2,3-Dichloropyrazine

Base Information

• Chemical Name: 2,3-Dichloropyrazine
• CAS No.: 4858-85-9
• Molecular Formula: C4H2Cl2N2
• Molecular Weight: 148.979
• Hs Code.: 29339900
• European Community (EC) Number: 225-460-1
• DSSTox Substance ID: DTXSID10197556
• Nikkaji Number: J262.498B
• Wikidata: Q72467800
• Mol file: 4858-85-9.mol

Synonyms:2,3-Dichloropyrazine;4858-85-9;Pyrazine, 2,3-dichloro-;dichloropyrazine;2,3-dichloro-pyrazine;EINECS 225-460-1;MFCD00040964;dichloro pyrazine;2,3 dichloropyrazine;2.3-dichloropyrazine;5,6-dichloropyrazine;2,3-dichloro pyrazine;2,3-Dichloropyrazine, 95%;SCHEMBL103808;MLCNOCRGSBCAGH-UHFFFAOYSA-;DTXSID10197556;BCP23193;STL195586;AKOS005259647;CS-W016328;PB15620;PS-8931;AC-16400;SY004668;AM20070355;BB 0242422;D3061;FT-0609580;EN300-56062;A23324;P10041;W-106047;F0001-1272;Z850504018

Chemical Property of 2,3-Dichloropyrazine

Chemical Property:

• Appearance/Colour: clear colorless to light yellow liquid
• Vapor Pressure: 0.745mmHg at 25°C
• Melting Point: 22.5-24.5 °C
• Refractive Index: 1.5645
• Boiling Point: 190.6 °C at 760 mmHg
• PKA: -4.23±0.10(Predicted)
• Flash Point: 86.1 °C
• PSA: 25.78000
• Density: 1.493 g/cm³
• LogP: 1.78340
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 147.9595035
• Heavy Atom Count: 8
• Complexity: 68.4

Purity/Quality:

98% ^*data from raw suppliers

2,3-Dichloropyrazine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 36/37/38-20/21/22
• Safety Statements: 36/37/39-26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CN=C(C(=N1)Cl)Cl
• Uses: 2,3-Dichloropyrazine is a substrate used for an efficient synthesis of aloisine (A575450), a potent cyclin-dependent kinase. Selective monosubstitution of this substrate provided an efficient synthesis of alloisines, potent cyclin-dependent kinases.

Technology Process of 2,3-Dichloropyrazine

There total 12 articles about 2,3-Dichloropyrazine 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: 90.0%

2-chloropyrazin (14508-49-7) → 2,3-dichloropyrazine (4858-85-9)

Guidance literature:

2-chloropyrazin; With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

With hexachloroethane; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

DOI:10.1021/jo0478196

Reference yield: 84.0%

2,3-dihydroxypyrazine (931-18-0,221303-71-5) → 2,3-dichloropyrazine (4858-85-9)

Guidance literature:

With trichlorophosphate;

Reference yield:

3-chloropyrazine 1-oxide (6863-76-9) → 2,5-dichloropyrazine (19745-07-4) + 2,3-dichloropyrazine (4858-85-9) + 2,6-dichloropyrazine (4774-14-5)

Guidance literature:

With trichlorophosphate; for 2h; Yield given. Yields of byproduct given; Heating;

upstream raw materials:

2-chloropyrazin

2,3-dihydroxypyrazine

3-chloropyrazine 1-oxide

Pyrazin-N_.N'-dioxyd

Downstream raw materials:

4-amino-N-(3-chloro-pyrazin-2-yl)-benzenesulfonamide

2-(3-chloropyrazin-2-yl)-2-(4-methylbenzenesulfonyl)acetonitrile

4-(2,3-Dichlorophenyl)-3-(ethoxycarbonyl)-5-(methoxycarbonyl)-6-methyl-2-<<2-<(2-chloropyrazin-3-yl)amino>ethoxy>methyl>-1,4-dihydropyridine

1,4-diazaphenoselenazine

Refernces

Practical syntheses of the adhesion molecule inhibitor ER-49890 and its stereoisomer

10.3987/COM-04-10279

The research focuses on the practical syntheses of the adhesion molecule inhibitor ER-49890 and its stereoisomer. The study reports improved synthetic routes for both the anti- and syn-isomers, with a key innovation being the stereoselective synthesis of the anti-(3-azabicyclo[3.3.1]non-9-yl)acetic acid side chain (anti-12) using Pd/C hydrogenation in the presence of HCl. The syn-isomer (syn-12) was obtained through a crystallization process as its oxalic acid salt from a mixture of anti- and syn-isomers. The 10H-pyrazino[2,3-b][1,4]benzothiazine core (7) was prepared from commercially available 4-chloro-3-nitrobenzyl alcohol (13) in a four-step process with good yield. The experiments involved various reactants, including sodium sulfide, 2,3-dichloropyrazine, triphenylphosphine, and iron powder, among others, and employed techniques such as HPLC, IR spectroscopy, NMR spectroscopy, and mass spectrometry for analysis. The study also detailed the effects of different solvents and additives on the hydrogenation process, leading to a selective synthesis of anti-12 with improved yields.