction with 3 steps

1: trichlorophosphate; zinc(II) chloride / Heating

2: nitric acid; acetic acid / 1.5 h / 80 - 85 °C

3: trichlorophosphate; N,N-dimethyl-formamide / 1 h / 0 - 5 °C

With nitric acid; acetic acid; N,N-dimethyl-formamide; zinc(II) chloride; trichlorophosphate;

DOI:10.14233/ajchem.2019.21860

upstream raw materials:

4-hydroxy-3-nitrocoumarin

4-hydroxy[1]benzopyran-2-one

phenol

Downstream raw materials:

6,12-Dihydro-1-benzopyrano<3,4-b><1,4>benzothiazin-6-one

4-(4-cyanophenylamino)-3-nitrocoumarin

3-nitro-4-phenylselanyl-2H-chromen-2-one

3-nitro-4-phenylamino-2H-chromen-2-one

Refernces

• 1、 Save'lev et al.. "-". . . Retrieved 1972.
• 2、 Radulovi?, Niko S.,Stojanovi?-Radi?, Zorica,Stojanovi?, Predrag,Stojanovi?, Nikola,Deki?, Vidoslav,Deki?, Biljana. "A small library of 4-(alkylamino)-3-nitrocoumarin derivatives with potent antimicrobial activity against gastrointestinal pathogens". . p. 315 - 327. Retrieved 2015/06/16.