1-Nitronaphthalene

Chemical properties

yellow crystalline solid

The Uses of 1-Nitronaphthalene

1-Nitronaphthalene as a nitroaromatic compound is studied for mutagenicity, as nitroaromatics are used in everyday products from polmers, dyes to drugs.

The Uses of 1-Nitronaphthalene

Usually used to study excited state dynamics of 1-nitropthalene in nonpolar, aprotic and protic solvents.

Definition

ChEBI: A mononitronaphthalene substituted by a nitro group at position 1.

Production Methods

One method to product 1-Nitronaphthalene: Naphthalene is charged to sulfuric acid alternately with mixed acid at 40 – 50 ℃ over 8 h, with the final temperature being 55 ℃. The acid strength used allows the molten product to be separated as an oil and washed. Continuous operation at 50 – 60 ℃ with mixed acid (33/48/19) gives a comparable product. The crude reaction product is obtained in 90 – 95 % yield and is purified by vacuum distillation.

General Description

1-Nitronaphthalene is a mutagenic nitroaromatic compound present in diesel exhaust and it causes acute liver and lung toxicity in rodents. 1-Nitronaphthalene is a cytochrome P450-bioactivated, nonciliated bronchiolar epithelial (Clara) cell cytotoxicant .

Biochem/physiol Actions

1-Nitronaphthalene binds covalently to protein and forms adducts in the rat airway epithelium in vivo.

Safety Profile

Poison by intraperitoneal route. Mutation data reported. A skin, eye, and mucous membrane irritant. Flammable solid and combustible liquid when exposed to heat or flame. To fight fire, use CO2, dry chemical, or water spray. Explosive reaction with nitric acid + sulfuric acid above 60°C. Forms a sensitive explosive mixture with tetranitromethane. When heated to decomposition it emits toxic fumes of NOx. See also 2-NITRONAPHTHALENE and NITRO COMPOUNDS OF AROMATIC HYDROCARBONS.

Purification Methods

Fractionally distil 1-nitronaphthalene under reduced pressure, then crystallise it from EtOH, aqueous EtOH or heptane. Chromatograph it on alumina with *benzene/pet ether as eluent. It sublimes in vacuo. The 1:1 picrate complex has m 72o (from EtOH). [Beilstein 5 H 553, 5 III 1593, 5 IV 1673.]