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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.

153-78-6

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153-78-6 Hazards Identification

Pictogram(s):

Signal:

Warning

GHS Hazard Statements:

H302 (33.33%): Harmful if swallowed [Warning Acute toxicity, oral]
H312 (16.67%): Harmful in contact with skin [Warning Acute toxicity, dermal]
H315 (16.67%): Causes skin irritation [Warning Skin corrosion/irritation]
H319 (16.67%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H332 (16.67%): Harmful if inhaled [Warning Acute toxicity, inhalation]
H335 (33.33%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
H341 (66.67%): Suspected of causing genetic defects [Warning Germ cell mutagenicity]
H351 (66.67%): Suspected of causing cancer [Warning Carcinogenicity]

Precautionary Statement Codes:

P203, P261, P264, P264+P265, P270, P271, P280, P281, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P318, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories:

Acute Tox. 4 (33.33%)
Acute Tox. 4 (16.67%)
Skin Irrit. 2 (16.67%)
Eye Irrit. 2 (16.67%)
STOT SE 3 (33.33%)

Hazards Summary:

Evidence for carcinogenicity in studies with rats and mice; [HSDB] An irritant; [MSDSonline] See POLYCYCLIC AROMATIC HYDROCARBONS.

153-78-6 Usage

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

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  • 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 academic research and scientific papers

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.

A new fluorene-based Schiff-base as fluorescent chemosensor for selective detection of Cr3?+ and Al3?+

Tajbakhsh, Mahmood,Chalmardi, Gholam Babaei,Bekhradnia, Ahmadreza,Hosseinzadeh, Rahman,Hasani, Nahid,Amiri, Mohammadreza Azizi

, p. 22 - 31 (2018)

2-((9H-fluoren-2-ylimino) methyl)phenol (F3) was synthesized by condensation reaction of 9H-fluoren-2-amine and 2-hydroxybenzaldehyde in EtOH and characterized by its melting point, 1H-,13C NMR and molecular mass. F3 exhibits a high selectivity for detection of Cr3?+ and Al3?+ ions as a fluorescent chemosensor and showed a single emission band at 536?nm upon excitation at 333?nm according to fluorescence emission studies. The addition of Cr3?+ and Al3?+ make a significant increase in fluorescent intensity at 536?nm in CH3CN, while other metal ions have almost no influence on the fluorescence. The fluorescence enhancement was attributed to the inhibited C[dbnd]N isomerization and the obstructed excited state intra-molecular proton transfer (ESIPT) of compound F3. Job's plot and DFT calculations data showed that the binding stoichiometries of F3 with Cr3?+ and Al3?+ are 2:1. The association constants (Ka) for Cr3?+ and Al3?+ were calculated and found to be 8.33?×?104?M??1 and 5.44?×?104?M??1, respectively. The detection limits were also calculated for Cr3?+ and Al3?+ and found to be 2.5?×?10??7?mol/L and 3.1?×?10??7?mol/L, respectively.

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.

Transfer hydrogenation of nitroarenes into anilines by palladium nanoparticles via dehydrogenation of dimethylamine borane complex

Patil, Nilesh M.,Bhosale, Manohar A.,Bhanage, Bhalchandra M.

, p. 86529 - 86535 (2015)

This work reports a simple and highly efficient protocol for reduction of nitroarenes to corresponding amines via dehydrogenation of dimethylamine borane using palladium nanoparticle (Pd NPs) as a versatile heterogeneous catalyst. The facile approach for the synthesis of Pd NPs within 15 min in aqueous medium has been reported. The Pd NPs were well characterized using various analytical techniques such as XRD, FEG-SEM, TEM, EDAX and XPS. The developed catalytic system uses environmentally benign dimethylamine borane as a reducing agent which is highly stable, water soluble and nontoxic. The various amines were synthesized from nitroarenes in excellent yields within 10-60 min at room temperature. The catalyst was reused up to four successive cycles without significant loss in its catalytic activity.

Comparative analysis to explore the suitability of a short chain dyad in its pristine and nanocomposite forms for designing artificial light energy conversion device

Paul, Somnath,Mitra, Ishani,Dutta, Rituparna,Bardhan, Munmun,Bose, Mridul,Das, Subrata,Saha, Mithu,Ganguly, Tapan

, p. 7873 - 7881 (2018)

From the UV-vis, steady state and time resolved spectroscopic investigations on the pristine dyad, dyad-spherical gold nanoparticles (GNP) and dyad-star shaped gold nanoparticles (GNS), it was observed that though in the ground state the dyad in its pristine form possesses trans-type (elongated and planar) isomer but on photoexcitation trans-form converts into cis-structure (folded). Interestingly, the dyad exhibits different behavior when it combines with GNP or GNS. In nanocomposite form, even on photoexcitation some ground state trans-structure still retains its identity in the excited state. The 60% of the trans-species remains unchanged in the excited state due to excitation of dyad-GNS system and possibly this configuration facilitates the hindrance of energy destructive charge recombination processes as in this conformer the donor and acceptor moieties tend to move far away from each other causing lack of overlapping of charge clouds within the two redox components. The dyad-GNS nanocomposite appears to be the best possible light energy conversion or storage device within the three system studied in the present investigation. Investigations are underway to examine how the degree of surface coverage of the dyad on the surface of gold nanoparticles affect its geometry or conformational changes on photoexcitation.

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.

Rabbit liver enzymes responsible for reduction of nitropolycyclic aromatic hydrocarbons

Kitamura,Narai,Hayashi,Tatsumi

, p. 776 - 779 (1983)

The present paper is the first description of mammalian nitroreductases acting upon nitropolycyclic aromatic hydrocarbons. Rabbit liver microsomal and cytosolic fractions have ability to reduce 1-nitropyrene or 2-nitrofluorene to the corresponding amine under anaerobic conditions. The nitroreductase activity in the former fraction is mainly due to a cytochrome P-450 system and that in the latter fraction is due to aldehyde oxidase.

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.

Ionothermal Synthesis of an Antimonomolybdate Cluster, [Sb8MoVI13MoV5O66]5-, and Its Catalytic Behavior to the Reduction of Nitrobenzene

Shi, Shu-Kui,Li, Xin,Guo, Hui-Li,Fan, Yan-Hua,Li, Hai-Yan,Dang, Dong-Bin,Bai, Yan

, p. 11213 - 11217 (2020)

The largest antimonomolybdate monomer, [Sb8MoVI13MoV5O66]5- (1-Sb8Mo18), has been isolated and displays a new breakthrough of polyoxometalates (POMs) with an ionothermal synthesis strategy. 1-Sb8Mo18 features the first hexanuclear sandwich-Type polymolybdate (POMo) with an unexpected metal ring {Sb6O12} to make its debut in Sb clusters. Furthermore, 1-Sb8Mo18 exhibits a prominent catalytic activity for reducing nitrobenzene to aniline with excellent sustainability.

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.

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