4-Bromo-3-hydroxymethylpyridine [Background and Overview]
4-Bromo-3-hydroxymethylpyridine, the English name is (4-Bromopyridin-3-yl)methanol, CAS number is 197007-87-7, and the molecular formula is C6H6BrNO, molecular weight 188.02200; PSA: 33.12000; LogP: 1.33640. Density 1.668g/cm3, boiling point 302.8ºC at 760 mmHg, flash point 136.9ºC, refractive index 1.598, vapor pressure 0.000427mmHg at 25°C.
If 4-bromo-3-hydroxymethylpyridine is inhaled, please move the patient to fresh air; if there is skin contact, take off contaminated clothing and wash the skin thoroughly with soap and water. If you feel discomfort, Seek medical attention; if eye contact occurs, separate eyelids, rinse with running water or saline, and seek medical attention immediately; if ingested, rinse mouth immediately, do not induce vomiting, and seek medical attention immediately. Advice to protect rescuers is as follows: Move the patient to a safe place, consult a doctor, and if conditions permit, please show this chemical safety data sheet to the doctor who comes to the scene. If there is a small leak, collect the leaked liquid in a sealable container as much as possible, absorb it with sand, activated carbon or other inert materials, and transfer it to a safe place. Do not flush it into the sewer; if there is a large leak, build a dike or dig a pit. Contain, seal the drainage pipe, cover it with foam to inhibit evaporation, use an explosion-proof pump to transfer it to a tanker or a special collector, and recycle or transport it to a waste treatment site for disposal.
4-Bromo-3-hydroxymethylpyridine [Synthesis]
4-Bromopyridine-3-carboxaldehyde can be used as the reaction raw material to react to generate 4-bromo-3-hydroxymethylpyridine with a yield of 70%. The reaction equation is as follows:
4-Bromo-3-hydroxymethylpyridine [Application]
4-Bromo-3-hydroxymethylpyridine can be used as an intermediate for the synthesis of other compounds with certain activity from chromium picolidine. Application examples of 4-bromo-3-hydroxymethylpyridine are as follows: n-butylboronic acid:
Compound 1 is prepared by Mitsunobu reaction between iodopyridine methanol solution of 4-bromo-3-hydroxymethylpyridine (6) and alkynylphenol (7). The reaction equation is as follows:
Afterwards, the alkyne aryl iodide (1) undergoes a palladium-catalyzed reaction in the presence of 3-nitrophenylboronic acid to obtain pyridine oxepane 2a. The reaction equation is as follows:
4-Bromo-3-hydroxymethylpyridine [Reference]
[1] https://baike.molbase.cn/cidian/976840_xianlu_1075254
[2] Carson M W, Giese M W, Coghlan M J. An intra/intermolecular Suzuki sequence to benzopyridyloxepines containing geometrically pure exocyclic tetrasubstituted alkenes[J]. Organic letters, 2008, 10(13): 2701-2704.
