2-Aminofluorene

181.23

181.23

1945861

205-817-8

3A69OS195N

26328|12274

2811

DTXSID1049223

NEEDLES FROM DIL ALC|LONG PLATES FROM DIL ALCOHOL

29214980

26

3.1

2-aminofluorene is a brown crystal powder. (NTP, 1992)

1.0941 (rough estimate)

131-132 °C

358.3°C at 760 mmHg

204.8±17.4 °C

1.6118 (estimate)

H2O: <0.1 g/100 mL at 19.5 ºC;estimated water solubility of 33 mg/l at 25 deg C

Store below +30°C.

2.56E-05mmHg at 25°C

UV: 2-350 (Organic Electronic Spectral Data, Phillips et al, John Wiley & Sons, New York) /Fluorene, 1-amino/|UV: 3-388 (Organic Electronic Spectral Data, Phillips et al, John Wiley & Sons, New York) /Fluorene, 9-amino/

This compound is sensitive to prolonged exposure to air. Insoluble in water.

Amines, Aromatic

2-AMINO FLUORENE forms salts with acids and can react with oxidizing materials. (NTP, 1992)

I; II; III

6.1

NONH for all modes of transport

3

68-40

45-36/37-24/25

LL5075000

Xn

Stable under normal temperatures and pressures.

P201, P202, P261, P264, P270, P271, P280, P281, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P308+P313, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, P501

H302

Flash point data for this material are not available, but it is probably combustible. (NTP, 1992)

Fires involving this compound may be controlled with carbon dioxide, dry chemical, or Halon extinguishers. (NTP, 1992)

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

SMALL SPILLS AND LEAKAGE: If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should keep this material in a tightly closed container under an inert atmosphere and store it under refrigerated temperatures. (NTP, 1992)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

2-Aminofluorene was detected in the wastewater effluent from sewage treatment facilities in Japan(1).

TERRESTRIAL FATE: Limited aqueous screening test data suggest the biodegradation of 2-aminofluorene in soil will be very slow(1,2). 2-Aminofluorene is not expected to undergo hydrolysis in soils. A calculated Koc range of 640 to 1100(3), indicates 2-aminofluorene is characterized by a low mobility in soil(4). An estimated Henry's Law constant of 3.62X10-8 atm-cu m/mole at 25 °C(5), suggests the volatilization of 2-aminofluorene from moist soils will not be important(3).|AQUATIC FATE: Limited aqueous screening test data suggest the biodegradation of 2-aminofluorene in aquatic systems will be very slow. 2-Aminofluorene is not expected to undergo hydrolysis in environmental waters. An estimated Koc ranging in the low mobility class for soil(1), indicates 2-aminofluorene will partition from the water column to organic matter contained in sediments and suspended solids. 2-Aminofluorene also has a low potential to bioconcentrate in aquatic systems. A Henry's Law constant of 3.62X10-8 atm-cu m/mole at 25 °C(2) suggests volatilization of 2-aminofluorene from environmental waters will not be important(3).|ATMOSPHERIC FATE: Based upon a calculated vapor pressure of 2.06X10-6 mm Hg at 25 °C(SRC), 2-aminofluorene is expected to exist in both the particulate and gaseous phases in ambient air(1). The vapor phase rection of 2-aminofluorene with photochemically produced hydroxyl radicals is likely to be an important fate process. The rate constant for the vapor-phase reaction of 2-aminofluorene with photochemically produced hydroxyl radicals has been estimated to be 2.21X(-10) cu cm/molecule-sec at 25 °C; which corresponds to an atmospheric half-life of about 2 hours at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(2). Washout by precipitation and gravitational settling may be important atmospheric removal mechanisms for 2-aminofluorene in particulate matter(SRC).

Aromatic-amines are generally resistant to hydrolysis(1). Therefore, 2-aminofluorene probably will not undergo hydrolysis in the environment. Vapor phase reactions with photochemically produced hydroxyl radicals may be important in ambient air. The rate constant for the vapor-phase reaction of 2-aminofluorene with photochemically produced hydroxyl radicals has been estimated to be 221X10-12 cu cm/molecule-sec at 25 °C, which corresponds to an atmospheric half-life of about 2 hours at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(2).

Based on an estimated water solubility of 33 mg/L at 25 °C(1) and an estimated log Kow of 3.00(2), the log BCF of 2-aminofluorene has been calculated to range from 1.93 to 2.05 from various regression-derived equations(3,SRC). These log BCF values suggest 2-aminofluorene has a low potential to bioconcentrate in aquatic systems(SRC).

Based on an estimated water solubility of 33 mg/L at 25 °C(1) and an estimated log Kow of 3.00(2), the Koc of 2-aminofluorene has been calculated to range from 650 to 1100 from various regression-derived equations(4,SRC). These Koc values indicate 2-aminofluorene is characterized by a low mobility class in soil(4). Furthermore, aromatic amines have been observed to undergo rapid and reversible covalent bonding with humic materials in aqueous solution; the initial bonding reaction is followed by a slower and much less reversible reaction believed to represent the addition of the amine to quinonal structures followed by oxidation of the product to give an amino-substituted quinone; these processes represent pathways by which aromatic amines may be converted to latent forms in the biosphere(5).

The Henry's Law constant of 3.62X10-8 atm-cu m/mole at 25 °C for 2-aminofluorene has been estimated using a bond contribution method(1). This Henry's Law constant suggests volatilization of 2-aminofluorene from environmental waters will not be important(2).

DRINKING WATER: 2-Aminofluorene was detected in groundwater wells in Japan(1).

Substances that increase the risk of NEOPLASMS in humans or animals. Both genotoxic chemicals, which affect DNA directly, and nongenotoxic chemicals, which induce neoplasms by other mechanism, are included. (See all compounds classified as Carcinogens.)|Chemical agents that increase the rate of genetic mutation by interfering with the function of nucleic acids. A clastogen is a specific mutagen that causes breaks in chromosomes. (See all compounds classified as Mutagens.)

N-HYDROXY METABOLITES ... /HAVE BEEN/ STRONGLY IMPLICATED AS PROXIMATE CARCINOGENIC DERIVATIVES OF AROMATIC AMINES & AMIDES. THUS, IN RAT & SOME OTHER SPECIES, N-HYDROXYAMIDES & THEIR CONJUGATES WERE DEMONSTRATED TO BE METABOLITES OF SOME AROMATIC AMINES & AMIDES, INCL 2-FLUORENAMINE ...|THE ENZYME-CATALYZED ACETYLATION OF 3 CARCINOGENIC AROMATIC AMINES, 2-AMINOFLUORENE, 4-AMINOBIPHENYL, & 2-AMINONAPHTHALENE, HAS BEEN MEASURED IN LIVER CYTOSOL FROM VARIOUS SPECIES. DOG LIVER CYTOSOL CONTAINED NO DETECTABLE ACTIVITY. THE LIVER OF THIS SPECIES IS UNSUSCEPTIBLE TO CARCINOGENIC ACTION OF THESE CMPD. THIS IS INDIRECT EVIDENCE INDICATING THAT ACETYLATION IS IMPORTANT IN TOXICITY OF THESE CMPD.|Activation of 2-AAF /2-acetylaminofluorene/ to N-hydroxy-2-aminofluorene, a potent mutagen to Salmonella strains, by guinea pig liver (S-9) mix afforded potent mutagen to Salmonella strains, by guinea pig 2-aminofluorene (AF) as well as N-OH-AAF /N-hydroxy-acetylaminofluorene/. Mutagenicities of 2-aminofluorene & N-hydroxy-2-aminofluorene were inhibited by antisera against NADPH-cytochrome C reductase & by paraoxon. While the mutagenic activity of 2-acetylaminofluorene to N-hydroxy-2-aminofluorene can be produced by N-hydroxylation of 2-aminofluorene or deacetylation of N-hydroxy-2-aminofluorene, the data suggested that deacetylation of 2-acetylaminofluorene (to 2-aminofluorene), followed by N-hydroxylation to produce N-hydroxy-2-aminofluorene, was the main pathway for the mutagenic activation of 2-acetylaminofluorene by guinea-pig liver (S-9) mix.|2-aminofluorene has known human metabolites that include 2-Acetylaminofluorene.

CANCERS OF THE GI TRACT, ESP OF THE COLON, ARE PREVALENT IN INDUSTRIALIZED NATIONS. NUTRITIONAL FACTORS & THE INTESTINAL FLORA HAVE BEEN ASSIGNED CAUSAL ROLES IN THE ETIOLOGY OF THESE NEOPLASIAS. ANAEROBIC BACTERIA (BACTEROIDES FRAGILIS G4841, B VULGATUS K871, & B THETAIOTAOMICRON T2979, ISOLATES OF HUMAN ORIGIN) POSSESS ENZYMATIC ABILITY TO CONVERT 2-AMINOFLUORENE TO SUBSTANCES MUTAGENIC TO SALMONELLA TYPHIMURIUM. THE AMES ASSAY HAVE BEEN ADAPTED TO THE STUDY OF POSSIBLE FACTORS CONTRIBUTING TO GI CANCERS. CULTURES OF THE ANAEROBES WERE GROWN FOR 28 HR AT 37 °C, DISRUPTED BY SONICATION, CENTRIFUGED, & THE SUPERNATANT COLLECTED. ONE ML OF THE BACTERIAL EXTRACT WAS MIXED WITH EITHER 2-NITROFLUORENE OR 2-AMINOFLUORENE (FINAL CONCN 5 MG/ML) & INCUBATED AT 37 °C FOR 24 HR & ASSAYED FOR MUTAGENICITY USING TA1538. IT WAS FOUND THAT FILTRATES OF CULTURES OF B VULGATUS GROWN IN THE PRESENCE OF EITHER 2-NITROFLUORENE OR 2-AMINOFLUORENE WERE DEVOID OF SUBSTANCES POSSESSING DIRECT-ACTING FRAMESHIFT MUTAGENIC ACTIVITY; HOWEVER SUCH ACTIVITY WAS EVIDENT WHEN THE FILTRATES WERE INCUBATED IN THE PRESENCE OF MICROSOMAL ENZYMES. THE PRESENT FINDINGS INDICATE THAT THE CONVERSION OF 2-NITROFLUORENE TO 2-AMINOFLUORENE BY ANAEROBIC BACTERIA IS PROBABLY NOT THE COMPLETE EXPLANATION FOR REDUCTION IN YIELD OF MUTANTS OBSERVED IN OTHER AMES/GI TRACT SHORT-TERM ASSAYS USING GERM-FREE ANIMALS THAT WERE COLONIZED WITH SALMONELLA & B VULGATUS.

ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits toxic fumes. (NTP, 1992)

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

2-aminofluorene

... N-2-fluorenylacetamide was discovered to be a powerful carcinogen prior to the possible use of the parent 2-fluorenamine as an insecticide. ... in 1938 before DDT was known & when insect pests were controlled with difficulty, 2-fluorenamine was a potent & promising insecticide.