2-Aminofluorene

Description

Occupational exposure to polycyclic aromatic amines (PAA) has occurred historically in the rubber, textile, and dye industries. Some sources of nonoccupational exposure to PAAs include inhalation of tobacco smoke, emissions from heated cooking oil and diesel engine exhaust, and dermal exposure to hair dyes.
During the 1870s, the first aromatic amine dyes were manufactured in Germany (dyes of natural origin were used prior to the synthesis of dyes). In 1895, a physician by the name Rehn reported a cluster of patients who had developed bladder cancer. He observed that all of the affected workers were employed at a site in Germany that manufactured fuschsin dye. The workers had all been exposed to large amounts of intermediate arylamines. The United States first started manufacturing dyes in the early 1900s when trade between the United States and Germany was halted during the First World War. DuPont was the first company to begin manufacturing synthetic dyes in the United States, and shortly thereafter (1930s) the physicians employed by DuPont also started reporting an increased incidence of workers who had developed bladder cancer. During 1947, a physician by the name of Mengellsdorf who was employed by DuPont reported that 100% of the workers who handled the chemical betanaphthylamine had developed bladder cancer. By the 1950s, Chinese dye manufacturers reported the development of bladder cancer in workers who handled benzidine. Evidence of the development of bladder cancer associated with the manufacture of dyes continued to mount, and during the 1970s dye manufacturing was discontinued in the United States and was taken over by developing nations. During the early 1970s, the US Occupational Safety and Health Administration (OSHA) began regulating aromatic amines that had been associated with the development of bladder cancers. During the 1980s, DuPont reported retrospectively that 316 of their dye manufacturing workers had developed bladder cancer prior to the discontinuation of dye manufacturing in the United States. During the 1990s, the first reports of bladder cancer in the Chinese dye manufacturing industry became public.
Hair dye products manufactured prior to the mid-1970s contained chemicals that were shown to produce cancer in rodents. Some of these chemical included aromatic amines. The manufacturers of hair coloring products began reformulating their products to remove these potentially carcinogenic compounds from their products beginning in the mid-1970s. It is not clear if some of the ingredients in contemporary hair products can cause an increased risk of cancer. The US National Cancer Institute reported that there may be an increased risk of developing non-Hodgkin’s lymphoma in people who used hair dyes prior to the 1980s; however, the data are limited and often inconsistent.

Chemical properties

WHITE TO SLIGHTLY BROWN CRYSTALLINE POWDER

The Uses of 2-Aminofluorene

PAAs are used in the rubber, textile, and dye industries. They are used as intermediates in the manufacture of plastics, drugs, and carbamate pesticides. The aromatic amines 2-aminofluorene and N-acetyl aminofluorene were being developed during the 1930s for use as pesticides; however, they were found to be carcinogenic in laboratory animals. They were never marketed as pesticides.

What are the applications of Application

2-Aminofluorene is used in the study of carcinogenesis

General Description

Brown crystal powder.

Air & Water Reactions

2-Aminofluorene is sensitive to prolonged exposure to air. Insoluble in water.

Reactivity Profile

2-AMINO FLUORENE forms salts with acids and can react with oxidizing materials.

Health Hazard

ACUTE/CHRONIC HAZARDS: When heated to decomposition 2-Aminofluorene emits toxic fumes.

Fire Hazard

Flash point data for 2-Aminofluorene are not available, but 2-Aminofluorene is probably combustible.

Safety Profile

Suspected carcinogen with experimental carcinogenic, neoplastigenic, and tumorigenic data. Poison by intraperitoneal route. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx. See also AMINES.

Environmental Fate

PAAs may be transported as vapor or adsorbed onto particulates. Due to low water solubility, PAAs are not transported in water but adsorb onto soil and sediments. Leaching is negligible. Bioaccumulation is not considered a concern.

Purification Methods

Wash the amine well with H2O and recrystallise it from Et2O or 50% aqueous EtOH (25g with 400mL), and dry it in a vacuum. Store it in the dark. [Bavin Org Synth Coll Vol V 30 1973, Beilstein 12 H 1331, 12 IV 337.]

Toxicity evaluation

N-hydroxy metabolites within the gastrointestinal tract transform fluoren-2-amine into a mutagen or carcinogen. A number of PAAs are potent bladder carcinogens. As noted previously, sequential hydroxylation and glucuronidation lead to urinary excretion, with metabolites in the urinary bladder. While glucuronidation enhances excretion via the urine, a glucuronidase in the bladder hydrolyzes the glucuronide and under acidic conditions N-hydroxylarylamines are formed. Subsequent conversion of the amine leads to an aryl nitrenium ion, which can initiate tumor formation. Sulfate esters can degrade to electrophilic nitronium ion–carbonium ion, which can form adducts with macromolecules.