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209562

Sigma-Aldrich

2,4-Dinitrophenylacetic acid

95%

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About This Item

Linear Formula:
(O2N)2C6H3CH2CO2H
CAS Number:
643-43-6
Molecular Weight:
226.14
Beilstein:
1990798
EC Number:
211-398-2
MDL number:
MFCD00007227
UNSPSC Code:
12352100
PubChem Substance ID:
24852576
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.

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).

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

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 simple rapid mixing device.
J F Eccleston et al.
Analytical biochemistry, 106(1), 73-77 (1980-07-15)
Synthesis of a parabactin photoaffinity label.
Bergeron RJ, et al.
The Journal of Organic Chemistry, 52(1), 144-149 (1987)
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
The coupling of diazonium salts with aliphatic carbon atoms.
Parmerter SM.
Org. React. (1959)
A G Lowe et al.
Analytical biochemistry, 144(2), 385-389 (1985-02-01)
A quenched-flow apparatus is described and applied to measurements of the hydrolysis of 2,4-dinitrophenyl acetate by sodium hydroxide and the entry of D-[U-14C]glucose into human red blood cells at 37 degrees C. Glucose influx into red cells was a saturable
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