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525693

Sigma-Aldrich

6-Bromo-2-pyridinecarboxaldehyde

97%

Synonym(s):

2-Bromo-6-formylpyridine, 2-Bromopyridine-6-carboxaldehyde, 2-Bromopyridyl-6-carboxaldehyde, 2-Formyl-6-bromopyridine, 6-Bromo-2-formylpyridine, 6-Bromo-2-pyridinecarbaldehyde, 6-Bromopicolinaldehyde, 6-Bromopyridine-2-aldehyde

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About This Item

Empirical Formula (Hill Notation):
C6H4BrNO
CAS Number:
34160-40-2
Molecular Weight:
186.01
MDL number:
MFCD02683546
UNSPSC Code:
12352100
PubChem Substance ID:
24874502
NACRES:
NA.22

Assay

97%

mp

81-85 °C (lit.)

storage temp.

2-8°C

SMILES string

[H]C(=O)c1cccc(Br)n1

InChI

1S/C6H4BrNO/c7-6-3-1-2-5(4-9)8-6/h1-4H

InChI key

QWFHFNGMCPMOCD-UHFFFAOYSA-N

General description

6-Bromo-2-pyridinecarboxaldehyde is a pyridine derivative. It participates in the synthesis of meso-substituted trans-A2B2-porphyrin.

Application

6-Bromo-2-pyridinecarboxaldehyde may be used in the synthesis of:
  • 6-([2,2′-bi(1,3-dithiolylidene)]-4-yl)picolinaldehyde
  • tris(2-pyridylmethyl)amine (Tpy) derivative having Tpy core bearing a 3-formyl-phenyl substituent on one of the three arms
  • syn- and anti- forms of 4-(6-bromopyridin-2-yl)-3-methyl-3-phenyloxetan-2-one
  • 6-(2,4,6-triisopropylphenyl)-2-pyridinecarboxaldehyde
Substrate used in a study of a rhodium-catalyzed, reductive aldol coupling with divinyl ketones leading to syn ß-hydroxyenones.
Useful building block for Tris[(pyridyl)methyl]amine ligands.

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Steric and Electronic Effects in the Formation and Carbon Disulfide Reactivity of Dinuclear Nickel Complexes Supported by Bis (iminopyridine) Ligands.
Bheemaraju A, et al.
Organometallics, 32(10), 2952-2962 (2013)
Francesca A Scaramuzzo et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 19(49), 16809-16813 (2013-11-01)
Reliable determination of the enantiomeric excess of free amino acids can be obtained by measuring the induced circular dichroism of a multicomponent assembly formed by a modified tris(2-pyridylmethyl)amine ligand, a zinc salt, and the amino acid of interest. The systems
Awatef Ayadi et al.
Beilstein journal of organic chemistry, 11, 1379-1391 (2015-10-02)
The synthesis and full characterization of two tetrathiafulvalene-appended azine ligands, namely 2-([2,2'-bi(1,3-dithiolylidene)]-4-yl)-6-((2,4-dinitrophenyl)hydrazono)methyl)pyridine (L1) and 5-([2,2'-bi(1,3-dithiolylidene)]-4-yl)-2-((2,4-dinitrophenyl)hydrazono)methyl)pyridine (L2) are described. The crystal structure of ligand L1 indicates that the ligand is completely planar with the presence of a strong intramolecular N3-H3···O1 hydrogen
Synthetic methodologies leading to porphyrin-quinone conjugates.
Cardoso MFDC, et al.
Journal of Porphyrins and Phthalocyanines, 1-23 (2015)
Soo Bong Han et al.
Organic letters, 8(24), 5657-5660 (2006-11-17)
Catalytic hydrogenation of divinyl ketones 1a and 1e in the presence of diverse aldehydes 2a-e at ambient temperature and pressure using cationic rhodium catalysts ligated by tri-2-furyl phosphine enables formation of aldol products 3a-e and 5a-e, respectively, with high levels
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