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Cas Database

1056246-70-8

1056246-70-8

Identification

  • Product Name:2-bromo-1-tetralone

  • CAS Number: 1056246-70-8

  • EINECS:

  • Molecular Weight:225.085

  • Molecular Formula: C10H9BrO

  • HS Code:

  • Mol File:1056246-70-8.mol

Synonyms:2-bromo-1-tetralone

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Safety information and MSDS view more

  • Signal Word:no data available

  • Hazard Statement:no data available

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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Relevant articles and documentsAll total 72 Articles be found

Acridine Orange Hemi(Zinc Chloride) Salt as a Lewis Acid-Photoredox Hybrid Catalyst for the Generation of α-Carbonyl Radicals

Das, Sanju,Mandal, Tanumoy,De Sarkar, Suman

supporting information, p. 755 - 765 (2021/12/10)

A readily accessible organic-inorganic hybrid catalyst is reported for the reductive fragmentation of α-halocarbonyl compounds. The robust hybrid catalyst is a self-stabilizing combination of ZnCl2 Lewis acid and acridine orange as the photoactive organic dye. Mechanistic specifics of this hybrid catalyst have been studied in detail using both photophysical and electrochemical experiments. A systematic study enabled the discovery of the appropriate Lewis acid for the effective LUMO stabilization of α-halocarbonyl compounds and thereby lowering of reduction potential within the range of a standard organic dye. This strategy resolves the issues like dehalogenative hydrogenation or homo-coupling of alkyl radicals by guiding the photoredox cycle through an oxidative quenching pathway. The cooperativity between the photoactive organic dye and the Lewis acid counterparts empowers functionalization with a wide range of coupling partners through efficient and controlled generation of alkyl radicals and serves as an appropriate alternative to the expensive late transition metal-based photocatalysts. To demonstrate the application potential of this cooperative catalytic system, four different synthetic transformations of α-carbonyl bromides were explored with broad substrate scopes.

Highly Deformed o-Carborane Functionalised Non-linear Polycyclic Aromatics with Exceptionally Long C?C Bonds

Marsh, Adam V.,Little, Mark,Cheetham, Nathan J.,Dyson, Matthew J.,Bidwell, Matthew,White, Andrew J. P.,Warriner, Colin N.,Swain, Anthony C.,McCulloch, Iain,Stavrinou, Paul N.,Heeney, Martin

supporting information, p. 1970 - 1975 (2020/12/25)

The effect of substituting o-carborane into the most sterically hindered positions of phenanthrene and benzo(k)tetraphene is reported. Synthesised via a Bull–Hutchings–Quayle benzannulation, the crystal structures of these non-linear acenes exhibited the highest aromatic deformation parameters observed for any reported carborane compound to date, and among the largest carboranyl C?C bond length of all organo-substituted o-carboranes. Photoluminescence studies of these compounds demonstrated efficient intramolecular charge-transfer, leading to aggregation induced emission properties. Additionally, an unusual low-energy excimer was observed for the phenanthryl compound. These are two new members of the family of carborane-functionalised non-linear acenes, notable for their peculiar structures and multi-luminescent properties.

Annulation reaction of cyclic pyridinium ylides with: In situ generated azoalkenes for the construction of spirocyclic skeletons

Quan, Bao-Xue,Yuan, Wei-Cheng,Zhang, Ming-Liang,Zhang, Xiao-Mei,Zhao, Jian-Qiang,Zhou, Ming-Qiang,Zhuo, Jun-Rui

supporting information, p. 1886 - 1891 (2020/03/23)

Two new types of cyclic pyridinium ylides were designed and further used in reactions with azoalkenes to access structurally diverse spirocyclic compounds. A range of spiropyrazoline oxindoles could be smoothly obtained in up to 99% yield via a [4 + 1] annulation process with oxindole 3-pyridinium ylides as C1 synthons. Similarly, a series of spiropyrazoline indanones could be prepared with indanone 2-pyridinium ylides as C1 synthons. This work represents the first example of cyclic pyridinium ylides as C1 synthons for the efficient construction of spirocyclic compounds.

Azologization and repurposing of a hetero-stilbene-based kinase inhibitor: Towards the design of photoswitchable sirtuin inhibitors

Grathwol, Christoph W.,W?ssner, Nathalie,Swyter, S?ren,Smith, Adam C.,Tapavicza, Enrico,Hofstetter, Robert K.,Bodtke, Anja,Jung, Manfred,Link, Andreas

supporting information, p. 2170 - 2183 (2019/09/30)

The use of light as an external trigger to change ligand shape and as a result its bioactivity, allows the probing of pharmacologically relevant systems with spatiotemporal resolution. A hetero-stilbene lead resulting from the screening of a compound that was originally designed as kinase inhibitor served as a starting point for the design of photoswitchable sirtuin inhibitors. Because the original stilbenoid structure exerted unfavourable photochemical characteristics it was remodelled to its heteroarylic diazeno analogue. By this intramolecular azologization, the shape of the molecule was left unaltered, whereas the photoswitching ability was improved. As anticipated, the highly analogous compound showed similar activity in its thermodynamically stable stretched-out (E)-form. Irradiation of this isomer triggers isomerisation to the long-lived (Z)-configuration with a bent geometry causing a considerably shorter end‐to‐end distance. The resulting affinity shifts are intended to enable real‐time photomodulation of sirtuins in vitro.

A Method for the Catalytic Enantioselective Synthesis of Chiral α-Azido and α-Amino Ketones from Racemic α-Bromo Ketones, and Its Generalization to the Formation of Bonds to C, O, and S

Da Silva Gomes, Roberto,Corey

supporting information, p. 20058 - 20061 (2019/12/27)

A new and practical method has been developed for the transformation of racemic α-bromo ketones to chiral α-azido and α-amino ketones with high enantioselectivity using phase transfer, ion-pair mediated reactions with a recoverable chiral quaternary salt (10 mol %) as catalyst in fluorobenzene-water. The process has been generalized to a variety of other attachments including of C, O, S, and NHR.

Process route upstream and downstream products

Process route

2,2-dibromo-1,2,3,4-tetrahydronaphthalen-1-one
51114-70-6

2,2-dibromo-1,2,3,4-tetrahydronaphthalen-1-one

2-bromo-1-tetralone
1056246-70-8,13672-07-6

2-bromo-1-tetralone

3,4-dihydronaphthalene-1(2H)-one
529-34-0

3,4-dihydronaphthalene-1(2H)-one

Conditions
Conditions Yield
With water; 1-methyl-3-pentyl-1H-imidazolium tetrafluoroborate; at 125 ℃; for 0.0333333h; under 2585.74 Torr; microwave irradiation;
86%
3,4-dihydronaphthalene-1(2H)-one
529-34-0

3,4-dihydronaphthalene-1(2H)-one

2-bromo-1-tetralone
1056246-70-8,13672-07-6

2-bromo-1-tetralone

Conditions
Conditions Yield
With bromine; In diethyl ether; for 2h; -10 deg C -> RT;
99%
With N-Bromosuccinimide; ammonium acetate; In diethyl ether; at 25 ℃; for 1.5h;
99%
With bromine; In diethyl ether; Cooling with ice;
99%
With Oxone; ammonium bromide; In methanol; for 0.333333h; regioselective reaction; Reflux;
98%
With sodium hydrogen sulfate; N-Bromosuccinimide; silica gel; at 20 ℃; for 1h;
97%
With bromine; at 0 - 20 ℃;
94%
With copper(II) nitrate trihydrate; hydrogen bromide; oxygen; at 70 ℃; for 2h; Green chemistry;
94%
With N-Bromosuccinimide; In various solvent(s); at 20 ℃; for 0.333333h;
92%
With Galden HT135; bromine; potassium carbonate; In chloroform; at 20 ℃; for 48h;
92%
With bromine; In diethyl ether; at 0 ℃; for 0.583333h; Inert atmosphere;
92%
With bromine; In diethyl ether; at 0 - 20 ℃;
91%
With copper(ll) bromide; In chloroform; ethyl acetate; for 5h; Heating;
90%
With N-Bromosuccinimide; In dimethyl sulfoxide; at 20 - 65 ℃;
90%
With bromine; In diethyl ether; at 0 ℃; for 2h;
90%
With hydrogen bromide; dihydrogen peroxide; In water; at 20 ℃; for 24h; Darkness;
88%
With bromine; In diethyl ether; at 0 ℃; for 0.333333h; regiospecific reaction; Inert atmosphere;
88%
With N-Bromosuccinimide; trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 20 ℃; for 24h;
87%
With ammonium cerium(IV) nitrate; at 25 - 28 ℃; for 4h;
87%
With N-Bromosuccinimide; toluene-4-sulfonic acid; at 20 ℃; for 2h;
86%
With trifluorormethanesulfonic acid; bromine; In dichloromethane; at 20 ℃; Inert atmosphere;
86%
With N-Bromosuccinimide; urea-hydrogen peroxide; 1-butyl-3-methylimidazolium Tetrafluoroborate; at 60 ℃;
85%
With N-Bromosuccinimide; copper(II) bis(trifluoromethanesulfonate); In chloroform; for 7h; Reflux; Inert atmosphere;
85%
With N-Bromosuccinimide; tetrachlorosilane; In acetonitrile; at 20 ℃; for 7h;
85%
With N-Bromosuccinimide; toluene-4-sulfonic acid; In acetonitrile; for 22h; Reflux;
82%
With triphenylphosphine hydrobromide; dimethyl sulfoxide; at 20 ℃; for 12h; chemoselective reaction; Inert atmosphere;
78%
With pyridinium hydrobromide perbromide; In methanol; stereoselective reaction; Reflux; Inert atmosphere;
76%
With aluminum oxide; hexamethylenetetramine; bromine; for 0.166667h; microwave irradiation;
75%
With hydrogen bromide; bromine; acetic acid; at 25 ℃; for 3h;
67%
With tert.-butylhydroperoxide; hydrogen bromide; In 1,4-dioxane; water; for 20h; Heating;
64%
With ferric(III) bromide; [bis(acetoxy)iodo]benzene; In acetic acid; at 20 ℃; for 16h; Inert atmosphere;
60%
With N-Bromosuccinimide; toluene-4-sulfonic acid; at 80 ℃; for 2h;
57%
With N-Bromosuccinimide; toluene-4-sulfonic acid; at 80 ℃; for 2h;
57%
With tetra-N-butylammonium tribromide; In methanol; dichloromethane; at 20 ℃;
50%
With bromine; acetic acid;
With carbon disulfide; bromine;
With bromine; acetic acid;
With bromine; In diethyl ether; chloroform;
With bromine; In tetrachloromethane;
With potassium bromide; copper(ll) bromide; In methanol; water; for 4h; Heating;
With bromine complrex of poly(styrene-co-4-vinylpyridine); dibenzoyl peroxide; In tetrachloromethane; for 4h; Heating;
With bromine; In methanol;
With hydrogen bromide; bromine; In acetic acid;
With bromine; In diethyl ether;
With bromine; In diethyl ether; at 10 ℃;
With N-Bromosuccinimide; toluene-4-sulfonic acid; at 20 ℃; for 2h;
86 % Chromat.
With N-Bromosuccinimide; In diethyl ether; at 30 ℃; for 2h; UV-irradiation;
With bromine; In ethyl acetate;
With sodium hypochlorite; bromine; In acetic acid;
With 1,1'-(ethane-1,2-diyl)dipyridinium bistribromide; In acetonitrile; for 0.166667h;
With N-Bromosuccinimide; amberlyst-15(R); In ethyl acetate; at 20 ℃; for 24h;
With N-Bromosuccinimide; toluene-4-sulfonic acid; In dichloromethane; at 0 - 20 ℃;
With N-Bromosuccinimide; acetic acid; at 20 ℃; Reflux;
With aluminum (III) chloride; bromine; In diethyl ether; at 0 - 20 ℃; Inert atmosphere;
With bromine; In tetrahydrofuran; diethyl ether; at 20 ℃; for 2h; Inert atmosphere; Cooling with ice;
Multi-step reaction with 2 steps
1: triphenyl phosphite; bromine; triethylamine / dichloromethane / 20 h / -78 - 20 °C / Inert atmosphere
2: toluene-4-sulfonic acid; [hydroxy(tosyloxy)iodo]benzene / acetonitrile / 0.03 h / 20 °C / Inert atmosphere
With triphenyl phosphite; [hydroxy(tosyloxy)iodo]benzene; bromine; toluene-4-sulfonic acid; triethylamine; In dichloromethane; acetonitrile;
With N-Bromosuccinimide; toluene-4-sulfonic acid; In dichloromethane; at 0 ℃; for 4h; Inert atmosphere; Reflux;
With N-Bromosuccinimide; ammonium acetate; In diethyl ether; at 0 - 20 ℃; for 2h;
With bromine; In methanol; at 8 ℃; Temperature;
With tetrabutylammomium bromide; dihydrogen peroxide; trifluoroacetic acid; In water; at 25 ℃; for 24h; Inert atmosphere;
76 %Spectr.
With bromine; In diethyl ether; at 0 - 20 ℃;
With N-Bromosuccinimide; toluene-4-sulfonic acid; In dichloromethane; at 40 ℃; for 1h; Reflux;
With hydrogen bromide; dimethyl sulfoxide; In ethyl acetate; at 60 ℃; for 6h;
With N-Bromosuccinimide; toluene-4-sulfonic acid; In dichloromethane; for 4h; Reflux;
With bromine; In chloroform; at 0 - 20 ℃; for 3h;
With copper(ll) bromide; In ethyl acetate; at 20 ℃;
1,2-Dihydronaphthalene
447-53-0

1,2-Dihydronaphthalene

2-bromo-1-tetralone
1056246-70-8,13672-07-6

2-bromo-1-tetralone

Conditions
Conditions Yield
With N-Bromosuccinimide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dimethyl sulfoxide; at 25 - 35 ℃; for 1h; regioselective reaction;
93%
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; water; at 60 ℃; for 2h; Green chemistry;
73%
With dipotassium peroxodisulfate; potassium bromide; In water; at 60 ℃; for 12h; Green chemistry;
65%
4-bromo-1,2-dihydronaphthalene
3333-24-2

4-bromo-1,2-dihydronaphthalene

2-bromo-1-tetralone
1056246-70-8,13672-07-6

2-bromo-1-tetralone

Conditions
Conditions Yield
With [hydroxy(tosyloxy)iodo]benzene; toluene-4-sulfonic acid; In acetonitrile; at 20 ℃; for 0.0333333h; Inert atmosphere;
82%
1-benzyloxy-1,2,3,4-tetrahydro-naphthalene
207398-88-7

1-benzyloxy-1,2,3,4-tetrahydro-naphthalene

2-bromo-1-tetralone
1056246-70-8,13672-07-6

2-bromo-1-tetralone

Conditions
Conditions Yield
With p-nitrobenzenesulfonamide; hydrogen bromide; oxygen; sodium nitrite; In water; acetonitrile; at 0 - 50 ℃; for 24.5h; under 760.051 Torr;
90%
3,4-dihydronaphthalen-1-yl acetate
19455-84-6

3,4-dihydronaphthalen-1-yl acetate

2-bromo-1-tetralone
1056246-70-8,13672-07-6

2-bromo-1-tetralone

Conditions
Conditions Yield
With lead(IV) acetate; sodium bromide; In methanol; at 0 ℃; for 2h;
95%
4-methoxy-1,2-dihydronaphthalene
84716-82-5

4-methoxy-1,2-dihydronaphthalene

2-bromo-1-tetralone
1056246-70-8,13672-07-6

2-bromo-1-tetralone

Conditions
Conditions Yield
With lead(IV) acetate; sodium bromide; In methanol; at 0 ℃; for 0.166667h;
93%
1-trimethylsiloxy-3,4-dihydronaphthalene
38858-72-9

1-trimethylsiloxy-3,4-dihydronaphthalene

2-bromo-1-tetralone
1056246-70-8,13672-07-6

2-bromo-1-tetralone

Conditions
Conditions Yield
With lead(IV) acetate; sodium bromide; In methanol; at 0 ℃; for 0.166667h;
96%
N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

3,4-dihydronaphthalene-1(2H)-one
529-34-0

3,4-dihydronaphthalene-1(2H)-one

2-bromo-1-tetralone
1056246-70-8,13672-07-6

2-bromo-1-tetralone

Conditions
Conditions Yield
amberlyst-15; In ethyl acetate; at 20 ℃; for 0.5h;
90%
1,2,3,4-Tetrahydro-1-naphthol
529-33-9

1,2,3,4-Tetrahydro-1-naphthol

2-bromo-1-tetralone
1056246-70-8,13672-07-6

2-bromo-1-tetralone

Conditions
Conditions Yield
With Oxone; ammonium bromide; In methanol; water; at 20 ℃; for 24h; Green chemistry;
88%

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