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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:
Molecular Weight:
206.24
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

96%

mp

99-103 °C (lit.)

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

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

Signal Word

Warning

Hazard Statements

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

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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"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)
Alternating copolymerization of carbon dioxide and epoxide by dinuclear zinc Schiff base complex.
Sugimoto H and Ogawa A.
Reactive functional Polymers, 67(11), 1277-1283 (2007)

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