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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
Molecular Weight:
165.15
MDL Number:
MFCD00007355
MOL File:
100-19-6.mol
MSDS File:
SDS
Last updated:2024-08-24 19:19:26

4-Nitroacetophenone Properties

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)
FDA UNII 4FM2J8HQ27
NIST Chemistry Reference Acetophenone, 4'-nitro-(100-19-6)
EPA Substance Registry System 4-Nitroacetophenone (100-19-6)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS07,GHS06
Signal word  Warning
Hazard statements  H302-H301
Precautionary statements  P301+P310a-P321-P405-P501a-P264-P270-P301+P312+P330-P501
Hazard Codes  Xn
Risk Statements  36-22
Safety Statements  22-24/25
WGK Germany  3
RTECS  AM9627000
Hazard Note  Harmful
HS Code  29147090
NFPA 704
0
1 0

4-Nitroacetophenone price More Price(36)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich N9608 4′-Nitroacetophenone 98% 100-19-6 5g $48.2 2024-03-01 Buy
Sigma-Aldrich N9608 4′-Nitroacetophenone 98% 100-19-6 100g $71.3 2024-03-01 Buy
TCI Chemical N0111 4'-Nitroacetophenone >98.0%(GC) 100-19-6 25g $32 2024-03-01 Buy
TCI Chemical N0111 4'-Nitroacetophenone >98.0%(GC) 100-19-6 100g $71 2024-03-01 Buy
Alfa Aesar A13877 4'-Nitroacetophenone, 98% 100-19-6 50g $29.8 2024-03-01 Buy
Product number Packaging Price Buy
N9608 5g $48.2 Buy
N9608 100g $71.3 Buy
N0111 25g $32 Buy
N0111 100g $71 Buy
A13877 50g $29.8 Buy

4-Nitroacetophenone Chemical Properties,Uses,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).

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.

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.

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.]

Global( 366)Suppliers
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View Lastest Price from 4-Nitroacetophenone manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
4-Nitroacetophenone pictures 2024-11-22 4-Nitroacetophenone
100-19-6
US $120.00 / kg 1kg 99% 20ton Hebei Zhuanglai Chemical Trading Co.,Ltd
4-Nitroacetophenone pictures 2024-11-22 4-Nitroacetophenone
100-19-6
US $0.00 / kg 50kg HPLC≥98% 10000kg Shaanxi Cuikang Pharmaceutical Technology Co., Ltd
4-Nitroacetophenone pictures 2024-10-25 4-Nitroacetophenone
100-19-6
US $40.00 / kg 1kg 0.99 10 tons Hebei Yanxi Chemical Co., Ltd.
  • 4-Nitroacetophenone pictures
  • 4-Nitroacetophenone
    100-19-6
  • US $0.00 / kg
  • HPLC≥98%
  • Shaanxi Cuikang Pharmaceutical Technology Co., Ltd
AURORA KA-7140 4'-NITROACETOPHENONE 4-NITROACETOPHENONE AKOS BBS-00003219 4'-Nitroacetophenone 1-(4-Nitrophenyl)ethan-1-one p-Nitroacetophenone ORTHO-NITROACETOPHENONE 4''-NITROACETOPHENONE CHLOAMPHENICOL p-Nitroacetophenone,97% 4′-Nitroacetophenone ,98% 1-(4-Nitrophenyl)ethan-1-one, 4-Acetylnitrobenzene p-Nitroacetophenone, 97% 100GR NSC 41590 4'-NITROACETOPHENONE FOR SYNTHESIS 1-Acetyl-4-nitrobenzene 4’-nitro-acetophenon 4-Acetylnitrobenzene 4-Nitrophenylmethylketone Acetophenone,4’-nitro- 1-(4-nitrophenyl)-ethanon Ethanone, 1-(4-nitrophenyl)- Ethanone,1-(4-nitrophenyl)- Methyl4-nitrophenylketone Methyl-p-nitrophenyl ketone methyl-p-nitrophenylketone Methylp-nitrophenylketone p-Acetylnitrobenzene Paranitroacetophenone p-Nitroacetophenon p-Nitrophenyl methyl ketone p-nitrophenylmethylketone Bromo-2&rsquo 4'-Nitroacetophenone, 98%, for synthesis 4'-Nitroacetophenone> 100-19-6 4-Nitroacetophenone 1-(4-NITROPHENYL)ETHAN-1-ONE 1-(4-nitrophenyl)ethanone P-NITROACETOPHENONE Nitroacetophenone PNAP 4'-Nitroacetophenone 100-19-6 O2NC6H4COCH3 KETONE Carbonyl Compounds C7 to C8 Building Blocks Ketones Organic Building Blocks C7 to C8 Carbonyl Compounds Chemical Synthesis Organic Building Blocks C7 to C8 Carbonyl Compounds Ketones Aromatic Acetophenones & Derivatives (substituted) Building Blocks 100-19-6