N-Hydroxy-2-acetamidofluorene

Base Information

• Chemical Name: N-Hydroxy-2-acetamidofluorene
• CAS No.: 53-95-2
• Molecular Formula: C15H13 N O2
• Molecular Weight: 239.274
• Hs Code.: 2924299090
• NSC Number: 46522
• UNII: 6AGD02HUQC
• DSSTox Substance ID: DTXSID2020719
• Nikkaji Number: J1.912G
• Wikipedia: Hydroxyacetylaminofluorene
• Wikidata: Q5955515
• Metabolomics Workbench ID: 51095
• ChEMBL ID: CHEMBL284464
• Mol file: 53-95-2.mol

Synonyms:Hydroxyacetylaminofluorene;Hydroxyfluorenylacetamide;N Hydroxy 2 acetamidofluorene;N-Hydroxy-2-acetamidofluorene

Chemical Property of N-Hydroxy-2-acetamidofluorene

Chemical Property:

• Appearance/Colour: cream powder
• Vapor Pressure: 4.51E-09mmHg at 25°C
• Melting Point: 136 - 137 C
• Refractive Index: 1.5500 (estimate)
• Boiling Point: 455.1°Cat760mmHg
• Flash Point: 229°C
• PSA: 40.54000
• Density: 1.322g/cm³
• LogP: 2.99990
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 239.094628657
• Heavy Atom Count: 18
• Complexity: 331

Purity/Quality:

98%min ^*data from raw suppliers

N-9H-Fluoren-2-yl-N-hydroxy-acetamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)N(C1=CC2=C(C=C1)C3=CC=CC=C3C2)O
• Uses: N-9H-Fluoren-2-yl-N-hydroxy-acetamide inactivates human arylamine N-acetyltransferases (NATs), NAT1 and NAT2. Mutagenicity examined in Salmonella typhimurium TA1538. Liver produced metabolite of the cancinogen 2-Acetamidofluorene (A158535), which is also a highly carcinogenic compound.

Technology Process of N-Hydroxy-2-acetamidofluorene

There total 12 articles about N-Hydroxy-2-acetamidofluorene 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: 84.0%

2-Nitrosofluoren (2508-20-5) + 2-oxo-propionic acid (127-17-3) → N-Hydroxy-2-acetylaminofluoren (53-95-2)

Guidance literature:

In water; acetic acid; for 0.5h; Ambient temperature;

DOI:10.1021/jo00279a039

Reference yield: 78.0%

N-(9H-fluoren-2-yl)hydroxylamine (53-94-1) + acetyl chloride (75-36-5) → N-Hydroxy-2-acetylaminofluoren (53-95-2)

Guidance literature:

With sodium hydrogencarbonate; In diethyl ether; at 20 ℃; for 1h;

DOI:10.1055/s-2007-990913

Reference yield: 30.0%

>-2-aminofluorene (137390-96-6) → N-Hydroxy-2-acetylaminofluoren (53-95-2) + 5'-<((2-Carboxy)ethyl)carbonyl> 2',3'-isopropylidene guanosine (137390-95-5) + Succinic acid 2-acetylamino-9H-fluoren-1-yl ester (3aR,4R,6R,6aR)-6-(2-amino-6-oxo-1,6-dihydro-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester (137390-97-7) + Succinic acid 2-acetylamino-9H-fluoren-3-yl ester (3aR,4R,6R,6aR)-6-(2-amino-6-oxo-1,6-dihydro-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester (137390-98-8) + 8--5'-<((2-carboxyethyl)carbonyl)>>-2',3'-isopropylideneguanosine (137390-99-9)

Guidance literature:

In water; acetone; at 40 ℃; Rate constant; pH 9.2 (also pH 4 and 7);

DOI:10.1016/S0040-4020(01)86525-X

upstream raw materials:

d⁽⁴⁾-methanol

N-(Pivaloyloxy)-2-(acetylamino)fluorene

NA-AAF

N-(9H-fluoren-2-yl)hydroxylamine

Downstream raw materials:

N-(Pivaloyloxy)-2-(acetylamino)fluorene

C₅₈H₆₄N₉O₈P

N-(deoxyguanosin-8-yl)-2-acetamidofluorene

N-(deoxyguanosin-8-yl)-2-aminofluorene

Refernces

• 1、 Krueger, Sarah,Meier, Chris. "Synthesis of site-specific damaged DNA strands by 8-(acetylarylamino)- 2′-deoxyguanosine adducts and effects on various DNA polymerases". . p. 1158 - 1169. Retrieved 2013/04/10.
• 2、 Novak, Michael,Rangappa, Kanchugarakoppal S.,Manitsas, Rebecca K.. "Nucleophilic Aromatic Substitution on Ester Derivatives of Carcinogenic N-Arylhydroxamic Acids by Aniline and N,N-Dimethylaniline". . p. 7813 - 7821. Retrieved 2007/10/02.