Description

(4-Bromopyridin-2-yl)methanol (CAS No. 131747-45-0) is a high-purity brominated pyridine derivative with the molecular formula C₆H₆BrNO. This compound features a hydroxymethyl group at the 2-position and a bromine substituent at the 4-position of the pyridine ring, making it a versatile intermediate for pharmaceutical, agrochemical, and materials science research. Its well-defined structure and reactivity enable precise modifications in synthetic organic chemistry.

Available in >95% purity (HPLC), this product is supplied as a white to off-white crystalline powder, rigorously tested via NMR, LC-MS, and elemental analysis to ensure batch-to-batch consistency. Ideal for cross-coupling reactions (e.g., Suzuki-Miyaura), nucleophilic substitutions, or as a precursor for heterocyclic scaffolds. Store under inert atmosphere at 2-8°C to maintain stability.

Key Applications: Ligand synthesis, medicinal chemistry building block, organocatalyst development.

Properties

• CAS Number: 131747-45-0
• Complexity: 89.1
• IUPAC Name: (4-bromo-2-pyridyl)methanol
• InChI: InChI=1S/C6H6BrNO/c7-5-1-2-8-6(3-5)4-9/h1-3,9H,4H2
• InChI Key: MHVUUSQGWMQSMH-UHFFFAOYSA-N
• Exact Mass: 186.96328
• Molecular Formula: C6H6BrNO
• Molecular Weight: 188.02
• SMILES: C1=CN=C(C=C1Br)CO
• Topological: 33.1
• Monoisotopic Mass: 186.96328
• Synonyms: (4-bromopyridin-2-yl)methanol, 131747-45-0, DTXSID80563704, DTXCID50514480, 812-912-3, 4-Bromo-2-pyridinemethanol, 2-PYRIDINEMETHANOL, 4-BROMO-, (4-BROMO-2-PYRIDYL)METHANOL, (4-Bromo-pyridin-2-yl)-methanol, MFCD09800557, (4-bromanylpyridin-2-yl)methanol, (4-Bromo-2-pyridinyl)methanol, 4-Bromo-2-(hydroxymethyl)pyridine, IJF, 4-bromo-2-pyridylmethanol, SCHEMBL1879544, SCHEMBL7667910, SCHEMBL29057155, MHVUUSQGWMQSMH-UHFFFAOYSA-N, BBL101441, STL555237, AKOS005259296, CS-W018599, PB31388, AC-23727, AS-19522, SY021911, B5291, EN300-217663

Application

(4-Bromopyridin-2-yl)methanol serves as a key intermediate in the synthesis of bioactive molecules, particularly in the development of kinase inhibitors and antiviral agents. Its bromine moiety enables palladium-catalyzed cross-coupling reactions for constructing complex heteroaromatic systems. Researchers also utilize it to prepare functionalized pyridine ligands for transition metal catalysis in asymmetric synthesis.

Safety and Hazards

GHS Hazard Statements

• H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H318 (33.3%): Causes serious eye damage [Danger Serious eye damage/eye irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H332 (66.7%): Harmful if inhaled [Warning Acute toxicity, inhalation]
• H335 (100%): 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, P305+P354+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Acute Tox. 4 (100%)
• Skin Irrit. 2 (100%)
• Eye Dam. 1 (33.3%)
• Eye Irrit. 2 (100%)
• Acute Tox. 4 (66.7%)
• STOT SE 3 (100%)

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Disclaimer: Sold exclusively for laboratory research. Prohibited for commercial use, diagnostics, or human/animal applications. Buyers assume all compliance liability.