| Identification | More | [Name]
2-Bromo-3-hydroxypyridine | [CAS]
6602-32-0 | [Synonyms]
2-BROMO-3-HYDROXYPYRIDINE
2-BROMO-3-PYRIDINOL
2-BROMOPYRIDIN-3-OL
3-HYDROXY-2-BROMOPYRIDINE
LABOTEST-BB LT01143272
TIMTEC-BB SBB003805
2-bromo-3-pyridino
2-Bromo-3-pyridine
2-BROMO-3-HYDROXYPYRIDINE 97%
2-Bromo-3-pyridinol(2-Bromo-3-hydroxypyridine)
(2-Bromo-pyridine-5-sulfonyl)acetic acid tert-butyl este
2-Bromo-3-hydroxy-4-picoline
2-Chloro-5-fluoro-4-picoline
2-Chloropyridine-5-acetate
3-(3-Methylsulfonylphenyl)pyridine methylsulfonate
3-Amino-5,6-dibromopyridine
4-Amino-2-chloro-3,5-dibromopyridine
5-Methylnicotinic acid HCl
2-Amino-3-nitro-5-methylpyridine
5-Bromo-3-chloro-2-methoxypyridine | [EINECS(EC#)]
229-547-5 | [Molecular Formula]
C5H4BrNO | [MDL Number]
MFCD00006220 | [Molecular Weight]
174 | [MOL File]
6602-32-0.mol |
| Chemical Properties | Back Directory | [Appearance]
LIGHT BROWN TO GREY CRYSTALLINE POWDER | [Melting point ]
185-188 °C(lit.)
| [Boiling point ]
321.7±22.0 °C(Predicted) | [density ]
1.5643 (rough estimate) | [refractive index ]
1.5500 (estimate) | [storage temp. ]
Inert atmosphere,Room Temperature | [form ]
Crystalline Powder | [pka]
4.32±0.10(Predicted) | [color ]
Light brown to gray | [Water Solubility ]
Soluble in alcohol. Insoluble in water. | [Detection Methods]
HPLC | [BRN ]
109829 | [InChI]
InChI=1S/C5H4BrNO/c6-5-4(8)2-1-3-7-5/h1-3,8H | [InChIKey]
YKHQFTANTNMYPP-UHFFFAOYSA-N | [SMILES]
C1(Br)=NC=CC=C1O | [CAS DataBase Reference]
6602-32-0(CAS DataBase Reference) | [NIST Chemistry Reference]
3-Pyridinol, 2-bromo-(6602-32-0) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H315-H319-H335 | [Precautionary statements ]
P261-P264-P271-P280-P302+P352-P305+P351+P338 | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [RTECS ]
UU7705000
| [F ]
10 | [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29333999 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
LIGHT BROWN TO GREY CRYSTALLINE POWDER | [Uses]
2-Bromo-3-hydroxypyridine is used to produce 2-bromo-4,6-diiodo-3-pyridinol. It is also used in azo dyes and in the synthesis of pterocellin A by reacting with kojic acid and in synthesis of orelline. | [Synthesis]
The general procedure for the synthesis of 2-bromo-3-hydroxypyridine from 3-hydroxypyridine was as follows:
(a) A hypobromite solution was prepared by slowly adding bromine (2.74 mL, 8.49 g, 5.31 mmol) to 10% sodium hydroxide solution (50 mL) at 5°C to 10°C. Subsequently, this hypobromite solution was added dropwise to 10% sodium hydroxide solution (50 mL) containing 3-hydroxypyridine (5.0 g, 52.6 mmol) over 20 minutes. The reaction mixture was continued to be stirred for 30 minutes. The pH of the reaction solution was adjusted to 6-7 with acetic acid. the mixture was cooled to 5°C and maintained for 1 h. The solid product was subsequently collected by filtration. The product was washed with water and dried under vacuum at 85°C to give 2-bromo-3-hydroxypyridine (6.22 g, 67% yield).
References: 1) GJ Clark and L W Deedy, Australian J Chem, (1981), 34, 927. | [References]
[1] Patent: US5646286, 1997, A
[2] Patent: US5726315, 1998, A
[3] Chemistry - A European Journal, 2010, vol. 16, # 28, p. 8439 - 8445
[4] Australian Journal of Chemistry, 1981, vol. 34, # 4, p. 927 - 932
[5] Helvetica Chimica Acta, 1988, vol. 71, p. 957 - 963 |
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