2-Aminofluorene

Base Information

• Chemical Name: 2-Aminofluorene
• CAS No.: 153-78-6
• Molecular Formula: C13H11N
• Molecular Weight: 181.237
• Hs Code.: 29214980
• European Community (EC) Number: 205-817-8
• NSC Number: 26328,12274
• UN Number: 2811
• UNII: 3A69OS195N
• DSSTox Substance ID: DTXSID1049223
• Nikkaji Number: J3.274C,J2.446.773B
• Wikipedia: 2-Aminofluorene
• Wikidata: Q26840753
• ChEMBL ID: CHEMBL84472
• Mol file: 153-78-6.mol

Synonyms:2-aminofluorene;2-fluorenamine;2-fluorenylamine

Chemical Property of 2-Aminofluorene

Chemical Property:

• Appearance/Colour: white to slightly brown crystalline powder
• Vapor Pressure: 2.56E-05mmHg at 25°C
• Melting Point: 124-128 °C(lit.)
• Refractive Index: 1.697
• Boiling Point: 379.3 °C at 760 mmHg
• PKA: 4.34±0.20(Predicted)
• Flash Point: 204.8 °C
• PSA: 26.02000
• Density: 1.203 g/cm³
• LogP: 3.42120
• Storage Temp.: Store below +30°C.
• Solubility.: soluble in Ether,Alcohol
• Water Solubility.: <0.1 g/100 mL at 19.5℃
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 181.089149355
• Heavy Atom Count: 14
• Complexity: 213
• Transport DOT Label: Poison

Purity/Quality:

2-Aminofluorene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 68-40
• Safety Statements: 45-36/37-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Polycyclic Aromatic Hydrocarbons
• Canonical SMILES: C1C2=CC=CC=C2C3=C1C=C(C=C3)N
• Description: Occupational exposure to polycyclic aromatic amines (PAA) has occurred historically in the rubber, textile, and dye industries. Some sources of nonoccupational exposure to PAAs include inhalation of tobacco smoke, emissions from heated cooking oil and diesel engine exhaust, and dermal exposure to hair dyes. During the 1870s, the first aromatic amine dyes were manufactured in Germany (dyes of natural origin were used prior to the synthesis of dyes). In 1895, a physician by the name Rehn reported a cluster of patients who had developed bladder cancer. He observed that all of the affected workers were employed at a site in Germany that manufactured fuschsin dye. The workers had all been exposed to large amounts of intermediate arylamines. The United States first started manufacturing dyes in the early 1900s when trade between the United States and Germany was halted during the First World War. DuPont was the first company to begin manufacturing synthetic dyes in the United States, and shortly thereafter (1930s) the physicians employed by DuPont also started reporting an increased incidence of workers who had developed bladder cancer. During 1947, a physician by the name of Mengellsdorf who was employed by DuPont reported that 100% of the workers who handled the chemical betanaphthylamine had developed bladder cancer. By the 1950s, Chinese dye manufacturers reported the development of bladder cancer in workers who handled benzidine. Evidence of the development of bladder cancer associated with the manufacture of dyes continued to mount, and during the 1970s dye manufacturing was discontinued in the United States and was taken over by developing nations. During the early 1970s, the US Occupational Safety and Health Administration (OSHA) began regulating aromatic amines that had been associated with the development of bladder cancers. During the 1980s, DuPont reported retrospectively that 316 of their dye manufacturing workers had developed bladder cancer prior to the discontinuation of dye manufacturing in the United States. During the 1990s, the first reports of bladder cancer in the Chinese dye manufacturing industry became public. Hair dye products manufactured prior to the mid-1970s contained chemicals that were shown to produce cancer in rodents. Some of these chemical included aromatic amines. The manufacturers of hair coloring products began reformulating their products to remove these potentially carcinogenic compounds from their products beginning in the mid-1970s. It is not clear if some of the ingredients in contemporary hair products can cause an increased risk of cancer. The US National Cancer Institute reported that there may be an increased risk of developing non-Hodgkin’s lymphoma in people who used hair dyes prior to the 1980s; however, the data are limited and often inconsistent.
• Uses: PAAs are used in the rubber, textile, and dye industries. They are used as intermediates in the manufacture of plastics, drugs, and carbamate pesticides. The aromatic amines 2-aminofluorene and N-acetyl aminofluorene were being developed during the 1930s for use as pesticides; however, they were found to be carcinogenic in laboratory animals. They were never marketed as pesticides.

Technology Process of 2-Aminofluorene

There total 19 articles about 2-Aminofluorene 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: 99.0%

2-nitro-9H-fluorene (607-57-8) → 2-aminofluorene (153-78-6)

Guidance literature:

With ammonium acetate; zinc; In water; Product distribution; Ambient temperature; influence of ammonium acetate; the lenght of the reducer column;;

DOI:10.1021/ac00154a001

Reference yield: 99.0%

→ 2-aminofluorene (153-78-6)

Guidance literature:

In methanol; water; at 20 ℃; for 0.0833333h;

With ammonia borane; In methanol; water; at 20 ℃;

Reference yield: 93.0%

→ 2-fluorenemaleimide + 2-aminofluorene (153-78-6)

Guidance literature:

upstream raw materials:

2-nitro-9H-fluorene

2-bromo-9H-fluorene

9-bromo-2-nitro-fluorene

2-acetylaminofluorene

Downstream raw materials:

N-fluoren-2-yl-succinamic acid

2-<2-Furoylamino>-fluoren

thiophene-2-carboxylic acid fluoren-2-ylamide

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

Refernces

• 1、 Tajbakhsh, Mahmood,Chalmardi, Gholam Babaei,Bekhradnia, Ahmadreza,Hosseinzadeh, Rahman,Hasani, Nahid,Amiri, Mohammadreza Azizi. "A new fluorene-based Schiff-base as fluorescent chemosensor for selective detection of Cr3?+ and Al3?+". . p. 22 - 31. Retrieved 2018.
• 2、 Patil, Nilesh M.,Bhosale, Manohar A.,Bhanage, Bhalchandra M.. "Transfer hydrogenation of nitroarenes into anilines by palladium nanoparticles via dehydrogenation of dimethylamine borane complex". . p. 86529 - 86535. Retrieved 2015.
• 3、 Paul, Somnath,Mitra, Ishani,Dutta, Rituparna,Bardhan, Munmun,Bose, Mridul,Das, Subrata,Saha, Mithu,Ganguly, Tapan. "Comparative analysis to explore the suitability of a short chain dyad in its pristine and nanocomposite forms for designing artificial light energy conversion device". . p. 7873 - 7881. Retrieved 2018.
• 4、 Kitamura,Narai,Hayashi,Tatsumi. "Rabbit liver enzymes responsible for reduction of nitropolycyclic aromatic hydrocarbons". . p. 776 - 779. Retrieved 1983.
• 5、 Shi, Shu-Kui,Li, Xin,Guo, Hui-Li,Fan, Yan-Hua,Li, Hai-Yan,Dang, Dong-Bin,Bai, Yan. "Ionothermal Synthesis of an Antimonomolybdate Cluster, [Sb8MoVI13MoV5O66]5-, and Its Catalytic Behavior to the Reduction of Nitrobenzene". . p. 11213 - 11217. Retrieved 2020.
• 6、 Tan, Fang-Fang,Tang, Kai-Li,Zhang, Ping,Guo, Yan-Jun,Qu, Mengnan,Li, Yang. "Utilization of a Hydrogen Source from Renewable Lignocellulosic Biomass for Hydrogenation of Nitroarenes". . p. 4189 - 4195. Retrieved 2019/03/07.