53638-54-3

Basic information

• Product Name: 8-NITROQUINAZOLIN-4-OL
• Synonyms: 8-NITROQUINAZOLIN-4-OL;8-Nitroquinazolin-4(3H)-one
• CAS NO: 53638-54-3
• Molecular Formula: C₈H₅N₃O₃
• Molecular Weight: 191.14
• Mol File: 53638-54-3.mol
• Article Data: 8

Chemical Properties

• Melting Point: 248 °C
• Boiling Point: 393 °C at 760 mmHg
• Flash Point: 191.5 °C
• Appearance: /
• Density: 1.64 g/cm³
• Vapor Pressure: 2.2E-06mmHg at 25°C
• Refractive Index: 1.739
• PKA: -0.96±0.20(Predicted)
• CAS DataBase Reference: 8-NITROQUINAZOLIN-4-OL(CAS DataBase Reference)
• NIST Chemistry Reference: 8-NITROQUINAZOLIN-4-OL(53638-54-3)
• EPA Substance Registry System: 8-NITROQUINAZOLIN-4-OL(53638-54-3)

Safety Data

• Hazardous Substances Data: 53638-54-3(Hazardous Substances Data)

Usage

General Description

8-NITROQUINAZOLIN-4-OL is a chemical compound with the molecular formula C8H5N3O3. It belongs to the class of nitroaromatic compounds and is primarily used in the synthesis of pharmaceuticals and other organic compounds. The presence of the nitro group makes this compound an important intermediate in the production of various functional materials such as dyes, resins, and pigments. 8-NITROQUINAZOLIN-4-OL may also be used as a reagent in chemical reactions in the laboratory and has potential applications in the field of medicinal chemistry. Its chemical structure and properties make it a versatile building block in organic synthesis and it is an important compound for research and development in the pharmaceutical and chemical industries.

InChI:InChI=1/C8H5N3O3/c12-8-5-2-1-3-6(11(13)14)7(5)9-4-10-8/h1-4H,(H,9,10,12)

Synthetic route

3-nitroanthranilic acid (606-18-8) + formamide (77287-34-4, 77287-35-5, 60100-09-6) → 8-nitroquinazoline-4(3H)-one (53638-54-3)

Conditions	Yield
at 140℃;	79%
at 210℃;
With trichlorophosphate at 100℃;

2-amino-3-nitro-benzamide (313279-12-8) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → 8-nitroquinazoline-4(3H)-one (53638-54-3) + 3-methyl-8-nitroquinazolin-4-one (221448-39-1) + cis-N'-(2-amino-3-nitrobenzoyl)-N,N-dimethylformamidine + trans-N'-(2-amino-3-nitrobenzoyl)-N,N-dimethylformamidine

Conditions	Yield
In tetrahydrofuran for 16h;	A 19% B 21% C n/a D n/a

3-nitroanthranilic acid (606-18-8) → 8-nitroquinazoline-4(3H)-one (53638-54-3)

Conditions	Yield
With formamide In 2-methoxy-ethanol at 200℃; for 17h;	14%

3-nitroanthranilic acid (606-18-8) + formamidine hydrochloride (6313-33-3) → 8-nitroquinazoline-4(3H)-one (53638-54-3)

Conditions	Yield
at 200℃;

N,N-dimethylformamide diisopropyl acetal (18503-89-4) + 2-amino-3-nitro-benzamide (313279-12-8) → 8-nitroquinazoline-4(3H)-one (53638-54-3) + 3-methyl-8-nitroquinazolin-4-one (221448-39-1) + 4-isopropoxy-8-nitroquinazoline + 8-nitro-3-(prop-2-yl)quinazolin-4-one (1332493-34-1)

Conditions	Yield
In N,N-dimethyl-formamide at 150℃;

3-nitroanthranilic acid (606-18-8) → 8-nitroquinazoline-4(3H)-one (53638-54-3) + 3-methyl-8-nitroquinazolin-4-one (221448-39-1) + cis-N'-(2-amino-3-nitrobenzoyl)-N,N-dimethylformamidine + trans-N'-(2-amino-3-nitrobenzoyl)-N,N-dimethylformamidine

Conditions	Yield
Multi-step reaction with 2 steps 1: thionyl chloride / tetrahydrofuran; N,N-dimethyl-formamide / 16 h 2: tetrahydrofuran / 16 h View Scheme

3-nitroanthranilic acid (606-18-8) → 8-nitroquinazoline-4(3H)-one (53638-54-3) + 3-methyl-8-nitroquinazolin-4-one (221448-39-1) + 4-isopropoxy-8-nitroquinazoline + 8-nitro-3-(prop-2-yl)quinazolin-4-one (1332493-34-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: thionyl chloride / tetrahydrofuran; N,N-dimethyl-formamide / 16 h 2: N,N-dimethyl-formamide / 150 °C View Scheme

3-nitroanthranilic acid (606-18-8) + ammonium acetate (631-61-8) → 8-nitroquinazoline-4(3H)-one (53638-54-3)

Conditions	Yield
at 150℃; for 2h; Sealed tube;	1.8 g

3-nitroanthranilic acid (606-18-8) → 8-nitroquinazoline-4(3H)-one

Conditions	Yield
at 140℃;	79%
at 210℃;
With trichlorophosphate at 100℃;

8-nitroquinazoline-4(3H)-one (53638-54-3) → 8-aminoquinazolin-4(3H)-one (130148-49-1)

Conditions	Yield
With stannous chloride dihydrate In ethyl acetate for 8h; Reflux;	72%
With methanol; nickel Hydrogenation;
With sodium sulfide; water
With 10% palladium on carbon; hydrogen In methanol; N,N-dimethyl-formamide

8-nitroquinazoline-4(3H)-one (53638-54-3) → 4-chloro-8-nitroquinazoline (19815-18-0)

Conditions	Yield
Stage #1: 8-nitroquinazoline-4(3H)-one With trichlorophosphate In N,N-dimethyl-aniline at 0 - 65℃; for 1.5h; Stage #2: With sodium hydrogencarbonate	59.63%
With phosphorus pentachloride; trichlorophosphate
With phosphorus pentachloride; trichlorophosphate for 4h; Reagent/catalyst; Reflux;	1 g

Conditions	Yield
Multi-step reaction with 3 steps 1: POCl3; PCl5 2: methanol 3: palladium/CaCO3; methanol / Hydrogenation View Scheme

Upstream product

• 606-18-8 3-nitroanthranilic acid 
• 3473-63-0 formamidine acetic acid 
• 631-61-8 ammonium acetate 
• 313279-12-8 2-amino-3-nitro-benzamide 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 18503-89-4 N,N-dimethylformamide diisopropyl acetal 
• 6313-33-3 formamidine hydrochloride 
• 77287-34-4 formamide 

Downstream Products

• 101421-74-3 quinazolin-8-ylamine 
• 653577-49-2 3,4-dihydro-quinazolin-8-ylamine 
• 653577-05-0 4-methoxy-quinazolin-8-ylamine 
• 1449736-67-7 tert-butyl 4-chloro-2-fluoro-3-((4-((3-(trifluoromethyl)phenyl)amino)quinazolin-8-yl)carbamoyl)benzylcarbamate 
• 1449736-86-0 8-nitro-4-(((1s,4s)-4-(trifluoromethyl)cyclohexyl)oxy)quinazoline 
• 1449736-87-1 8-nitro-4-(((1r,4r)-4-(trifluoromethyl)cyclohexyl)oxy)quinazoline 
• 1449737-51-2 4-(((1s,4s)-4-(trifluoromethyl)cyclohexyl)oxy)quinazolin-8-amine 
• 1449736-01-9 (S)-N-(4-chloro-2-fluoro-3-((4-((3-(trifluoromethyl)phenyl)amino)quinazolin-8-yl)carbamoyl)benzyl)tetrahydrofuran-2-carboxamide 
• 845509-38-8 4-methyl-N'-(8-nitroquinazolin-4-yl)benzene-1-sulfonohydrazide 
• 19815-18-0 4-chloro-8-nitroquinazoline 
• 130148-49-1 8-aminoquinazolin-4(3H)-one 
• 1449736-84-8 N⁴-(4-fluoro-3-(trifluoromethyl)phenyl)quinazoline-4,8-diamine 
• 1449736-85-9 N-(4-fluoro-3-(trifluoromethyl)phenyl)-8-nitroquinazolin-4-amine 
• 1449736-83-7 N-(4,4-dimethylcyclohexyl)-8-nitroquinazolin-4-amine 

Relevant articles and documents

A in the aqueous phase under microwave conditions using halogenated benzamide fast synthesis of quinazoline compounds of the method

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