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130648

Sigma-Aldrich

4-Nitroacetanilide

98%

Synonym(s):

4′-Nitroacetanilide, Acetic acid 4-nitroanilide

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About This Item

Linear Formula:
CH3CONHC6H4NO2
CAS Number:
104-04-1
Molecular Weight:
180.16
Beilstein:
2211962
EC Number:
203-169-0
MDL number:
MFCD00007303
UNSPSC Code:
12352100
PubChem Substance ID:
24847974
NACRES:
NA.22

Assay

98%

mp

213-215 °C (lit.)

SMILES string

CC(=O)Nc1ccc(cc1)[N+]([O-])=O

InChI

1S/C8H8N2O3/c1-6(11)9-7-2-4-8(5-3-7)10(12)13/h2-5H,1H3,(H,9,11)

InChI key

NQRLPDFELNCFHW-UHFFFAOYSA-N

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Application

4-Nitroacetanilide was used as a test substrate and its hydrolysis was determined by UV spectroscopic measurements. It was also used to prepare 4-aminoacetanilide.

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)

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Ross L Stein
Biochemistry, 41(3), 991-1000 (2002-01-16)
Aryl acylamidase (EC 3.1.5.13; AAA) catalyzes the hydrolysis of p-nitroacetanilide (PNAA) via the standard three-step mechanism of serine hydrolases: binding of substrate (K(s)), acylation of active-site serine (k(acyl)), and hydrolytic deacylation (k(deacyl)). Key mechanistic findings that emerged from this study
Shinji Takenaka et al.
Journal of bioscience and bioengineering, 107(1), 27-32 (2009-01-17)
Bacillus cereus strain 10-L-2 synthesizes two arylamine N-acetyltransferases (Nat-a and Nat-b) with broad substrate specificities toward aniline and its derivatives. In southern blot analysis using probes encoding the NH2-terminus of Nat-b and a conserved region of N-acetyltransferases, digested total DNA
Dirk Volkmer et al.
Inorganic chemistry, 35(13), 3792-3803 (1996-06-19)
Dinuclear nickel(II) complexes of the ligands 2,6-bis[bis((2-benzimidazolylmethyl)amino)methyl]-p-cresol (bbapOH), N,N,N',N'-tetrakis(2-benzimidazolylmethyl)-2-hydroxy-1,3-diaminopropane (tbpOH), N-methyl-N,N',N'-tris(2-benzimidazolylmethyl)-2-hydroxy-1,3-diaminopropane (m-tbpOH) and 1-[N,N-bis(2-benzimidazolylmethyl)amino]-3-[2-(3,5-dimethyl-1H-pyrazol-1-yl)ethoxy]-2-hydroxypropane (bpepOH) were prepared in order to model the active site of urease. The novel asymmetric structures of the dinuclear complexes were characterized by X-ray structure analysis.
Short-column liquid chromatographic assay for caffeine and chloramphenicol in serum.
R S Markin et al.
Journal of chromatography, 525(2), 464-470 (1990-02-23)
María F Montenegro et al.
Biological chemistry, 389(4), 425-432 (2008-01-23)
Apart from its esterase activity, butyrylcholinesterase (BuChE) displays aryl acylamidase (AAA) activity able to hydrolyze o-nitroacetanilide (ONA) and its trifluoro-derivative (F-ONA). We report here that, despite amidase and esterase sites residing in the same protein, in human samples depleted of
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