Diaziquone

Base Information

• Chemical Name: Diaziquone
• CAS No.: 57998-68-2
• Molecular Formula: C16H20 N4 O6
• Molecular Weight: 364.358
• NSC Number: 182986
• UNII: FQL5EUP13W
• DSSTox Substance ID: DTXSID40206721
• Nikkaji Number: J22.970I
• Wikidata: Q27162386
• NCI Thesaurus Code: C1363
• Metabolomics Workbench ID: 144626
• ChEMBL ID: CHEMBL36016
• Mol file: 57998-68-2.mol

Synonyms:1,4-cyclohexadiene-1,4-dicarbamic acid, 2,5-(bis-(1-aziridinyl))-3,6-dioxo diethyl ester;2,5-bis(1-aziridinyl)-3,6-bis(carbethoxyamino)-1,4-benzoquinone;2,5-diaziridinyl-3,6-bis(carboethoxyamino)-1,4-benzoquinone;3,6-diaziridinyl-2,5-bis(carboethoxyamino)-1,4-benzoquinone;AZQ;CI-904;diaziquone;diaziquone ion (1-);NSC 182986;NSC-182986

Chemical Property of Diaziquone

Chemical Property:

• Vapor Pressure: 5.72E-09mmHg at 25°C
• Melting Point: 230° (dec)
• Refractive Index: 1.6000 (estimate)
• Boiling Point: 469°Cat760mmHg
• Flash Point: 237.4°C
• PSA: 116.82000
• Density: 1.45g/cm³
• LogP: 0.34240
• XLogP3: 0
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 8
• Exact Mass: 364.13828437
• Heavy Atom Count: 26
• Complexity: 671

Purity/Quality:

99% ^*data from raw suppliers

DIAZIQUONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 40
• Safety Statements: 22-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)NC1=C(C(=O)C(=C(C1=O)N2CC2)NC(=O)OCC)N3CC3
• Uses: Antineoplastic.

Technology Process of Diaziquone

There total 8 articles about Diaziquone 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: 85.5%

1-ethyleneimine (17619-22-6) + 2,5-dichloro-3,6-bis(ethoxycarbonylamino)-1,4-benzoquinone (33251-22-8) → diaziquone (57998-68-2)

Guidance literature:

With triethylamine; In tetrahydrofuran; water;

Reference yield: 79.0%

ethyleneimine (151-56-4,9002-98-6) + 2,5-dichloro-3,6-bis(ethoxycarbonylamino)-1,4-benzoquinone (33251-22-8) → diaziquone (57998-68-2)

Guidance literature:

With triethylamine; In tetrahydrofuran; for 10h; Ambient temperature;

DOI:10.1055/s-1989-27348

Reference yield:

2,5-diamino-3,6-dichloro-1,4-benzoquinone (3908-48-3) → diaziquone (57998-68-2)

Guidance literature:

Multi-step reaction with 4 steps

1: Na₂S₂O₄ / H₂O; cyclohexane / 0.33 h / 25 °C

2: H₂O; cyclohexane / 20 h / 25 °C

3: FeCl₃, aq. HCl / 3 h / 25 °C

4: 79 percent / Et₃N / tetrahydrofuran / 10 h / Ambient temperature

With hydrogenchloride; sodium dithionite; iron(III) chloride; triethylamine; In tetrahydrofuran; cyclohexane; water;

DOI:10.1055/s-1989-27348

upstream raw materials:

ethyleneimine

2,5-dichloro-3,6-bis(ethoxycarbonylamino)-1,4-benzoquinone

2,5-diamino-3,6-dichloro-1,4-benzoquinone

3,6-diamino-2,5-dichloro-1,4-hydroquinone

Downstream raw materials:

2-aziridinyl-5-(2'-hydroxyethylamino)-3,6-bis(carboethoxyamino)-1,4-benzoquinone

Refernces

• 1、 -. "Method for producing 3,6-bis(carboethoxyamino)-2,5-diaziridinyl-1,4-benzoquinone". . . Retrieved 2008/06/13.