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525693

Sigma-Aldrich

6-Bromo-2-pyridinecarboxaldehyde

97%

Sinónimos:

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

Fórmula empírica (notación de Hill):
C6H4BrNO
Número de CAS:
34160-40-2
Peso molecular:
186.01
MDL number:
MFCD02683546
UNSPSC Code:
12352100
PubChem Substance ID:
24874502
NACRES:
NA.22

Quality Level

100

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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

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NHC-Promoted asymmetric β-lactone formation from arylalkylketenes and electron-deficient benzaldehydes or pyridinecarboxaldehydes.
Douglas J, et al.
The Journal of Organic Chemistry, 78(8), 3925-3938 (2013)
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
Magdalena M Makowska-Grzyska et al.
Inorganic chemistry, 42(23), 7472-7488 (2003-11-11)
Divalent manganese, cobalt, nickel, and zinc complexes of 6-Ph(2)TPA (N,N-bis((6-phenyl-2-pyridyl)methyl)-N-((2-pyridyl)methyl)amine; [(6-Ph(2)TPA)Mn(CH(3)OH)(3)](ClO(4))(2) (1), [(6-Ph(2)TPA)Co(CH(3)CN)](ClO(4))(2) (2), [(6-Ph(2)TPA)Ni(CH(3)CN)(CH(3)OH)](ClO(4))(2) (3), [(6-Ph(2)TPA)Zn(CH(3)CN)](ClO(4))(2) (4)) and 6-(Me(2)Ph)(2)TPA (N,N-bis((6-(3,5-dimethyl)phenyl-2-pyridyl)methyl)-N-((2-pyridyl)methyl)amine; [(6-(Me(2)Ph)(2)TPA)Ni(CH(3)CN)(2)](ClO(4))(2) (5) and [(6-(Me(2)Ph)(2)TPA)Zn(CH(3)CN)](ClO(4))(2) (6)) have been prepared and characterized. X-ray crystallographic characterization of 1A.CH(3)()OH and 1B.2CH(3)()OH (differing solvates
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)
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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