3,5-Dithiocyanatopyridine-2,6-diamine

Base Information

• Chemical Name: 3,5-Dithiocyanatopyridine-2,6-diamine
• CAS No.: 2645-32-1
• Molecular Formula: C7H5N5S2
• Molecular Weight: 223.27800
• European Community (EC) Number: 803-549-1
• DSSTox Substance ID: DTXSID00384716
• Nikkaji Number: J1.402.686J
• Wikidata: Q72462861
• ChEMBL ID: CHEMBL4303622
• Mol file: 2645-32-1.mol

Synonyms:2,6-diaminopyridine-3,5-bis(thiocyanate);PR-619

Chemical Property of 3,5-Dithiocyanatopyridine-2,6-diamine

Chemical Property:

• Melting Point: 210℃
• Boiling Point: 406.0±45.0 °C(Predicted)
• PKA: -0.19±0.50(Predicted)
• PSA: 163.84000
• Density: 1.61±0.1 g/cm3(Predicted)
• LogP: 1.90366
• Storage Temp.: ?20°C
• Solubility.: DMSO: soluble5mg/mL (clear solution)
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 222.99863753
• Heavy Atom Count: 14
• Complexity: 261

Purity/Quality:

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

PR 619 ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22-37/38-41-43
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C(=NC(=C1SC#N)N)N)SC#N
• Description: PR-619 (2645-32-1) is a nonselective, reversible inhibitor of cysteine-reactive deubiquitinating enzymes (DUBs; 5-20 μM)1. PR-619 is highly useful for preserving ubiquitinated proteins during cell lysis. DUBs become unregulated in cell lysates and will act quickly to deubiquitinate proteins of interest during cell lysis. To preserve maximum amounts of ubiquitinated protein, include PR-619 (50-100 μM) in lysis buffers. PR-619 is also useful for interrogating the role of DUBs in intact cell systems2, and treatment of cells results in an overall accumulation of ubiquitinated proteins and many other phenotypes.
• Uses: PR 619 is a broad-range DUB inhibitor. A selective and general inhibitior of cellular DUB activity without direct impairment of proteasomal proteolysis. Used in the preparation of thiazolopyridines an d bisthiazolopyridines. PR-619 has been used:as a component of lysis buffer and also as a deubiquitinase inhibitor to treat proteins derived from SILAC-labeled Jurkat cellsas a pan-deubiquitinase inhibitor to study its effect on adenoassociated virus (AAV) transductionin radioimmunoprecipitation assay buffer (RIPA) buffer used for ubiquitination assays

Technology Process of 3,5-Dithiocyanatopyridine-2,6-diamine

There total 2 articles about 3,5-Dithiocyanatopyridine-2,6-diamine 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: 68.0%

ammonium thiocyanate + 2.6-diaminopyridine (141-86-6) → PR-619 (2645-32-1)

Guidance literature:

In methanol; at 20 ℃; for 1h;

DOI:10.1021/ja026118s

Reference yield:

→ PR-619 (2645-32-1)

Guidance literature:

2,6-Diamino-pyridin, NH4SCN, wss. Eg., Br2/Eg. (20-25grad); neben 2,6-Diamino-3-thiocyanato-pyridin;

DOI:10.1039/jr9620003464

Reference yield:

PR-619 (2645-32-1) → 3,5-bis(methylthio)pyridine (70999-08-5)

Guidance literature:

Multi-step reaction with 3 steps

1: NaNO₂-HCl

2: tributylphosphine

3: LiAlH₄

With hydrogenchloride; lithium aluminium tetrahydride; tributylphosphine; sodium nitrite;

DOI:10.1039/c39800001139

upstream raw materials:

2.6-diaminopyridine

Downstream raw materials:

2,6-diphenyl-bisthiazolo[4,5-b;5',4'-e]pyridine

3,5-bis(methylthio)pyridine

Refernces