ChemicalBook > CAS DataBase List > 4-Nitroacetophenone

4-Nitroacetophenone

Product Name
4-Nitroacetophenone
CAS No.
100-19-6
Chemical Name
4-Nitroacetophenone
Synonyms
1-(4-NITROPHENYL)ETHAN-1-ONE;Nitroacetophenone;1-(4-nitrophenyl)ethanone;PNAP;P-NITROACETOPHENONE;NSC 41590;Bromo-2’AURORA KA-7140;AKOS BBS-00003219;p-Nitroacetophenon
CBNumber
CB5118997
Molecular Formula
C8H7NO3
Formula Weight
165.15
MOL File
100-19-6.mol
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4-Nitroacetophenone Property

Melting point:
75-78 °C(lit.)
Boiling point:
202 °C(lit.)
Density 
1.3450 (rough estimate)
refractive index 
1.5468 (estimate)
Flash point:
201-202°C
storage temp. 
Sealed in dry,Room Temperature
form 
Crystalline Powder
color 
Yellow
Water Solubility 
Insoluble in water.
BRN 
607777
InChIKey
YQYGPGKTNQNXMH-UHFFFAOYSA-N
CAS DataBase Reference
100-19-6(CAS DataBase Reference)
NIST Chemistry Reference
Acetophenone, 4'-nitro-(100-19-6)
EPA Substance Registry System
4-Nitroacetophenone (100-19-6)
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Safety

Hazard Codes 
Xn
Risk Statements 
36-22
Safety Statements 
22-24/25
WGK Germany 
3
RTECS 
AM9627000
Hazard Note 
Harmful
HS Code 
29147090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H301Toxic if swalloed

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P321Specific treatment (see … on this label).

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
N9608
Product name
4′-Nitroacetophenone
Purity
98%
Packaging
5g
Price
$48.2
Updated
2024/03/01
Sigma-Aldrich
Product number
N9608
Product name
4′-Nitroacetophenone
Purity
98%
Packaging
100g
Price
$71.3
Updated
2024/03/01
TCI Chemical
Product number
N0111
Product name
4'-Nitroacetophenone
Purity
>98.0%(GC)
Packaging
25g
Price
$32
Updated
2024/03/01
TCI Chemical
Product number
N0111
Product name
4'-Nitroacetophenone
Purity
>98.0%(GC)
Packaging
100g
Price
$71
Updated
2024/03/01
Alfa Aesar
Product number
A13877
Product name
4'-Nitroacetophenone, 98%
Packaging
50g
Price
$29.8
Updated
2024/03/01
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4-Nitroacetophenone Chemical Properties,Usage,Production

Chemical Properties

The pure product is pale yellow crystal or needle crystal. Soluble in hot ethanol, ether and benzene, insoluble in water. 4-Nitroacetophenone is the raw material for the manufacture of synthomycin and chloramphenicol.

Uses

4''-Nitroacetophenone is used as a reagent in the synthesis of 4-Nitroacetophenone thiosemicarbazone derivatives and their copper(II) complexes which have potential anti-trypanosomal activity in vitro. Also used as a reagent in the synthesis of (R)-(4-Nitrophenyl)oxirane (N504430) and (S)-(4-Nitrophenyl)oxirane (N504435).

Preparation

In the presence of catalyst cobalt stearate, p-nitroethylbenzene is oxidized to synthesize 4-nitroacetophenone with air at 140-150°C and 0.2MPa pressure. The reaction product is washed with water, neutralized, centrifugally dehydrated, and dried to obtain a finished product.

Application

One of several alternative routes to synthetic chloroamphenicol uses 4-nitroacetophenone as starting material with a first-stage bromination to α-bromo-4-nitroacetophenone followed by buildup of the side chain. α-bromo-4-nitroacetophenone is the key precursor in the synthesis of the bronchodilator clenbuterol.

Definition

ChEBI: 4-nitroacetophenone is a member of the class of acetophenones that is acetophenone substituted at the para-position by a nitro group. It is a C-nitro compound and a member of acetophenones.

Synthesis Reference(s)

The Journal of Organic Chemistry, 48, p. 4634, 1983 DOI: 10.1021/jo00172a038
Synthetic Communications, 26, p. 291, 1996 DOI: 10.1080/00397919608003617

General Description

P-nitroacetophenone appears as yellow prisms or bright yellow powder. (NTP, 1992)

Air & Water Reactions

Insoluble in water.

Reactivity Profile

A nitrated ketone. Ketones are reactive with many acids and bases liberating heat and flammable gases (e.g., H2). The amount of heat may be sufficient to start a fire in the unreacted portion of the ketone. Ketones react with reducing agents such as hydrides, alkali metals, and nitrides to produce flammable gas (H2) and heat. Ketones are incompatible with isocyanates, aldehydes, cyanides, peroxides, and anhydrides. They react violently with aldehydes, HNO3, HNO3 + H2O2, and HClO4.

Fire Hazard

Flash point data for 4-Nitroacetophenone are not available. 4-Nitroacetophenone is probably combustible.

Purification Methods

Crystallise the ketone from EtOH or aqueous EtOH. [Beilstein 7 IV 657.]

4-Nitroacetophenone Preparation Products And Raw materials

Raw materials

4-Nitrobenzoyl chloride Ethylbenzene Cobalt stearate 4-Nitroethylbenzene p-Nitroethylbenzene 2-Ethylnitrobenzene Nitric acid Sodium hydroxide Sulfuric acid

Preparation Products

3-(4-NITRO-PHENYL)-ISOXAZOL-5-YLAMINE A-BROMO-4-NITROACETOPHENONE HEXAMINE DL-THREO-2-ACETAMIDO-L-(4-NITROPHENYL)-L,3-PROPANEDIOL 5-(4-NITROPHENYL)-2H-PYRAZOL-3-YLAMINE CLENBUTEROL 4-(1,2,3-THIADIAZOL-4-YL)ANILINE 4-(4-NITROPHENYL)-1,2,3-THIADIAZOLE Chloramphenicol DIETHOXYMETHANE 2-Ethylnitrobenzene 4-AMINO-ALPHA-TERT-BUTYLAMINE-3,5-DICHLOROACETOPHENONE 4-Aminoacetophenone N-[1-(hydroxymethyl)-2-(4-nitrophenyl)-2-oxoethyl]acetamide
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View Lastest Price from 4-Nitroacetophenone manufacturers

Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
4-Nitroacetophenone 100-19-6
Price
US $120.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20ton
Release date
2024-06-04
Shaanxi Cuikang Pharmaceutical Technology Co., Ltd
Product
4-Nitroacetophenone 100-19-6
Price
US $0.00/kg
Min. Order
50kg
Purity
HPLC≥98%
Supply Ability
10000kg
Release date
2024-03-21
Hebei Yanxi Chemical Co., Ltd.
Product
4-Nitroacetophenone 100-19-6
Price
US $40.00/kg
Min. Order
1kg
Purity
0.99
Supply Ability
10 tons
Release date
2023-09-05

100-19-6, 4-NitroacetophenoneRelated Search:

4'-Methoxyacetophenone 4'-Bromoacetophenone 4-Aminoacetophenone 3-Aminoacetophenone 4-Nitrobenzophenone 4'-Methylacetophenone 2-Nitroacetophenone Acetophenone 4'-Hydroxyacetophenone p-Nitrophenylacetonitrile L-PICEIN 4-Nitrophenylacetic acid 4'-Chloroacetophenone 3-Nitroacetophenone 4'-(Trifluoromethyl)acetophenone 4-NITROPHENYLACETYLENE 4-Nitrobenzyl alcohol 2-BROMO-2'-NITROACETOPHENONE

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  • 100-19-6