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153-78-6

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153-78-6 Usage

Description

2-Aminofluorene is a polycyclic aromatic amine (PAA) that appears as a brown crystal powder. It has been historically used in various industries, including rubber, textile, and dye manufacturing. However, it was found to be carcinogenic in laboratory animals and was never marketed as a pesticide.

Uses

Used in Rubber Industry:
2-Aminofluorene is used as an intermediate in the rubber industry for the production of various rubber products.
Used in Textile Industry:
2-Aminofluorene is used as an intermediate in the textile industry for the production of dyes and other textile-related products.
Used in Dye Industry:
2-Aminofluorene is used as an intermediate in the dye industry for the manufacture of synthetic dyes.
Used in Plastics Industry:
2-Aminofluorene is used as an intermediate in the plastics industry for the production of various types of plastics.
Used in Drug Industry:
2-Aminofluorene is used as an intermediate in the drug industry for the synthesis of certain pharmaceutical compounds.
Used in Pesticide Industry:
Although 2-Aminofluorene was being developed for use as a pesticide during the 1930s, it was found to be carcinogenic and was never marketed for this purpose.

Air & Water Reactions

2-Aminofluorene is sensitive to prolonged exposure to air. Insoluble in water.

Reactivity Profile

2-AMINO FLUORENE forms salts with acids and can react with oxidizing materials.

Health Hazard

ACUTE/CHRONIC HAZARDS: When heated to decomposition 2-Aminofluorene emits toxic fumes.

Fire Hazard

Flash point data for 2-Aminofluorene are not available, but 2-Aminofluorene is probably combustible.

Safety Profile

Suspected carcinogen with experimental carcinogenic, neoplastigenic, and tumorigenic data. Poison by intraperitoneal route. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx. See also AMINES.

Environmental Fate

PAAs may be transported as vapor or adsorbed onto particulates. Due to low water solubility, PAAs are not transported in water but adsorb onto soil and sediments. Leaching is negligible. Bioaccumulation is not considered a concern.

Purification Methods

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.]

Toxicity evaluation

N-hydroxy metabolites within the gastrointestinal tract transform fluoren-2-amine into a mutagen or carcinogen. A number of PAAs are potent bladder carcinogens. As noted previously, sequential hydroxylation and glucuronidation lead to urinary excretion, with metabolites in the urinary bladder. While glucuronidation enhances excretion via the urine, a glucuronidase in the bladder hydrolyzes the glucuronide and under acidic conditions N-hydroxylarylamines are formed. Subsequent conversion of the amine leads to an aryl nitrenium ion, which can initiate tumor formation. Sulfate esters can degrade to electrophilic nitronium ion–carbonium ion, which can form adducts with macromolecules.

Check Digit Verification of cas no

The CAS Registry Mumber 153-78-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,5 and 3 respectively; the second part has 2 digits, 7 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 153-78:
(5*1)+(4*5)+(3*3)+(2*7)+(1*8)=56
56 % 10 = 6
So 153-78-6 is a valid CAS Registry Number.
InChI:InChI=1/C13H11N/c14-13-7-3-6-11-10-5-2-1-4-9(10)8-12(11)13/h1-7H,8,14H2

153-78-6 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (B22769)  2-Aminofluorene, 98%   

  • 153-78-6

  • 1g

  • 281.0CNY

  • Detail
  • Alfa Aesar

  • (B22769)  2-Aminofluorene, 98%   

  • 153-78-6

  • 5g

  • 521.0CNY

  • Detail
  • Alfa Aesar

  • (B22769)  2-Aminofluorene, 98%   

  • 153-78-6

  • 25g

  • 2188.0CNY

  • Detail
  • Aldrich

  • (A55500)  2-Aminofluorene  98%

  • 153-78-6

  • A55500-5G

  • 519.48CNY

  • Detail
  • Aldrich

  • (A55500)  2-Aminofluorene  98%

  • 153-78-6

  • A55500-25G

  • 2,185.56CNY

  • Detail

153-78-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Aminofluorene

1.2 Other means of identification

Product number -
Other names 9H-Fluoren-2-amine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:153-78-6 SDS

153-78-6Related news

First Principles Study of Linear and Nonlinear Optical Properties of 2-Aminofluorene (cas 153-78-6) (C13H11N)09/30/2019

In this study, electronic band structure, linear and nonlinear optical properties of crystalline 2-aminofluorene are calculated following the density functional theory. The exchange correlation effects are taken into account by generalized gradient approximation and modified Becke–Johnson poten...detailed

Activation of 2-Aminofluorene (cas 153-78-6) by Prostaglandin Endoperoxide H Synthase 209/29/2019

Prostaglandin endoperoxide H synthase is the key enzyme in the conversion of arachidonic acid to tissue prostanoids. Two isoforms of prostaglandin endoperoxide H synthase have been identified: PHS-1 is constitutively expressed in most tissues under normal physiological conditions and PHS-2 is ex...detailed

153-78-6Relevant articles and documents

A new and efficient pyridine-2,6-dicarboxamide-based fluorescent and colorimetric chemosensor for sensitive and selective recognition of Pb2+ and Cu2+

Hosseinzadeh, Rahman,Rahimi, Hannaneh,Tajbakhsh, Mahmood

, (2021)

A new fluorene-bearing pyridine-2,6-dicarboxamide (3) as an effectint fluorescent and colorimetric cation sensor was successfully synthesized and well-characterized using FT-IR, NMR, ESI+-MS and elemental analysis. The metal ion binding ability of the chemosensor 3 in the presence of different metal ions was investigated using UV–vis, fluorescence experiments and results exhibited a desirable selectivity and significant sensitivity of the chemosensor 3 for the detection of Cu2+ and Pb2+ ions. The association constant (Ka) of 3-Cu2+ and 3-Pb2+ complexes were determined to be 8.89 × 103 M?1 and 5.65 × 108 M-2, respectively. The obtained limit of detection (LOD) values (1.49 × 10?6 M for Cu2+ and 2.31 × 10?6 M for Pb2+) clearly revealed the considerable sensitivity of the chemosensor 3.

Ultrasound-promoted highly efficient reduction of aromatic nitro compounds to the aromatic amines by samarium/ammonium chloride

Basu, Manas K.,Becker, Frederick F.,Banik, Bimal K.

, p. 5603 - 5606 (2000)

Ultrasound-promoted, highly efficient reduction of several aromatic nitro compounds to the aromatic amines was achieved by samarium/ammonium chloride mediated reaction. (C) 2000 Elsevier Science Ltd.

Route to the tritiation of carbon atom 9 of carcinogenic fluorenylhydroxamic acids

Gutmann,Bell

, p. 255 - 270 (1974)

-

Non-specific tritiation of some carcinogenic aromatic amines

Breeman,Kaspersen,Westra

, p. 741 - 750,748,749 (1978)

2-Aminofluorene, 4-amino-3-methylbiphenyl, 4-amino-biphenyl and 4-amino-4'-fluorobiphenyl were tritiated by acid catalyzed exchange of the corresponding nitro compounds followed by catalytic reduction. The exchange reactions were carried out by heating the nitro compounds in [3H]-trifluoroacetic acid with a catalytic amount of trifluoromethanesulphonic acid (TFMS). No loss of tritium could be detected during the conversion of the tritiated nitro compounds into the corresponding amines by catalytic hydrogenation. Incorporation into the ortho position is very low (4%). During the metabolic activation and binding of the tritiated N-acetyl-2-aminofluorene to rat liver DNA in vivo, no tritium exchange occurred.

Amidofluorene-appended lower rim 1,3-diconjugate of calix[4]arene: Synthesis, characterization and highly selective sensor for Cu2+

Hosseinzadeh, Rahman,Nemati, Mohammad,Zadmard, Reza,Mohadjerani, Maryam

, p. 1749 - 1757 (2016)

Functionalization of calix[4]arene with amidofluorene moieties at the lower rim led to formation of the 1,3-diconjugate of calix[4]arene L as a novel fluorescent chemosensor for Cu2+. The receptor molecule L exhibited a pronounced selectivity towards Cu2+ over other mono and divalent ions. The formation of the complex between L and Cu2+ was evaluated by absorption, fluorescence and 1H NMR spectroscopy. The sensor L showed a remarkable color change from colorless to purple and a fluorescence quenching only upon interaction with Cu2+. The 1:1 stoichiometry of the obtained complex has been determined by Job's plot. The association constant determined by fluorescence titration was found to be 1.8 × 106 M-1. The sensor showed a linear response toward Cu2+ in the concentration range from 1 to 10 μM with a detection limit of 9.6 × 10-8 M.

Half-Sandwich Ruthenium Complexes of Amide-Phosphine Based Ligands: H-Bonding Cavity Assisted Binding and Reduction of Nitro-substrates

Pachisia, Sanya,Kishan, Ram,Yadav, Samanta,Gupta, Rajeev

, p. 2009 - 2022 (2021/02/06)

We present synthesis and characterization of two half-sandwich Ru(II) complexes supported with amide-phosphine based ligands. These complexes presented a pyridine-2,6-dicarboxamide based pincer cavity, decorated with hydrogen bonds, that participated in the binding of nitro-substrates closer to the Ru(II) centers, which is further supported with binding and docking studies. These ruthenium complexes functioned as the noteworthy catalysts for the borohydride mediated reduction of assorted nitro-substrates. Mechanistic studies not only confirmed the intermediacy of [Ru-H] in the reduction but also asserted the involvement of several organic intermediates during the course of the catalysis. A similar Ru(II) complex that lacked pyridine-2,6-dicarboxamide based pincer cavity substantiated its unique role both in the substrate binding and the subsequent catalysis.

Hydrogenation of nitroarenes catalyzed by a dipalladium complex

Hung, Ming-Uei,Yang, Shu-Ting,Ramanathan, Mani,Liu, Shiuh-Tzung

, (2017/09/06)

A dipalladium complex [Pd2(L)Cl2](PF6)2 (2), via the substitution of (PhCN)2PdCl2 with 5-phenyl-2,8-bis(6′-bipyridinyl)-1,9,10-anthyridine (L) followed by the anion exchange, was found to be a good pre-catalyst for the reduction of nitroarenes to yield the corresponding anilines under atmospheric pressure of hydrogen in methanol. This method provides a straightforward access to a diverse array of functionalized anilines, exhibiting a possible application in synthetic chemistry. The catalytic activity of this complex is enhanced by the di-metallic system via the synergistic effect.

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