Никотиноилхлорид

Description

Nicotinoyl chloride is an acid chloride of nicotinic (pyridine-3-carboxylic) acid, a reactive acylating reagent of the pyridine series. It is obtained by chlorinating nicotinic acid (niacin) with phosphorus oxychloride in pyridine.

Basic Attributes

• CAS No: 10400-19-8
• Chemical formula: C6H4ClNO
• English name: Nicotinoyl chloride
• Molecular weight: 141.55506; molecular weight: 141.55
• Exact weight: 141.56; exact and monoisotopic mass (refined): 140.9981414
• EU number: 233-863-9
• DSSTox ID: DTXSID40146214
• HS code: 2933399090

Physico-chemical characteristics

• Density: 1.3±0.1 g/cm3
• Melting point: 15-16 °C
• Boiling point: 110-113 °C at 25-26 torr pressure
• Flash point: 84 °C
• Refractive index: 1.547
• PSA: 30
• XLogP3: 1.13 (also given as 1.3)

Molecular descriptors

• Hydrogen bond acceptors: 2
• Rotating links: 1
• Heavy atoms: 9
• Molecule Complexity: 116
• Covalently linked units: 1
• Connection canonized: yes

Method of obtaining

Nicotinic acid (niacin) is chlorinated with phosphorus oxychloride in a pyridine medium to obtain the desired acid chloride.

Scope of application

Primary use is as an intermediate for the synthesis of inositol nicotinate (an ester of nicotinic acid and inositol), used in pharmaceutical and food additive applications. As a reactive acyl chloride, it is also used more widely - for the introduction of a nicotinoyl group (pyridine-3-carbonyl fragment) into other molecules through reactions with alcohols and amines.

Toxicity and hazard classification

• Hazard class code: 34
• Safety instructions: 26-27-36/37/39-45
• Hazard label: C (caustic)

Storage and handling

Store in an airtight container, away from moisture and nucleophilic reagents - the acyl chloride group reacts vigorously with water. Wear gloves and safety goggles when working under traction; in case of contact with skin or eyes, rinse immediately with running water.

Chemical nature

The pyridine ring with the electron-withdrawing nitrogen atom reduces the electron density on the carbonyl carbon of the acid chloride, increasing its reactivity compared to benzoyl chloride. This accelerates the acylation reactions of alcohols and amines, but at the same time increases the sensitivity of the substance to hydrolysis - contact with air moisture quickly returns the original nicotinic acid.

Place in the series of acyl chlorides of pyridine carboxylic acids

Nicotinoyl chloride is a derivative of pyridine-3-carboxylic acid; In a similar way, by chlorination with phosphorus oxychloride, the acid chlorides of isomeric pyridinecarboxylic acids are obtained - picolinic (2-position) and isonicotinic (4-position). Their reactivity and areas of application are similar, however, it is the 3-isomer that is in demand in the production of nicotinic acid esters for pharmaceuticals and food additives.