3-Formyl-6-nitrochromone

Base Information

• Chemical Name: 3-Formyl-6-nitrochromone
• CAS No.: 42059-80-3
• Molecular Formula: C10H5NO5
• Molecular Weight: 219.153
• Hs Code.: 2914400090
• European Community (EC) Number: 623-595-4
• DSSTox Substance ID: DTXSID20361448
• Nikkaji Number: J1.047.412D
• Wikidata: Q72495084
• ChEMBL ID: CHEMBL314564
• Mol file: 42059-80-3.mol

Synonyms:3-Formyl-6-nitrochromone;42059-80-3;6-Nitro-4-oxo-4H-chromene-3-carbaldehyde;6-nitro-4-oxochromene-3-carbaldehyde;6-Nitro-4-oxo-4H-1-benzopyran-3-carboxaldehyde;CHEMBL314564;6-nitro-4-oxo-chromene-3-carbaldehyde;MFCD00192184;4H-1-benzopyran-3-carboxaldehyde, 6-nitro-4-oxo-;6-nitrochromone-3-carbaldehyde;SCHEMBL1997539;SCHEMBL13978670;DTXSID20361448;3-Formyl-6-nitrochromone, 99%;BDBM50131072;AKOS009157145;AKOS015916578;BP-12628;BS-23117;CS-0155777;EN300-55225;D84190;A825742;AQ-358/42007337;Z825901322;1-Isopropyl-2,3,4,9-tetrahydro-1H-?-carboline-3-carboxylicacid

Chemical Property of 3-Formyl-6-nitrochromone

Chemical Property:

• Vapor Pressure: 8.26E-07mmHg at 25°C
• Melting Point: 157-161 °C(lit.)
• Refractive Index: 1.723
• Boiling Point: 406.2 °C at 760 mmHg
• Flash Point: 207.6 °C
• PSA: 93.10000
• Density: 1.641 g/cm³
• LogP: 2.03690
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 219.01677226
• Heavy Atom Count: 16
• Complexity: 370

Purity/Quality:

98%min ^*data from raw suppliers

6-Nitro-4-oxo-4H-chromene-3-carbaldehyde ^*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

Useful:

• Canonical SMILES: C1=CC2=C(C=C1[N+](=O)[O-])C(=O)C(=CO2)C=O
• Uses: 3-Formyl-6-nitrochromone is the suitable reagent used in a study to investigate the multidrug resistance reversal by some 3- formylchromones in human colon cancer and mouse lymphoma cells transfected with the human MDR1 gene. It is the suitable reagent used in the synthesis of uridine-based library.

Technology Process of 3-Formyl-6-nitrochromone

There total 5 articles about 3-Formyl-6-nitrochromone 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: 91.0%

1-(2-hydroxy-5-nitrophenyl)ethanone (1450-76-6) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 6-nitro-4-oxo-4H-chromene-3-carbaldehyde (42059-80-3)

Guidance literature:

N,N-dimethyl-formamide; With bis(trichloromethyl) carbonate; In 1,2-dichloro-ethane; at 0 - 20 ℃;

1-(2-hydroxy-5-nitrophenyl)ethanone; In 1,2-dichloro-ethane; at 0 - 20 ℃; for 6.5h; Further stages.;

DOI:10.1080/00304940709458601

Reference yield:

1-(2-hydroxy-5-nitrophenyl)ethanone (1450-76-6) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → C9H6O4NCl + 6-nitro-4-oxo-4H-chromene-3-carbaldehyde (42059-80-3)

Guidance literature:

N,N-dimethyl-formamide; With bis(trichloromethyl) carbonate; In 1,2-dichloro-ethane; at 0 - 20 ℃;

1-(2-hydroxy-5-nitrophenyl)ethanone; In 1,2-dichloro-ethane; at 0 - 20 ℃; for 6.5h; Further stages.;

DOI:10.1080/00304940709458601

Reference yield:

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) → 6-nitro-4-oxo-4H-chromene-3-carbaldehyde (42059-80-3)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / dichloromethane

2: aluminum (III) chloride / 120 °C

3: oxalyl dichloride / 0 - 20 °C

With pyridine; aluminum (III) chloride; oxalyl dichloride; In dichloromethane; 2: Fries rearrangement / 3: Vilsmeier reaction;

DOI:10.1016/j.bmcl.2011.03.079

upstream raw materials:

1-(2-hydroxy-5-nitrophenyl)ethanone

N,N-dimethyl-formamide

4-nitro-phenol

4-nitrophenol acetate

Refernces

• 1、 Yuan, Jiaqi,He, Qian,Song, Shanshan,Zhang, Xiaofei,Miao, Zehong,Yang, Chunhao. "One pot and metal-free approach to 3-(2-Hydroxybenzoyl)-1-aza-anthraquinones". supporting information. . Retrieved 2019/08/30.
• 2、 China Raju,Nageswara Rao,Suman,Yogeeswari,Sriram,Shaik, Thokhir Basha,Kalivendi, Shasi Vardhan. "Synthesis, structure-activity relationship of novel substituted 4H-chromen-1,2,3,4-tetrahydropyrimidine-5-carboxylates as potential anti-mycobacterial and anticancer agents". supporting information; experimental part. p. 2855 - 2859. Retrieved 2011/06/24.