2,4,6-Triaminoquinazoline

Base Information

• Chemical Name: 2,4,6-Triaminoquinazoline
• CAS No.: 13741-90-7
• Molecular Formula: C8H9 N5
• Molecular Weight: 175.193
• Hs Code.: 2933990090
• European Community (EC) Number: 674-087-4
• NSC Number: 158574
• UNII: WZD2M6Q8CC
• DSSTox Substance ID: DTXSID50303497
• Nikkaji Number: J477.991F
• Wikidata: Q27093512
• Metabolomics Workbench ID: 147112
• ChEMBL ID: CHEMBL6885
• Mol file: 13741-90-7.mol

Synonyms:2,4,6-Triaminoquinazoline;quinazoline-2,4,6-triamine;13741-90-7;2,4,6-Quinazolinetriamine;WZD2M6Q8CC;NSC-158574;CHEMBL6885;MERCURICTHIOCYANATE;UNII-WZD2M6Q8CC;2,4,6 triaminoquinazoline;TAQ;SCHEMBL335027;2,4,6-Quinazolinetriamine #;DTXSID50303497;BDBM50404663;NSC158574;AKOS005266286;DB02532;FT-0691410;A18184;EN300-1087105;Q27093512

Chemical Property of 2,4,6-Triaminoquinazoline

Chemical Property:

• Vapor Pressure: 1.37E-12mmHg at 25°C
• Boiling Point: 560.5°C at 760 mmHg
• Flash Point: 327.2°C
• PSA: 103.84000
• Density: 1.499g/cm³
• LogP: 2.12000
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 175.08579531
• Heavy Atom Count: 13
• Complexity: 185

Purity/Quality:

98%min ^*data from raw suppliers

Quinazoline-2,4,6-triamine 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C1N)C(=NC(=N2)N)N

Technology Process of 2,4,6-Triaminoquinazoline

There total 7 articles about 2,4,6-Triaminoquinazoline 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%

2,4-diamino-6-nitroquinazoline (7154-34-9) → 2,4,6-triaminoquinazoline (13741-90-7)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; acetic acid; In N,N-dimethyl-formamide; for 5h; under 2585.81 Torr;

DOI:10.1021/jacs.8b08249

Reference yield:

4-chloro-3-cyanonitrobenzene (16588-02-6) → 2,4,6-triaminoquinazoline (13741-90-7)

Guidance literature:

Multi-step reaction with 2 steps

1: N,N-dimethyl-formamide / 24 h / 140 °C

2: acetic acid; palladium 10% on activated carbon; hydrogen / methanol / 12 h / 50 °C

With palladium 10% on activated carbon; hydrogen; acetic acid; In methanol; N,N-dimethyl-formamide;

Reference yield:

5-nitroanthranilonitrile (17420-30-3) → 2,4,6-triaminoquinazoline (13741-90-7)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium hydroxide / ethanol; propan-1-ol / 6 h / 90 °C

2: palladium 10% on activated carbon; hydrogen / methanol

With palladium 10% on activated carbon; hydrogen; potassium hydroxide; In methanol; propan-1-ol; ethanol;

DOI:10.1007/s00044-018-2188-7

upstream raw materials:

2,2',4,4'-tetra-amino-6,6'-azoquinazoline

2,4-diamino-6-azidoquinazoline

2,4-diamino-6-nitroquinazoline

4-chloro-3-cyanonitrobenzene

Downstream raw materials:

2,4-diamino-6-quinazoline-6-carbonitrile

N⁶-(2-chlorobenzyl)quinazoline-2,4,6-triamine

N⁶-(3-chlorobenzyl)quinazoline-2,4,6-triamine

N⁶-(4-chlorobenzyl)quinazoline-2,4,6-triamine

Refernces

• 1、 Rosowsky,Fu,Queener. "Synthesis of 2,4-diaminopyrido[2,3-d]pyrimidines and 2,4-diamino-quinazolines with bulky dibenz[b,f]azepine and dibenzo[a,d]-cycloheptene substituents at the 6-position as inhibitors of dihydrofolate reductases from Pneumocystis carinii, Toxoplasma gondii, and Mycobacterium avium". . p. 921 - 926. Retrieved 2000.
• 2、 -. "PHOTOISOMERIZABLE DERIVATIVES OF DIHYDROFOLATE REDUCTASE INHIBITORS". Page/Page column 29. . Retrieved 2019/07/13.