6-Chloroquinazoline-2,4(1H,3H)-dione

Base Information

• Chemical Name: 6-Chloroquinazoline-2,4(1H,3H)-dione
• CAS No.: 1640-60-4
• Molecular Formula: C8H5ClN2O2
• Molecular Weight: 196.5905
• Hs Code.: 2933599590
• NSC Number: 194820
• DSSTox Substance ID: DTXSID60307724
• Nikkaji Number: J856.752B
• Wikidata: Q82055242
• Mol file: 1640-60-4.mol

Synonyms:6-Chloroquinazoline-2,4(1H,3H)-dione;1640-60-4;6-chloro-1H-quinazoline-2,4-dione;6-chloro-1,2,3,4-tetrahydroquinazoline-2,4-dione;6-chloroquinazoline-2,4-diol;6-Chloro-quinazoline-2,4-diol;MFCD00030678;NSC194820;SCHEMBL404118;SCHEMBL13009776;IGWJEWGQUFOVDP-UHFFFAOYSA-;DTXSID60307724;BCP23047;CS-D0596;AKOS006345687;6-chloranyl-1H-quinazoline-2,4-dione;6-Chloro-2,4[1H,3H]quinazolinedione;NSC-194820;6-Chloro-2,4(1H,3H)-quinazolinedione;DS-11548;SY042887;6-Chloro-(1h,3h)-Quinazolin-2,4-Dione;A3643;FT-0660506;EN300-131197;A810534;J-518662;Z1201617625;6-chloroquinazoline-2,4(1H,3H)-dione;6-Chloro-1,2,3,4-tetrahydroquinazoline-2,4-dione;InChI=1/C8H5ClN2O2/c9-4-1-2-6-5(3-4)7(12)11-8(13)10-6/h1-3H,(H2,10,11,12,13)

Chemical Property of 6-Chloroquinazoline-2,4(1H,3H)-dione

Chemical Property:

• Vapor Pressure: 2.62E-11mmHg at 25°C
• Melting Point: 360℃ (acetic acid )
• Refractive Index: 1.601
• Boiling Point: 517 °C at 760 mmHg
• PKA: 10.02±0.20(Predicted)
• Flash Point: 266.5 °C
• PSA: 65.72000
• Density: 1.475g/cm³
• LogP: 0.86980
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 196.0039551
• Heavy Atom Count: 13
• Complexity: 257

Purity/Quality:

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

6-Chloroquinazoline-2,4(1H,3H)-dione ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C1Cl)C(=O)NC(=O)N2

Technology Process of 6-Chloroquinazoline-2,4(1H,3H)-dione

There total 21 articles about 6-Chloroquinazoline-2,4(1H,3H)-dione 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: 100.0%

carbon dioxide (124-38-9,18923-20-1) + 2-amino-5-chlorobenzonitrile (5922-60-1) → 6-chloro-1,2,3,4-tetrahydroquinazoline-2,4-dione (1640-60-4)

Guidance literature:

With bicarbonate salt of 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 80 ℃; for 4h; under 750.075 Torr; Inert atmosphere;

DOI:10.1002/hc.21014

Reference yield: 98.0%

urea (57-13-6) + 5-chloroanthranilic acid (635-21-2) → 2,4-dihydroxy-6-chloroquinazoline (1640-60-4)

Guidance literature:

at 200 ℃;

DOI:10.3390/molecules23020417

Reference yield: 95.6%

2-amino-5-chlorobenzonitrile (5922-60-1) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 6-chloro-1,2,3,4-tetrahydroquinazoline-2,4-dione (1640-60-4)

Guidance literature:

With carbon dioxide; In water; at 150 ℃; for 5h; under 37503.8 Torr;

DOI:10.1021/acs.oprd.6b00244

upstream raw materials:

4-chlorobenzenesulfonyl chloride

2,4,6-trichloroquinazoline

2-ureido-5-chlorobenzoic acid

carbon dioxide

Downstream raw materials:

2,4,6-trichloroquinazoline

1-(3,5-di-O-p-toluoyl-2-deoxy-α,β-D-erythro-pentofuranosyl)-6-chloro-quinazoline-2,4(3H)-dione

2-amino-6-chloro-4-[3-(3-methoxycarbonyl-propionylamino)-phenyl]-quinazoline

2,6-dichloro-4-(3-nitro-phenyl)-quinazoline

Refernces

• 1、 Fujii, Akira,Matsuo, Hideaki,Choi, Jun-Chul,Fujitani, Tadahiro,Fujita, Ken-ichi. "Efficient synthesis of 2-oxazolidinones and quinazoline-2,4(1H,3H)-diones from CO2 catalyzed by tetrabutylammonium fluoride". . p. 2914 - 2920. Retrieved 2018.
• 2、 Sadeghzadeh, Seyed Mohsen. "Ionic liquid immobilized onto fibrous nano-silica: A highly active and reusable catalyst for the synthesis of quinazoline-2,4(1 H,3 H)-diones". . p. 91 - 96. Retrieved 2015.
• 3、 Kumar, Subodh,Verma, Sanny,Shawat, Efrat,Nessim, Gilbert Daniel,Jain, Suman L.. "Amino-functionalized carbon nanofibres as an efficient metal free catalyst for the synthesis of quinazoline-2,4(1H,3H)-diones from CO2 and 2-aminobenzonitriles". . p. 24670 - 24674. Retrieved 2015.
• 4、 Nikpour, Farzad,Paibast, Touraj. "A green, facile, and one-pot synthesis of 2,4-(1H,3H)-quinazolinediones under microwave irradiations". . p. 1438 - 1439. Retrieved 2005.
• 5、 Li, Pengfa,Zhan, Chuanlang,Zhang, Shanlin,Ding, Xunlei,Guo, Fengqi,He, Shenggui,Yao, Jiannian. "Alkali metal cations control over nucleophilic substitutions on aromatic fused pyrimidine-2,4-[1H,3H]-diones: Towards new PNA monomers". . p. 8908 - 8915. Retrieved 2012.
• 6、 -. "Proton type ionic liquid [HDBN] [2-PyOH] and preparation and application thereof". Paragraph 0021; 0025-0029; 0055-0059. . Retrieved 2021/11/21.