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Sigma-Aldrich

3,5-Di-tert-butyl-2-hydroxybenzaldehyde

99%

Synonym(s):

3,5-Di-tert-butylsalicylaldehyde

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About This Item

Linear Formula:
HOC6H2[C(CH3)3]2CHO
CAS Number:
37942-07-7
Molecular Weight:
234.33
MDL number:
MFCD00191998
UNSPSC Code:
12352100
PubChem Substance ID:
24848469
NACRES:
NA.22

Assay

99%

form

powder or crystals

mp

59-61 °C (lit.)

SMILES string

CC(C)(C)c1cc(C=O)c(O)c(c1)C(C)(C)C

InChI

1S/C15H22O2/c1-14(2,3)11-7-10(9-16)13(17)12(8-11)15(4,5)6/h7-9,17H,1-6H3

InChI key

RRIQVLZDOZPJTH-UHFFFAOYSA-N

General description

3,5-Di-tert-butyl-2-hydroxybenzaldehyde undergoes condensation reaction with
  • methyl-2-{N-(2′-aminoethane)}-amino-1-cyclopentenedithiocarboxylate to yield Schiff base ligand
  • N,N-diethyl-2-methyl-1,4-phenylenediamine during the synthesis of copper(II) and cobalt(II) complexes of salicylaldimine

Application

3,5-Di-tert-butyl-2-hydroxybenzaldehyde was used in the synthesis of
  • Mn(III)-salen complex and its diamino precursor 5,6-diamino-5,6-dideoxy-1,2-O-isopropylidene-3-O-methyl-β-L-idofuranose
  • chiral Schiff base ligand for an enantioselective copper-catalyzed addition of phenylacetylene to imines
  • chiral oxazolidine ligand for the enantioselective addition of diethylzinc to aldehydes
  • tin Schiff base complexes with histidine analogues

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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Mild and efficient synthesis of 5, 6-diamino-5, 6-dideoxy-1, 2-O-isopropylidene-3- O -methyl-?-l-idofuranose: precursor of the first carbohydrate-derived chiral Mn (III)-salen complex.
Yan S and Klemm D.
Tetrahedron, 58(50), 10065-10071 (2002)
Co (II) and Cu (II) Schiff base complexes of bis (N-(4-diethylamino-2-methylphenyl)-3, 5-di-tert-butylsalicylaldimine): Electrochemical and X-ray structural study.
Ulusoy M, et al.
Structural Chemistry, 19(5), 749-755 (2008)
Ariadna Garza-Ortiz et al.
Bioinorganic chemistry and applications, 2013, 502713-502713 (2013-07-19)
Five novel tin Schiff base complexes with histidine analogues (derived from the condensation reaction between L-histidine and 3,5-di-tert-butyl-2-hydroxybenzaldehyde) have been synthesized and characterized. Characterization has been completed by IR and high-resolution mass spectroscopy, 1D and 2D solution NMR ((1)H, (13)C  and
Tetrahedron Asymmetry, 18, 1124-1124 (2007)
Tetrahedron Asymmetry, 18, 377-377 (2007)
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