Welcome to LookChem.com Sign In|Join Free

Cas Database

108-86-1

108-86-1

Identification

  • Product Name:Bromobenzene

  • CAS Number: 108-86-1

  • EINECS:203-623-8

  • Molecular Weight:157.01

  • Molecular Formula: C6H5Br

  • HS Code:2903 99 80

  • Mol File:108-86-1.mol

Synonyms:Benzene, bromo-;Monobromobenzene;Benzene,bromo-;10005-81-9;NCI-C55492;Bromobenzene [UN2514] [Flammable liquid];

Post Buying Request Now
Entrust LookChem procurement to find high-quality suppliers faster

Safety information and MSDS view more

  • Pictogram(s):IrritantXi,DangerousN

  • Hazard Codes:Xi,N,F,T

  • Signal Word:Warning

  • Hazard Statement:H226 Flammable liquid and vapourH315 Causes skin irritation H411 Toxic to aquatic life with long lasting effects

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled Fresh air, rest. Refer for medical attention. In case of skin contact Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention . In case of eye contact First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention. If swallowed Do NOT induce vomiting. Refer for medical attention . Contact with liquid causes irritation of eyes and mild irritation of skin. Ingestion causes mild irritation of mouth and stomach. (USCG, 1999) Minimum/Potential Fatal Human Dose4 (?). 4= VERY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) IS 50-500 MG/KG, BETWEEN 1 TEASPOON & 1 OUNCE FOR 70 KG PERSON (150 LB).Absorption, Distribution and ExcretionABSORBED THROUGH LUNGS, GI TRACT & INTACT SKIN. EXCRETED AS CATECHOL DERIVATIVES BOTH FREE & CONJUGATED WITH SULFATE OR MERCAPTURIC ACID.

  • Fire-fighting measures: Suitable extinguishing media If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped or safely confined. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use foam, dry chemical or carbon dioxide. Special Hazards of Combustion Products: Irritating hydrogen bromide and other gases may be produced in fire. (USCG, 1999) 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. Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Remove all ignition sources. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Do NOT let this chemical enter the environment. Collect leaking and spilled liquid in sealable containers as far as possible. 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. Fireproof. Ventilation along the floor.

  • 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

Supplier and reference price

  • Manufacture/Brand
  • Product Description
  • Packaging
  • Price
  • Delivery
  • Purchase
  • Manufacture/Brand:TRC
  • Product Description:1-Bromobenzene
  • Packaging:25g
  • Price:$ 140
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:TCI Chemical
  • Product Description:Bromobenzene >99.0%(GC)
  • Packaging:25g
  • Price:$ 16
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:TCI Chemical
  • Product Description:Bromobenzene >99.0%(GC)
  • Packaging:500g
  • Price:$ 28
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:Bromobenzene
  • Packaging:500 g
  • Price:$ 26
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:Bromobenzene
  • Packaging:2.5 kg
  • Price:$ 125
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Bromobenzene Bromobenzene for synthesis. CAS 108-86-1, molar mass 157 g/mol., for synthesis
  • Packaging:8017869026
  • Price:$ 3100
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Bromobenzene for synthesis
  • Packaging:25 L
  • Price:$ 2969.25
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Bromobenzene ReagentPlus , 99%
  • Packaging:18l
  • Price:$ 952
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Bromobenzene solution certified reference material, 5000 μg/mL in methanol
  • Packaging:u
  • Price:$ 44.6
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Bromobenzene ReagentPlus , 99%
  • Packaging:500ml
  • Price:$ 66.4
  • Delivery:In stock
  • Buy Now

Relevant articles and documentsAll total 306 Articles be found

Gilman,Brown

, p. 1181,1185 (1930)

Comments on a Conversion of Epoxides to Halohydrins with Elemental Halogen Catalyzed by Phenylhydrazine: Tandem Electrophilic Halogenation of Aromatic Compounds and Epoxide Ring Opening to Halohydrins

Soroka, Miroslaw,Goldeman, Waldemar,Malysa, Piotr,Stochaj, Monika

, p. 2341 - 2344 (2003)

The halogenation of aromatic compounds by bromine or chlorine in the presence of an epoxide gives the corresponding halogenated aromatics and 2-halohydrins, both with good yields.

A convenient new method for the bromination of deactivated aromatic compounds

Duan, Jianxin,Zhang, Lian Hao,Dolbier Jr., William R.

, p. 1245 - 1246 (1999)

Treatment of deactivated aromatic compounds with N-bromosuccinimide in trifluoroacetic acid solvent in the presence of sulfuric acid gave the corresponding monobromoaromatic compounds in good to excellent yields.

Photoelectrochemistry with Quinone Radical Anions-Photoassisted Reduction of Halobenzenes and Carbonyl Compounds

Robertson, Peter K. J.,Eggins, Brian R.

, p. 1829 - 1832 (1994)

Photoexcited electrochemically generated quinone radical anions reduced 1,2-dibromobenzene to bromobenzene, 1,4-dibromobenzene to bromobenzene and 4-chlorobenzonitrile to benzonitrile.In the presence of anthracene, 2-bromophenyl-, 4-bromophenyl- and 4-cyanophenyl-anthracenes were formed.With acetaldehyde, acetone, acetophenone, benzaldehyde and benzophenone, the major products were the corresponding pinacols, with small amounts of the two-electron secondary alcohols.In acetonitrile as solvent, cinnamonitriles, hydrocinnamonitriles and phenylglutaronitriles were formed in addition to the alcohols.Glyoxylic acid was reduced to tartaric, glycolic and malic acids.The reduction of CO2 was unsuccessful.

C?I-Selective Cross-Coupling Enabled by a Cationic Palladium Trimer

Diehl, Claudia J.,Scattolin, Thomas,Englert, Ulli,Schoenebeck, Franziska

, p. 211 - 215 (2019)

While there is a growing interest in harnessing synergistic effects of more than one metal in catalysis, relatively little is known beyond bimetallic systems. This report describes the straightforward access to an air-stable Pd trimer and presents unambiguous reactivity data of its privileged capability to differentiate C?I over C?Br bonds in C?C bond formations (arylation and alkylation) of polyhalogenated arenes, which typical Pd0 and PdI-PdI catalysts fail to deliver. Experimental and computational reactivity data, including the first location of a transition state for bond activation by the trimer, are presented, supporting direct trimer reactivity to be feasible.

Directly Observed Reductive Elimination of Aryl Halides from Monomeric Arylpalladium(II) Halide Complexes

Roy, Amy H.,Hartwig, John F.

, p. 13944 - 13945 (2003)

Monomeric, three-coordinate arylpalladium(II) halide complexes undergo reductive elimination of aryl halide to form free haloarene and Pd(0). Reductive elimination of aryl chlorides, bromides, and iodides were observed upon the addition of P(t-Bu)3/

Vibrational Spectroscopy and Photodissociation Properties of Ions As Determined by Two-Laser Photodissociation Techniques.

Honovich, Jeffrey P.,Dunbar, Robert C.

, p. 3755 - 3758 (1983)

Iodobenzene, bromobenzene, and m-iodotoluene cations trapped in an ion cyclotron resonance (ICR) mass spectrometer undergo an enhanced visible photodissociation process in the presence of infrared irradiation.The infrared wavelength dependence in the 9.7-10.7-μm region for this effect exhibits features wich relate to the infrared spectroscopy of these ions.The variation in extent of the infrared enhancement with visible wavelength is interpreted as reflecting two different mechanisms: at short wavelengths the enhancement is attributed to changes invisible-absorption cross section with increasing internal energy and gives a useful means of observing such effects, while at long wavelengths the enhancement is attributed to a perturbation of the two-photon dissociation kinetics.The photodissociation rates of several other ions were shown not to undergo an enhancement effect when irradiated with the infrared laser.

Effects of Solvent and Additives on the Rearrangement Pathway of the Seyferth Reaction

Lambert, Joseph B.,Boch, Richard J.,Larson, Eric G.

, p. 3054 - 3059 (1985)

The Seyferth reagent has dual reactivity with electron-deficient alkenes. trans-1,2-Dichloroethene reacts both with the free carbene to give cyclopropane stereospecifically and with a complex between carbene and a second molecule of Seyferth reagent (homogeneous catalysis) to give a rearranged propene.The addition of other materials to the reaction mixture can have a profound effect on the ratio of the two pathways.Good ? donors such as p-xylene decrease the pathway to rearranged propene via the complexed carbene.Such materials thus serve as inhibitors to the process of homogeneous catalysis by forming a competing complex that does not go on to propene but instead reverts to free carbene.The existence of the inhibitor-carbene complex is supported by concentration studies.The presence of insoluble materials such as zinc chloride, on the other hand , serves to decrease the pathway that leads through free carbene to the cyclopropane.Free carbene may react with the surface of the additive and be removed as a reactive species.This latter process would have no effect on carbene previously complexed with the homogeneous catalyst, the Seyferth reagent , which could still proceed to rearranged propene.

A study on Zr-Ir multiple bonding active for C-H bond cleavage

Oishi, Masataka,Oshima, Masato,Suzuki, Hiroharu

, p. 6634 - 6654 (2014)

Zr-Ir hydrido complexes with ansa-(cyclopentadienyl)(amide) as the supporting ligand in the zirconium fragment, e.g., (L1ZrR) (Cp*Ir)(μ-H)3 [L1 = Me2Si(η 5-C5Me4)(NtBu), R = Cl (5), Ph (7), Me (10), alkyl, and aryl] were designed, synthesized, and isolated as tractable early-late heterodinuclear complexes. Despite the presence of the three supporting hydride ligands, Zr-Ir distances in the crystal structures of 5, alkyl, and aryl complexes [2.74-2.76 A] were slightly longer than the sum of the element radii of Zr and Ir [2.719 A]. These hydrocarbyl complexes displayed the thermolytic C-H activation of a variety of aromatic compounds and several organometallic compounds. Also, the substrate scope and limitation in the Zr-Ir system were studied. The regiochemical outcomes during the C-H activation of pyridine derivatives and methoxyarenes suggested the in situ generation of a Lewis acidic active intermediate, i.e., (L1Zr) (Cp*IrH2) (III). The existence of III and relevant σ-complex intermediates {L1Zr(η2-R-H)} (Cp*IrH2) (IIR) (R = Me, Ph) in the ligand exchange was demonstrated by the direct isolation of a Et3PO-adduct of III (39b) from 7 and kinetic studies. The structure of the direct Zr-Ir bonds in IIPh, IIMe, III, and 39b were probed using computational studies. The unprecedented strong M-M′ interactions in the early-late heterobimetallic (ELHB) complexes have been proposed herein.

The Addition Reaction of Benzynes Generated Electrochemically from Dihalobenzenes with Tertiary Amines

Egashira, Naoyoshi,Takenga, Jun,Hori, Fumikai

, p. 2671 - 2673 (1987)

The electroreduction of dihalobenzenes was carried out in the presence of tertiary amines as benzyne acceptors in DMF-TBAP, giving the addition products in yields more than 10percent.For o-dibromobenzene, the yield of the addition product, N-phenylpiperidine, increased to 21percent in the presence of N-ethylpiperidine.

ON THE ABSOLUTE REACTIVITY OF ARYL CATIONS: SELECTIVITY TOWARD HALIDE IONS AS A FUNCTION OF VISCOSITY

Lorand, John P.

, p. 7337 - 7340 (1989)

The selectivities toward bromide and chloride ions observed in the dediazoniation of three arenediazonium salts are found to be independent of viscosity.It is inferred that the capture of aryl cations by these halide ions is diffusion controlled.

Generation, structure, and reactivity of o-iodobenzoyloxyl radicals. Pulsed laser photolysis of 1-(o-halobenzoyloxy)-2-pyridones

Hashimoto, Ji-Ichiro,Segawa, Katsunori,Itoh, Hiroki,Sakuragi, Hirochika

, p. 362 - 363 (2000)

The transient absorption spectrum of o-iodobenzoyloxyl radicals was observed for the first time in acetonitrile using 1-(o-iodobenzoyloxy)-2-pyridone as a precursor. On the basis of the comparison of the spectra of o-halobenzoyloxyl radicals, it is proposed that the o-iodobenzoyloxyl radicals take a planar structure with a strong interaction between the radical center oxygen atom and the neighboring iodine atom.

Photochemically Switching Diamidocarbene Spin States Leads to Reversible Büchner Ring Expansions

Perera, Tharushi A.,Reinheimer, Eric W.,Hudnall, Todd W.

, p. 14807 - 14814 (2017)

The discovery of thermal and photochemical control by Woodward and Hoffmann revolutionized how we understand chemical reactivity. Similarly, we now describe the first example of a carbene that exhibits differing thermal and photochemical reactivity. When a singlet ground-state N,N'-diamidocarbene 1 was photolyzed at 380 nm, excitation to a triplet state was observed. The triplet-state electronic structure was characteristic of the expected biradical σ1pπ1 spin configuration according to a combination of spectroscopic and computational methods. Surprisingly, the triplet state of 1 was found to engage a series of arenes in thermally reversible Büchner ring expansion reactions, marking the first examples where both cyclopropanation and ring expansion of arenes were rendered reversible. Not only are these photochemical reactions different from the known thermal chemistry of 1, but the reversibility enabled us to perform the first examples of photochemically induced arene exchange/expansion reactions at a single carbon center.

Nucleophilic substitution of hydrogen in naphthalene by chloride (Cl -) in ionic liquids

Shi, Shen Yi,Kong, Ai Guo,Zhao, Xin Hua,Ding, Han Ming,Yang, Fan,Shan, Yong Kui

, p. 147 - 150 (2011)

Nucleophilic aromatic substitution of hydrogen in non-activated aromatic ring, a very rare phenomenon in organic chemistry, is found in ionic liquids containing Cl- as anion under mild reaction conditions. The reaction may be carried out by the addition of the halogen-bonding adduct (Br 2Cl-) as nucleophile to aromatic ring carbon atom, leading to the formation of the nucleophilic substitution product.

Hydroxyl radical induced reactions in aqueous solutions of halogenated benzenes: Effect of electronegativity of halogen

Mohan, Hari,Mittal, Jai P.

, p. 599 - 607 (2002)

The .OH radicals, generated by radiolysis, are found to react only in acidic conditions with halogenated benzenes by an electron transfer mechanism. The concentration of acid, at which solute radical cation of halogenated benzenes appear, is observed to depend strongly on the nature and number of halogen atoms in halogenated benzenes. A linear increase in the acid concentration required for solute radical cation formation is observed with electronegativity of halogen.

Cope rearrangement versus a novel tandem retro-diels-alder-diels-alder reaction with role reversal

Su, Kuan-Jen,Mieusset, Jean-Luc,Arion, Vladimir B.,Brecker, Lothar,Brinker, Udo H.

, p. 113 - 115 (2007)

A reinvestigation of the thermolysis of 4,4-dibromotetracyclo[6.2.1.0 2,7.03,5]undec-9-ene (2) affords diene 8 with a completely rearranged hydrocarbon skeleton via the isolable intermediate 4, along with cyclopentadiene and bromobenzene. DFT calculations show that the novel tandem retro-Diels-Alder-Diels-Alder reaction with role reversal is slightly less favored than the overall single-step Cope rearrangement. (Chemical Equation Presented)

REDUCTION BY A MODEL OF NAD(P)H. 42. DIRECT EVIDENCE FOR ONE ELECTRON TRANSFER MECHANISM IN THE REDUCTION OF ARENEDIAZONIUM SALTS.

Yasui, Shinro,Nakamura, Kaoru,Ohno, Atsuyoshi

, p. 3331 - 3334 (1983)

Arenediazonium salts are reduced by an NAD(P)H- model in methanol at room temperature to afford the corresponding reduction product, ArH.The reaction proceeds partially with a radical-chain mechanism involving initial one electron transfer from the NAD(P)H-model to the diazonium salt.

Through-Space Activation Can Override Substituent Effects in Electrophilic Aromatic Substitution

Guan, Liangyu,Holl, Maxwell Gargiulo,Pitts, Cody Ross,Struble, Mark D.,Siegler, Maxime A.,Lectka, Thomas

, p. 14913 - 14916 (2017)

Electrophilic aromatic substitution (EAS) represents one of the most important classes of reactions in all of chemistry. One of the "iron laws" of EAS is that an electron-rich aromatic ring will react more rapidly than an electron-poor ring with suitable electrophiles. In this report, we present unique examples of electron-deficient arenes instead undergoing preferential substitution in intramolecular competition with more electron-rich rings. These results were made possible by exploiting the heretofore unknown propensity of a hydrogen-bonding OH-arene interaction to switch to the alternative HO-arene interaction in order to provide activation. In an extreme case, this through-space HO-arene activation is demonstrated to overcome the deactivating effect of a trifluoromethyl substituent, making an otherwise highly electron-deficient ring the site of exclusive reactivity in competition experiments. Additionally, the HO-arene activation promotes tetrabromination of an increasingly more electron-deficient arene before the unactivated "control" ring undergoes monobromination. It is our hope that these results will shed light on biological interactions as well as provide new strategies for the electrophilic substitution of aromatic rings.

-

Ainley,Challenger

, p. 2171,2176 (1930)

-

-

Beringer et al.

, p. 141,143 (1956)

-

Bromination of Deactivated Aromatics Using Potassium Bromate

Harrison, J.J.,Pellegrini, J.P.,Selwitz, C.M.

, p. 2169 - 2171 (1981)

-

Pd-catalyzed reduction of aryl halides using dimethylformamide as the hydride source

Zawisza, Anna Maria,Muzart, Jacques

, p. 6738 - 6742 (2007)

The Pd-catalyzed homocoupling of aryl halides in a basic DMF solution is often accompanied by the dehalogenation of the substrate as side reaction. When an inorganic base such as sodium bicarbonate is used, the reducing role of the solvent has been demonstrated using DMF-d7 and GC/MS analysis.

Kupchik, E. J.,Lanigan, T.

, p. 3661 - 3665 (1962)

-

Summers,Larson

, p. 4498 (1952)

-

Properties of PTFE tape as a semipermeable membrane in fluorous reactions

Parsons, Brendon A.,Smith, Olivia Lin,Chae, Myeong,Dragojlovic, Veljko

, p. 980 - 993 (2015)

In a PTFE tape phase-vanishing reaction (PV-PTFE), a delivery tube sealed with PTFE tape is inserted into a vessel which contains the substrate. The reagent diffuses across the PTFE tape barrier into the reaction vessel. PTFE co-polymer films have been found to exhibit selective permeability towards organic compounds, which was affected by the presence of solvents. In this study, we attempted to establish general trends of permeability of PTFE tape to different compounds and to better describe the process of solvent transport in PV-PTFE bromination reactions. Though PTFE tape has been reported as impermeable to some compounds, such as dimethyl phthalate, solvent adsorption to the tape altered its permeability and allowed diffusion through channels of solvent within the PTFE tape. In this case, the solvent-filled pores of the PTFE tape are chemically more akin to the adsorbed solvent rather than to the PTFE fluorous structure. The solvent uptake effect, which was frequently observed in the course of PV-PTFE reactions, can be related to the surface tension of the solvent and the polarity of the solvent relative to the reagent. The lack of pores in bulk PTFE prevents solvents from altering its permeability and, therefore, bulk PTFE is impermeable to most solvents and reagents. However, bromine, which is soluble in liquid fluorous media, diffused through the bulk PTFE. A better understanding of the PTFE phase barrier will make it possible to further optimize the PV-PTFE reaction design.

Bromine and iodine-cucurbit[6]uril complexes: Preparation and applications in synthetic organic chemistry

Reddy,Cavallini,Demets,Silva

, p. 2262 - 2264 (2014)

Iodine and bromine inclusion compounds were easily prepared by gas diffusion of the halogens using finely powdered CB[6]. A brown powder consisting of I2-CB[6]·4H2O and an orange one of (Br 2)4-CB[6]·10H2O were employed in several different reactions. I2-CB[6] can be used in catalytic reactions giving yields comparable to those reported in the literature. Br 2-CB[6] was effectively applied in electrophilic bromination of benzene and formation of bromohydrin. However, the radical substitution at cyclohexene could not be performed. Overall, based on these results, several applications can be envisioned for these complexes. This journal is the Partner Organisations 2014.

-

Leicester

, p. 619 (1938)

-

-

Henry

, p. 1886,1888 (1971)

-

Photochemical Decomposition of Dibenzoyl Peroxide and Phenyl Benzoate in Solid KBr Matrix

Owen, David J.,O'Donnell, Jennifer,Schutt, Wendy,Morrow, Jeffrey,Li, Yuzhuo

, p. 6203 - 6207 (1993)

Physical and photochemical properties of dibenzoyl peroxide (DBPO) and phenyl benzoate (PB) in a solid KBr matrix were investigated.The photoinduced decompositions of DBPO and PB were monitored with infrared spectroscopy and HPLC.The organic molecules at different locations in the matrix contribute to the overall IR absorption differently.Therefore, they are affected differently during a photochemical decomposition.The bromide ions in the matrix intercept some of the radical intermediates in the decomposition of DBPO but have no influence on the radical pair in the rearrangement of phenyl benzoate.

-

Bunnett et al.

, p. 367 (1966)

-

-

Kohn,Mueller

, p. 407 (1909)

-

-

Rice,Morganroth

, p. 1388 (1956)

-

Noncatalytic bromination of benzene: A combined computational and experimental study

Shernyukov, Andrey V.,Genaev, Alexander M.,Salnikov, George E.,Rzepa, Henry S.,Shubin, Vyacheslav G.

, p. 210 - 225 (2016)

The noncatalytic bromination of benzene is shown experimentally to require high 5-14 M concentrations of bromine to proceed at ambient temperatures to form predominantly bromobenzene, along with detectable (6-benzene of 0.97 ± 0.03 at 298 K. These results are rationalized using computed transition states models at the B3LYP+D3/6-311++G(2d,2p) level with an essential continuum solvent field for benzene applied. The model with the lowest predicted activation free energies agrees with the high experimental kinetic order in bromine and involves formation of an ionic, concerted, and asynchronous transition state with a Br8 cluster resembling the structure of the known Br9-. This cluster plays three roles; as a Br+ donor, as a proton base, and as a stabilizing arm forming weak interactions with two adjacent benzene C-H hydrogens, these aspects together combining to overcome the lack of reactivity of benzene induced by its aromaticity. The computed inverse kinetic isotope effect of 0.95 agrees with experiment, and arises because C-Br bond formation is essentially complete, whereas C-H cleavage has not yet commenced. The computed free energy barriers for the reaction with 4Br2 and 5Br2 for a standard state of 14.3 M in bromine are reasonable for an ambient temperature reaction, unlike previously reported theoretical models involving only one or two bromines.

-

Le Fevre,Markham

, p. 703 (1934)

-

Formation and Reactivity of the Radical Cation of Bromobenzene in Aqueous Solution: A Pulse Radiolysis Study

Mohan, Hari,Mittal, Jai P.

, p. 6519 - 6524 (1995)

A transient optical absorption band (λmax=325 nm) is formed upon reaction of . OH radical with bromobenzene in neutral aqueous solution and is assigned to the OH adduct.In strongly acidic solution (HClO4 > 3 mol dm3), the OH adduct undergoes H+-catalyzed dehydroxylation to form the bromobenzene radical cation.This radical cation absorbs at 550 nm and at 270-310 nm.Even at this high H+ concentration, only a fraction of the OH adduct is converted to the radical cation.SO4.- reacts with bromobenzene to form the hydroxycyclohexadienyl radical (λmax=325 nm) and the phenoxyl radical (λmax=400 nm).The bromobenzene radical cation is also observed in irradiated 1,2-dichloroethane solutions.C6H5Br.+ is a strong one-electron oxidant and oxidizes Br-, SCN-, and organic sulfides with high rate constants.C6H5Br.+ undergoes electron transfer reaction with Cl- to establish an equilibrium, from which a reduction potential value for C6H5Br.+/C6H5Br was determined to be 2.31+/-0.15 V versus NHE.

-

Huyser,Wang

, p. 3901 (1968)

-

Radical Rearrangements of Bicyclohexane: Homolytic Substitution of a Cyclobutane Ring

Walton, John C.

, p. 1252 - 1254 (1987)

Bromine atoms react with bicyclohexane in an SH2 reaction at the bridgehead carbon atoms; the bicyclohex-2-yl radical rearranges by β-scission of the inter-ring bond.

Remarkably stable ortho-halophenylcopper reagents

Ebert, Greg W.,Pfennig, Deborah R.,Suchan, Scott D.,Donovan Jr., Thomas A.

, p. 2279 - 2282 (1993)

We wish to report the generation of remarkably stable o-halophenlycopper reagents at room temperature by the direct oxidative addition of activated copper to o-flouro-and o-choloriodobenzene. The reagents will undergo substitution reactions with suitable organic halides at 25°C.

Reactivity of alkali and alkaline earth metal tetrafluorobromates towards aromatic compounds and pyridine

Sobolev, Vasily I.,Filimonov, Victor D.,Ostvald, Roman V.,Radchenko, Vyacheslav B.,Zherin, Ivan I.

, p. 120 - 123 (2016)

The bromination activity of tetrafluorobromates of alkali and alkali-earth metals increases in the order KBrF4, CsBrF4, RbBrF4and Ba(BrF4)2. The most active tetrafluorobromate—Ba(BrF4)2is able to selectively brominate the deactivated aromatic compounds nitrobenzene and 4-nitrotoluene, but not the activated compounds benzene and toluene. In all cases bromination of methyl groups of methylbenzenes does not occur. Ba(BrF4)2forms the known complex C6H5N·BrF3when reacted with pyridine. Due to dilution by inert BaF2, this pyridine-based complex is air stable and can be considered as safer and more convenient reagent in comparison with the original fluorobromates; it can selectively brominate benzene and toluene in contrast with tetrafluorobromates.

-

Kohn,Fink

, p. 187 (1923)

-

Ogata et al.

, p. 960 (1964)

Silk?Fibroin-Supported Palladium Catalyst for Suzuki-Miyaura and Ullmann Coupling Reactions of Aryl Chlorides

Albano, Gianluigi,Farinola, Gianluca M.,Giannini, Cinzia,Musio, Roberta,Omenetto, Fiorenzo G.,Rizzo, Giorgio,Sibillano, Teresa

supporting information, (2022/02/03)

Recently, we have reported the preparation of a silk fibroin-supported Palladium catalyst (Pd/SF) and its use in the Suzuki-Miyaura cross-coupling of aryl iodides. Since its synthetic applicability and structural features are still far from being fully ex

Radical Hydrodehalogenation of Aryl Halides with H2 Catalyzed by a Phenanthroline-Based PNNP Cobalt(I) Complex

Iizuka, Kosuke,Ishizaka, Yusuke,Jheng, Nai-Yuan,Minami, Yasunori,Naganawa, Yuki,Nakajima, Yumiko,Sekiguchi, Akira

, p. 2320 - 2329 (2022/02/16)

Radical hydrodehalogenation of aryl halides (Ar-X; X = Cl, Br, I) is achieved in the presence of atmospheric pressure H2 as a H-atom donor using a Co(I) catalyst bearing a phenanthroline-based PNNP ligand (2,9-bis((diphenylphosphanyl)methyl)-1,10-phenanthroline). The reaction proceeds under mild conditions (1 atm H2) and is applicable to aryl bromides and aryl chlorides with various functional groups. A mechanistic study revealed that the PNNP-Co complex underwent facile H-H cleavage and facilitated a H-atom transfer. This process is mediated by a long-range metal-ligand cooperation of the PNNP-Co system, which includes the dearomatization/aromatization sequence of the phenanthroline ligand backbone. A radical clock experiment demonstrated the Ar-X bond cleavage via a radical mechanism. Further kinetic study supported that the rate-determining step includes electron transfer from the Co center to the substrate, affording a radical pair ArX?- and an odd-electron metal-halide complex [Co(II) + ArX?-]? as a transition state.

Alternative method for the synthesis of triazenes from aryl diazonium salts

Abrams

, (2021/05/10)

An alternative mild method for access to 1-aryl-3,3-dimethyl alkyl triazenes is described. This protocol employs the dropwise addition of a methanolic solution of a carboxylate (RCO2M) or carbonate (CO32?) to a gently heated DMF solution containing an aryl diazonium salt (ArN2+), that had been previously isolated. Presumably homolysis of the weak N–O bond of diazo ether adducts formed in this operation initiates radical pathways that lead to the generation of triazene product. DMF serves as not only a one-electron donor to the diazonium salts employed in this process, but also as a source of dimethylamine radicals that act as a nucleophilic coupling partner. The reaction provides modest yields (ca. 20–40%) across an array of aryl diazonium salts that contain various substitution. Furthermore this unique approach to triazenes contrasts with traditional methods that employ dimethyl amine in reagent form which directly couples with diazonium salts. Seemingly, only one other example employing somewhat similar reaction conditions to this current investigation en route to triazenes has been reported, albeit with lower yields and for one representative example furnished as a side-product. The current work here improves upon the efficiency of this reported result, and further expands the reaction scope.

Poly-N-bromosulfonamide-melamine as a novel brominating reagent for regioselective ipso-bromination of arylboronic acids

Alavinia, Sedigheh,Ghorbani-Vaghei, Ramin

, p. 1269 - 1276 (2021/08/27)

A practical synthetic method for the synthesis of aryl bromide was developed through regioselective bromination of boronic acid in the presence of poly-N-bromosulfonamide-melamine (PBBSM). In this regard, a novel heterogeneous support, cross-linked poly sulfonamide-melamine, has been successfully synthesized to stabilize bromine with high surface functional group density (6.6?mmol Br+/g). The prepared reagent is a novel brominating reagent that combines the effective functions of N-bromosulfonamide, N-bromosulfonamide-melamine, and melamine groups. The structure of PBBSM was characterized using XRD, FT–IR, 1H NMR, TGA, FE-SEM, EDX, and TGA analysis. Graphic abstract: [Figure not available: see fulltext.]

The graphite-catalyzed: ipso -functionalization of arylboronic acids in an aqueous medium: metal-free access to phenols, anilines, nitroarenes, and haloarenes

Badgoti, Ranveer Singh,Dandia, Anshu,Parewa, Vijay,Rathore, Kuldeep S.,Saini, Pratibha,Sharma, Ruchi

, p. 18040 - 18049 (2021/05/29)

An efficient, metal-free, and sustainable strategy has been described for the ipso-functionalization of phenylboronic acids using air as an oxidant in an aqueous medium. A range of carbon materials has been tested as carbocatalysts. To our surprise, graphite was found to be the best catalyst in terms of the turnover frequency. A broad range of valuable substituted aromatic compounds, i.e., phenols, anilines, nitroarenes, and haloarenes, has been prepared via the functionalization of the C-B bond into C-N, C-O, and many other C-X bonds. The vital role of the aromatic π-conjugation system of graphite in this protocol has been established and was observed via numerous analytic techniques. The heterogeneous nature of graphite facilitates the high recyclability of the carbocatalyst. This effective and easy system provides a multipurpose approach for the production of valuable substituted aromatic compounds without using any metals, ligands, bases, or harsh oxidants.

Process route upstream and downstream products

Process route

diethyl ether
60-29-7,927820-24-4

diethyl ether

phenyllithium
591-51-5

phenyllithium

1,1-dibromomethane
74-95-3

1,1-dibromomethane

bromobenzene
108-86-1,52753-63-6

bromobenzene

benzyl bromide
100-39-0

benzyl bromide

1,1'-(1,2-ethanediyl)bisbenzene
103-29-7

1,1'-(1,2-ethanediyl)bisbenzene

Conditions
Conditions Yield
zuletzt bei Raumtemperatur;
bromine
7726-95-6

bromine

acetic acid
64-19-7,77671-22-8

acetic acid

phenylboronic acid
98-80-6

phenylboronic acid

bromobenzene
108-86-1,52753-63-6

bromobenzene

hydrogen bromide
10035-10-6,12258-64-9

hydrogen bromide

Conditions
Conditions Yield
at 25 ℃; Rate constant;
1,2,3,4,5,6-hexabromocyclohexane
1837-91-8

1,2,3,4,5,6-hexabromocyclohexane

bromobenzene
108-86-1,52753-63-6

bromobenzene

1,3-dibromobenzene
108-36-1

1,3-dibromobenzene

1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

benzyl bromide
100-39-0

benzyl bromide

1,1'-(1,2-ethanediyl)bisbenzene
103-29-7

1,1'-(1,2-ethanediyl)bisbenzene

2,3-dibromobenzene
583-53-9

2,3-dibromobenzene

Conditions
Conditions Yield
at 55 ℃; for 16h; Product distribution; Irradiation; other solvents;
tetrachloromethane
56-23-5

tetrachloromethane

3,6-dibromo-cyclohexa-1,4-diene

3,6-dibromo-cyclohexa-1,4-diene

bromobenzene
108-86-1,52753-63-6

bromobenzene

hydrogen bromide
10035-10-6,12258-64-9

hydrogen bromide

Conditions
Conditions Yield
bromine
7726-95-6

bromine

phenylboronic acid
98-80-6

phenylboronic acid

bromobenzene
108-86-1,52753-63-6

bromobenzene

hydrogen bromide
10035-10-6,12258-64-9

hydrogen bromide

Conditions
Conditions Yield
In acetic acid; 20% aq. acetic acid;;
In acetic acid;
Conditions
Conditions Yield
With iron(III) chloride; at 75 - 105 ℃; for 10h; Reagent/catalyst; Temperature; Industrial scale;
425.6 kg
477.2 kg
4-bromophenyliodonium-(5-[2,2-dimethyl-1,3-dioxane-4,6-dione])ylide
1250409-86-9

4-bromophenyliodonium-(5-[2,2-dimethyl-1,3-dioxane-4,6-dione])ylide

bromobenzene
108-86-1,52753-63-6

bromobenzene

1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

1-Bromo-4-fluorobenzene
460-00-4

1-Bromo-4-fluorobenzene

Conditions
Conditions Yield
With potassium fluoride; [2.2.2]cryptande; In N,N-dimethyl-formamide; at 130 ℃; for 0.25h; Reactivity; sealed tube;
4-bromobenzenediazonium tetrafluoroborate
673-40-5

4-bromobenzenediazonium tetrafluoroborate

bromobenzene
108-86-1,52753-63-6

bromobenzene

1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

Conditions
Conditions Yield
With ferrocene; Iodoacetic acid; In isopropyl alcohol; for 0.166667h; Heating;
81 % Chromat.
10 % Chromat.
With trimethylsilyl iodide; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate; at 65 ℃; for 2h;
95 % Chromat.
5 % Chromat.
4-bromobenzenediazonium hexafluorophosphate
20566-57-8

4-bromobenzenediazonium hexafluorophosphate

bromobenzene
108-86-1,52753-63-6

bromobenzene

1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

Conditions
Conditions Yield
With ferrocene; Iodoacetic acid; In various solvent(s);
65 % Chromat.
20 % Chromat.
ethanol
64-17-5

ethanol

4-bromobenzenediazonium tetrafluoroborate
673-40-5

4-bromobenzenediazonium tetrafluoroborate

bromobenzene
108-86-1,52753-63-6

bromobenzene

1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

4-bromoethoxybenzene
588-96-5

4-bromoethoxybenzene

Conditions
Conditions Yield
With Iodoacetic acid; for 0.166667h; Heating;
11 % Chromat.
58 % Chromat.
4 % Chromat.

Global suppliers and manufacturers

Global( 163) Suppliers
  • Company Name
  • Business Type
  • Contact Tel
  • Emails
  • Main Products
  • Country
  • Simagchem Corporation
  • Business Type:Manufacturers
  • Contact Tel:+86-592-2680277
  • Emails:sale@simagchem.com
  • Main Products:110
  • Country:China (Mainland)
  • Chemwill Asia Co., Ltd.
  • Business Type:Manufacturers
  • Contact Tel:021-51086038
  • Emails:sales@chemwill.com
  • Main Products:30
  • Country:China (Mainland)
  • EAST CHEMSOURCES LIMITED
  • Business Type:Manufacturers
  • Contact Tel:86-532-81906761
  • Emails:josen@eastchem-cn.com
  • Main Products:97
  • Country:China (Mainland)
  • Amadis Chemical Co., Ltd.
  • Business Type:Lab/Research institutions
  • Contact Tel:86-571-89925085
  • Emails:sales@amadischem.com
  • Main Products:29
  • Country:China (Mainland)
close
Post a RFQ

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

1

What can I do for you?
Get Best Price

Get Best Price for 108-86-1
Post Buying Request Now
close
Remarks: The blank with*must be completed