ChemicalBook--->CAS DataBase List--->37669-64-0

37669-64-0

37669-64-0 Structure

37669-64-0 Structure
IdentificationBack Directory
[Name]

(5-BROMO-PYRIDIN-3-YL)-METHANOL
[CAS]

37669-64-0
[Synonyms]

AURORA KA-3029
5-Bromo-3-pyridinemethanol
3-Bromopyridine-5-methanol
3-Bromo-5-pyridinemethanol
5-Bromopyridine-3-methanol
3-Pyridinemethanol, 5-bromo-
(5-BROMO-3-PYRIDINYL)METHANOL
(3-Bromo-pyridin-5-yl)methanol
5-Bromo-3-pyridinemethanol >
(5-BROMO-PYRIDIN-3-YL)-METHANOL
3-BROMO-5-HYDROXYMETHYLPYRIDINE
5-Bromo-3-hydroxymethylpyridine
5-BroMo-3-pyridineMethanol, 95+%
(5-BROMO-PYRIDIN-3-YL)-METHANOL ISO 9001:2015 REACH
[Molecular Formula]

C6H6BrNO
[MDL Number]

MFCD03265757
[MOL File]

37669-64-0.mol
[Molecular Weight]

188.02
Chemical PropertiesBack Directory
[Melting point ]

27°
[Boiling point ]

291.5±25.0 °C(Predicted)
[density ]

1.67
[refractive index ]

1.5940-1.5980
[storage temp. ]

Keep in dark place,Inert atmosphere,Room temperature
[form ]

Liquid or Low Melting Solid
[pka]

13.29±0.10(Predicted)
[color ]

Clear pale yellow
[InChIKey]

WDVDHJLKXYCOFS-UHFFFAOYSA-N
Safety DataBack Directory
[Hazard Codes ]

Xi
[Hazard Note ]

Irritant
[HS Code ]

2933399990
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Tetrahydrofuran-->Thionyl chloride-->Bromine-->Sodium borohydride-->Nicotinic acid-->iodine-->1-(5-bromopyridin-3-yl)-N,N-dimethylmethanamine-->Ethyl 5-bromonicotinate-->5-Bromonicotinoyl chloride-->Nicotinoyl chloride hydrochloride-->5-Hydroxynicotinic acid-->Methyl 5-bromonicotinate-->5-Bromo-3-pyridinecarboxaldehyde-->5-Bromonicotinic acid
[Preparation Products]

(5-Bromo-pyridin-3-yl)-acetonitrile-->3-Bromo-5-(Chloromethyl)Pyridine Hydrochloride-->(5-(Furan-2-yl)pyridin-3-yl)methanol
Hazard InformationBack Directory
[Uses]

5-Bromo-3-pyridinemethanol serves as a precursor for synthesizing [3-(benzyloxy)methyl]-5-bromopyridine via reaction with sodium hydride and benzyl bromide[6].
[Synthesis]

Sodium borohydride (2.2 g, 59.1 mmol) was added to a suspension of 5-bromo-pyridine-3-carbaldehyde (10.0 g, 53.7 mmol) in MeOH (100 mL) at 0° C. The mixture was stirred at 0° C. for 1 hour before it was quenched by adding water (5.0 mL). Evaporation of solvents afforded a light yellowish oil, which was re-dissolved in EtOAc and washed with water. The organic layer was dried over anhy. Na2SO4, filtered and concentrated in vacuo to give 5-Bromo-3-pyridinemethanol (9.6 g, 95 per cent) as a colourless oil.
[References]

[1] Patent: WO2013/79452, 2013, A1. Location in patent: Page/Page column 143
[2] Patent: US2013/143863, 2013, A1. Location in patent: Paragraph 1076; 1077; 1078
[3] Journal of Medicinal Chemistry, 2016, vol. 59, # 10, p. 4913 - 4925
[4] Patent: US2013/267495, 2013, A1. Location in patent: Paragraph 0454-0455
[5] Patent: US2013/296302, 2013, A1. Location in patent: Paragraph 0549
Spectrum DetailBack Directory
[Spectrum Detail]

(5-BROMO-PYRIDIN-3-YL)-METHANOL(37669-64-0)1HNMR
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