2-Mercapto-4(3H)-quinazolinone

Base Information

• Chemical Name: 2-Mercapto-4(3H)-quinazolinone
• CAS No.: 13906-09-7
• Molecular Formula: C8H6 N2 O S
• Molecular Weight: 178.214
• Hs Code.: 2933990090
• European Community (EC) Number: 237-676-3
• DSSTox Substance ID: DTXSID50160880
• Nikkaji Number: J227.622D
• Wikidata: Q27459048
• ChEMBL ID: CHEMBL1232053
• Mol file: 13906-09-7.mol

Synonyms:2-mercapto-4(3H)-quinazolinone

Chemical Property of 2-Mercapto-4(3H)-quinazolinone

Chemical Property:

• Vapor Pressure: 0.000165mmHg at 25°C
• Melting Point: >300 °C(lit.)
• Boiling Point: 330.5°Cat760mmHg
• PKA: 9.49±0.20(Predicted)
• Flash Point: 153.7°C
• PSA: 84.55000
• Density: 1.46g/cm³
• LogP: 1.21180
• Storage Temp.: 2-8°C
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 178.02008399
• Heavy Atom Count: 12
• Complexity: 229

Purity/Quality:

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

2-thioxo-2,3-dihydroquinazolin-4(1{H})-one ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=O)NC(=S)N2
• Uses: 2-Mercapto-4(3H)-quinazolinone was employed as a modifier for the carbon paste electrode, for voltammetric determination of mercury. It was used in the synthesis of 4-quinazolinone derivatives, inhibitors of the DNA repair enzyme poly(ADP-ribose) polymerase.

Technology Process of 2-Mercapto-4(3H)-quinazolinone

There total 72 articles about 2-Mercapto-4(3H)-quinazolinone 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: 96.0%

methyl 2-isothiocyanatobenzoate (16024-82-1) → 2-thioxo-2,3-dihydro-1H-quinazolin-4-one (13906-09-7)

Guidance literature:

With pyridine; ammonia; In toluene; at -34 - 20 ℃; for 1h; under 1500.15 Torr; Inert atmosphere; Sealed tube;

DOI:10.3987/COM-15-S(T)12

Reference yield: 85.0%

anthranilic acid (118-92-3,159201-01-1,50816-84-7,80206-34-4,104809-47-4) + thiourea (17356-08-0) → 2-thioxo-2,3-dihydro-1H-quinazolin-4-one (13906-09-7)

Guidance literature:

at 40 ℃; for 2.5h; Inert atmosphere; Ionic liquid;

DOI:10.1016/j.tetlet.2013.08.090

Reference yield: 84.0%

3,6-dimethyl-2-phenylpyrimidine-4(3H)-one (20959-22-2) → 2-thioxo-2,3-dihydro-1H-quinazolin-4-one (13906-09-7)

Guidance literature:

With Lawessons reagent; In benzene; for 10h; Heating;

upstream raw materials:

4-amino-1H-quinazoline-2-thione

2-(Thioureido)benzoic acid methyl ester

2-thioureido-benzoic acid ethyl ester

anthranilic acid

Downstream raw materials:

2-[2-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-1-methyl-2-oxo-ethylsulfanyl]-3H-quinazolin-4-one

2-butyl thioquinazolin-4(3H)-one

2-[1-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carbonyl)-propylsulfanyl]-3H-quinazolin-4-one

2-<3-<3-(1-piperidinylmethyl)phenoxy>propylthio>-4(3H)-quinazolinone hydrochloride

Refernces

• 1、 Singh, Harjit,Kumar, Subodh. "Synthesis of heterocycles via enamines-XIII1 1 H. Singh, S. Kumar, J. Chem. Soc., Perkin Trans 1, 1987, in press. Steric control on the mode of reactions of β-isothiocyanatoketones with amino-acids". . p. 2177 - 2180. Retrieved 1987.
• 2、 Yun, L. M.,Yangibaev, S.,Shakhidoyatov, Kh. M.,Kadyrov, Ch. Sh.. "NEW METHOD FOR THE SYNTHESIS OF 2-THIOXO-4-QUINAZOLONES". . p. 221. Retrieved 1983.
• 3、 Murugesan, Dinakaran,Ray, Peter C.,Bayliss, Tracy,Prosser, Gareth A.,Harrison, Justin R.,Green, Kirsteen,Soares De Melo, Candice,Feng, Tzu-Shean,Street, Leslie J.,Chibale, Kelly,Warner, Digby F.,Mizrahi, Valerie,Epemolu, Ola,Scullion, Paul,Ellis, Lucy,Riley, Jennifer,Shishikura, Yoko,Ferguson, Liam,Osuna-Cabello, Maria,Read, Kevin D.,Green, Simon R.,Lamprecht, Dirk A.,Steyn, Adrie J. C.,Ioerger, Thomas R.,Sacchettini, Jim,Rhee, Kyu Y.,Arora, Kriti,Barry, Clifton E.,Wyatt, Paul G.,Boshoff, Helena I. M.. "2-Mercapto-Quinazolinones as Inhibitors of Type II NADH Dehydrogenase and Mycobacterium tuberculosis: Structure-Activity Relationships, Mechanism of Action and Absorption, Distribution, Metabolism, and Excretion Characterization". . p. 954 - 969. Retrieved 2018.
• 4、 Nikpour, Farzad,Mozafari, Roya,Paibast, Touraj. "A facile and convenient method to the one-pot synthesis of 2-mercapto-4(3H)-quinazolinones". . p. 1569 - 1571. Retrieved 2009.
• 5、 -. "Preparation method and application of quinazolinone derivatives containing disulfide structure". Paragraph 0041-0043. . Retrieved 2022/01/12.