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1-Amino-2-bromonaphthalene is an organic compound characterized by the chemical formula C10H8BrN. It is a derivative of naphthalene, featuring a naphthalene ring with a bromine atom and an amino group attached to it. 1-Amino-2-bromonaphthalene is notable for its potential applications in various fields due to its unique chemical structure.

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  • 771-14-2 Structure
  • Basic information

    1. Product Name: 1-Amino-2-bromonaphthalene
    2. Synonyms: 1-Amino-2-bromonaphthalene;2-Bromo-1-naphthylamine;2-bromonaphthalen-1-amine
    3. CAS NO:771-14-2
    4. Molecular Formula: C10H8BrN
    5. Molecular Weight: 222.08
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 771-14-2.mol
  • Chemical Properties

    1. Melting Point: 67.0 to 71.0 °C
    2. Boiling Point: 339.4°C at 760 mmHg
    3. Flash Point: 159.1°C
    4. Appearance: /
    5. Density: 1.563g/cm3
    6. Vapor Pressure: 9.22E-05mmHg at 25°C
    7. Refractive Index: 1.718
    8. Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
    9. Solubility: N/A
    10. PKA: 1.05±0.10(Predicted)
    11. CAS DataBase Reference: 1-Amino-2-bromonaphthalene(CAS DataBase Reference)
    12. NIST Chemistry Reference: 1-Amino-2-bromonaphthalene(771-14-2)
    13. EPA Substance Registry System: 1-Amino-2-bromonaphthalene(771-14-2)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 771-14-2(Hazardous Substances Data)

771-14-2 Usage

Uses

Used in Pharmaceutical Synthesis:
1-Amino-2-bromonaphthalene is used as a key intermediate in the synthesis of various pharmaceuticals. Its presence in these compounds can contribute to their therapeutic properties, making it a valuable component in drug development.
Used in Dye Production:
In the dye industry, 1-Amino-2-bromonaphthalene is utilized as a precursor for the production of dyes. Its chemical structure allows for the creation of dyes with specific color characteristics, which are important for various applications such as textiles, printing, and other industrial processes.
Used in Organic Material Synthesis:
1-Amino-2-bromonaphthalene is employed as a building block in the synthesis of organic materials. Its unique structure can be incorporated into the design of new materials with tailored properties, such as improved stability or specific interactions with other molecules.
Used in Organic Electronic Devices:
1-Amino-2-bromonaphthalene is used as a component in the development of organic electronic devices and materials. Its electronic properties, such as its ability to act as a donor or acceptor in electronic systems, make it a promising candidate for applications in organic photovoltaics, organic light-emitting diodes (OLEDs), and other electronic components.
While the provided materials do not specify the exact applications in different industries, the above uses are inferred based on the compound's properties and typical applications of similar organic compounds in various fields.

Check Digit Verification of cas no

The CAS Registry Mumber 771-14-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 7,7 and 1 respectively; the second part has 2 digits, 1 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 771-14:
(5*7)+(4*7)+(3*1)+(2*1)+(1*4)=72
72 % 10 = 2
So 771-14-2 is a valid CAS Registry Number.
InChI:InChI=1/C10H8BrN/c11-9-6-5-7-3-1-2-4-8(7)10(9)12/h1-6H,12H2

771-14-2SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-Amino-2-bromonaphthalene

1.2 Other means of identification

Product number -
Other names 2-bromonaphthalen-1-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:771-14-2 SDS

771-14-2Relevant articles and documents

Catalyst-Free 1,2-Dibromination of Alkenes Using 1,3-Dibromo-5,5-dimethylhydantoin (DBDMH) as a Bromine Source

Wang, Lei,Zhai, Lele,Chen, Jinyan,Gong, Yulin,Wang, Peng,Li, Huilin,She, Xuegong

supporting information, p. 3177 - 3183 (2022/02/23)

A direct 1,2-dibromination method of alkenes is realized using 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) as a bromine source. This reaction proceeds under mild reaction conditions without the use of a catalyst and an external oxidant. Various sorts of alkene substrates are transformed into the corresponding 1,2-dibrominated products in good to excellent yields with broad substrate scope and exclusive diastereoselectivity. This method offers a green and practical approach to synthesize vicinal dibromide compounds.

Atroposelective Synthesis, Structure and Properties of a Novel Class of Axially Chiral N-Aryl Quinolinium Salt

Sweet, Jamie S.,Rajkumar, Sundaram,Dingwall, Paul,Knipe, Peter C.

supporting information, p. 3980 - 3985 (2021/03/31)

Inspired by naturally occurring molecules containing atropisomeric N+-C axes, we have developed a novel synthetic approach to generate a library of axially chiral N-aryl quinolinium salts. Enantiopurities up to 93 % ee were obtained via a four-step route from commercially available precursors. Axial stereochemistry was controlled through an enantioselective ring-closing Buchwald–Hartwig coupling reaction. The structure and properties of the salts were examined by X-ray crystallography, DFT, UV-Vis, and fluorescence spectroscopy, revealing high rotational barriers and solvatochromic behaviour.

Compound for organic photoelectric device Composition for organic photoelectric device, organic photoelectric device, and display device

-

Paragraph 0225-0229, (2021/10/13)

A compound for an organic optoelectronic device, a composition for an organic optoelectronic device including the same, an organic optoelectronic device, and a display device, the compound being represented by a combination of Chemical Formula 1 and Chemical Formula 2:

Mild and Selective Method of Bromination of Flavonoids

Hurtová, Martina,Biedermann, David,Kuzma, Marek,K?en, Vladimír

, p. 3324 - 3331 (2020/11/30)

A new method was developed for the mild and selective bromination of simple aromatic compounds and flavonoids in good yields using α,β-dibromohydrocinnamic acid in the presence of a base. This procedure enables selective mono- or dibromination of compounds highly sensitive to oxidative or radical attack. New brominated derivatives of silymarin flavonolignans and related flavonoids were prepared. These brominated derivatives can be used as valuable synthetic intermediates in further synthesis.

Making endo-cyclizations favorable again: A conceptually new synthetic approach to benzotriazoles via azide group directed lithiation/cyclization of 2-azidoaryl bromides

Ageshina, Alexandra A.,Chesnokov, Gleb A.,Topchiy, Maxim A.,Alabugin, Igor V.,Nechaev, Mikhail S.,Asachenko, Andrey F.

supporting information, p. 4523 - 4534 (2019/05/17)

Although benzotriazoles are important and ubiquitous, currently there is only one conceptual approach to their synthesis: bridging the two ortho-amino groups with an electrophilic nitrogen atom. Herein, we disclose a new practical alternative-the endo-cyclization of 2-azidoaryl lithiums obtained in situ from 2-azido-aryl bromides. The scope of the reaction is illustrated using twenty-four examples with a variety of alkyl, alkoxy, perfluoroalkyl, and halogen substituents. We found that the directing effect of the azide group allows selective metal-halogen exchange in aryl azides containing several bromine atoms. Furthermore, (2-bromophenyl)diazomethane undergoes similar cyclization to give an indazole. Thus, cyclizations of aryl lithiums containing an ortho-X = Y = Z group emerge as a new general approach for the synthesis of aromatic heterocycles. DFT computations suggested that the observed endo-selectivity applies to the anionic cyclizations of other functionalities that undergo "1,1-additions" (i.e., azides, diazo compounds, and isonitriles). In contrast, cyclizations with the heteroatomic functionalities that follow the "1,2-addition" pattern (cyanates, thiocyanates, isocyanates, isothiocyanates, and nitriles) prefer the exo-cyclization path. Hence, such reactions expand the current understanding of stereoelectronic factors in anionic cyclizations.

Synthesis, kinetics, and mechanism of bromophenols by N-bromophthalimide in aqueous acetic acid

Anjaiah, Birla,Prameela, Kethavath,Srinivas, Pabba,Rajanna, Kamatala Chinna

, p. 804 - 812 (2018/09/11)

The kinetics and mechanism of bromination of phenol and its substituents, viz. 4-chlorophenol, 4-bromophenol, 4-methylphenol, and 4-methoxyphenol by N-bromophthalimide (NBP) in the presence of mercuric acetate in the temperature range of 303–318?K in aqueous acetic acid medium have been investigated. The reaction follows first-order dependence on [NBP] and fractional order dependence of rate on [Phenol]. The activation parameters have been evaluated, and based on the observed kinetic results the probable mechanism has been proposed. Observed kinetic features and Hammett's reaction constant (ρ) suggests that bromination occurs through electrophilic substitution of bromonium ion (Br+) into the aromatic ring in the transition state. Large negative entropy of activation values probably suggests the rigid nature of transition state.

Synthesis of indole-fused heteroacenes by cascade cyclisation involving rhodium(ii)-catalysed intramolecular C-H amination

Matsuda, Takanori,Ito, Hirotaka

supporting information, p. 6703 - 6707 (2018/09/29)

Heteroacenes are potentially important materials for organic electronics and their syntheses are of topical interest. Herein we report the development of a catalytic, redox-neutral reaction for the synthesis of the 5,10-dihydroindolo[3,2-b]indole class of

Molecular propellers that consist of dehydrobenzo[14]annulene blades

Nobusue, Shunpei,Mukai, Yuichi,Fukumoto, Yo,Umeda, Rui,Tahara, Kazukuni,Sonoda, Motohiro,Tobe, Yoshito

supporting information, p. 12814 - 12824,11 (2020/09/14)

A new class of propel- ler-shaped compound (4), which consisted of dehydrobenzo[14]annulene ([14]DBA) blades, as well as its naphtho homologues (5 and 6), have been prepared. Although NMR studies of compound 4 did not provide useful information regarding

Coarctate versus pericyclic reactivity in naphthalene-fused azo-ene-ynes: Synthesis of benzocinnolines and benzoisoindazoles

McClintock, Sean P.,Zakharov, Lev N.,Herges, Rainer,Haley, Michael M.

scheme or table, p. 6798 - 6806 (2011/08/06)

The cyclization reactions of naphthalene-fused azo-ene-yne compounds are explored both computationally and experimentally. Calculations reveal that naphtho-fusion to an azo- ene-yne scaffold does not significantly alter the transition state energies compared to the benzene-based systems; however, fusing the naphthalene in an angular fashion leads to lower energy intermediates due to the creation of arenes possessing greater aromaticity. Experimentally, the cyclization of the angular systems yields not only the expected monomeric benzocinnolines and benzoisoindazoles, but also several dimeric structures, including one that readily isomerizes in the presence of light and/or trace acid. Copyright

Lewis acid-promoted synthesis of unsymmetrical and highly functionalized carbazoles and dibenzofurans from biaryl triazenes: Application for the total synthesis of clausine C, clausine R, and clauraila A

Yang, Weijun,Zhou, Jun,Wang, Binjie,Ren, Hongjun

supporting information; scheme or table, p. 13665 - 13669 (2012/01/15)

A natural approach: A Lewis acid-promoted nucleophilic aromatic substitution approach to the regioselective synthesis of highly substituted carbazoles and dibenzofurans has been developed. The annulation process is applied to the total synthesis of carbazole alkaloids clausine C, clausine R, and clauraila A (see scheme).

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