ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
化工社オープンプロジェクト：[email protected]AIアクセス：llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.7.8
戻る
化工社化工社 化学情報印刷レポート · 研究参考用
HCID 5897作成日：2026年10月27日

2-アセトアミドフルオレン

2-アセトアミドフルオレン · 2-アセチルアミノフルオレン · N-(9H-フルオレン-2-イル)アセトアミド · N-アセチル-9H-フルオレン-2-アミン · 2-アセチルアミノ-9H-フルオレン · 2-(アセチルアミノ)-9H-フルオレン · 2-アセトアミドフルオレン標準品 · ２アセチルアミノフルオレン

https://huagongshe.com/ja/chemical/5897

2-アセトアミドフルオレン の分子構造式

識別子と物理属性

CAS No.53-96-3
分子式C15H13NO
平均分子量223.27 g/mol
単同位体質量223.09971404 g/mol
SMILESCC(=O)Nc1ccc2c(c1)Cc1ccccc1-2
InChIKeyCZIHNRWJTSTCEX-UHFFFAOYSA-N
PubChem CID5897
ChEMBLCHEMBL311469
ChEBICHEBI:17356
EC No.200-188-6
DTXSIDDTXSID0039227
現地名2-アセトアミドフルオレン

化学・物理的性質

XLogP3.3
極性表面積29.1
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1
重原子数17
形式電荷0
複雑度301
物質分類Hazardous Air Pollutants (HAPs)Carcinogens
PolymersOther Classes -> Polycyclic Aromatic Hydrocarbons
Color/FormCrystals from alcohol + waterTan, crystalline powder
溶解度less than 1 mg/mL at 68.9 °F (NTP, 1992)Soluble in glycols, fat solventsSoluble in ether, acetic acidInsolubleアセトン、酢酸、アルコール (Weast, 1986)、エチレングリコール、脂肪族溶剤 (Windholze et al., 1983) に可溶26.3 °C で 10.13 mg/L (Ellington et al., 1987)
DecompositionWhen heated to decomposition it emits toxic fumes of /nitrogen oxides/.
融点381 °F (NTP, 1992)194 °C192-196 °C(lit.)
蒸気圧0.00023 mmHg at 212 °F (NTP, 1992)
Physical Description2-acetylaminofluorene appears as white powder or light beige solid. (NTP, 1992)Tan, crystalline powder[NIOSH]Tan, crystalline powder.
Other Experimental PropertiesNeedles crystallized from 50% alcohol or 50% acetic acid
沸点364.56°C (rough estimate)
密度1.0707 (rough estimate)
屈折率1.5500 (estimate)
貯蔵条件Store below +30°C.
pKa（酸解離定数）14.89±0.20(Predicted)
外観・状態結晶性粉末
色オフホワイトからタン
Merck14,4157
BRN2807677
ヘンリー定数5.2×104 mol/(m3Pa) at 25℃, HSDB (2015)
InChI1S/C15H13NO/c1-10(17)16-13-6-7-15-12(9-13)8-11-4-2-3-5-14(11)15/h2-7,9H,8H2,1H3,(H,16,17)
InChIKeyCZIHNRWJTSTCEX-UHFFFAOYSA-N
SMILESCC(=O)Nc1ccc-2c(Cc3ccccc-23)c1
CAS データベース53-96-3(CAS DataBase Reference)
EPAの化学物質情報2-Acetylaminofluorene (53-96-3)

化学的特性

WHITE TO YELLOW-BROWN CRYSTALLINE POWDER

安全性と法規制

GHS 分類DangerH302 (95.8%): Harmful if swallowed [Warning Acute toxicity, oral]P203, P264, P270, P280, P301+P317, P318, P330, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 71 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
規制情報Chemical: Acetamide, N-9H-fluoren-2-yl-Hazard Traits - CarcinogenicityAcetamide, N-9H-fluoren-2-yl-: Does not have an individual approval but may be used under an appropriate group standardThe New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)
その他の安全情報IMAP assessments - Acetamide, N-9H-fluoren-2-yl-: Environment tier I assessment
輸送ラベル（DOT）Class 9
火災危険Flash point data for this chemical are not availablehowever, it is probably combustible. (NTP, 1992)
健康有害性Excerpt from NIOSH Pocket Guide for 2-Acetylaminofluorene:
有害性の概要2-Acetylaminofluorene is used by scientists to study the carcinogenicity and mutagenicity of aromatic amines. No information is available on the acute (short-term), chronic (long-term), reproductive, or developmental effects of 2-acetylaminofluorene in humans. It has caused a variety of tumors in laboratory animals. EPA has not classified 2-acetylaminofluorene for carcinogenicity.Potential for cancer--see 29 CFR 1910.1003. An animal carcinogen (liver, bladder, and kidneys)[ACGIH]The major hazards encountered in the use and handling of 2-acetylaminofluorene stem from its toxicologic properties. Toxic by inhalation and skin absorption, exposure to this tan, crystalline solid may occur from its use in biomedical research. The major toxic effect from exposure is cancer. OSHA considers 2-acetylaminofluorene to be an occupational carcinogen, and has established strict standards regulating its industrial use. Engineering controls are required to prevent exposure. However, in activities or situations where exposure may occur, wear a self-contained breathing apparatus and personal protective clothing. If contact should occur, immediately wash the affected skin, and remove contaminated clothing at the site. Waste 2-acetylaminofluorene is a candidate for rotary kiln and fluidized bed forms of incineration. Before implementing land disposal of 2-acetylaminofluorene consult with environmental regulatory agencies for guidance.

用途

用途

有機合成原料。

使用

N-(2-Fluorenyl)acetamide (2-Acetamidofluorene, 2-AAF), a genotoxic carcinogen, is used to induce liver cancer in animal models such as the 2-AAF/partial hepatectomy rat. 2-AAF may be used to study the mechanism of liver carcinogenesis and as a reference material during its identification or quantitation.

一般的な説明

White powder or light beige solid.

製法・合成法

調製方法

2-Acetylaminofluorene is produced for research purposes only with an estimated U.S. annual usage of less than 20 lb. It was originally developed as a possible insecticide but has never been used for this purpose after discovery of its carcinogenicity. It is now almost exclusively used in the laboratory studies as a model carcinogen and mutagen.

純化方法

Recrystallise it from toluene (1.3mg in 100mL). Its solubility in H2O is 1.3mg/L at 25o, UV: max nm(log ) : 288(4.43), 313(4.13). [Sawicki J Org Chem 21 271 1956.] It can also be recrystallised from 50% AcOH. [Diels et al. Chem Ber 35 3285 1902]. 9-14C and -14C 2-acetamidofluorene were recrystallised from aqueous EtOH and had m 194-195o and 194o respectively. Potent CARCINOGEN. [Miller et al. Cancer Res 9 504 1949, 10 616 1950, Sadin et al. J Am Chem Soc 74 5073 1952, Beilstein 12 H 3287, 12 IV 3373.]

反応性グループAmides and Imides
Special ReportsU.S. Department of Health & Human Services/National Toxicology ProgramTwelfth Report on Carcinogens (2011). The Report on Carcinogens is an informational scientific and public health document that identifies and discusses substances (including agents, mixtures, or exposure circumstances) that may pose a carcinogenic hazard to human health. 2-Acetylaminofluorene (53-96-3) is listed as reasonably anticipated to be a human carcinogen. First listed in the Second Annual Report on Carcinogens (1981).[Available from, as of March 1, 2012: http://ntp.niehs.nih.gov/?objectid=03C9AF75-E1BF-FF40-DBA9EC0928DF8B15]
RCRA 要件U005As stipulated in 40 CFR 261.33, when 2-acetylaminofluorene, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).
OSHA StandardsWorkers' exposure to 2-acetylaminofluorene is to be controlled through the required use of engineering controls, work practices, and personal protective equipment, incl respirators. Identified as an occupational carcinogen without establishing a PEL.
Reactivity Profile2-ACETYLAMINOFLUORENE is incompatible with acids, bases and oxidizing agents. Ozone and chlorinating agents oxidize this compound (NTP, 1992).
大気基準Listed as a hazardous air pollutant (HAP) generally known or suspected to cause serious health problems. The Clean Air Act, as amended in 1990, directs EPA to set standards requiring major sources to sharply reduce routine emissions of toxic pollutants. EPA is required to establish and phase in specific performance based standards for all air emission sources that emit one or more of the listed pollutants. 2-Acetylaminofluorene is included on this list.
消火Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (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.(General first aid procedures)
非火災時の漏出対応SMALL SPILLS AND LEAKAGE: In cleanup of leaks or spills outside the laboratory hood, maintenance or repair operations on contaminated systems or equipment, where direct contact with this compound could result, each person entering that area should be provided with and required to wear, clean impervious garments, including gloves, boots and continuous air supplied hood-style respirator. To perform cleanup FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol 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.
処分方法SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U005, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.[A potential candidate for rotary kiln incineration at a temperature range of 820 to 1,600 °C and residence times of seconds for liquids and gases, and hours for solids. A potential candidate for fluidized bed incineration at a temperature range of 450 to 980 °C and residence times of seconds for liquids and gases, and longer for solids.
Preventive MeasuresSRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. The completeness of the cleaning procedures should be considered before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at the end of shift, but should remain at employee's place of work for cleaning.The worker should immediately wash the skin when it becomes contaminated.The worker should wash daily at the end of each work shift, and prior to eating, drinking, smoking, etc.Work clothing that becomes wet or significantly contaminated should be removed and replaced.Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premises.
Isolation and EvacuationExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
Respirator Recommendations(See OSHA respirator requirements for selected chemicals)
Permissible Exposure Limit (PEL)Ca[1910.1014] See Appendix B
Protective Action Criteria (PAC)2.2 [mg/m3]25 [mg/m3]69 [mg/m3]
Recommended Exposure Limit (REL)Ca See Appendix A
Personal Protective Equipment (PPE)Excerpt from NIOSH Pocket Guide for 2-Acetylaminofluorene:Wear appropriate personal protective clothing to prevent skin contact.Wear appropriate eye protection to prevent eye contact.Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to the substancethis is irrespective of the recommendation involving the wearing of eye protection.Facilities for quickly drenching the body should be provided within the immediate work area for emergency use where there is a possibility of exposure. [Note: It is intended that these facilities provide a sufficient quantity or flow of water to quickly remove the substance from any body areas likely to be exposed. The actual determination of what constitutes an adequate quick drench facility depends on the specific circumstances. In certain instances, a deluge shower should be readily available, whereas in others, the availability of water from a sink or hose could be considered adequate.]For more Personal Protective Equipment (PPE) (Complete) data for 2-ACETYLAMINOFLUORENE (6 total), please visit the HSDB record page.
Immediately Dangerous to Life or Health (IDLH)A potential occupational carcinogen. (NIOSH, 2024)NIOSH considers 2-acetylaminofluorene to be a potential occupational carcinogen.Ca [N.D.]
Cancer Sites[in animals: tumors of the liver, bladder, lungs, skin & pancreas]
相互作用CONFIRMATORY EVIDENCE FOR INVOLVEMENT OF N-SULFATE IN CARCINOGENESIS WAS DISCOVERY THAT DEPLETION OF INTRACELLULAR GLUTATHIONE LEVEL WITH ACETANILIDE REDUCES CARCINOGENICITY OF 2-ACETYLAMINOFLUORENE.ETHIONINE COMPLETELY INHIBITS ... HYDROXYLATION OF ACETYLAMINOFLUORENE.... /It has been/ found that dietary intake of 500 ppm BHT following an initiating treatment with ... 2-acetylaminofluorene appeared to exert a promoting effect, which was ... not as strong as that of phenobarbital. This was subsequently confirmed /in other studies/. ... /In one study it was/ observed that BHT enhanced pulmonary carcinogenesis in mice. In a study on BHT inhibition of liver carcinogenesis ... /it was/ noted that with rats fed 2-acetylaminofluorene, liver carcinogenesis was inhibited, as ... /demonstrated in other studies/, but that, at high levels of BHT, induction of bladder cancer was seen. Probably, metabolic shifts are involved that protect the liver & yields a higher level of excretion of metabolites that could affect the bladder, but a promoting effect may also be involved. The findings ... /in some of these studies/ are consistent with a promoting effect of these antioxidants, but more work needs to be done before assignment can be confidently made.The synergism of two carcinogenic aromatic amines with different tissue specificities was studied at the level of initiation in Wistar rats. Gamma-glutamyl transpeptidase and glutathione S-transferase P were used as markers for preneoplastic foci in liver. 2-Acetylaminofluorene (AAF) is a complete rat liver carcinogen, whereas trans-4-acetylaminostilbene (AAS) produces ear duct tumors quite selectively, but also acts as a strong initiator in rat liver. When these carcinogens were administered sequentially as two doses of each or simultaneously as four doses of a mixture to neonate animals, which then were treated with phenobarbital in the drinking water for promotion, the initiating activity was additive. When these chemicals were given to young adult animals within 4 weeks in two series of four doses, followed by partial hepatectomy and phenobarbital in the drinking water, the number of preneoplastic foci was greater in groups which had received AAS in both series or in the second series after AAF than in those groups which had received only AAF or AAF in the second series. The average size of foci depended clearly on the sequence in which the two carcinogens were administered. The foci were larger when AAF was given after AAS. The results support the notion that AAS is a strong initiator in rat liver, and that AAF, which is a complete liver carcinogen, has promoting properties under certain circumstances in addition to its initiating properties. The two carcinogens seem to produce the initiating lesions independently but the extent of initiation is additive in this model situation. The simplified neonatal rat liver model appears to be particularly suitable for investigating initiating properties and is proposed for studies of synergistic effects of genotoxic chemicals on the initiation stage, independent of organotropism. It avoids a number of complicating factors related to treatment schedule, forced proliferation rate and toxicity in other models.
標的器官Liver, bladder, kidneys, pancreas, skin
生態毒性値EC50Species: Xenopus laevis (African Clawed Frog) embryoConditions: freshwater, renewal, 23 °CConcentration: 6900 ug/L for 96 hr (95% confidence interval: 6500-7300 ug/L)Effect: abnormal development, malformations /100% purity formulation/LC50Concentration: 87000 ug/L for 96 hr (95% confidence interval: 84000-89000 ug/L) /100% purity formulation/
環境中動態TERRESTRIAL FATE: Based on a classification scheme(1), a log Koc value of 3.14(2), corresponding to a Koc of 1380(SRC), indicates that 2-acetylaminofluorene is expected to have moderate mobility in soil(SRC). Volatilization of 2-acetylaminofluorene from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.9X10-10 atm-cu m/mole(SRC), using a fragment constant estimation method(3). 2-Acetylaminofluorene is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.9X10-5 mm Hg at 25 °C(SRC), determined from a fragment constant method(4). Utilizing activated sludge, 7-12% of the Theoretical BOD was reached in 6 days(5) indicating that biodegradation is not an important environmental fate process in soil(SRC).AQUATIC FATE: Based on a classification scheme(1), a log Koc value of 3.14(2), corresponding to a Koc of 1380(SRC), indicates that 2-acetylaminofluorene is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.9X10-10 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 53(SRC), from an estimated log Kow of 3.12(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Utilizing activated sludge, 7-12% of the Theoretical BOD was reached in 6 days(8) indicating that biodegradation is not an important environmental fate process in water(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-acetylaminofluorene, which has an estimated vapor pressure of 2.9X10-5 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase 2-acetylaminofluorene is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC)the half-life for this reaction in air is estimated to be 5 hours(SRC), calculated from its rate constant of 2.7X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase 2-acetylaminofluorene may be removed from the air by wet or dry deposition(SRC). 2-Acetylaminofluorene absorbs at wavelengths >290 nm(4), and therefore may be susceptible to direct photolysis by sunlight(SRC).
有害作用NTP Carcinogen - Reasonably anticipated to be a human carcinogen.
暴露経路inhalation, skin absorption, ingestion, skin and/or eye contact
Signs and SymptomsReduced function of liver, kidneys, bladder, pancreas[potential occupational carcinogen]
Ongoing Test StatusThe following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical.[Available from: http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=53-96-3]
Soil Adsorption/MobilityA log Koc of 3.14 has been reported for 2-acetylaminofluorene(1), corresponding to a Koc of 1380(SRC). According to a classification scheme(2), this estimated Koc value suggests that 2-acetylaminofluorene is expected to have low mobility in soil.
TSCA Test SubmissionsThe mutagenicity of N-2-fluorenylacetamide (NFA) was evaluated in Salmonella tester strains TA98, TA100, TA1535, TA1537 and TA1538 (Ames Test), both in the presence and absence of added metabolic activation by Aroclor-induced rat liver S9 fraction. Based on the results of preliminary bacterial toxicity determinations, NFA, diluted with DMSO, was tested for mutagenicity at concentrations up to 1 mg/plate using the plate incorporation assay. NFA caused a positive response in strains TA1535, TA100, and TA98 following metabolic activation.
Artificial Pollution Sources2-Acetylaminofluorene's production and use in cancer research(1) may result in its release to the environment through various waste streams(SRC).
CERCLA 報告数量Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 1 lb or 0.454 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).
水環境危害等級（WGK）3
TSCA 収載状態TSCA listed
RTECS 番号AB9450000
輸送番号（UN）UN 3077 9/PG 3
毒性Acute oral LD50 for mice 1,020 mg/kg (quoted, RTECS, 1985).
税関コード2924 29 70
危険文句（R）45-22-51/53
危険表示T,N
安全措置（S）53-36/37/39-45
危険等級6.1(b)Acute Tox. 4 OralCarc. 1B
包装等級III
貯蔵分類6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
有害物質データ53-96-3(Hazardous Substances Data)