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4-Chloronicotinic acid

Product Name4-Chloronicotinic acid
CAS10177-29-4
MFC6H4ClNO2
MW157.55
EINECS628-434-1
MOL File10177-29-4.mol

Chemical Properties

Melting point	139-143 °C
Boiling point	301.9±22.0 °C(Predicted)
Density	1.470±0.06 g/cm3(Predicted)
storage temp.	Inert atmosphere,2-8°C
solubility	Soluble in organic solvents at 20°C
form	powder
pka	0.78±0.25(Predicted)
color	White
BRN	9255849
InChI	1S/C6H4ClNO2/c7-5-1-2-8-3-4(5)6(9)10/h1-3H,(H,9,10)
InChIKey	IMRGVWZLCZERSQ-UHFFFAOYSA-N
SMILES	OC(=O)c1cnccc1Cl
CAS DataBase Reference	10177-29-4(CAS DataBase Reference)

Safety Information

Hazard Codes	Xn,Xi
Risk Statements	22-36/37/38
Safety Statements	26-36
WGK Germany	3
Hazard Note	Irritant
HazardClass	IRRITANT, KEEP COLD
PackingGroup	III
HS Code	29333990
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2

MSDS

Provider	Language
SigmaAldrich	English
ALFA	English

Usage And Synthesis

Chemical Properties

White to light brown solid

Uses

Building block used in a synthesis of benzocanthinones via tributyltin hydride radical induced cyclization. Also used in a synthesis of heterocyclic analogues of xanthone.

Uses

4-Chloronicotinic Acid is a building block used in a synthesis of benzocanthinones via tributyltin hydride radical induced cyclization. It is also used in a synthesis of heterocyclic analogues of xanthone.

Synthesis

626-61-9

124-38-9

10177-29-4

1. Neutralization reaction: Neutralize 4-chloropyridine hydrochloride using 10% NaOH solution to obtain 4-chloropyridine (1). 2. lithiation reaction: 4-chloropyridine (1) (15 mmol) was dissolved in THF (250 ml) under nitrogen protection, cooled to -78 °C, and 1.2 equivalents of lithium diisopropylammonium was slowly added (1.5 M hexane solution containing 1 equivalent of THF, ALDRICH). 3. carboxylation reaction: the resulting anion is reacted with dry CO to produce 4-chloropyridine-3-carboxylic acid (3, i.e. 4-chloronicotinic acid). 4. Isolation and purification: The reaction mixture was treated and isolated to obtain 4-chloronicotinic acid as a colorless solid in 60-80% yield.

References

[1] Journal of Organic Chemistry, 1995, vol. 60, # 2, p. 292 - 296
[2] Patent: US2011/53975, 2011, A1. Location in patent: Page/Page column 60
[3] Patent: WO2009/87238, 2009, A2. Location in patent: Page/Page column 97; 98-99
[4] Patent: WO2005/21546, 2005, A1. Location in patent: Page/Page column 124-125
[5] Journal of Medicinal Chemistry, 2016, vol. 59, # 5, p. 1869 - 1879

4-Chloronicotinic acid

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

Preparation Products And Raw materials

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