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Cas Database

100-39-0

100-39-0

Identification

  • Product Name:Benzene,(bromomethyl)-

  • CAS Number: 100-39-0

  • EINECS:202-847-3

  • Molecular Weight:171.037

  • Molecular Formula: C7H7Br

  • HS Code:2903 99 80

  • Mol File:100-39-0.mol

Synonyms:Toluene,a-bromo- (8CI);(Bromomethyl)benzene;(Bromophenyl)methane;1-Bromomethylbenzene;NSC 8041;Phenylmethyl bromide;a-Bromotoluene;w-Bromotoluene;

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Safety information and MSDS view more

  • Pictogram(s):IrritantXi

  • Hazard Codes:Xi

  • Signal Word:Warning

  • Hazard Statement:H315 Causes skin irritationH319 Causes serious eye irritation H335 May cause respiratory irritation

  • 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. 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 Rinse mouth. Do NOT induce vomiting. Give one or two glasses of water to drink. Refer for medical attention . Inhalation causes irritation of nose and throat; severe exposure may cause pulmonary edema. Vapors cause severe eye irritation; liquid can burn eyes. Skin contact causes irritation. Ingestion causes irritation of mouth and stomach. (USCG, 1999) Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Aromatic hydrocarbons and related compounds/

  • Fire-fighting measures: Suitable extinguishing media Water spray, dry chemical, foam or carbon dioxide is effective. Water is effective not only for dispersing of leaked chemicals prior to its ignition, but also for cooling fire-exposed containers. Special Hazards of Combustion Products: Irritating hydrogen bromide gas may be formed. Behavior in Fire: Forms vapor that is a powerful tear gas. (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. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Personal protection: chemical protection suit including self-contained breathing apparatus. Evacuate and restrict persons not wearing protective equipment from area of spill or leak until cleanup is complete. Remove all ignition sources. Ventilate area of spill or leak. ... If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters.

  • 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. Separated from strong oxidants, strong bases and food and feedstuffs. Dry. Well closed.In general, materials which are toxic as stored or which can decomposition into toxic components due to heat, moisture, acids, or acid fumes, should be stored in cool, well ventilated place, out of sun, away from area of high fire hazard and should be periodically inspected and monitored. Incompatible materials should be isolated.

  • 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

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  • Manufacture/Brand:TRC
  • Product Description:Benzyl bromide
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Benzyl Bromide (stabilized with Propylene Oxide) >98.0%(GC)
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  • Manufacture/Brand:TCI Chemical
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  • Manufacture/Brand:TCI Chemical
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:Benzyl bromide
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:Benzyl bromide
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:Benzyl bromide
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:Benzyl bromide
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Benzyl bromide for synthesis. CAS No. 100-39-0, EC Number 202-847-3., for synthesis
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Relevant articles and documentsAll total 370 Articles be found

Simple synthesis of fresh alkyl iodides using alcohols and hydriodic acid

Klein, Suzane M.,Zhang, Cungen,Jiang, Yu Lin

, p. 2638 - 2641 (2008)

A simple synthesis of fresh alkyl iodides using alcohols and hydriodic acid (HI) is reported. The alkyl iodides were obtained in quick and easy work-up with good to excellent yields (66-94%) and very high purities (97-99%). Freshly prepared iodomethane and 1-iodobutane were applied to synthesize biologically relevant 3,7-dimethyladenine and 9-butyladenine, which were characterized thoroughly using 1D and 2D NMR, individually.

REACTIVITY OF t-BUTYLDIMETHYLSILYL ETHERS : A FACILE CONVERSION INTO BROMIDE

Mattes, Henri,Benezra, Claude

, p. 1697 - 1698 (1987)

TBDMS ether can be efficiently converted in one step into the corresponding bromides by a CBr4, PPh3 and acetone mixture.

-

Kubiczek,Neugebauer

, p. 917,919 (1950)

-

Kinetics of the nucleophilic substitution of benzyltributylammonium bromide with allyl, butyl, and benzyl chlorides and with benzyl acetate and benzyl ether

Wang, Ten-Tsai,Chang, Chyi-Huang,Huang, Ting-Chia

, p. 615 - 626 (1996)

In this study, we investigated the kinetics of the nucleophilic substitutions, RX + (BzBu3NBr) ? RBr + (BzBu3NX), where R = allyl, Bu and Bz, when X = Cl; and X = AcO and BzO when R = Bz. The forward and backward rate constants in addition to the activation energies for R = allyl and Bu were also determined. However, only the rate constants at 35°C were determined for the benzyl compounds with toluene as the solvent to reduce the reaction rate. Moreover, the effects of the structures of the groups R and the leaving groups X on the reactivity were compared. Results in this study can provide valuable information for future studies involving the phase transfer catalyzed displacements.

Organic synthesis in water/carbon dioxide emulsions

Jacobson,Lee C.T.,DaRocha,Johnston

, p. 1207 - 1210 (1999)

The synthetic reaction between a hydrophobe, benzyl chloride, and a hydrophilic nucleophile, KBr, is reported in water-in-carbon dioxide (w/c) and carbon dioxide-in-water (c/w) emulsions. Emulsions containing equal amounts of water and CO2 were

Kinetics of the gas-phase elimination of α-bromophenylacetic acid under maximum inhibition

Chuchani, Gabriel,Dominguez, Rosa M.

, p. 725 - 728 (1999)

The gas phase elimination kinetics of the title compound was studied over the temperature range of 260.1-315.0 °C and pressure range of 20-70 Torr. This elimination, in seasoned static reaction system and in the presence of at least fourfold of the free r

Chlorotrimethylsilane/Lithium Bromide and Hexamethyldisilane/Pyridinium Bromide Perbromide: Effective and Selective Reagents for the Conversion of Alkyl (Cycloalkyl and Aralkyl) Alcohols into Bromides

Olah, George A.,Gupta, B. G. Balaram,Malhotra, Ripudaman,Narang, Subhash C.

, p. 1638 - 1639 (1980)

Alkyl bromides were obtained in high yield in the reaction of the corresponding alcohols with chlorotrimethylsilane/lithium bromide.The reaction was equally applicable to primary, secondary, and tertiary alcohols as well as to allylic and benzylic alcohols.High regioselectivity was observed in related conversions in which hexamethyldisilane/pyridinium bromide perbromide was used.Tertiary alcohols, for example, were converted selectively into the corresponding tertiary bromides in the presence of primary and secondary hydroxylic functions.The reactions were also highly steroselective.

STEREOSPECIFIC DISPLACEMENT OF SULFUR FROM CHIRAL CENTERS. ACTIVATION VIA THIAPHOSPHONIUM SALTS.

Krafft, Grant A.,Siddall, Thomas L.

, p. 4867 - 4870 (1985)

The first general method for direct displacement of sulfur from chiral carbon centers has been developed.Chiral mercaptans are readily converted to the corresponding thiaphosphonium salts by treatment with t-butyl hypochlorite and hexamethylphosphorous triamide.Metathesis with ammonium hexafluorophosphate provides stable, isolable, crystalline salts which undergo clean nucleophilic diplacement with a variety of heteroatom and carbon based nucleophiles, affording products in which the stereochemistry has been inverted.

Simple and rapid determination of the activation parameters of organic reactions by temperature-dependent NMR spectroscopy II. Application to reversible reactions

Satoh, Masahiro,Hirota, Minoru

, p. 2619 - 2624 (1996)

A non-isothermal (NIT) method for evaluating the activation enthalpies and entropies of reactions in solutions was applied to several reversible reactions. This was realized by a stepwise elevation of the temperature of a reaction system using a variable-temperature apparatus comprising on NMR spectrometer and a quick collection of FID (free induction decay) at every plateau of the step. The rate from NIT experiments agreed well with the previously measured rates by the conventional methods.

Regiospecific Synthesis of Calcium-Independent Daptomycin Antibiotics using a Chemoenzymatic Method

Mupparapu, Nagaraju,Lin, Yu-Hsin Cindy,Kim, Tae Ho,Elshahawi, Sherif I.

, p. 4176 - 4182 (2021)

Daptomycin (DAP) is a calcium (Ca2+)-dependent FDA-approved antibiotic drug for the treatment of Gram-positive infections. It possesses a complex pharmacophore hampering derivatization and/or synthesis of analogues. To mimic the Ca2+-binding effect, we used a chemoenzymatic approach to modify the tryptophan (Trp) residue of DAP and synthesize kinetically characterized and structurally elucidated regiospecific Trp-modified DAP analogues. We demonstrated that the modified DAPs are several times more active than the parent molecule against antibiotic-susceptible and antibiotic-resistant Gram-positive bacteria. Strikingly, and in contrast to the parent molecule, the DAP derivatives do not rely on calcium or any additional elements for activity.

-

Harnish,Tarbell

, p. 4123,4125, 4126 (1948)

-

-

Offermann,Voegtle

, p. 272 (1977)

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Visible light induced 'on water' benzylic bromination with N-bromosuccinimide

Podgor?ek, Ajda,Stavber, Stojan,Zupan, Marko,Iskra, Jernej

, p. 1097 - 1099 (2006)

Benzylic bromination of various 4-substituted toluenes (Me, tert-Bu, COOEt and COMe) was effectively conducted with NBS in pure water and with a 40 W incandescent light-bulb as an initiator of the radical chain process, while electron donating groups (OMe and NHAc) directed the reaction to electrophilic aromatic substitution.

Association of fluorous "phase-vanishing" method with visible-light activation in benzylic bromination by bromine

Podgorsek, Ajda,Stavber, Stojan,Zupan, Marko,Iskra, Jernej

, p. 483 - 488 (2006)

In this study the "phase-vanishing" method for diffusion-controlled addition of a reagent (Br2) to a reaction phase via a fluorous membrane (C8F18) is combined with an additional mode of activation (visible-light) to achieve the benzyl bromination of various alkyl-substituted aromatic compounds in a concentrated solution. Benzyl bromination of p-tert-butyl-toluene proceeded in various solvents including hexane and methanol, while the reaction of the neat substrate showed a similar selectivity as in carbon tetrachloride. The effect of the substituent on the para position of toluene on the course of bromination revealed three processes: benzyl bromination with H, Me, tBu and CO2Et substituents, aromatic bromination with OMe and NHAc substituents and the reaction of the 4-acetyl derivative at the substituent to form an α-bromo ketone. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

Poly(N,N′-dibromo-N-ethyl-benzene-1,3-disulfonamide), N,N,N′,N′-tetrabromobenzene-1,3-disulfonamide and novel poly(N,N′-dibromo-N-phenylbenzene-1,3-disulfonamide) as powerful reagents for benzylic bromination

Ghorbani-Vaghei, Ramin,Chegini, Mohammad,Veisi, Hojat,Karimi-Tabar, Mehdi

, p. 1861 - 1865 (2009)

N,N,N′,N′-Tetrabromobenzene-1,3-disulfonamide [TBBDA], poly(N,N′-dibromo-N-ethyl-benzene-1,3-disulfonamide) [PBBS], and novel poly(N,N′-dibromo-N-phenylbenzene-1,3-disulfonamide) [PBPS] can be used for bromination of benzylic positions in solvent.

Facile continuous process for gas phase halogen exchange over supported alkyl phosphonium salts

Sharma, Priti,Sasson, Yoel

, p. 2824 - 2828 (2018)

Chloride-bromide halogen exchange was realized when a mixture of an alkyl chloride and an alkyl bromide were reacted over a supported molten alkyl phosphonium catalyst. Conversion was found to be near equilibrium in a tubular flow reactor at 150 °C and 1500 GHSV. The catalyst was prepared by impregnation of alumina or silica support and found to be highly stable for relatively long periods of time. A pathway for the catalytic cycle is proposed.

-

Olah,G.A.,Welch,J.

, p. 652 (1974)

-

Efficient dehydrative alkylation of thiols with alcohols catalyzed by alkyl halides

Yang, Yaqi,Ye, Zihang,Zhang, Xu,Zhou, Yipeng,Ma, Xiantao,Cao, Hongen,Li, Huan,Yu, Lei,Xu, Qing

, p. 9638 - 9642 (2017)

Alcohols can be efficiently converted into the useful thioethers by a transition metal- and base-free dehydrative S-alkylation reaction with thiols or disulfides by employing alkyl halides as the effective catalyst. This simple and efficient method is a green and practical way for the preparation of thioethers, as it tolerates a wide range of substrates such as aryl and alkyl thiols, as well as benzylic, allylic, secondary, tertiary, and even the less reactive aliphatic alcohols.

A facile conversion of thiols to alkyl halides by triphenylphosphine/N-halosuccinimides

Iranpoor,Firouzabadi,Aghapour

, p. 1176 - 1178 (2001)

Thiols are efficiently converted to alkyl halides in high to excellent yields when treated with triphenylphosphin/N-halosuccinimide (halogen: Br,Cl, and I) in dichloromethane at room temperature.

Quadraphasic phase-vanishing method: Application to bromination reactions that produce acidic by-products

Rahman, Md. Taifur,Kamata, Naoya,Matsubara, Hiroshi,Ryu, Ilhyong

, p. 2664 - 2666 (2005)

A quadraphasic phase-vanishing method was developed that employs water as the fourth phase acting as an 'acid scavanger phase'. This protocol worked well for bromination of acetophenones giving high yields of the corresponding α-bromo ketones. Georg Thieme Verlag Stuttgart.

Pure branch effect on the optical properties of novel conjugated derivatives

Yang, Long,Gao, Fang,Liu, Jian,Zhong, Xiaolin,Li, Hongru,Zhang, Shengtao

, p. 582 - 583 (2010)

Pure cooperative branch effects on one- and two-photon optical properties of conjugated derivatives are presented. AMI calculations demonstrate that the electron density distribution of the frontier orbital and the dipole moment changes of the derivatives are related to the number of branches. The theoretical results show that not only the energy level of the frontier orbital could be mediated by the number of branches, but the HOMOLUMO gap could be regulated.

-

Walling,Padwa

, p. 2976 (1962)

-

-

Jung,M.E.,Hatfield,G.L.

, p. 4483 - 4486 (1978)

-

Graphite-catalyzed acylative cleavage of ethers with acyl halides

Suzuki, Yoshitada,Matsushima, Masayuki,Kodomari, Mitsuo

, p. 319 - 320 (1998)

Graphite is found to catalyze acylative cleavage of ethers such as benzylic, allylic, tert-butylic and cyclic ethers with acyl halides to give the corresponding esters in good to excellent yields. Benzylic ether was cleaved chemoselectively, when a variety of other functional groups was present, to produce the corresponding ester along with benzyl halide.

Direct halogenation of alcohols and their derivatives with tert-Butyl halides in the ionic liquid [pmIm]Br under sonication conditions - A novel, efficient and green methodology

Ranu, Brindaban C.,Jana, Ranjan

, p. 755 - 758 (2005)

A novel halogenating reagent system for direct halogenation of alcohols has been developed. tert-Butyl bromide, chloride and iodide in combination with the ionic liquid [pmIm]Br have been found to convert alcohols into the corresponding bromides, chlorides and iodides under sonication conditions (or heating) in good yields. Although a variety of primary and secondary alcohols participated in this reaction without any difficulty, tertiary alcohols remained inert. Several alcohol derivatives such as OTMS, OTBDMS, OAc, OTS and OTHP are also transformed into the corresponding halides in one-pot fashion by this procedure. A plausible rationale for this transformation is also presented. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.

Nickel-Catalyzed Benzylation of C?H Bonds in Aromatic Amides with Benzyltrimethylammonium Halides

Sasagawa, Akane,Yamaguchi, Mao,Ano, Yusuke,Chatani, Naoto

, p. 964 - 967 (2017)

Nickel-catalyzed benzylation reactions of C?H bonds in aromatic amides with benzyltrimethylammonium halides are developed by using a 5-chloro-8-aminoquinoline derivative as a bidentate directing group. Benzylation occurs selectively at the ortho-C?H bonds in aromatic amides, and no methylation was detected. The presence of a 5-chloro-8-aminoquinoline moiety is essential for the success of this reaction, in which a variety of functional groups can be tolerated.

Tribromoisocyanuric acid/triphenylphosphine: A new system for conversion of alcohols into alkyl bromides

De Andrade, Vitor S.C.,De Mattos, Marcio C.S.

, p. 975 - 979 (2014)

An efficient and facile method has been developed for the conversion of alcohols into alkyl bromides under neutral conditions using tribromoisocyanuric acid and triphenylphosphine (molar ratio 1.0:0.7:2.0, alcohol/ tribromoisocyanuric acid/triphenylphosphine) in dichloromethane at room temperature. This method can be applied for the conversion of primary, secondary, benzylic and allylic alcohols, and their corresponding bromides are obtained in 67-82 percent yield. Tertiary alcohols do not react under these conditions.

Inorganic Micelles (Hydrophilic Core@Amphiprotic Shell) for Multiple Applications

Islam, Md. Shahinul,Choi, Won San,Kim, Sun Ha,Han, Oc Hee,Lee, Ha-Jin

, p. 6061 - 6070 (2015)

A facile approach for synthesizing superhydrophobic hollow silica micelles (SHSMs) with hydrophilic cores and amphiprotic (superhydrophobic/hydrophilic) shell structures that act as "all-in-one" smart nanomaterials is presented. The particles possess hydr

Direct bromination of hydrocarbons catalyzed by Li2MnO 3 under oxygen and photo-irradiation conditions

Nishina, Yuta,Morita, Junya,Ohtani, Bunsho

, p. 2158 - 2162 (2013)

A method for the direct bromination of hydrocarbons with Br2 using a ubiquitous and inexpensive catalyst is highly desirable. Herein, we report the selective mono-bromination of hydrocarbons in good yield using Li2MnO3 as a catalyst under irradiation with a fluorescent room light. This new catalyst can be recycled. The effect of light was investigated using action spectra, which revealed that the reaction occurred on the surface of the catalyst.

-

Schmidt

, p. 1144,1147, 1148 (1946)

-

REACTIONS IN MICROEMULSION MEDIA. NUCLEOPHILIC DISPLACEMENT REACTION OF BENZYL CHLORIDE WITH BROMIDE ION

Martin, Craig A.,McCrann, Patrick M.,Angelos, George H.,Jaeger, David A.

, p. 4651 - 4654 (1982)

A kinetic and synthetic study of the reaction of benzyl chloride with bromide ion has been performed in microemulsions composed of cetyltrimethylammonium bromide, 1-butanol, water, potassium bromide, and hexane; rates and yields of benzyl bromide formatio

A Simple Method for the Conversions of Adamantyl, Benzyl and Benzhydryl Alcohols to Their Corresponding Bromides and Chlorides and the Transhalogenation of Adamantyl, Benzyl, Benzhydryl and tertiary Alkyl Bromides and Chlorides

Amrollah-Madjdabadi, A.,Pham, Tung N.,Ashby, E. C.

, p. 614 - 616 (1989)

Adamantyl, benzyl, and benzhydryl alcohols have been converted to their corresponding bromides and chlorides in the absence of a solvent, rapidly and in high yield using boron tribromide and tin(IV) chloride, respectively.Additionally the above bromides and chlorides can be interconverted by a transhalogenation process using the same reagents in the absence of solvent.

SYNTHESIS OF BENZYL HALIDES FROM ALDEHYDES PROMOTED BY HALOSILANES AND 1,1,3,3-TETRAMETHYLDISILOXANE (TMDS).

Aizpurua, Jesus M.,Palomo, Claudio

, p. 1103 - 1104 (1984)

Direct synthesis of monoalkyl halides from aldehydes by a new reductive halogenation method is briefly described.

A simple and efficient iodination of alcohols on polymer-supported triphenylphosphine

Anilkumar, Gopinathan,Nambu, Hisanori,Kita, Yasuyuki

, p. 190 - 191 (2002)

A simple, mild, and high-yielding procedure for the iodination of allylic, benzylic, and other primary alcohols using a combination of iodine and imidazole on polymer-supported triphenyl phosphine is described.

Highly Reactive Manganese(IV)-Oxo Porphyrins Showing Temperature-Dependent Reversed Electronic Effect in C-H Bond Activation Reactions

Guo, Mian,Seo, Mi Sook,Lee, Yong-Min,Fukuzumi, Shunichi,Nam, Wonwoo

, p. 12187 - 12191 (2019)

We report that Mn(IV)-oxo porphyrin complexes, MnIV(O)(TMP) (1) and MnIV(O)(TDCPP) (2), are capable of activating the C-H bonds of hydrocarbons, including unactivated alkanes such as cyclohexane, via an oxygen non-rebound mechanism. Interestingly, 1 with an electron-rich porphyrin is more reactive than 2 with an electron-deficient porphyrin at a high temperature (e.g., 0 °C). However, at a low temperature (e.g., -40 °C), the reactivity of 1 and 2 is reversed, showing that 2 is more reactive than 1. To the best of our knowledge, the present study reports the first example of highly reactive Mn(IV)-oxo porphyrins and their temperature-dependent reactivity in C-H bond activation reactions.

Ionic liquid promoted regioselective monobromination of aromatic substrates with N-bromosuccinimide

Rajagopal,Jarikote,Lahoti,Daniel, Thomas,Srinivasan

, p. 1815 - 1817 (2003)

Aromatic substrates were monobrominated regioselectively with NBS in the ionic liquid 1,3-di-n-butylimidazolium tetrafluoroborate [bbim]BF4 in 5 min at 28°C in excellent isolated yields (80-98%) in the absence of a catalyst.

Mild Aliphatic and Benzylic Hydrocarbon C-H Bond Chlorination Using Trichloroisocyanuric Acid

Combe, Sascha H.,Hosseini, Abolfazl,Parra, Alejandro,Schreiner, Peter R.

, p. 2407 - 2413 (2017)

We present the controlled monochlorination of aliphatic and benzylic hydrocarbons with only 1 equiv of substrate at 25-30 °C using N-hydroxyphthalimide (NHPI) as radical initiator and commercially available trichloroisocyanuric acid (TCCA) as the chlorine source. Catalytic amounts of CBr4 reduced the reaction times considerably due to the formation of chain-carrying ·CBr3 radicals. Benzylic C-H chlorination affords moderate to good yields for arenes carrying electron-withdrawing (50-85%) or weakly electron-donating groups (31-73%); cyclic aliphatic substrates provide low yields (24-38%). The products could be synthesized on a gram scale followed by simple purification via distillation. We report the first direct side-chain chlorination of 3-methylbenzoate affording methyl 3-(chloromethyl)benzoate, which is an important building block for the synthesis of vasodilator taprostene.

Synthesis and application of new phenyl-functionalized zeolites as protection against radical bromination at the benzylic position

Itoh, Akichika,Masaki, Yukio

, p. 1450 - 1452 (1997)

New zeolites functionalized with phenyl group have been synthesized from phenyltriethoxysilane and/or tetraethylorthosilicate with dodecylamine as a template at room temperature. These zeolites have proved to have an ability to protect the benzylic position against radical bromination. 4-Chloromethylstyrene was brominated at the double bond selectively and the benzylic position was intact under irradiation with visible light in the presence of phenyl-functionalized zeolites, although without the zeolite, the both sites were brominated.

THE CINE O-ALKYLATION OF OXIRANYLCARBINOLS

Bird, C. W.,Hormozi, N.

, p. 705 - 706 (1988)

The reaction of the alkoxides derived from some oxyranylcarbinols with alkyl halides occurs by electrophilic attack on the oxiranyl oxygen rather than the alkoxide one leading to formation of the rearranged oxiranylcarbinyl ether.

Coomber, J. W.,Whittle, E.

, p. 608 - 619 (1967)

BORON TRIFLUORIDE ETHERATE/HALIDE ION, A NOVEL REAGENT FOR THE CONVERSION OF ALLYL, BENZYL AND TERTIARY ALCOHOLS TO THE HALIDES

Mandal, Arun K.,Mahajan, S. W.

, p. 3863 - 3866 (1985)

A combination of boron trifluoride etherate and halide ion is found to be an excellent reagent for the conversion of allyl, benzyl and tertiary alcohols to the halides.

The complex synergy of water in the metal/bromide autoxidation of hydrocarbons caused by benzylic bromide formation

Partenheimer, Walt

, p. 297 - 306 (2004)

One of the most active and selective catalysts in homogeneous liquid phase oxidation using molecular oxygen (O2) is a mixture of cobalt, manganese and bromide salts in acetic acid. It has been used to produce hundreds of different carboxylic acids in high yield and purity including the commercial production of terephthalic acid from p-xylene. Water is normally a by-product in these reactions and it is shown here that its concentration is an important reaction variable. In anhydrous acetic acid, with reagents with sufficiently strong electron-withdrawing substitutents (toluene, 4-carboxytoluene, 4-chlorotoluene), all of the active bromide becomes inactive via benzylic bromide formation. The Co/Mn/ Br catalyst is therefore converted to a Co/Mn catalyst which is dubbed 'catalyst failure' because of its undesirable characteristics of lower activity, decreased selectivity especially towards over-oxidation and color formation. For 4-chlorotoluene, increasing the water concentration to 5 weight % initially decreases the rate of reaction but eventually is more active and selective because the oxidation and hydrolysis of the benzylic bromide allows for sufficient active catalytic bromide. It is shown that benzylic bromides do not 'promote' the reaction and that both oxidation and solvolysis of the benzylic bromide occurs during autoxidation. During polymethylbenzene oxidation, benzylic bromide formation occurs only with the most reactive methyl group. The complex factors during metal/bromide autoxidation -some favored by increased water concentration and others detrimental - are outlined.

A new synthesis and application of N, N'-dibromo-N, N'-1,2-ethylene bis(2,5-dimethyl benzene sulfonamide); as a novel selective bromination agent for aromatic compounds

Ardeshir, Khazaei,Abbas, Shirdarreh

, p. 4079 - 4085 (1999)

Reaction Between Novel Compound; N, N' dibromo-N, N'-1,2- ethylene bis(2,5- dimethyl benzene sulfonamide) and aromatic compounds in the carbontetrachloride produces bromo aromatic compounds. In the case of benzene rings that contain mono activated substituted, only para - bromo isomer was formed. At the presence of benzoyl peroxide in the reaction mixture α - Hydrogen from alkyl side chain was substituted with bromine.

Positive shift in corrole redox potentials leveraged by modest β-CF3-substitution helps achieve efficient photocatalytic C-H bond functionalization by group 13 complexes

Zhan, Xuan,Yadav, Pinky,Diskin-Posner, Yael,Fridman, Natalia,Sundararajan, Mahesh,Ullah, Zakir,Chen, Qiu-Cheng,Shimon, Linda J. W.,Mahammed, Atif,Churchill, David G.,Baik, Mu-Hyun,Gross, Zeev

, p. 12279 - 12286 (2019)

Tris- A nd tetrakis-β-trifluoromethylated gallium (3CF3-Ga, 4CF3-Ga) and aluminum (3CF3-Al, 4CF3-Al) corrole systems were synthesized by a facile "one-pot" approach from the respective tri- A nd tetra-iodo starting compounds using the FSO2CF2CO2Me reagent. The isolated 5,10,15-(tris-pentafluorophenyl)corrole-based compounds set the groundwork for another important β-substituent study in inorganic photocatalysis. As seen previously,-CF3 group substitution leads to red shifts in both the absorption and emission spectra compared to their unsubstituted counterparts (X. Zhan, et al., Inorg. Chem., 2019, 58, 6184-6198). All CF3-substituted corrole complexes showed strong fluorescence; 3CF3-Al possessed the highest fluorescence quantum yield (0.71) among these compounds. The photocatalytic production of bromophenol by way of these photosensitizing complexes was studied demonstrating that tris-trifluoromethylation is an important substitution class, especially when Ga3+ is present (experimental TON value in parentheses): 3CF3-Ga (192) > 4CF3-Ga (146) > 3CF3-Al (130) > 4CF3-Al (56) > 1-Ga (43) > 1-Al (18). The catalytic performance (turn-over number, TON) for benzylbromide formation (from toluene) was found to be: 3CF3-Ga (225) > 1-Ga (138) > 3CF3-Al (130) > 4CF3-Ga (126) > 1-Al (95) > 4CF3-Al (89); in these trials, benzaldehyde was also detected as a product in which 3CF3-Ga outperforms the other compounds (TON = 109). The tetra-CF3-substituted 4CF3-Ga and 4CF3-Al species exhibit a dramatic formal positive shift of 116 mV and 126 mV per [CF3] group, respectively, compared to the unsubstituted parent species 1-Ga and 1-Al. However, the absorbance values (λabs = 400 nm) of these corrole complexes (all equally concentrated: 4.0 × 10-6 M) were 3CF3-Al (0.23) > 3CF3-Ga (0.22) > 1-Al (0.21) > 1-Ga (0.20) > 4CF3-Al (0.19) > 4CF3-Ga (0.15), which helps rationalize why 3CF3-Ga performs the best among these catalysts. These new photosensitizers were carefully characterized by 1H and 19F NMR spectroscopy to help verify the number and position (symmetry) of the CF3 groups; 3CF3-Ga and 3I-Al were structurally characterized. Distortions in the corrole macrocycle imposed by the multiple β-substitution were quantified.

Free-Radical Bromination of Selected Organic Compounds in Water

Shaw, Henry,Perlmutter, Howard D.,Gu, Chen,Arco, Susan D.,Quibuyen, Titos O.

, p. 236 - 237 (1997)

-

-

Ford,Waters

, p. 2240,2245 (1952)

-

A new synthetic approach to novel spiro-β-lactams

Bhalla, Aman,Venugopalan, Paloth,Bari, Shamsher S.

, p. 4943 - 4950 (2006)

An operationally simple and efficient approach for the synthesis of novel spiro-β-lactams is described. The key reaction is a halogen-mediated intrasulfenyl cyclization of a cis-3-benzylthio-3-(prop-2-ynyloxy/-enyloxy)- β-lactam procured through a Lewis acid-mediated C-3-alkylation of the trans-3-benzylthio-3-chloro-β-lactam carbocation equivalent. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

Increasing the selectivity of bromination of aromatic compounds using Br2/SiO2

Ghiaci,Asghari

, p. 1151 - 1152 (2001)

Br2/SiO2 possessed considerable practical advantages over traditional reagents for the bromination of aromatic hydrocarbons, e.g., toluene, o-, m-, and p-xylene, anthracene and phenol. In the presence of SiO2, toluene reacted with bromine instantly. Compounds containing electron-donating substituents showed mainly bromination on the rings. The behavior of o-, m-, and p-xylene showed predominant substitution on the rings. The bromination of phenol to p-bromophenol showed good yield at 81%. Naphthalene was monobrominated to 1-bromonaphthalene with a yield of 84% in 2 has the potential to alter reaction selectivity. It may be able to switch a mechanism from radical to polar, or to influence the regioselectivity of the products formed. In the absence of SiO2, selectivity was lost and a mixture of products by substitution of bromine atom on the ring and on the side chain without any preferability was obtained. The nature of silica gel was important for the success of the reaction. Optimal results were obtained with silica gel dried at 250°C for 1 hr.

-

Koeroesi,J.

, p. 1222 - 1232 (1969)

-

Benton,Dillon

, p. 1128 (1942)

NHC-palladium-catalyzed ionic liquid-accelerated regioselective oxyarylation of alkynes with diaryl ethers?

Cen, Liying,He, Dan,Jiang, Huanfeng,Li, Jianxiao,Lin, Zidong,Wu, Wanqing

supporting information, p. 1983 - 1988 (2022/04/03)

The first NHC-palladium-catalyzed regioselective oxyarylation of oxime ether in a task-specific ionic liquid via C(sp3)-O and C(sp2)-O bond cleavage of two different types of ethers for the assembly of structurally diverse 4-arylisoxazoles is described. Both the basic ionic liquid [C3NH2mim]Br and NHC-Pd catalyst IPr-Pd-Im-Cl2 played an important role in this transformation. Notably, this new approach provides a practical and straightforward route to access a broad range of privileged 4-arylisoxazole structures with good yields and excellent regioselectivities. Significantly, this catalytic system can be recycled up to eight times without significant loss of catalytic activity.

Synthesis, Docking, and Biological activities of novel Metacetamol embedded [1,2,3]-triazole derivatives

Battu, Satyanarayana,Joolakanti, Hima Bindhu,Kamepalli, Ramanjaneyulu,Miryala, Jeevanreddy

, (2021/06/18)

ERα controls the breast tissue development and progression of breast cancer. In our search for novel compounds to target Estrogen Receptor Alpha Ligand-Binding Domain, we identified “N-(3-((1H-1,2,3-triazol-4-yl)methoxy)phenyl)acetamide” derivatives as lead compounds. The Docking studies indicated good docking score for Metacetamol derivatives when docked into the 1XP6. A series of metacetamol derivatives have been synthesized, characterized and evaluated for cytotoxicity, anti bacterial and anti oxidant activities. Among the tested twelve hybrid compounds, “7a, 7g, 7h and 7i” derivatives showed promising cytotoxicity with IC50 value of 50 value of 30 μM, whereas Compounds “7a, 7b, 7c, 7d, 7g, 7j, 7k and 7l” showed moderate anti bacterial activity with the MIC value of 300 μM.

[1,3]-Claisen rearrangement via removable functional group mediated radical stabilization

Alam, Md Nirshad,Dash, Soumya Ranjan,Mukherjee, Anirban,Pandole, Satish,Marelli, Udaya Kiran,Vanka, Kumar,Maity, Pradip

supporting information, p. 890 - 895 (2021/02/01)

A thermal O-to-C [1,3]-rearrangement of α-hydroxy acid derived enol ethers was achieved under mild conditions. The 2-aminothiophenol protection of carboxylic acids facilitates formation of the [1,3] precursor and its thermal rearrangement via stabilization of a radical intermediate. Experimental and theoretical evidence for dissociative radical pair formation, its captodative stability via aminothiophenol, and a unique solvent effect are presented. The aminothiophenol was deprotected from rearrangement products as well as after derivatization to useful synthons.

One-Step Synthesis of Triphenylphosphonium Salts from (Het)arylmethyl Alcohols

Abaev, Vladimir T.,Chalikidi, Petrakis N.,Demidov, Oleg P.,Gutnov, Andrey V.,Magkoev, Taimuraz T.,Trushkov, Igor V.,Uchuskin, Maxim G.

, p. 9838 - 9846 (2021/07/28)

Two approaches for the synthesis of substituted phosphonium salts from easily available benzyl alcohols and their heterocyclic analogs have been developed. The developed protocols are complementary: the direct mixing of alcohol, trimethylsilyl bromide, and triphenylphosphine in 1,4-dioxane followed by heating at 80 °C was found to be more efficient for acid-sensitive substrates, such as salicyl or furfuryl alcohols as well as secondary benzyl alcohols, while a one-pot procedure including sequential addition of trimethylsilyl bromide and triphenylphosphine gave higher yields for benzyl alcohols bearing electroneutral or electron-withdrawing substituents.

Process route upstream and downstream products

Process route

1,2-propylene cyclic carbonate
108-32-7

1,2-propylene cyclic carbonate

N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

chloranil
118-75-2

chloranil

para-bromotoluene
106-38-7

para-bromotoluene

2-methylphenyl bromide
95-46-5

2-methylphenyl bromide

benzyl bromide
100-39-0

benzyl bromide

Conditions
Conditions Yield
at 100 ℃; Product distribution;
1,2-propylene cyclic carbonate
108-32-7

1,2-propylene cyclic carbonate

N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

dibenzoyl peroxide
94-36-0

dibenzoyl peroxide

para-bromotoluene
106-38-7

para-bromotoluene

2-methylphenyl bromide
95-46-5

2-methylphenyl bromide

benzyl bromide
100-39-0

benzyl bromide

Conditions
Conditions Yield
at 100 ℃; Product distribution;
1,2-propylene cyclic carbonate
108-32-7

1,2-propylene cyclic carbonate

N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

para-bromotoluene
106-38-7

para-bromotoluene

2-methylphenyl bromide
95-46-5

2-methylphenyl bromide

benzyl bromide
100-39-0

benzyl bromide

Conditions
Conditions Yield
at 100 ℃; Product distribution;
n-butyl magnesium bromide
693-03-8

n-butyl magnesium bromide

dibutyl ether
142-96-1

dibutyl ether

benzyl 2,4,6-trimethylbenzoate
4909-77-7

benzyl 2,4,6-trimethylbenzoate

mesitylenecarboxylic acid
480-63-7

mesitylenecarboxylic acid

benzyl bromide
100-39-0

benzyl bromide

Conditions
Conditions Yield
n-butyl magnesium bromide
693-03-8

n-butyl magnesium bromide

benzyl 2,4,6-trimethylbenzoate
4909-77-7

benzyl 2,4,6-trimethylbenzoate

benzyl bromide
100-39-0

benzyl bromide

Conditions
Conditions Yield
With dibutyl ether;
tetrachloromethane
56-23-5

tetrachloromethane

N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

dibenzyl ether
103-50-4

dibenzyl ether

benzyl bromide
100-39-0

benzyl bromide

benzaldehyde
100-52-7

benzaldehyde

Conditions
Conditions Yield
UV-Licht.Irradiation;
tetrachloromethane
56-23-5

tetrachloromethane

N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

dibenzoyl peroxide
94-36-0

dibenzoyl peroxide

benzyl bromide
100-39-0

benzyl bromide

Conditions
Conditions Yield
ethyl bromide
74-96-4

ethyl bromide

benzoic acid benzyl ester
120-51-4

benzoic acid benzyl ester

benzoic acid ethyl ester
93-89-0,99341-95-4

benzoic acid ethyl ester

benzyl bromide
100-39-0

benzyl bromide

Conditions
Conditions Yield
With magnesium; benzene;
diethyl ether
60-29-7,927820-24-4

diethyl ether

phenylmagnesium bromide

phenylmagnesium bromide

benzyl bromide
100-39-0

benzyl bromide

benzaldehyde
100-52-7

benzaldehyde

Conditions
Conditions Yield
phenylmagnesium bromide

phenylmagnesium bromide

benzyl bromide
100-39-0

benzyl bromide

Conditions
Conditions Yield
With diethyl ether;

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