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化工社化工社 化学情報印刷レポート · 研究参考用
HCID 1539作成日：2026年10月27日

2-アミノフルオレン

2-アミノフルオレン · 9H-フルオレン-2-アミン · 2-アミノ-9H-フルオレン · 2-フルオレンアミン · 2‐アミノフルオレン標準品 · 2-アミノフルオレン IN TOLUENE · 2-アミノフルオレン, 100 µg/mL in Toluene · 2-アミノフルオレン標準品

https://huagongshe.com/ja/chemical/1539

2-アミノフルオレン の分子構造式

識別子と物理属性

CAS No.153-78-6
分子式C13H11N
平均分子量181.23 g/mol
単同位体質量181.08914936 g/mol
SMILESNc1ccc2c(c1)Cc1ccccc1-2
InChIKeyCFRFHWQYWJMEJN-UHFFFAOYSA-N
PubChem CID1539
ChEMBLCHEMBL84472
EC No.205-817-8
DTXSIDDTXSID1049223
現地名2-アミノフルオレン

化学・物理的性質

XLogP3.1
極性表面積26
水素結合供与体数1
水素結合受容体数1
回転可能結合数0
重原子数14
形式電荷0
複雑度213
PolymersOther Classes -> Polycyclic Aromatic Hydrocarbons
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
LogP（分配係数）3.14
Color/FormNEEDLES FROM DIL ALCLONG PLATES FROM DIL ALCOHOL
溶解度less than 1 mg/mL at 67.1 °F (NTP, 1992)SOL IN ALCOHOL, ETHERestimated water solubility of 33 mg/l at 25 °Csoluble in Ether,Alcohol<0.1 g/100 mL で 19.5 ºC
DecompositionWhen heated to decomp it emits NO(x).
融点257 to 261 °F (NTP, 1992)131-132 °C124-128 °C (lit.)
蒸気圧0.0000279 [mmHg]
Physical Description2-aminofluorene is a brown crystal powder. (NTP, 1992)Brown solid[CAMEO] Off-white powder[MSDSonline]
Other Experimental PropertiesUV: 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/
沸点304.35°C (rough estimate)
密度1.0941 (rough estimate)
屈折率1.6118 (estimate)
貯蔵条件Keep in dark place,Inert atmosphere,Room temperature
外観・状態powder to crystal
pKa（酸解離定数）4.34±0.20(Predicted)
色White to Orange to Green
BRN1945861
ヘンリー定数2.7×102 mol/(m3Pa) at 25℃, HSDB (2015)
InChIInChI=1S/C13H11N/c14-11-5-6-13-10(8-11)7-9-3-1-2-4-12(9)13/h1-6,8H,7,14H2
InChIKeyCFRFHWQYWJMEJN-UHFFFAOYSA-N
SMILESC1C2=C(C=CC=C2)C2=C1C=C(N)C=C2
CAS データベース153-78-6(CAS DataBase Reference)
NISTの化学物質情報Fluoren-2-amine(153-78-6)
EPAの化学物質情報2-Aminofluorene (153-78-6)

化学的特性

WHITE TO SLIGHTLY BROWN CRYSTALLINE POWDER

安全性と法規制

GHS 分類WarningH302 (37.5%): Harmful if swallowed [Warning Acute toxicity, oral]P203, P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P318, P319, P321, P330, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 8 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
規制情報Hazard Traits - Carcinogenicity9H-Fluoren-2-amine: Does not have an individual approval but may be used under an appropriate group standard
輸送ラベル（DOT）Poison
火災危険Flash point data for this material are not available, but it is probably combustible. (NTP, 1992)
健康有害性ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits toxic fumes. (NTP, 1992)
有害性の概要Evidence for carcinogenicity in studies with rats and mice[HSDB] An irritant[MSDSonline] See POLYCYCLIC AROMATIC HYDROCARBONS.
反応性グループAmines, Aromatic
Reactivity Profile2-AMINOFLUORENE forms salts with acids and can react with oxidizing materials. (NTP, 1992)
Air and Water ReactionsThis compound is sensitive to prolonged exposure to air. Insoluble in water.
Hazard Classes and CategoriesAcute Tox. 4 (37.5%)
消火Fires involving this compound may be controlled with carbon dioxide, dry chemical, or Halon extinguishers. (NTP, 1992)
応急処置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.

用途

使用

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.

一般的な説明

Brown crystal powder.

製法・合成法

純化方法

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.]

非火災時の漏出対応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.
Isolation and EvacuationExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Personal Protective Equipment (PPE)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)
環境中動態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 °Cwhich 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).
Effluent Concentrations2-Aminofluorene was detected in the wastewater effluent from sewage treatment facilities in Japan(1).
Soil Adsorption/MobilityBased 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 solutionthe 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 quinonethese processes represent pathways by which aromatic amines may be converted to latent forms in the biosphere(5).
Environmental BiodegradationLevels of oxygen uptake for 500 mg/L of 2-aminofluorene oxidized in activated sewage sludge suspensions with suspended solid concn of 2,500 mg/L did not differ from the controls(1,2). After 144 hours, oxygen consumptions were about 1600, 1400 and 250 mg/L for Franklin, Nashville and Ashland sludge, respectively(1), whereas, corresponding controls accounted for losses of approximately 1650, 1500 and 450 mg of oxygen per liter(1).
Environmental BioconcentrationBased 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).
Volatilization from Water/SoilThe 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).
Non-Human Toxicity Excerpts2-FLUORENAMINE GIVEN TO MICE & RATS BY VARIOUS ROUTES PRODUCED LIVER TUMORS IN MICE & LIVER, INTESTINE, EAR DUCT, BREAST, AND LUNG TUMORS IN RATS. /FROM TABLE/2-AMINOFLUORENE ... & ITS ACETYL DERIVATIVE WERE DISCOVERED TO BE CARCINOGENIC IN MOST SPECIES /IN CHRONIC TOXICITY STUDIES/ EXCEPT THE GUINEA PIG & STEPPE LEMMING. TESTS IN RHESUS MONKEY ARE NEGATIVE SO FAR, EVEN THOUGH EXPOSURES HAVE BEEN UNDERWAY FOR MORE THAN 10 YEARS. THE 1 & 3 ISOMERS OF FLUOURENAMINE CMPD ARE WEAKLY CARCINOGENIC, IF AT ALL, & THE 4-ISOMER DOES NOT SEEM TO BE CARCINOGENIC TO RODENTS.BECAUSE SHORT IN VITRO TREATMENTS OF CHINESE HAMSTER CELLS WITH 2-AMINOFLUORENE (2-AF) DID NOT INCREASE SISTER CHROMATID EXCHANGE (SCE) EVEN IN THE PRESENCE OF A METABOLIC ACTIVATION SYSTEM, EXPT WERE CARRIED OUT WITH RABBITS TO SEE WHETHER IN VIVO ACTIVATION OCCURRED. RABBITS INJECTED WITH 2-AMINOFLUORENE COULD ACTIVATE THE CMPD & A TRANSIENT DOSE DEPENDENT INCREASE IN SCE WAS FOUND IN PERIPHERAL LYMPHOCYTES CULTURED AT VARIOUS TIMES AFTER THE INJECTION. THE ADDITION OF PHYTOHEMAGGLUTININ /TO THE PERIPHERAL LYMPHOCYTES/ & THE CONSEQUENT METABOLIC STIMULATION AFFECTS THE INDUCTION OF ENZYMES INVOLVED IN THE ACTIVATION OF 2-AMINOFLUORENE.CARCINOGENS WHICH CAUSE STRAIN TA1538 TO REVERT TO HISTIDINE INDEPENDENCE IN THE IN VITRO ASSAYS DEVELOPED BY AMES WILL, WHEN INGESTED, CAUSE AN INCREASED CONCN OF HISTIDINE INDEPENDENT REVERTANTS TO APPEAR IN THE FECES. THIS HOST MEDIATED ASSAY OFFERS A POSSIBLE MEANS OF STUDYING THE RELATIONSHIP OF THE BACTERIAL FLORA TO THE FORMATION OF REACTIVE INTERMEDIATES THAT MAY BE RELATED TO GI CARCINOGENESIS. GNOTOBIOTIC SPRAGUE DAWLEY RATS, ASSOC WITH SALMONELLA TYPHIMURIUM TA1538, MAY ALSO BE ASSOC WITH LACTOBACILLUS PLANTARUM OR BACTERIODES VULGATUS AS WELL AS WITH BOTH OF THESE STRAINS. AFTER THE INGESTION OF 2-NITROFLUORENE (3.4 MG), FECAL CONCENTRATION OF HIS+ REVERTANTS WAS GREATLY INCREASED IN ALL GROUPS OF RATS EXCEPT THOSE ASSOCIATED WITH STRAIN TA1538 AND BACTERIODES VULGATUS. THE CONCN OF THE VARIOUS BACTERIA WERE MEASURED AT 8 SITES IN THE GI TRACT. BACTERIODES VULGATUS ACHIEVED HIGH CONCN IN THE STOMACH WHEN IT WAS ASSOC WITH STRAIN TA1538, BUT ITS CONCN WAS NOT AS HIGH WHEN IT WAS ASSOC WITH LACTOBACILLUS PLANTARUM TOGETHER WITH STRAIN TA1538. BACTERIODES VULGATUS READILY REDUCES 2-NITROFLUORENE TO 2-AMINOFLUORENE, A REACTION WHICH IS NEGLIGIBLE IN CULTURES OF LACTOBACILLUS PLANTARUM & STRAIN TA1538. SINCE 2-AMINOFLUORENE IS LESS MUTAGENIC THAN 2-NITROFLUORENE, BACTERIODES VULGATUS APPEARS TO DIMINISH THE REVERTANT RESPONSE BY REMOVING THE MORE POTENT MUTAGEN FROM WITHIN THE GI TRACT.
Environmental Abiotic DegradationAromatic-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).
Environmental Water ConcentrationsDRINKING WATER: 2-Aminofluorene was detected in groundwater wells in Japan(1).
Environmental Fate/Exposure SummaryInformation regarding the production of 2-aminofluorene was not available. 2-Aminofluorene is expected to biodegrade very slowly and is not expected to hydrolyze in the environment. A calculated Koc range of 640 to 1100, indicates 2-aminofluorene is characterized by a low mobility class in soil. In aquatic systems, 2-aminofluorene may 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, suggests volatilization of 2-aminofluorene from environmental waters will not be important. 2-Aminofluorene is expected to exist in both the particulate and vapor phases in ambient air. For vapor phase 2-aminofluorene in the atmosphere, the vapor phase reaction with photochemically produced hydroxyl radicals (half-life of 2 hr) is likely to be an important fate process. Otherwise, washout by precipitation and gravitational settling may be an important removal mechanism for 2-aminofluorene in atmospheric particulate matter. (SRC)
水環境危害等級（WGK）3
RTECS 番号LL5075000
税関コード29214980
危険文句（R）68-40
危険表示Xn
安全措置（S）45-36/37-24/25
危険等級Aquatic Chronic 2Carc. 2
貯蔵分類11 - Combustible Solids
有害物質データ153-78-6(Hazardous Substances Data)