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116203

Sigma-Aldrich

2-Chloro-3-hydroxypyridine

98%

Synonym(s):

2-Chloro-3-pyridinol

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About This Item

Empirical Formula (Hill Notation):
C5H4ClNO
CAS Number:
6636-78-8
Molecular Weight:
129.54
EC Number:
229-635-3
MDL number:
MFCD00006235
UNSPSC Code:
12352100
PubChem Substance ID:
24847271
NACRES:
NA.22

Quality Level

100

Assay

98%

mp

170-172 °C (lit.)

SMILES string

Oc1cccnc1Cl

InChI

1S/C5H4ClNO/c6-5-4(8)2-1-3-7-5/h1-3,8H

InChI key

RSOPTYAZDFSMTN-UHFFFAOYSA-N

Application

2-Chloro-3-hydroxypyridine has been used in the preparation of 3-hydroxypyridine-2( 1 H)-selone. It has also been used in the synthesis of all four possible benzo[4,5]furopyridine tricyclic heterocycles: benzo[4,5]furo[2,3-b]pyridine, benzo[4,5]furo[2,3-c]pyridine, benzo[4,5]furo[3,2-c]pyridine, and benzo[4,5]furo[3,2-b]pyridine. the synthesis involves α and γ-activation of chloropyridines, as well as palladium-mediated reactions.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
STBK1866
STBH5934
STBD1805V
STBC4719V
STBB6482V

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Novel heterocyclic systems. Part 21. Synthesis of 3-hydroxypyridine-2 (1H)-selone and its application in the synthesis of 1-azaphenoxaselenine and its substituted derivatives.
Smith K, et al.
Journal of the Chemical Society. Perkin Transactions 1, 2075-2079 (1986)
Wen Song Yue et al.
Organic letters, 4(13), 2201-2203 (2002-06-21)
[reaction: see text] By taking advantage of the alpha- and gamma-activation of chloropyridines as well as palladium-mediated reactions, all four possible benzo[4,5]furopyridine tricyclic heterocycles, benzo[4,5]furo[2,3-b]pyridine, benzo[4,5]furo[2,3-c]pyridine, benzo[4,5]furo[3,2-c]pyridine, and benzo[4,5]furo[3,2-b]pyridine, are efficiently synthesized from 2-chloro-3-iodopyridine, 3-chloro-4-stannylpyridine, 4-chloro-3-iodopyridine, and 2-chloro-3-hydroxypyridine, respectively.

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