Description

6-Chloro-3-pyridinecarbonitrile (CAS No. 33252-28-7) is a high-purity organic compound with the molecular formula C₆H₃ClN₂, widely utilized in pharmaceutical and agrochemical research. This heterocyclic nitrile derivative, also known by its IUPAC name 6-chloropyridine-3-carbonitrile, features a chloro-substituted pyridine ring with a cyano functional group at the 3-position, making it a versatile intermediate for nucleophilic substitution and cross-coupling reactions. Available in crystalline solid form, it is characterized by excellent stability under standard laboratory conditions. Ideal for use in Suzuki-Miyaura, Buchwald-Hartwig, and other palladium-catalyzed transformations, this compound is rigorously tested via HPLC, GC, and NMR to ensure ≥98% purity, meeting the stringent requirements of synthetic chemists and process development teams.

Properties

• CAS Number: 33252-28-7
• Complexity: 137
• IUPAC Name: 6-chloropyridine-3-carbonitrile
• InChI: InChI=1S/C6H3ClN2/c7-6-2-1-5(3-8)4-9-6/h1-2,4H
• InChI Key: ORIQLMBUPMABDV-UHFFFAOYSA-N
• Exact Mass: 137.9984758
• Molecular Formula: C6H3ClN2
• Molecular Weight: 138.55
• SMILES: C1=CC(=NC=C1C#N)Cl
• Topological: 36.7
• Monoisotopic Mass: 137.9984758
• Synonyms: 6-Chloronicotinonitrile, 6-Chloro-3-pyridinecarbonitrile, 608-851-5, 2-Chloro-5-cyanopyridine, 33252-28-7, 6-chloropyridine-3-carbonitrile, 6-chloro-nicotinonitrile, 2-CHLORO-5-PYRIDINECARBONITRILE, 2-Chloropyridine-5-carbonitrile, MFCD00084941, 6-chloro nicotinonitrile, 6-Chloro-3-cyanopyridine, 3-PYRIDINECARBONITRILE, 6-CHLORO-, 2-chloro-5-cyano-pyridine, 6-Chloronicotinitrile, 6-chloronicotino-nitrile, 6-chloro-nicotino-nitrile, 2-Chloro,5-cyanopyridine, 5-Cyano-2-chloropyridine, 2-chloro -5-cyanopyridine, 2-chloro- 5-cyanopyridine, 2-chloro-5-(cyano)pyridine, SCHEMBL75830, 2-chloro -5-(cyano)pyridine, SCHEMBL7757978, SCHEMBL20178180, 2-Chloro pyridine-5-carbonitrile, 2-chloro-pyridine-5-carbonitrile, 6-chloro-3-pyridine carbonitrile, 6-chloro-3-pyridine-carbonitrile, DTXSID80408888, BCP11416, BBL100899, CL0236, SBB054388, STL554693, AKOS000121128, 6-Chloro-3-pyridinecarbonitrile, 97%, AB03166, AC-2475, CS-W020115, SB11104, BP-21215, HY-59197, SY001536, DB-010164, C2056, NS00124151, EN300-25566, 6-Chloro-3-cyanopyridine6-Chloronicotinonitrile, A15490, 11X-0845, F0001-0983

Application

6-Chloro-3-pyridinecarbonitrile serves as a key building block in the synthesis of active pharmaceutical ingredients (APIs), particularly for antiviral and antihypertensive agents. It is also employed in the development of neonicotinoid insecticides due to its pyridine core. Researchers value its reactivity in palladium-catalyzed C–N bond formations and cyanation reactions for functionalized heterocycles. Additionally, it finds use in material science for constructing nitrogen-rich molecular scaffolds.

Safety and Hazards

GHS Hazard Statements

• H302+H312+H332 (37.2%): Harmful if swallowed, in contact with skin or if inhaled [Warning Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]
• H302 (97.4%): Harmful if swallowed [Warning Acute toxicity, oral]
• H312 (91%): Harmful in contact with skin [Warning Acute toxicity, dermal]
• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H332 (47.4%): Harmful if inhaled [Warning Acute toxicity, inhalation]
• H335 (98.7%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Acute Tox. 4 (97.4%)
• Acute Tox. 4 (91%)
• Skin Irrit. 2 (100%)
• Eye Irrit. 2 (100%)
• Acute Tox. 4 (47.4%)
• STOT SE 3 (98.7%)

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