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554154

Sigma-Aldrich

4-tert-Butyl-2,6-diformylphenol

96%

Synonym(s):

5-(1,1-Dimethylethyl)-2-hydroxy-1,3-benzenedicarboxaldehyde

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About This Item

Linear Formula:
(CH3)3CC6H2(CHO)2OH
CAS Number:
84501-28-0
Molecular Weight:
206.24
MDL number:
MFCD01567135
UNSPSC Code:
12352100
PubChem Substance ID:
24879380
NACRES:
NA.22

Assay

96%

mp

99-103 °C (lit.)

functional group

aldehyde

SMILES string

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

InChI

1S/C12H14O3/c1-12(2,3)10-4-8(6-13)11(15)9(5-10)7-14/h4-7,15H,1-3H3

InChI key

WQNTWZJPCLUXQC-UHFFFAOYSA-N

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General description

4-tert-Butyl-2,6-diformylphenol can be prepared from 4-tert-butylphenol and hexamethylenetetramine.

Application

4-tert-Butyl-2,6-diformylphenol may be used to synthesize:
  • symmetrical macrocyclic Schiff′s base
  • 2,6-bis(N-(4′-methyl-2′-hydroxyphenyl)iminomethyl)-4-tert-butylphenol
  • isostructural C3-symmetrical triple stranded dinuclear lanthanide analogs
  • 5-tert-butyl-2 hydroxy-isophthalaldehyde-bis-2-pyridinehydrazone via reaction with 2-hydrazinopyridine
  • 5-tert-butyl-2-hydroxyisophthalaldehyde-bisphenylhydrazone via reaction with phenylhydrazine

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

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCP9771
MKCM0912
MKCJ7503
MKCD5819
MKCB3249V

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Adam Gorczyński et al.
Dalton transactions (Cambridge, England : 2003), 44(38), 16833-16839 (2015-09-09)
A series of isostructural C3-symmetrical triple stranded dinuclear lanthanide [Ln2L3](NO3)3 molecules have been synthesized using subcomponent self-assembly of Ln(NO3)3 with 2-(methylhydrazino)benzimidazole and 4-tert-butyl-2,6-diformylphenol, where Ln = Tb (1), Dy (2), Ho (3), Er (4), Tm (5), and Yb (6). The
"A ?turn-on? fluorescent chemosensor for zinc ion with facile synthesis and application in live cell imaging"
Wang XLK and Tong A
Analytica Chimica Acta, 776, 69- 73 (2013)
Binuclear and polynuclear transition metal complexes with macrocyclic ligands. 2. New macrocyclic Schiff" s base in the reaction of 4-tert-butyl-2, 6-diformylphenol with 1, 2-diaminobenzene. Synthesis and structural, spectroscopic, and theoretical study.
Ustynyuk YA, et al.
Russian Chemical Bulletin, 51(3), 488- 498 (2002)
Eswaran Chinnaraja et al.
Inorganic chemistry, 58(7), 4465-4479 (2019-04-02)
The ligand L1 of 4-methyl-2,6-diformylphenol and L2 of 4- tert-butyl-2,6-diformylphenol are synthesized through Schiff base condensation with rac-, ( R)-(+), or ( S)-(-)-1,1'-binaphthyl-2,2'-diamine (BNDA). As a result, the racemic L1rac, L2rac, and enantiopure L1RR, L1SS, L2RR, and L2SS ligands are
Mono-and diformylation of 4-substituted phenols: a new application of the Duff reaction.
Lindoy LF, et al.
Synthesis, 07, 1029-1032 (1998)
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