6-Azauracil

Base Information

• Chemical Name: 6-Azauracil
• CAS No.: 461-89-2
• Deprecated CAS: 19241-95-3,31952-63-3,31952-63-3
• Molecular Formula: C3H3N3O2
• Molecular Weight: 113.076
• Hs Code.: 29336980
• European Community (EC) Number: 207-318-0
• NSC Number: 3425
• UNII: I14TWN70LR
• DSSTox Substance ID: DTXSID2060042
• Nikkaji Number: J9.363G
• Wikidata: Q27124185
• Metabolomics Workbench ID: 58732
• ChEMBL ID: CHEMBL2260276
• Mol file: 461-89-2.mol

Synonyms:6-azauracil;azauracil

Chemical Property of 6-Azauracil

Chemical Property:

• Appearance/Colour: white to light yellow fine crystalline powder
• Melting Point: 274-275 °C(lit.)
• Refractive Index: 1.463
• Boiling Point: 503.4 °C at 760 mmHg
• PKA: 7.78±0.20(Predicted)
• Flash Point: 258.3 °C
• PSA: 78.61000
• Density: 1.86 g/cm³
• LogP: -1.54180
• Storage Temp.: Store below +30°C.
• Water Solubility.: Partly soluble in water, ethanol, DMSO, and 1 M NH4OH (50 mg/ml).
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 113.022526347
• Heavy Atom Count: 8
• Complexity: 162

Purity/Quality:

99% ^*data from raw suppliers

6-Azauracil ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T, Xi
• Hazard Codes: Xi,T
• Statements: 36/37/38-63-25
• Safety Statements: 26-36-45-38-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NNC(=O)NC1=O
• Uses: 6-Azauracil (6-AU) is used as a growth inhibitor of various microorganisms via depletion of intracellular GTP and UTP nucleotide pools. 6-Azauracil has been widely used in investigations on modulation of transcription, especially in yeast models.

Technology Process of 6-Azauracil

There total 7 articles about 6-Azauracil 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: 61.6%

glyoxylic acid semicarbazone (928-73-4) → 6-azauracil (461-89-2)

Guidance literature:

With sodium hydroxide; In methanol; 1,2-dimethoxyethane; at 80 ℃; for 24h;

Reference yield:

3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acid (13924-15-7) → 6-azauracil (461-89-2)

Guidance literature:

at 230 - 250 ℃; under 10 Torr;

DOI:10.1021/ja01587a049

Reference yield:

6-aza-5,6-dihydrouracil (18802-37-4) → 6-azauracil (461-89-2)

Guidance literature:

With water; bromine;

DOI:10.1021/jo01104a033

upstream raw materials:

6-aza-5,6-dihydrouracil

6-aza-2-thiouracil

3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acid

glyoxylic acid semicarbazone

Downstream raw materials:

3,5-dichloro-1,2,4-triazine

6-aza-5,6-dihydrouracil

6-aza-4-thiouracil

3,5-dithioxo-2,3,4,5-tetrahydrotriazine

Refernces

• 1、 Chang,Ulbricht. "-". . p. 976,977. Retrieved 1958.
• 2、 -. "Full synthesis method of eptapirone". Paragraph 0089; 0102; 0103; 0104. . Retrieved 2018/09/12.