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Key Documents

209562

Sigma-Aldrich

2,4-Dinitrophenylacetic acid

95%

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About This Item

Linear Formula:
(O2N)2C6H3CH2CO2H
CAS Number:
Molecular Weight:
226.14
Beilstein/REAXYS Number:
1990798
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

assay

95%

mp

169-175 °C (lit.)

SMILES string

OC(=O)Cc1ccc(cc1[N+]([O-])=O)[N+]([O-])=O

InChI

1S/C8H6N2O6/c11-8(12)3-5-1-2-6(9(13)14)4-7(5)10(15)16/h1-2,4H,3H2,(H,11,12)

Inchi Key

KCNISYPADDTFDO-UHFFFAOYSA-N

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General description

Coupling of 2,4-dinitrophenylacetic acid with diazonium salts has been reported[1].

Application

2,4-Dinitrophenylacetic acid was used in the preparation of 2-hydroxy-4-nitrohenzonitrile, required for the synthesis of parabactin azide (catecholamide siderophore photoaffinity label)[2].

Pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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The coupling of diazonium salts with aliphatic carbon atoms.
Parmerter SM.
Org. React. (1959)
A simple rapid mixing device.
J F Eccleston et al.
Analytical biochemistry, 106(1), 73-77 (1980-07-15)
Guofeng Zhang et al.
Biochemistry, 41(45), 13370-13377 (2002-11-06)
Phosphonoacetaldehyde hydrolase (phosphonatase) from Bacillus cereus catalyzes hydrolytic P-C bond cleavage of phosphonoacetaldehyde (Pald) via a Schiff base intermediate formed with Lys53. A single turnover requires binding of Pald to the active site of the core domain, closure of the
Synthesis of a parabactin photoaffinity label.
Bergeron RJ, et al.
The Journal of Organic Chemistry, 52(1), 144-149 (1987)
A self-assembled nanofiber catalyst for ester hydrolysis.
Mustafa O Guler et al.
Journal of the American Chemical Society, 129(40), 12082-12083 (2007-09-15)

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