4-Chloro-6,7-dimethoxyquinazoline

Base Information

• Chemical Name: 4-Chloro-6,7-dimethoxyquinazoline
• CAS No.: 13790-39-1
• Molecular Formula: C10H9ClN2O2
• Molecular Weight: 224.647
• Hs Code.: 2933990090
• European Community (EC) Number: 672-791-6
• DSSTox Substance ID: DTXSID10377694
• Nikkaji Number: J645.451H
• Wikidata: Q72518632
• Mol file: 13790-39-1.mol

Synonyms:4-Chloro-6,7-dimethoxyquinazoline;13790-39-1;4-Chloro-6,7-dimethoxy-quinazoline;Quinazoline, 4-chloro-6,7-dimethoxy-;MFCD01570172;6,7-dimethoxy-4-chloro-quinazoline;6,7-DIMETHOXY-4-CHLOROQUINAZOLINE;SCHEMBL364049;4-chloro-6,7dimethoxyquinazoline;4-chloro6,7-dimethoxyquinazoline;4chloro-6,7-dimethoxyquinazoline;DTXSID10377694;LLLHRNQLGUOJHP-UHFFFAOYSA-N;BCP27482;CS-D1184;4-chloro-6,7-di-methoxyquinazoline;4-chloro-6,7-dimethoxy quinazoline;4-Chloro-6,7-dimethoxyqui nazoline;6,7-Dimethoxy-4-chloroquinazol ine;STL083702;4-chloro-6, 7-dimethoxy-quinazoline;4-chloro-6,7- dimethoxy-quinazoline;AKOS000282524;AC-2724;PB21757;PS-6299;4-chloro-6,7-bis(methyloxy)quinazoline;SY002685;AM20020453;C2574;FT-0636960;EN300-23058;J-007074;J-515088;F2113-0651;Z147652346

Chemical Property of 4-Chloro-6,7-dimethoxyquinazoline

Chemical Property:

• Appearance/Colour: white or almost white power
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 185 °C
• Refractive Index: 1.605
• Boiling Point: 345.52 °C at 760 mmHg
• PKA: 0.77±0.30(Predicted)
• Flash Point: 162.765 °C
• PSA: 44.24000
• Density: 1.321 g/cm³
• LogP: 2.30040
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Water Solubility.: Insoluble in water.
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 224.0352552
• Heavy Atom Count: 15
• Complexity: 218

Purity/Quality:

99% ^*data from raw suppliers

4-Chloro-6,7-dimethoxyquinazoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39-37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C2C(=C1)C(=NC=N2)Cl)OC
• Uses: 4-Chloro-6,7-dimethoxyquinazoline is a useful synthetic intermediate in the preparation of epidermal growth factors A useful synthetic intermediate in the preparation of epidermal growth factors.

Technology Process of 4-Chloro-6,7-dimethoxyquinazoline

There total 26 articles about 4-Chloro-6,7-dimethoxyquinazoline 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: 98.0%

3H-6,7-dimethoxyquinazolin-4-one (13794-72-4) → 6,7-dimethoxy-4-chloroquinazoline (13790-39-1)

Guidance literature:

With thionyl chloride; In N,N-dimethyl-formamide; for 6h; Heating / reflux;

Reference yield: 93.0%

6,7-dimethoxy-4-hydroxyquinazoline (13794-72-4) → 6,7-dimethoxy-4-chloroquinazoline (13790-39-1)

Guidance literature:

With thionyl chloride; Reflux;

DOI:10.3390/molecules21050612

Reference yield: 93.0%

6,7-dimethoxy quinazolin-4-one (13794-72-4) → 6,7-dimethoxy-4-chloroquinazoline (13790-39-1)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; trichlorophosphate; In toluene; Heating;

DOI:10.1016/j.tetlet.2006.02.043

upstream raw materials:

3H-6,7-dimethoxyquinazolin-4-one

6,7-dimethoxy-4-hydroxyquinazoline

6,7-dimethoxy quinazolin-4-one

methyl 2-amino-4,5-dimethoxybenzoate

Downstream raw materials:

(6,7-dimethoxy-quinazolin-4-yl)-(2-fluoro-4-nitro-phenyl)-amine

4-[(3-Fluorophenyl)amino]-6,7-dimethoxyquinazoline

2-[3-fluoro-4-(6,7-dimethoxyquinazolin-4-yloxy)phenyl]acetic acid

Refernces

• 1、 Tian, Houru,Liu, Di,Li, Jiuyan,Ma, Mengyao,Lan, Ying,Wei, Wenkui,Niu, Rui,Song, Kai. "Pure red phosphorescent iridium(iii) complexes containing phenylquinazoline ligands for highly efficient organic light-emitting diodes". . p. 11253 - 11260. Retrieved 2021.
• 2、 Devegowda, Preethi Saligrama,Balaji, Kyathegowdanadoddi Srinivas,Prasanna, Doddakunche Shivaramu,Swaroop, Toreshettahally Ramesh,Jayarama, Shankar,Siddalingaiah, Lokesh,Rangappa, Kanchugarakoppal Subbegowda. "Pro-apoptotic activity of novel 4-anilinoquinazoline derivatives mediated by up-regulation of bax and activation of poly(ADP-ribose) phosphatase in ehrlich ascites carcinoma cells". . p. 896 - 904. Retrieved 2017.
• 3、 Hassan, Hani Mutlak A.,Denetiu, Iuliana,Khan, Salman A.,Rehan, Mohd,Sakkaf, Kaltoom,Gauthaman, Kalamegam. "Synthesis and biological evaluation of novel triazolyl 4-anilinoquinazolines as anticancer agents". . p. 1766 - 1772. Retrieved 2019.
• 4、 Myers, Michael R.,Setzer, Natalie N.,Spada, Alfred P.,Zulli, Allison L.,Hsu, Chin-Yi J.,Zilberstein, Asher,Johnson, Susan E.,Hook, Linda E.,Jacoski, Mary V.. "The preparation and SAR of 4-(anilino), 4-(phenoxy), and 4-(thiophenoxy)-quinazolines: Inhibitors of p56(lck) and EGF-R tyorsine kinase activity". . p. 417 - 420. Retrieved 1997.
• 5、 Gibson,Grundy,Godfrey,Woodburn,Ashton,Curry,Scarlett,Barker,Brown. "Epidermal growth factor receptor tyrosine kinase: Structure-activity relationships and antitumour activity of novel quinazolines". . p. 2723 - 2728. Retrieved 1997.
• 6、 Amin, Jahangir,Chuckowree, Irina,Tizzard, Graham J.,Coles, Simon J.,Wang, Minghua,Bingham, John P.,Hartley, John A.,Spencer, John. "Targeting epidermal growth factor receptor with ferrocene-based kinase inhibitors". . p. 509 - 513. Retrieved 2013.
• 7、 Ashok, Abhishek,Thanukrishnan, Kannan,Naik, Halehatty S. Bhojya,Ghosh, Soma. "Novel 4-[5-(substituted-1,2,4-oxadiazol-3-yl)phenylamine] derivatives of 6,7-dimethoxy-quinazolines as potent inhibitors of VEGF receptors I and II". . p. 2122 - 2130. Retrieved 2016.
• 8、 Zou, Min,Jin, Bo,Liu, Yanrong,Chen, Huiping,Zhang, Zhuangli,Zhang, Changzheng,Zhao, Zhihong,Zheng, Liyun. "Synthesis and biological evaluation of some novel thiophene-bearing quinazoline derivatives as EGFR inhibitors". . p. 102 - 110. Retrieved 2018.
• 9、 -. "Method suitable for industrial production and preparation of gefitinib". Paragraph 0022-0029. . Retrieved 2021/08/19.
• 10、 Zhang, Zixue,Zhang, Qingwei,Zhang, Hao,Jiao, Minru,Guo, Zheng,Peng, Xinyan,Fu, Lei,Li, Jianqi. "Discovery of quinazolinyl-containing benzamides derivatives as novel HDAC1 inhibitors with in vitro and in vivo antitumor activities". . . Retrieved 2021/10/16.