
CAS Number: 93271-59-1
Chemical Name: 2-Hydroxy-4-methylpyridine-3-carbonitrile
IUPAC Name: 2-Hydroxy-4-methylpyridine-3-carbonitrile
Synonyms:
4-Methyl-2-hydroxynicotinonitrile;
2-Hydroxy-4-methylnicotinonitrile;
4-Methyl-3-cyano-2-pyridinol
Molecular Formula: C₇H₆N₂O
Molecular Weight: ~134.14 g/mol
Appearance: Off-white to light beige crystalline powder
Physical State: Solid
Melting Point: Typically reported in the range of 170–180 °C (may vary depending on purity)
Boiling Point: Not applicable (decomposes before boiling under normal atmospheric pressure)
Solubility:
Soluble in polar organic solvents such as methanol, ethanol, DMSO, and acetone; slightly soluble in water
Stability:
Stable under standard laboratory conditions; may be sensitive to strong oxidizing agents and prolonged exposure to moisture
Functional Groups:
Hydroxyl group (–OH)
Nitrile group (–C≡N)
Heteroaromatic pyridine ring
Methyl substituent (–CH₃)
Chemical Class:
Substituted pyridine derivative / Heterocyclic nitrile compound
SMILES (representative):
CC1=NC(=C(C=N1)C#N)O
InChI Key (representative):
(Varies by database; available from chemical registries)
93271-59-1 is widely used as a heterocyclic building block in organic synthesis. Its structure contains both hydroxyl and nitrile functional groups, enabling versatile chemical transformations.
Applications include:
Synthesis of pharmaceutical intermediates
Preparation of agrochemical compounds
Development of biologically active heterocycles
Intermediate in specialty chemical production
The nitrile group allows further derivatization into amides, acids, or amines, while the hydroxyl group participates in substitution and condensation reactions.
Commonly employed in:
Medicinal chemistry research
Structure–activity relationship (SAR) studies
Development of pyridine-based drug candidates
Multi-step heterocyclic synthesis
Its dual functional groups make it valuable for constructing complex nitrogen-containing molecular frameworks.
GHS Classification (typical for similar compounds):
Harmful if swallowed
Causes skin and eye irritation
May cause respiratory irritation
Common Hazard Statements:
H302: Harmful if swallowed
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
Precautionary Statements:
P261: Avoid breathing dust
P280: Wear protective gloves and eye protection
P305 + P351 + P338: IF IN EYES, rinse cautiously with water and remove contact lenses
P301 + P312: IF SWALLOWED, call a doctor if you feel unwell
Handle in a well-ventilated laboratory environment using appropriate personal protective equipment (PPE).
Typical Purity: 97–99% (Research and Industrial Grade)
Storage Conditions:
Store in a tightly sealed container
Keep in a cool, dry, and well-ventilated area
Protect from moisture and direct sunlight
Keep away from strong oxidizing agents
Commercial Use:
Available from specialty chemical manufacturers for research and industrial organic synthesis applications.
Not intended for direct pharmaceutical, food, or diagnostic use without proper regulatory compliance.
93271-59-1 (2-Hydroxy-4-methylpyridine-3-carbonitrile) is a versatile heterocyclic intermediate widely utilized in pharmaceutical and fine chemical synthesis. Its combination of hydroxyl and nitrile functional groups enables diverse chemical transformations, making it an important building block in medicinal chemistry, agrochemical development, and advanced organic research applications.
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