2-Acetylaminofluorene

Base Information

• Chemical Name: 2-Acetylaminofluorene
• CAS No.: 53-96-3
• Deprecated CAS: 2508-21-6
• Molecular Formula: C15H13 N O
• Molecular Weight: 223.274
• Hs Code.: 2924299090
• European Community (EC) Number: 200-188-6
• NSC Number: 12279
• UN Number: 3077
• UNII: 9M98QLJ2DL
• DSSTox Substance ID: DTXSID0039227
• Nikkaji Number: J2.312D
• Wikipedia: 2-Acetylaminofluorene
• Wikidata: Q4382200
• NCI Thesaurus Code: C29791
• Pharos Ligand ID: 8NYVAV557GDX
• Metabolomics Workbench ID: 50878
• ChEMBL ID: CHEMBL311469
• Mol file: 53-96-3.mol

Synonyms:2 Acetamidofluorene;2 Acetylaminofluorene;2 Fluorenylacetamide;2-AAF;2-Acetamidofluorene;2-Acetylaminofluorene;2-Fluorenylacetamide;AAF, aminofluorene;Acetylaminofluorene;Aminofluorene AAF;Fluoren 2 ylacetamide;Fluoren-2-ylacetamide;N 2 Fluorenylacetamide;N Acetyl 2 Aminofluorene;N-2-Fluorenylacetamide;N-acetyl-2-aminofluorene

Chemical Property of 2-Acetylaminofluorene

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 4.73E-09mmHg at 25°C
• Melting Point: 194
• Refractive Index: 1.5500 (estimate)
• Boiling Point: 303
• PKA: 14.89±0.20(Predicted)
• Flash Point: 277.2°C
• PSA: 29.10000
• Density: 1.23g/cm³
• LogP: 3.28920
• Storage Temp.: Store below +30°C.
• Solubility.: Soluble in acetone, acetic acid, alcohol (Weast, 1986), glycols, and fat solvents (Windholz et al., 1983)
• Water Solubility.: 0.000529 g/100 mL
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 223.099714038
• Heavy Atom Count: 17
• Complexity: 301
• Transport DOT Label: Class 9

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-Acetamidofluorene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T,N
• Statements: 45-22-51/53
• Safety Statements: 53-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Polycyclic Aromatic Hydrocarbons
• Canonical SMILES: CC(=O)NC1=CC2=C(C=C1)C3=CC=CC=C3C2
• Description: 2-Acetylaminofluorene (2-AAF) was originally synthesized to be used as a pesticide but due to its profound carcinogenicity it is now purely used in research laboratories for research purposes only. The occupations at greatest risk to acetylaminofluorene exposure are organic chemists, chemical stockroom workers, and biomedical researchers. 2-AAF is a tan-colored compound insoluble in water (melting point. 194
  C). It is soluble in glycols, alcohols, ether, and acetic acid. 2-AAF is no longer produced in commercial quantities anywhere in the world. In 2009, 2-AAF was distributed in small quantities by 17 specialty chemical companies, including 11 in the United States. As per the US Environmental Protection Agency (EPA), environmental release of 2-AAF rose from w10 000 to w81 000 lb from 1998 to 2001, and then was contained below 1000 lb in 2003. Although neither the National Institute of Occupational Safety and Health (NIOSH) nor the Occupational Safety and Health Administration (OSHA) has estimated the number of US workers exposed to acetylaminofluorene, perhaps fewer than 1000 workers in 200 laboratories may have come in contact with this compound. In order to debate ‘threshold level,’ dose–response relationships, and carcinogenic potential of 2-AAF, a few studies employed very large numbers of female BALB/c StCrlfC3Hf/ Nctr mice, and exposed them to low doses of 2-AAF for up to 33 months. Study findings showed two different types of dose– response relationships for urinary bladder neoplasms and liver neoplasms; bladder neoplasms exhibited a minimum effect level (or a nonlinear response) for specific conditions. In contrast, the late-appearing liver neoplasms displayed a nearly linear response that extrapolated directly to zero dose. Time of exposure (18, 24, and 33 months) was shown to be an important factor for incremental positive response. Induction of bladder neoplasms was shown to occur early in the study, but was dependent on the continuous presence of 2-AAF, whereas the liver neoplasms appeared very late in the study but were shown to be induced at a very early point in the exposures and did not require the continuous presence of the carcinogen in order to develop. Results of this type of studies were consistent with ‘no threshold concept.’ Overall, most studies advocate the importance of the time factor in safety evaluation or risk assessment in carcinogenesis because carcinogen dose, length of exposure, and gender all may play roles in cancer/ tumor development.
• Uses: As a positive control to study the carcinogenicity and mutagenicity of aromatic amines. As a laboratory reagent for research purposes (specifically, a positive control for carcinogenicity and mutagenicity studies) Acetylaminofluorene is found as a contaminant in coal gasification processes. It was intended to be used as a pesticide but was never marketed due to its carcinogenicity. It has no known use. 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.

Technology Process of 2-Acetylaminofluorene

There total 21 articles about 2-Acetylaminofluorene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

2-nitro-9H-fluorene (607-57-8) + acetic anhydride (108-24-7) → 2-acetylaminofluorene (53-96-3)

Guidance literature:

With indium; acetic acid; In methanol; at 20 ℃; for 2h;

DOI:10.1016/S0040-4039(02)02479-6

Reference yield: 75.0%

2-nitro-9H-fluorene (607-57-8) + potassium thioacetate (10387-40-3) → 2-acetylaminofluorene (53-96-3)

Guidance literature:

In N,N-dimethyl-formamide; at 130 ℃; for 2h;

DOI:10.1016/j.tetlet.2005.09.196

Reference yield: 35.0%

GLUTATHIONE (70-18-8) + N-(sulfonatooxy)-N-acetyl-2-aminofluorene (16808-85-8) → 2-acetylaminofluorene (53-96-3) + 7-(glutathion-S-yl)-2-acetylaminofluorene (82332-94-3) + 1-(glutathion-S-yl)-2-acetylaminofluorene (82332-95-4) + 3-(glutathion-S-yl)-2-acetylaminofluorene (82332-96-5) + 4-(glutathion-S-yl)-2-acetylaminofluorene (82332-97-6)

Guidance literature:

With sodium perchlorate; In acetonitrile; at 20 ℃; Product distribution; Mechanism; pH = 8.5;

DOI:10.1021/ja9534563

upstream raw materials:

2-aminofluorene

acetic anhydride

acetic acid

NA-AAF

Downstream raw materials:

8-(N-2-amino-fluorene)-O⁶-benzyl-3',5'-O-bis(tert-butyldimethylsilyl)-N²-dimethoxytrityl-2'-deoxyguanosine

9-oxo-2-acetylamino-7-nitrofluorene

N-2-(3-Nitro-9-oxo-fluorenyl)-acetamid

2,7-diaminofluoren-9-one

Refernces

• 1、 Chung, Jing-Gung,Chang, Huei-Ling,Lin, Wen-Chuan,Yeh, Feng-Tsgh,Hung, Chi-Fu. "Effects of ibuprofen on arylamine N-acetyltransferase activity in human colon tumor cells". . p. 1 - 6. Retrieved 1999.
• 2、 Chung. "The effects of vitamin E on arylamine N-Acetyltransferase activity in strains of Helicobacter pylori from peptic ulcer patients". . p. 655 - 661. Retrieved 1999.
• 3、 Chung, Jing G.,Tsou, Mei F.,Wang, Hwang H.,Lo, Hsueh H.,Hsieh, Sue E.,Yen, Yee S.,Wu, Lii T.,Chang, Shih H.,Ho, Chin C.,Hung, Chi F.. "Rhein affects arylamine N-acetyltransferase activity in Helicobacter pylori from peptic ulcer patients". . p. 117 - 123. Retrieved 1998.
• 4、 Kim, Byeong Hyo,Han, Rongbi,Piao, Fengyu,Jun, Young Moo,Baik, Woonphil,Lee, Byung Min. "Indium-mediated one-pot reductive conversion of nitroarenes to N-arylacetamides". . p. 77 - 79. Retrieved 2007/10/03.