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122130

Sigma-Aldrich

3,5-Dibromosalicylaldehyde

98%

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About This Item

Linear Formula:
Br2C6H2-2-(OH)CHO
CAS Number:
90-59-5
Molecular Weight:
279.91
EC Number:
202-003-4
MDL number:
MFCD00003318
UNSPSC Code:
12352100
PubChem Substance ID:
24847478
NACRES:
NA.22

Assay

98%

form

solid

mp

82-83.5 °C (lit.)

solubility

methanol: soluble 25 mg/mL, clear, yellow to brown

functional group

aldehyde

SMILES string

Oc1c(Br)cc(Br)cc1C=O

InChI

1S/C7H4Br2O2/c8-5-1-4(3-10)7(11)6(9)2-5/h1-3,11H

InChI key

JHZOXYGFQMROFJ-UHFFFAOYSA-N

Related Categories

General description

3,5-Dibromosalicylaldehyde reacts with alkyl cyanoacetates in the presence of ammonium acetate to yield 4H- chromenes.

Application

3,5-Dibromosalicylaldehyde was used in the synthesis of Schiff base, 15N-Labeled N-(3,5-dibromosalicylidene)-methylamine. It was used as reactant for synthesis of Schiff base ligands which forms mononuclear complexes with copper(II), nickel(II), zinc(II) and cobalt(II).

Pictograms

Exclamation markEnvironment
GHS07,GHS09

Signal Word

Warning

Hazard Statements

H315,H319,H335,H400

Hazard Classifications

Aquatic Acute 1 - 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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Z Rozwadowski
Magnetic resonance in chemistry : MRC, 44(9), 881-886 (2006-06-03)
Deuterium isotope effects on 13C chemical shift of tetrabutylammonium salts of Schiff bases, derivatives of amino acids (glycine, L-alanine, L-phenylalanine, L-valine, L-leucine, L-isoleucine and L-methionine) and various ortho-hydroxyaldehydes in CDCl3 have been measured. The results have shown that the tetrabutylammonium
Shasad Sharif et al.
Journal of the American Chemical Society, 128(10), 3375-3387 (2006-03-09)
The tautomeric equilibrium in a Schiff base, N-(3,5-dibromosalicylidene)-methylamine 1, a model for the hydrogen bonded structure of the cofactor pyridoxal-5'-phosphate PLP which is located in the active site of the enzyme, was measured by means of 1H and 15N NMR
Haibo Ni et al.
Experimental neurology, 304, 102-113 (2018-03-09)
Receptor for activated protein kinase C 1 (RACK1) is a multifaceted scaffolding protein known to be involved in the regulation of signaling events required for neuronal protection. In the present study, we investigated the role of RACK1 in secondary brain
[Colorimetric determination of 4-chloro-2-(o-chlorobenzoyl)-N-methyl-N alpha-glycylglycinanilide with 3,5-dibromsalicyladehyde (author's transl)].
R Ikenishi et al.
Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan, 101(6), 532-537 (1981-06-01)
Nazanin Kordestani et al.
Dalton transactions (Cambridge, England : 2003), 49(24), 8247-8264 (2020-06-09)
The enantiopure Schiff bases (R or S)-N-1-(phenyl)ethyl-2,4-X1,X2-salicylaldimine (X1, X2 = Cl, Br, I) coordinate to copper(ii) and provide pseudotetrahedral bis[(S or R)-N-1-(phenyl)ethyl-(2,4-X1,X2-salicylaldiminato-κ2N,O)]-Δ/Λ-Cu(ii) (Λ/Δ-Cu-R or Δ/Λ-Cu-S). An induced Λ and Δ-chirality at-metal centre has been launched along the C2-axis of the
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