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Safety Information

384305

Sigma-Aldrich

6-Hydroxypyridine-2-carboxylic acid

95%

Synonym(s):

6-Hydroxypicolinic acid, 6-Hydroxypyridine-2-carboxylic acid

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About This Item

Empirical Formula (Hill Notation):
C6H5NO3
CAS Number:
19621-92-2
Molecular Weight:
139.11
Beilstein:
115842
MDL number:
MFCD00192220
UNSPSC Code:
12352100
PubChem Substance ID:
24863659
NACRES:
NA.22

Quality Level

100

Assay

95%

form

solid

mp

270 °C (dec.) (lit.)

SMILES string

OC(=O)c1cccc(O)n1

InChI

1S/C6H5NO3/c8-5-3-1-2-4(7-5)6(9)10/h1-3H,(H,7,8)(H,9,10)

InChI key

VRCWSYYXUCKEED-UHFFFAOYSA-N

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General description

6-Hydroxypyridine-2-carboxylic acid (6HPA, 6-Hydroxypicolinic acid) is a picolinic acid derivative. It has been reported to exhibit enol-keto tautomerism. It is a chelating ligand exhibiting potential complexing ability (via N,O-chelation or N,O,O-chelation). Intramolecular proton transfer (IPT) in tautomeric forms of 6HPA has been investigated by density functional theory (DFT) calculations.

Application

6-Hydroxypyridine-2-carboxylic acid may be used in the preparation of ruthenium(II) complex, [RuH(CO)(6-OH-py-2-COO)(PPh3)2].

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

384305-VAR:
384305-25G:
384305-5G:
384305-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
MKCD9895
MKBR2617V
MKBN4946V
MKBG4645V
MKBF2856

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Computational study of the intramolecular proton transfer between 6-hydroxypicolinic acid tautomeric forms and intermolecular hydrogen bonding in their dimers.
Kazemi Riabi SH, et al.
Physical Chemistry Research, 1, 117-125 (2013)
Synthesis, molecular, spectroscopic and catalytic characterization of ruthenium (II) complexes with pyridine-2-carboxylic acid derivatives ligands.
Malecki JG, et al.
Polyhedron, 48(1), 21-30 (2012)
Jennifer A Jacobsen et al.
Journal of medicinal chemistry, 54(2), 591-602 (2010-12-30)
Fragment-based lead design (FBLD) has been used to identify new metal-binding groups for metalloenzyme inhibitors. When screened at 1 mM, a chelator fragment library (CFL-1.1) of 96 compounds produced hit rates ranging from 29% to 43% for five matrix metalloproteases

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