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20260-53-1

20260-53-1 Structure

20260-53-1 Structure
IdentificationMore
[Name]

NICOTINOYL CHLORIDE HYDROCHLORIDE
[CAS]

20260-53-1
[Synonyms]

3-PYRIDINECARBONYL CHLORIDE
3-PYRIDINECARBOXYLIC ACID CHLORIDE HYDROCHLORIDE
3-PYRIDINOYL CHLORIDE HYDROCHLORIDE
NICOTINIC ACID CHLORIDE HYDROCHLORIDE
NICOTINOYL CHLORIDE HYDROCHLORIDE
NICOTINYL CHLORIDE HYDROCHLORIDE
PYRIDINE-3-CARBONYL CHLORIDE HYDROCHLORIDE
3-pyridinecarbonylchloride,hydrochloride
NicotinoylchlorideHcl
[EINECS(EC#)]

243-648-1
[Molecular Formula]

C6H5Cl2NO
[MDL Number]

MFCD00012820
[Molecular Weight]

178.02
[MOL File]

20260-53-1.mol
Chemical PropertiesBack Directory
[Appearance]

white to off-white crystalline powder
[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 DataBack Directory
[Symbol(GHS) ]

Corrosion (GHS05)
GHS05
[Signal word ]

Danger
[Hazard statements ]

H314
[Precautionary statements ]

P260-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338-P363
[Hazard Codes ]

C
[Risk Statements ]

R34:Causes burns.
[Safety Statements ]

S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S28:After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer) .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
[RIDADR ]

UN 3261 8/PG 2
[WGK Germany ]

3
[TSCA ]

Yes
[HazardClass ]

8
[PackingGroup ]

III
[HS Code ]

29333990
[Storage Class]

8A - Combustible corrosive hazardous materials
[Hazard Classifications]

Skin Corr. 1B
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Nicotinic acid hydrochloride-->Nicotinic acid-->Thionyl chloride-->N,N-Dimethylformamide
[Preparation Products]

Nicorandil-->N-Methoxy-N-methylnicotinamide-->NICOTINANILIDE-->MYRISTYL NICOTINATE-->nicotinic anhydride-->Hexyl nicotinate-->Picamilon-->Nicotinyl chloride hydrochloride-->5-Bromo-3-pyridinemethanol-->3-Iodopyridine-->6-[(Pyridine-3-carbonyl)-amino]-hexanoic acid-->N-[1,4,5,6,7,8-Hexahydro-6,7-dimethyl-4-oxo-5-(3-pyridinylcarbonyl)-2-pteridinyl]-2-methyl-propanamide-->(2S)-2-(pyridin-3-ylformamido)propanoic acid-->1H-indol-3-yl(pyridin-3-yl)methanone
Hazard InformationBack Directory
[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
  • 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.
[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.
[Synthesis]

Nicotinic acid

59-67-6

Nicotinoyl chloride hydrochloride

20260-53-1

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
Spectrum DetailBack Directory
[Spectrum Detail]

Nicotinoyl chloride hydrochloride(20260-53-1)MS
Nicotinoyl chloride hydrochloride(20260-53-1)1HNMR
Nicotinoyl chloride hydrochloride(20260-53-1)13CNMR
Nicotinoyl chloride hydrochloride(20260-53-1)IR1
Nicotinoyl chloride hydrochloride(20260-53-1)IR2
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

Nicotinoyl chloride hydrochloride, 97%(20260-53-1)
[Alfa Aesar]

Nicotinoyl chloride hydrochloride, 98%(20260-53-1)
[Sigma Aldrich]

20260-53-1(sigmaaldrich)
[TCI AMERICA]

Nicotinoyl Chloride Hydrochloride,>95.0%(T)(20260-53-1)
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