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D198501

Sigma-Aldrich

2,4-Dinitrophenol

moistened with water, ≥98.0%

Synonym(s):

α-Dinitrophenol, 2,4-DNP, DNP

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About This Item

Linear Formula:
(O2N)2C6H3OH
CAS Number:
51-28-5
Molecular Weight:
184.11
Beilstein:
1246142
MDL number:
MFCD00007115
UNSPSC Code:
12352100
PubChem Substance ID:
24893583
NACRES:
NA.22

vapor density

6.35 (vs air)

Assay

≥98.0%

contains

≥15% water

mp

108-112 °C (lit.)

SMILES string

Oc1ccc(cc1[N+]([O-])=O)[N+]([O-])=O

InChI

1S/C6H4N2O5/c9-6-2-1-4(7(10)11)3-5(6)8(12)13/h1-3,9H

InChI key

UFBJCMHMOXMLKC-UHFFFAOYSA-N

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Application

2,4-Dinitrophenol (DNP) can be used:
  • As a reactant for catalytic reduction reactions.
  • To activate carboxylic acids by converting them into dinitrophenyl (DNP) esters.
  • To prepare the corresponding ester via acylation reaction using isobutyric anhydride catalyzed by hafnium triflate.
  • As an effective cocatalyst to accelerate the activity and enantioselectivity of primary amine organocatalyst derived from natural primary amino acids for direct asymmetric aldol reaction.
  • As an alternative activator to tetrazoles in the reaction of phosphoroamidites with nucleosides.

Signal Word

Danger

Hazard Classifications

Acute Tox. 2 Oral - Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Aquatic Acute 1 - Desen. Expl. 4 - STOT RE 1

Storage Class Code

4.1B - Flammable solid hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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Sukhanova A A, et al.
Tetrahedron Asymmetry, 28(12), 1834-1841 (2017)
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Hafnium inspired activation of highly hindered anhydrides in the acylation of alcohols and polyols.
Mensah E, et al.
Tetrahedron Letters, 59(12), 1094-1098 (2018)
2, 4-Dinitrophenol: a novel activating reagent in nucleotide synthesis via the phosphoramidite route. Design of new effective phosphitylating reagents.
Dabkowski W, et al.
Tetrahedron Letters, 41(39), 7535-7539 (2000)
2, 4-Dinitrophenol as an effective cocatalyst: greatly improving the activities and enantioselectivities of primary amine organocatalysts for asymmetric aldol reactions.
Da C S, et al.
The Journal of Organic Chemistry, 74(6), 2541-2546 (2009)
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