ChemicalBook Product Catalog Pharmaceutical intermediates Heterocyclic compound Pyridine compound Pyridine derivatives 2-Chloro-6-methyl-3-pyridinecarbonitrile

2-Chloro-6-methyl-3-pyridinecarbonitrile

Product Name2-Chloro-6-methyl-3-pyridinecarbonitrile
CAS28900-10-9
MFC7H5ClN2
MW152.58
EINECS628-229-7
MOL File28900-10-9.mol

Chemical Properties

Melting point	114-116 °C (lit.)
Boiling point	140-145 °C (lit.)
Density	1.2763 (rough estimate)
refractive index	1.5500 (estimate)
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
solubility	Chloroform, Methanol
form	Solid
pka	-1.21±0.10(Predicted)
color	Pale Yellow
BRN	120414
InChI	InChI=1S/C7H5ClN2/c1-5-2-3-6(4-9)7(8)10-5/h2-3H,1H3
InChIKey	YSBNBAYNISAUIT-UHFFFAOYSA-N
SMILES	C1(Cl)=NC(C)=CC=C1C#N
CAS DataBase Reference	28900-10-9(CAS DataBase Reference)
NIST Chemistry Reference	2-Chloro-3-cyano-6-methylpyridine(28900-10-9)

Safety Information

Hazard Codes	Xn,T
Risk Statements	20/21/22-36/37/38
Safety Statements	26-37/39-36/37/39-22
RIDADR	3276
WGK Germany	3
Hazard Note	Toxic
HazardClass	6.1
PackingGroup	III
HS Code	29333990
Storage Class	11 - Combustible Solids
Hazard Classifications	Acute Tox. 4 Oral Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
ACROS	English
SigmaAldrich	English
ALFA	English

Usage And Synthesis

Uses

2-Chloro-6-methyl-3-pyridinecarbonitrile, is a building block used for the synthesis of various biologically active compounds. It can be used for the preparation of 2-(Alkoxycarbonyl)-3-Anilinobenzo[b]thiophenes and Thieno[2,3-b]pyridines as new potent anticancer agents.

Chemical Properties

light yellow to brown cryst. flakes or needles

Uses

2-Chloro-6-methyl-3-pyridinecarbonitrile (2-chloro-6-methylnicotinonitrile) may be used in the preparation of methyl-2-nitropyridinecarboxamides.

Uses

Synthesis

4241-27-4

2-Chloro-6-methyl-3-pyridinecarbonitrile

28900-10-9

Step 1: 6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (45.0 g, 335 mmol) was added to phosphorochloridic acid (652 g, 4250 mmol) and the reaction was stirred at 130°C for 2 hours. After the reaction was completed, the reaction solution was concentrated and the resulting residue was dissolved in dichloromethane and the pH was adjusted to 8 by slowly adding 4 M aqueous sodium hydroxide.The organic layer was separated, washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure to give 2-chloro-6-methylnicotinonitrile (51.0 g, 99% yield).1H NMR (400 MHz, CDCl3) δ 2.65 (s, 3H), 7.24 (d, J = 8.0 Hz, 1H), 7.89 (d, J = 8.0 Hz, 1H).

References

[1] Patent: US2017/145005, 2017, A1. Location in patent: Paragraph 0149; 0150; 0151; 0152
[2] Heterocycles, 1995, vol. 41, # 6, p. 1307 - 1318
[3] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 6, p. 2206 - 2210
[4] Polish Journal of Chemistry, 1982, vol. 56, # 2, p. 419 - 423
[5] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2014, vol. 69, # 5, p. 509 - 518

2-Chloro-6-methyl-3-pyridinecarbonitrile

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

Preparation Products And Raw materials

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