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2-Bromo-3-hydroxypyridine

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Name

2-Bromo-3-hydroxypyridine

EINECS 229-547-5
CAS No. 6602-32-0 Density 1.788 g/cm3
PSA 33.12000 LogP 1.54970
Solubility Soluble in alcohol. Insoluble in water. Melting Point 185-188 °C(lit.)
Formula C5H4BrNO Boiling Point 321.7 °C at 760 mmHg
Molecular Weight 173.997 Flash Point 148.4 °C
Transport Information N/A Appearance Light brown to grey crystalline powder
Safety 26-36-24/25 Risk Codes 36/37/38-20/21/22
Molecular Structure Molecular Structure of 6602-32-0 (2-Bromo-3-hydroxypyridine) Hazard Symbols HarmfulXn,IrritantXi
Synonyms

3-Pyridinol, 2-bromo-;2-Bromo-3-pyridinol;2-Bromopyridin-3-ol;3-Hydroxy-2-bromopyridine;

Article Data 20

2-Bromo-3-hydroxypyridine Synthetic route

24100-18-3

2-bromo-3-methoxypyridine

6602-32-0

2-bromo-pyridin-3-ol

Conditions
ConditionsYield
With hydrogen bromide In dichloromethane at 140℃; Inert atmosphere;94%
109-00-2

3-HYDROXYPYRIDINE

6602-32-0

2-bromo-pyridin-3-ol

Conditions
ConditionsYield
With bromine; sodium hydroxide In water at -10 - 20℃; for 3h;75%
With bromine; sodium hydroxide In water at -10 - 20℃; for 3h; Temperature;75%
With bromine; acetic acid In sodium hydroxide67%
109-00-2

3-HYDROXYPYRIDINE

A

6602-32-0

2-bromo-pyridin-3-ol

B

6602-33-1

2,6-dibromopyridin-3-ol

C

129611-31-0

2,4-Dibromo-3-hydroxypyridine

Conditions
ConditionsYield
With sodium hydroxide; bromine In water for 3h;A 68%
B n/a
C n/a
With bromine; sodium hydroxide In water for 24h; Cooling with ice;A 16%
B 18%
C 7%
With sodium hydroxide; bromine In water for 3h; Product distribution; other reaction conditions;

methanesulfonic acid 2-bromopyridin-3-yl ester

6602-32-0

2-bromo-pyridin-3-ol

Conditions
ConditionsYield
With lithium diisopropyl amide In tetrahydrofuran at 23℃; for 0.5h;57%
109-00-2

3-HYDROXYPYRIDINE

A

6602-32-0

2-bromo-pyridin-3-ol

B

6602-33-1

2,6-dibromopyridin-3-ol

Conditions
ConditionsYield
With bromine In sodium hydroxide; water; ethyl acetateA n/a
B 29%
Stage #1: 3-HYDROXYPYRIDINE With bromine; sodium hydroxide In water at 0℃; for 1.5h;
Stage #2: With hydrogenchloride In water pH=2;
Stage #3: In hexane; ethyl acetate for 72h;
A n/a
B 20%
15128-82-2

3-hydroxy-2-nitropyridine

6602-32-0

2-bromo-pyridin-3-ol

Conditions
ConditionsYield
With phosphorus tribromide
74037-50-6

3-ethoxy-2-nitropyridine

6602-32-0

2-bromo-pyridin-3-ol

Conditions
ConditionsYield
With water; hydrogen bromide; acetic acid at 130℃; unter Druck;
38729-14-5

2-nitro-1-oxy-pyridin-3-ol

6602-32-0

2-bromo-pyridin-3-ol

Conditions
ConditionsYield
With chloroform; phosphorus tribromide
110-86-1

pyridine

109-00-2

3-HYDROXYPYRIDINE

7726-95-6

bromine

6602-32-0

2-bromo-pyridin-3-ol

109-00-2

3-HYDROXYPYRIDINE

A

6602-32-0

2-bromo-pyridin-3-ol

B

6602-33-1

2,6-dibromopyridin-3-ol

C

6602-34-2

2,4,6-tribromo-3-hydroxypyridine

Conditions
ConditionsYield
With N-Bromosuccinimide In tetrachloromethane at 20℃; for 48h;A 28 % Spectr.
B 32 % Spectr.
C 4 % Spectr.

2-Bromo-3-hydroxypyridine Specification

The 2-Bromo-3-hydroxypyridine, with the CAS registry number 6602-32-0, is also known as 2-Bromo-3-pyridinol. It belongs to the product categories of Blocks; Bromides; Pyridines; Pyridine; Pyridine Series; Pyridines, Pyrimidines, Purines and Pteredines; Pyridines derivatives; Halides; API intermediates; Bromopyridines; Halopyridines; Boronic Acid. Its EINECS number is 207-857-1. This chemical's molecular formula is C5H4BrNO and molecular weight is 174.00. What's more, its systematic name is 2-bromopyridin-3-ol. It should be sealed and stored in a cool and dry place. Moreover, it should be protected from light. It is used in organic synthesis.

Physical properties of 2-Bromo-3-hydroxypyridine are: (1)ACD/LogP: 1.66; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.64; (4)ACD/LogD (pH 7.4): 0.96; (5)ACD/BCF (pH 5.5): 10.25; (6)ACD/BCF (pH 7.4): 2.13; (7)ACD/KOC (pH 5.5): 181.48; (8)ACD/KOC (pH 7.4): 37.75; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 22.12 Å2; (13)Index of Refraction: 1.614; (14)Molar Refractivity: 33.91 cm3; (15)Molar Volume: 97.2 cm3; (16)Polarizability: 13.44×10-24cm3; (17)Surface Tension: 56.7 dyne/cm; (18)Density: 1.788 g/cm3; (19)Flash Point: 148.4 °C; (20)Enthalpy of Vaporization: 58.6 kJ/mol; (21)Boiling Point: 321.7 °C at 760 mmHg; (22)Vapour Pressure: 0.000155 mmHg at 25°C.

Preparation: this chemical can be prepared by pyridin-3-ol at the temperature of 20 °C. This reaction will need reagents Br2, HCl and solvent aq. NaOH. The yield is about 52%.

2-Bromo-3-hydroxypyridine can be prepared by pyridin-3-ol at the temperature of 20 °C

Uses of 2-Bromo-3-hydroxypyridine: it can be used to produce 2-bromo-3-isopropoxypyridine at the temperature of 80 °C. It will need reagent K2CO3 and solvent dimethylformamide with the reaction time of 2 hours. The yield is about 99%.

2-Bromo-3-hydroxypyridine can be used to produce 2-bromo-3-isopropoxypyridine at the temperature of 80 °C

When you are using this chemical, please be cautious about it as the following:
This chemical is harmful by inhalation, in contact with skin and if swallowed. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need wear suitable protective clothing and must avoid contact with eyes.

You can still convert the following datas into molecular structure:
(1)SMILES: Brc1ncccc1O
(2)Std. InChI: InChI=1S/C5H4BrNO/c6-5-4(8)2-1-3-7-5/h1-3,8H
(3)Std. InChIKey: YKHQFTANTNMYPP-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 320mg/kg (320mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#04679.

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