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Merck
CN

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:
1990798
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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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

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

Regulatory Information

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The coupling of diazonium salts with aliphatic carbon atoms.
Parmerter SM.
Org. React. (1959)
M N Camien et al.
Analytical biochemistry, 138(2), 329-334 (1984-05-01)
A method employing high-speed infrasonic mixing for obtaining timed samples for following the progress of a moderately rapid chemical reaction is described. Drops of 10 to 50 microliter each of two reagents are mixed to initiate the reaction, followed, after
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
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
A simple rapid mixing device.
J F Eccleston et al.
Analytical biochemistry, 106(1), 73-77 (1980-07-15)

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