Nicotinoyl chloride hydrochloride Chemical Properties

Melting point:

151-157 °C(lit.)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

Crystalline Powder

color 

White to off-white

Water Solubility 

It decomposes in water.

Sensitive 

Moisture Sensitive

BRN 

3655772

InChI

InChI=1S/C6H4ClNO.ClH/c7-6(9)5-2-1-3-8-4-5;/h1-4H;1H

InChIKey

MSYBLBLAMDYKKZ-UHFFFAOYSA-N

SMILES

C(Cl)(=O)C1=CN=CC=C1.[H]Cl

CAS DataBase Reference

20260-53-1(CAS DataBase Reference)

EPA Substance Registry System

3-Pyridinecarbonyl chloride, hydrochloride (20260-53-1)

Safety Information

Hazard Codes 

C

Risk Statements 

34

Safety Statements 

26-28-36/37/39-45

RIDADR 

UN 3261 8/PG 2

WGK Germany 

3

TSCA 

Yes

HazardClass 

8

PackingGroup 

III

HS Code 

29333990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Nicotinoyl chloride hydrochloride Usage And Synthesis

Chemical Properties

white to off-white crystalline powder

Uses

Nicotinoyl chloride hydrochloride was used in the preparation of 1-[5-O-tert-butyldimethylsilyl-2-deoxy-2-fluoro-3-O-(3-pyridylcarbonyl)-β-D-ribofuranosyl]uracil, bis(ethylenedithio)tetrathiafulvalene derivatives and 7,16-dinicotinoylated or 7,16-diisonicotinoylated compounds via reaction with tetraaza[14]annulene and its complexes.

Uses

Nicotinoyl chloride hydrochloride was used in the preparation of :

• 1-[5-O-tert-butyldimethylsilyl-2-deoxy-2-fluoro-3-O-(3-pyridylcarbonyl)-β-D-ribofuranosyl]uracil
• 7,16-dinicotinoylated and/or 7,16-diisonicotinoylated compounds via reaction with tetraaza[14]annulene and its complexes
• bis(ethylenedithio)tetrathiafulvalene derivatives

Uses

As a Nicotinic Acid analog, Nicotinoyl chloride hydrochloride can be used in the preparation of cardiovascular agents and renal drugs.

Synthesis

Niacin (8.12 mmol) and 2 drops of anhydrous DMF were added to SOCl2 (10 mL) under anhydrous conditions with vigorous stirring at 0°C. The reaction mixture was heated to 78 °C and refluxed for 3 hours. Upon completion of the reaction, the excess SOCl2 was removed by evaporation under reduced pressure to give a yellow solid. Subsequently, 10 mL of diethyl ether was added to the solid and refluxed for 1 hour. The reaction mixture was filtered to give a white solid nicotinoyl chloride hydrochloride in a yield of 1.388 g (yield: 96.0%).

References

[1] Dalton Transactions, 2005, # 3, p. 424 - 426
[2] Journal of Organic Chemistry, 2009, vol. 74, # 17, p. 6691 - 6702
[3] Green Chemistry, 2009, vol. 11, # 1, p. 83 - 90
[4] Molecules, 2014, vol. 19, # 4, p. 4791 - 4801
[5] Phosphorus, Sulfur and Silicon and the Related Elements, 2011, vol. 186, # 3, p. 552 - 557

Nicotinoyl chloride hydrochloride(20260-53-1)Related Product Information

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