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168637

Sigma-Aldrich

2,4-Dihydroxybenzaldehyde

98%

Synonym(s):

β-Resorcylaldehyde

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About This Item

Linear Formula:
(HO)2C6H3CHO
CAS Number:
95-01-2
Molecular Weight:
138.12
Beilstein:
878548
EC Number:
202-383-1
MDL number:
MFCD00011686
UNSPSC Code:
12352100
PubChem Substance ID:
24850248
NACRES:
NA.22

Assay

98%

form

powder

bp

220-228 °C/22 mmHg (lit.)

mp

135-137 °C (lit.)

SMILES string

[H]C(=O)c1ccc(O)cc1O

InChI

1S/C7H6O3/c8-4-5-1-2-6(9)3-7(5)10/h1-4,9-10H

InChI key

IUNJCFABHJZSKB-UHFFFAOYSA-N

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General description

2,4-Dihydroxybenzaldehyde undergoes regioselective mono-benzylation reaction under extremely mild basic conditions. It undergoes condensation reaction with isonicotinic acid hydrazide in methanol to yield 2,4-dihydroxybenzaldehyde isonicotinoyl hydrazone, a new fluorescent reagent.

2,4-Dihydroxybenzaldehyde is a potential building block for bioactive compounds, specialty chemicals and dyes.

Application

2,4-Dihydroxybenzaldehyde was used in two-step synthesis of ethyl 3,5-dibromo-2,4-dihydroxycinnamate.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335

Hazard Classifications

Acute Tox. 4 Oral - 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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The regioselective 4-benzylation of 2, 4-dihydroxybenzaldehyde.
Mendelson WL, et al.
Synthetic Communications, 26(3), 593-601 (1996)
Direct and derivative spectrophotometric determination of zinc with 2, 4-dihydroxybenzaldehyde isonicotinoyl hydrazone in potable water and pharmaceutical samples.
Sivaramaiah S and Reddy PR.
Journal of Analytical Chemistry, 60(9), 828-832 (2005)
Antibacterial activity and molecular studies of non-symmetric POCOP-Pd (II) pincer complexes derived from 2, 4-dihydroxybenzaldehyde (2, 4-DHBA)
Aragn-Muriel, A et al.
Polyhedron, 227, 116115-116115 (2022)
Two-photon uncaging with the efficient 3,5-dibromo-2,4-dihydroxycinnamic caging group.
Nathalie Gagey et al.
Angewandte Chemie (International ed. in English), 46(14), 2467-2469 (2007-02-21)
Chao-Bin Xue et al.
Bioorganic & medicinal chemistry, 15(5), 2006-2015 (2007-01-30)
Phenoloxidase (PO), also known as tyrosinase, is a key enzyme in insect development, responsible for catalyzing the hydroxylation of tyrosine into o-diphenols and the oxidation of o-diphenols into o-quinones. Inhibition of PO may provide a basis for novel environmentally friendly
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