7321-27-9

Basic information

• Product Name: 2-Bromoanthracene
• Synonyms: 2-BROMOANTHRACENE;2-BroMoantharacene;Anthracene, 2-broMo-;2-Bromonatthracene;2-Bromoanthracene,97%
• CAS NO: 7321-27-9
• Molecular Formula: C₁₄H₉Br
• Molecular Weight: 257.13
• EINECS: 1312995-182-4
• Product Categories: Electronic Chemicals;Anthracenes;Anthracene series;Anthracene derivatives;OLED materials,pharm chemical,electronic
• Mol File: 7321-27-9.mol

Chemical Properties

• Melting Point: 220 °C
• Boiling Point: 389.679 °C at 760 mmHg
• Flash Point: 190.306 °C
• Appearance: /
• Density: 1.479 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.733
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), DMSO (Sparingly), Methanol (Very Slightly)
• CAS DataBase Reference: 2-Bromoanthracene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromoanthracene(7321-27-9)
• EPA Substance Registry System: 2-Bromoanthracene(7321-27-9)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 7321-27-9(Hazardous Substances Data)

Usage

Chemical Properties

Yellow solid

InChI:InChI=1/C14H9Br/c15-14-6-5-12-7-10-3-1-2-4-11(10)8-13(12)9-14/h1-9H

Upstream product

• 572-83-8 2-bromoanthracene-9,10-dione 
• 2269-22-9 aluminum tri-sec-butoxide 

Downstream Products

• 676578-20-4 2-(anthracene-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1250-59-5 Bianthryl-(2,2') 
• 1247-92-3 2-anthryldiphenylphosphine 
• 1172-98-1 anthracen-2-yldiphenylphosphine oxide 
• 960071-98-1 (2R,3S,5R)-5-(2-anthrylethynyl)-3-hydroxy-2-(4,4'-dimethoxytrityloxymethyl)tetrahydrofuran 
• 141981-64-8 anthracene-2-ylboronic acid 
• 1301205-51-5 C₂₁H₁₃ClO 
• 1430417-85-8 2-(1-pyreno-ethynyl)anthracene 
• 1593560-78-1 2,5-di(anthracen-2-yl)-1-methyl-1,3,4-triphenylsilole 
• 1593560-75-8 2,5-di(anthracen-2-yl)-1,1-dimethyl-3,4-diphenylsilole 
• 78053-56-2 2-Ethynylanthracene 
• 109871-20-7 [2]anthryl-phenyl-amine 
• 248-93-1 13H-indeno[1,2-b]anthracene 

Relevant articles and documents

Thermally stable organic thin film transistors based on 2-(anthracen-2-yl)tetracene

Organic semiconductors with high mobility and high thermal stability are of great importance for practical application of organic electronics. To explore new semiconductors by taking advantage of the intrinsic properties of tetracene molecule, herein, we report the design and synthesis of a novel p-type tetracene derivatives, 2-(anthracen-2-yl)tetracene (TetAnt). Top contact organic thin-film transistors (OTFTs) based on TetAnt show a hole mobility of up to 0.79 cm2 V?1 s?1. In addition, a high mobility of ~0.4 cm2 V?1 s?1 is maintained even after thermal stressed to a high temperature of 290 °C, indicating the excellent thermal stability of TetAnt.

Naked eye detection of anions by 2,2¤-bianthracene derivative bearing urea groups in various organic solvents

A highly fluorescent 2,2¤-bianthryl derivative bearing urea groups (2) was prepared as an anion receptor. The UV-vis and fluorescence titrations of 2 in various organic solvents revealed that the association constants (K11) were correlated with acceptor number and Swain acity of the solvents used, and tetrahydrofuran was found to strongly enhance the K11 for Cl1 and AcO1 due to enthalpy driven complexation, in which naked eye detection of AcO1 was achieved.

Aerobic C(sp2)-H Hydroxylations of 2-Aryloxazolines: Fast Access to Excited-State Intramolecular Proton Transfer (ESIPT)-Based Luminophores

The direct hydroxylation of 2-aryloxazolines via a deprotonative magnesiation using TMPMgCl·LiCl and subsequent oxidation with molecular oxygen or air as a green oxidant is reported. This method proceeds under mild conditions at room temperature with high regioselectivity and chemoselectivity. The obtained phenols exhibit tunable luminescence properties, induced by excited-state intramolecular proton transfer. This method opens a new opportunity for the sustainable synthesis of luminescent organic molecules.

Preparation method of 2-bromoanthracene

The invention relates to a preparation method of 2-bromoanthracene. The preparation method comprise following steps: a, an aluminium chloride solid is added into diglyme so as to obtain a first solution, wherein the preparation temperature is controlled to be 30 to 70 DEG C, and after preparation, the temperature is reduced to 20 to 40 DEG C; b, 2-bromoanthraquinone, potassium borohydride, and diglyme are mixed, an obtained mixture is heated to 80 to 120 DEG C, the temperature is maintained for 0.5 to 5h, the first solution is added dropwise, the temperature of an obtained system is maintained to be 90 to 130 DEG C so as to obtain a second solution; c, the second solution is cooled to 90 to 120 DEG C, a hydrochloric acid aqueous solution is added for hydrolysis at 20 to 60 DEG C, after hydrolysis, cooling and pumping filtration are carried out so as to obtain a crude product; and d, absolute ethyl alcohol is added into the crude product, the temperature is increased to 50 to 70, and is maintained for 0.5 to 3.0h, and then an obtained product is cooled to 10 to 40 DEG C, and is subjected to pumping filtration so as to obtain a 2-bromoanthracene refined product. The beneficial effects of the preparation method are that: synthesis is simple, post-treatment is convenient; the preparation method is suitable for industrialized production; and relatively high referential value and commercial value are achieved in the field of halogenated anthracene preparation.

A small molecule composed of anthracene and thienothiophene devised for high-performance optoelectronic applications

An asymmetric small molecule composed of anthracene and alkylated thienothiophene (2-(anthracen-2-yl)-5-hexylthieno[3,2-b]thiophene) was synthesized via the Suzuki coupling reaction. The thermal stability, photochemical properties, and morphological characteristics were investigated using thermogravimetric analysis, differential scanning calorimetry, cyclic voltammetry, UV-visible spectroscopy, and X-ray diffraction techniques. The compound demonstrated a good thermal stability of 5% at a decomposition temperature of 336 °C. The solution-processed single-crystal transistor, devised with 2-(anthracen-2-yl)-5-hexylthieno[3,2-b]thiophene, exhibited high performance with a hole mobility of 0.1 cm2/Vs. Furthermore, by utilizing the high mobility of 2-(anthracen-2-yl)-5-hexylthieno[3,2-b]thiophene, we demonstrated its unprecedented high photoresponsivity of 3370 A/W, a finding that can be attributed to the very efficient photoconductive behavior of a single crystal of 2-(anthracen-2-yl)-5-hexylthieno[3,2-b]thiophene.

Fluorescent cytotoxic compounds specific for the cellular polyamine transport system

Cyano-substituted anthracene containing polyamines were synthesized and shown to be efficient polyamine transporter ligands. Moreover, these compounds (3 and 4) had improved fluorescence properties over previously known anthryl-polyamine conjugates, which facilitated their intracellular trafficking by confocal microscopy. These cytotoxic fluorescent agents may find use as molecular probes which traffic into cells via the polyamine transport system and may also be viable anticancer drugs which are readily quantified in human tissues due to their excellent fluorescence properties: (excitation: λ 405 nm) and emission (420 nm) occurs in the visible light range. The ability to excite and emit in the visible range provides an advantage to these probes as these wavelengths are not toxic to human cells (versus ultraviolet mediated excitations, λ400 nm) and visible light lasers are less costly to purchase and operate than UV laser sources.

A first synthesis and physical properties of asymmetric anthracenes-thiophenes bridged with ethylene

Here we report our recent result of a new semiconductor material, which has an asymmetric structure. The synthesized molecules consist of anthracene and thiophene connected by bridged ethylene and substituted with hexyl or dodecyl groups as pendants. The semiconductors were synthesized using a McMurry coupling reaction between anthracene-2-carbaldehyde and corresponding 5-hexyl(or dodecyl)thiophene-2-carbaldehyde. A first investigation of synthesized asymmetry AVHT (9a) and AVDT (9b) for the physical properties showed that they have high oxidation potential and thermal stability. The devices prepared by using AVHT (9a) and AVDT (9b) showed the mobility of 2.6 × 10-2 cm 2/Vs and 4.4 × 10-3 cm2/Vs, respectively, in solution processed OTFTs.

Synthesis and characterization of anthracene derivative for organic field-effect transistor fabrication

Here we report on the synthesis and characterization of anthracene derivative for solution processable organic field-effect transistors. The transistor devices with bottom-contact geometry provided a maximum field-effect mobility of 3.74×10-4 cm2 V-1 s -1 as well as current on/off ratio of 5.05×104 and low threshold voltage. Structural information in the solid state is obtained by thermal analysis and two-dimensional wide angle X-ray scattering (2D-WAXS). From the 2D-WAXS, it is clear that the planes of anthracene rings and benzene ring of the molecule are different in solid state. We assume similar arrangement in the thin-film which limit the effective hopping and thus charge mobility. Copyright

A new InCl3-catalyzed reduction of anthrones and anthraquinones by using aluminum powder in aqueous media

InCl3-catalyzed reduction of anthrones and anthraquinones was investigated under different conditions. A new synthetic method for anthracenes in aqueous media under mild conditions is described.

Bis(2-acenyl)acetylene semiconductors

Bis(2-acenyl)acetylene compounds that are useful as organic semiconductors are disclosed. The compounds, when used as the active layer in OTFTs exhibit device characteristics, like charge-carrier mobilities and current on/off ratios, that are comparable to those of pentacene. Also described are semiconductor devices comprising at least one compound of the invention; and articles comprising the semiconductor devices such as thin film transistors or transistor arrays, and electroluminescent lamps.