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About This Item
Empirical Formula (Hill Notation):
C6H4BrNO
CAS Number:
Molecular Weight:
186.01
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
MDL number:
Assay:
97%
InChI
1S/C6H4BrNO/c7-6-3-1-2-5(4-9)8-6/h1-4H
SMILES string
[H]C(=O)c1cccc(Br)n1
InChI key
QWFHFNGMCPMOCD-UHFFFAOYSA-N
assay
97%
mp
81-85 °C (lit.)
functional group
aldehyde, bromo
storage temp.
2-8°C
Quality Level
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 β-hydroxyenones.
Useful building block for Tris[(pyridyl)methyl]amine ligands.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
ppe
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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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
Synthetic methodologies leading to porphyrin-quinone conjugates.
Cardoso MFDC, et al.
Journal of Porphyrins and Phthalocyanines, 1-23 (2015)
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
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)
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
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