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2-Bromo-3-pyridinol

2-Bromo-3-pyridinol structure

CAS No:
6602-32-0
Formula:
C5H4BrNO
Chemical Name:
2-Bromo-3-pyridinol
Synonyms:
3-Pyridinol,2-bromo-;2-Bromo-3-pyridinol;2-Bromo-3-hydroxypyridine;SKF 75250
Categories:
Pharmaceutical Intermediates > Heterocyclic Compound

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Description

LIGHT BROWN TO GREY CRYSTALLINE POWDER

2-Bromo-3-pyridinol Basic Attributes

Molecular Weight：

174

Exact Mass：

174.00

BRN：

109829

EC Number：

229-547-5

UNII：

9DAB85H359

DSSTox ID：

DTXSID8022242

HScode：

29333999

Characteristics

PSA：

33.1

XLogP3：

1.5

Appearance：

Light brown to gray Crystalline Powder

Density：

1.8±0.1 g/cm3

Melting Point：

186.5-187 °C

Boiling Point：

321.7°C at 760 mmHg

Flash Point：

148.4±22.3 °C

Refractive Index：

1.614

Water Solubility：

soluble in alcohol. Insoluble in water.

Storage Conditions：

Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

Safety Information

Hazard category：

IRRITANT

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

36/37/38-20/21/22

safety instructions：

26-36-24/25

RTECS Number：

UU7705000

Marks：

Xi,Xn

Hazard note：

Irritant

Stability/Shelf Life：

Stable under normal temperatures and pressures.

Precautionary statement(s)：

P261-P305 + P351 + P338

Hazard Statements：

H315-H319-H335

GHS Classification：

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 47 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

2-Bromo-3-pyridinol Use and Manufacturing

Methods of Manufacturing

(a) (a) 2-bromo-3-methoxypyridine (295 mg, 1.57 mmol) was heated in hydrobromide acid (5 ml) to 140 °C and stirred overnight. The solution was neutralized with a saturated sodium bicarbonate solution and extracted three times with ethyl acetate. The combined organic layers were dried over NaEXAMPLE 7 [0594] Preparation of 71 [0595] Prepared according to the method of Wishka et al, WO 2002/100857. [0596] Bromine (21.6 mL, 421 mmol) was added dropwise to a stirred solution of sodium hydroxide (39.2 g, 976 mmol)) in water (800 mL) at 0° C. The resultant bromate solution was then added dropwise to a stirred solution of 3-hydroxypyridine (20.0 g, 210 mmol), and sodium hydroxide (8.4 g, 34.3 mmol) in water (50 mL) at 0° C. The reaction mixture was stirred at 0° C. for 90 minutes, acidified to pH 2 by addition of 12M HCl soln., and the resultant precipitate collected, washed with water and dried on the filter. The solid was dissolved in EtOAc (170 mL), the solution diluted with heptane (620 mL) and allowed to crystallise for 3 days. The solid was collected, to give 2-bromopyridin-3-ol, and the mother liquor concentrated in vacuo to give a pale yellow solid. The crude solid was recrystallised from EtOH/water and dried in vacuo to afford 71 as a pale yellow crystalline solid (10.8 g, 42.7 mmol, 20percent).

Uses

Used as pharmaceutical intermediate

Computed Properties

Molecular Weight:174.00
XLogP3:1.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:172.94763
Monoisotopic Mass:172.94763
Topological Polar Surface Area:33.1
Heavy Atom Count:8
Complexity:78.8
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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