2-Amino-3-chloro-5-cyanopyridine

Base Information

• Chemical Name: 2-Amino-3-chloro-5-cyanopyridine
• CAS No.: 156361-02-3
• Molecular Formula: C₆H₄ClN₃
• Molecular Weight: 153.571
• Hs Code.: 2933399990
• European Community (EC) Number: 815-326-6
• DSSTox Substance ID: DTXSID30363271
• Wikidata: Q82146879
• Mol file: 156361-02-3.mol

Synonyms:2-Amino-3-chloro-5-cyanopyridine;156361-02-3;6-Amino-5-chloronicotinonitrile;6-amino-5-chloropyridine-3-carbonitrile;6-Amino-5-chloro-nicotinonitrile;3-Pyridinecarbonitrile,6-amino-5-chloro-;6-amino-5-chloro-pyridine-3-carbonitrile;MFCD03617768;6-amino-5-chloro-3-pyridinecarbonitrile;SCHEMBL1726985;DTXSID30363271;BCP11958;AKOS005069285;AB15576;CS-W019832;3-Pyridinecarbonitrile, 6-amino-5-chloro-;FT-0645859;2-amino-3-chloro-5-cyanopyridine, AldrichCPR;A809739;10T-0065;J-518241

Chemical Property of 2-Amino-3-chloro-5-cyanopyridine

Chemical Property:

• Vapor Pressure: 0.00559mmHg at 25°C
• Melting Point: 185-188 °C
• Refractive Index: 1.615
• Boiling Point: 273.9 °C at 760 mmHg
• PKA: 0.72±0.49(Predicted)
• Flash Point: 119.4 °C
• PSA: 62.70000
• Density: 1.42 g/cm³
• LogP: 1.77008
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 153.0093748
• Heavy Atom Count: 10
• Complexity: 162

Purity/Quality:

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

2-Amino-3-chloro-5-cyanopyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-37/38-41
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C=NC(=C1Cl)N)C#N

Technology Process of 2-Amino-3-chloro-5-cyanopyridine

There total 2 articles about 2-Amino-3-chloro-5-cyanopyridine 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: 93.0%

potassiumhexacyanoferrate(II) trihydrate + 5-bromo-3-chloropyridin-2-ylamine (38185-55-6) → 2-amino-3-chloro-5-cyanopyridine (156361-02-3)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1,8-diazabicyclo[5.4.0]undec-7-ene; In water; tert-butyl alcohol; at 85 ℃; for 16h; Inert atmosphere;

DOI:10.1039/c2cc17468e

Reference yield: 87.0%

6-aminonicotinonitrile (4214-73-7) → 2-amino-3-chloro-5-cyanopyridine (156361-02-3)

Guidance literature:

With N-chloro-succinimide; In N,N-dimethyl-formamide; at 80 ℃; for 4h;

Reference yield:

2-amino-3-chloro-5-cyanopyridine (156361-02-3) + 4-chlorosulfonyl-benzoic acid methyl ester (69812-51-7) → C14H10ClN3O4S

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1016/j.bmcl.2014.10.074

upstream raw materials:

6-aminonicotinonitrile

5-bromo-3-chloropyridin-2-ylamine

Refernces

• 1、 Zhang, Dengyou,Sun, Haifeng,Zhang, Lei,Zhou, Yu,Li, Chunpu,Jiang, Hualiang,Chen, Kaixian,Liu, Hong. "An expedient Pd/DBU mediated cyanation of aryl/heteroaryl bromides with K4[Fe(CN)6]". supporting information; experimental part. p. 2909 - 2911. Retrieved 2012/03/27.