3-Nitroacetophenone Property

Melting point:

76-78 °C(lit.)

Boiling point:

202 °C(lit.)

Density 

1.3450 (rough estimate)

vapor pressure 

0.32Pa at 25℃

refractive index 

1.5468 (estimate)

Flash point:

202°C

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Crystalline Powder

color 

Yellow to yellow-green

Odor

Odorless

Water Solubility 

<0.01 g/100 mL at 20 ºC

BRN 

743002

Stability:

Stable. Incompatible with strong oxidizing agents, strong bases.

InChIKey

ARKIFHPFTHVKDT-UHFFFAOYSA-N

LogP

1.42

NIST Chemistry Reference

3-Nitroacetophenone(121-89-1)

EPA Substance Registry System

3-Nitroacetophenone (121-89-1)

Safety

Hazard Codes 

Xn

Risk Statements 

21

Safety Statements 

22-24/25

WGK Germany 

2

RTECS 

AM9625000

TSCA 

Yes

HS Code 

29147090

Hazardous Substances Data

121-89-1(Hazardous Substances Data)

Toxicity

mouse,LD50,intraperitoneal,200mg/kg (200mg/kg),National Technical Information Service. Vol. AD277-689,

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

3-Nitroacetophenone Chemical Properties,Usage,Production

Chemical Properties

white to light beige crystalline powder or yellow needle-like crystals. soluble in hot water and ether, slightly soluble in ethanol. can be volatile with water vapor.

Uses

3''-Nitroacetophenone is used as a reactant in the synthesis of fluorine based aminothiazoles with antimicrobial activity.

Uses

3′-Nitroacetophenone can undergo high hydrostatic pressure-assisted reduction with Ni–Al alloy in water to form 1-(3-aminophenyl)ethanol.

Preparation

3-Nitroacetophenone is synthesized from acetophenone by nitration.
Synthesis of 3-nitroacetophenone

Production Methods

Acetophenone is carefully dissolved in concentrated sulfuric acid at 0 ℃, and mixed acid is added slowly below 0 ℃. The crude product is precipitated by quenching into ice, filtered, and washed acid free. Purification, mainly from the ortho isomer, is achieved by recrystallization from ethanol with significant lowering of the overall yield to ca. 55 %.

General Description

3-nitroacetophenone is a light beige powder. It is an anthropogenic compound which is used as a synthetic intermediate in the production of dyes and other organic compounds. (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 3-Nitroacetophenone are not available, however 3-Nitroacetophenone is probably combustible.

Purification Methods

Distil the ketone in steam and crystallise it from EtOH. [Beilstein 7 IV 656.]