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100-58-3

100-58-3

Identification

Synonyms:Phenylmagnesiumbromide (6CI);Bromomagnesiobenzene;Bromophenylmagnesium;

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Safety information and MSDS view more

  • Pictogram(s):HighlyF+, CorrosiveC, FlammableF

  • Hazard Codes:F+,C,F

  • Signal Word:Danger

  • Hazard Statement:H314 Causes severe skin burns and eye damage

  • 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

Supplier and reference price view more

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  • Manufacture/Brand:Usbiological
  • Product Description:Phenylmagnesium Bromide
  • Packaging:25ml
  • Price:$ 319
  • Delivery:In stock
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  • Manufacture/Brand:TRC
  • Product Description:PhenylmagnesiumBromide(1.0MsolutioninTHF)
  • Packaging:500ml
  • Price:$ 250
  • Delivery:In stock
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  • Manufacture/Brand:TRC
  • Product Description:PhenylmagnesiumBromide(1.0MsolutioninTHF)
  • Packaging:50ml
  • Price:$ 80
  • Delivery:In stock
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Phenylmagnesium Bromide (16% in Tetrahydrofuran, ca. 1mol/L)
  • Packaging:250g
  • Price:$ 124
  • Delivery:In stock
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  • Manufacture/Brand:Strem Chemicals
  • Product Description:Phenylmagnesium bromide, 2.9M (45wt% ±1wt%) in 2-methyltetrahydrofuran
  • Packaging:1mole
  • Price:$ 178
  • Delivery:In stock
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  • Manufacture/Brand:Strem Chemicals
  • Product Description:Phenylmagnesium bromide, 3M in ether
  • Packaging:1mole
  • Price:$ 155
  • Delivery:In stock
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  • Manufacture/Brand:Strem Chemicals
  • Product Description:Phenylmagnesium bromide, 2.9M (45wt% ±1wt%) in 2-methyltetrahydrofuran
  • Packaging:0.25mole
  • Price:$ 78
  • Delivery:In stock
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  • Manufacture/Brand:Strem Chemicals
  • Product Description:Phenylmagnesium bromide, 3M in ether
  • Packaging:0.25mole
  • Price:$ 52
  • Delivery:In stock
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Phenylmagnesium bromide solution 3.0M in diethyl ether
  • Packaging:800ml
  • Price:$ 217
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Phenylmagnesium bromide solution 3.0M in diethyl ether
  • Packaging:200ml
  • Price:$ 204
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Relevant articles and documentsAll total 55 Articles be found

Scalable Continuous Synthesis of Grignard Reagents from in Situ-Activated Magnesium Metal

Deitmann, Eva,G?ssl, Lars,Hofmann, Christian,L?b, Patrick,Menges-Flanagan, Gabriele

, p. 315 - 321 (2020)

The continuous synthesis of Grignard reagents has been investigated under continuous processing conditions using Mg turnings at variable liquid throughputs and concentrations. A novel process window easily accessible through continuous processing was employed, namely, using a large molar access of Mg turnings within the reactor and achieving Mg activation by mechanical means. A laboratory and a 10-fold-increased pilot-scale reactor setup were built and evaluated, including integrated inline analytics via ATR-IR measurements. The main goal of this work was to explore the full potential of classic Grignard reagent formation through the use of scalable flow chemistry and to allow for fast and safe process optimization. It was found that on both the laboratory and pilot scales, full conversion of the employed halides could be achieved with a single passage through the reactor. Furthermore, Grignard reagent yields of 89-100% were reached on the laboratory scale.

Formation of phenylmagnesium halides in toluene

Simuste, Hannes,Panov, Dmitri,Tuulmets, Ants,Nguyen, Binh T.

, p. 3061 - 3066 (2005)

Formation reactions of phenylmagnesium chloride and bromide in toluene in the presence of one or two equivalents of diethyl ether or THF were investigated kinetically. Also, the reaction in diethyl ether and in chlorobenzene was addressed. Kinetic features of the reactions are similar to those found previously for the formation of alkylmagnesium halides in toluene and consist of rapid formation of a disolvated Grignard reagent followed by a slower formation of a monosolvated reagent. The latter is able of catalyzing the conversion of different halides into Grignard reagents. However, the contribution of Wurtz-type side reactions is considerable except when THF is used in toluene. Involving the kinetic data and the activation parameters some details of the reaction mechanism were discussed.

Nickel-Catalyzed Alkyl-Alkyl Cross-Electrophile Coupling Reaction of 1,3-Dimesylates for the Synthesis of Alkylcyclopropanes

Chen, Pan-Pan,Hong, Xin,Jarvo, Elizabeth R.,McGinnis, Tristan M.,Sanford, Amberly B.,Thane, Taylor A.

, (2020)

Cross-electrophile coupling reactions of two Csp3-X bonds remain challenging. Herein we report an intramolecular nickel-catalyzed cross-electrophile coupling reaction of 1,3-diol derivatives. Notably, this transformation is utilized to synthesize a range of mono- and 1,2-disubstituted alkylcyclopropanes, including those derived from terpenes, steroids, and aldol products. Additionally, enantioenriched cyclopropanes are synthesized from the products of proline-catalyzed and Evans aldol reactions. A procedure for direct transformation of 1,3-diols to cyclopropanes is also described. Calculations and experimental data are consistent with a nickel-catalyzed mechanism that begins with stereoablative oxidative addition at the secondary center.

Formation of Transient Anionic Metal Clusters in Palladium/Diene-Catalyzed Cross-Coupling Reactions

Kolter, Marlene,Koszinowski, Konrad

, p. 13376 - 13384 (2019)

Despite their considerable practical value, palladium/1,3-diene-catalyzed cross-coupling reactions between Grignard reagents RMgCl and alkyl halides AlkylX remain mechanistically poorly understood. Herein, we probe the intermediates formed in these reactions by a combination of electrospray-ionization mass spectrometry, UV/Vis spectroscopy, and NMR spectroscopy. According to our results and in line with previous hypotheses, the first step of the catalytic cycle brings about transmetalation to afford organopalladate anions. These organopalladate anions apparently undergo SN2-type reactions with the AlkylX coupling partner. The resulting neutral complexes then release the cross-coupling products by reductive elimination. In gas-phase fragmentation experiments, the occurrence of reductive eliminations was observed for anionic analogues of the neutral complexes. Although the actual catalytic cycle is supposed to involve chiefly mononuclear palladium species, anionic palladium nanoclusters [PdnR(DE)n]?, (n=2, 4, 6; DE=diene) were also observed. At short reaction times, the dinuclear complexes usually predominated, whereas at longer times the tetra- and hexanuclear clusters became relatively more abundant. In parallel, the formation of palladium black pointed to continued aggregation processes. Thus, the present study directly shows dynamic behavior of the palladium/diene catalyst system and degradation of the active catalyst with increasing reaction time.

Room-Temperature Palladium(II)-Catalyzed Direct 2-Arylation of Indoles with Tetraarylstannanes

Liu, Yuxia,Wang, Chao,Huang, Linjuan,Xue, Dong

supporting information, p. 1613 - 1618 (2020/09/15)

A palladium(II)-catalyzed direct 2-arylation of indoles by tetraarylstannanes with oxygen (balloon) as the oxidant at room temperature has been developed. Various tetraarylstannanes can be employed as aryl sources for 2-arylation of indoles in up to 89% yield, providing a practical and efficient catalytic protocol for accessing 2-arylindoles.

Process route upstream and downstream products

Process route

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

bromobenzene

magnesium
7439-95-4

magnesium

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

Conditions
Conditions Yield
In tetrahydrofuran;
In tetrahydrofuran; for 1.5h; Inert atmosphere; Reflux;
With iodine; In tetrahydrofuran; for 2h; Inert atmosphere; Reflux;
With iodine; In tetrahydrofuran; for 1h; Heating / reflux;
bromobenzene
108-86-1,52753-63-6

bromobenzene

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

Conditions
Conditions Yield
With magnesium; In tetrahydrofuran; at 40 ℃; for 0.25h; Inert atmosphere; Flow reactor;
100%
With magnesium; In tetrahydrofuran;
With magnesium; In diethyl ether; at 19.9 ℃; Rate constant; various concentrations of aryl halide;
With magnesium; In diethyl ether; benzene; at 19.85 ℃; Rate constant; Product distribution; Thermodynamic data; magnesium oxidation with hydrocarbon halides; character of adsorption; diffusion of reagent to metal surface; rate of oxidation; energy of activation; kinetics; formation of Grignard reagents;
With 18-crown-6 ether; magnesium; In tetrahydrofuran; at 20 ℃; Further Variations:; Reagents; Solvents; Product distribution;
With magnesium; In diethyl ether; at 35 ℃; Further Variations:; Solvents; Kinetics;
With magnesium; In diethyl ether;
With magnesium; In diethyl ether;
With magnesium; In tetrahydrofuran;
With ammonium chloride; magnesium; In tetrahydrofuran;
With magnesium; In tetrahydrofuran;
With iodine; magnesium; In tetrahydrofuran; at 40 ℃; for 1h; Heating / reflux;
With iodine; magnesium; In tetrahydrofuran; at 25 ℃; for 0.5h; Inert atmosphere;
With magnesium; In diethyl ether;
With magnesium; iodine; In tetrahydrofuran;
With magnesium; In tetrahydrofuran;
With magnesium; In tetrahydrofuran; Inert atmosphere;
With magnesium; In tetrahydrofuran; for 1h; Inert atmosphere; Reflux;
With magnesium; In tetrahydrofuran; Inert atmosphere;
With magnesium; In tetrahydrofuran; at 83 ℃;
With iodine; magnesium; In tetrahydrofuran; for 2h; Inert atmosphere; Reflux;
With magnesium; In tetrahydrofuran;
With magnesium; In diethyl ether; at 20 - 50 ℃; Inert atmosphere; Sealed tube;
With magnesium; In diethyl ether; at 20 ℃;
With magnesium; In diethyl ether;
With magnesium; In tetrahydrofuran; Inert atmosphere;
With magnesium; In tetrahydrofuran;
With magnesium; In tetrahydrofuran-d8; at 20 ℃; Inert atmosphere; Schlenk technique;
With iodine; magnesium; In diethyl ether; at 20 ℃; for 2.5h; Reflux; Inert atmosphere;
With iodine; magnesium; at 30 ℃; for 1h; Inert atmosphere;
With iodine; magnesium; In diethyl ether; for 1h; Inert atmosphere; Reflux;
With magnesium; In tetrahydrofuran; at 30 ℃; for 0.5h; Inert atmosphere; Cooling with ice;
With magnesium; In tetrahydrofuran; for 1h; Inert atmosphere; Reflux;
bromobenzene
108-86-1,52753-63-6

bromobenzene

1-phenyltetrafluoro-2-propenylacetate

1-phenyltetrafluoro-2-propenylacetate

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

Conditions
Conditions Yield
With magnesium; In tetrahydrofuran;
24%
bromobenzene
108-86-1,52753-63-6

bromobenzene

N-Z-(S)-serine methyl ester

N-Z-(S)-serine methyl ester

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

Conditions
Conditions Yield
With hydrogenchloride; In diethyl ether;
[NitriphosCl]PF6

[NitriphosCl]PF6

1,2-dichloro-benzene
95-50-1

1,2-dichloro-benzene

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

Conditions
Conditions Yield
With biphenyl; ethylmagnesium bromide; phenylmagnesium bromide; In o-xylene;
1-phenyl-2-bromoethane
103-63-9

1-phenyl-2-bromoethane

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

Conditions
Conditions Yield
With hydrogenchloride; iodine; In magnesium;
2-amino-5-chlorobenzonitrile
5922-60-1

2-amino-5-chlorobenzonitrile

(2-amino-5-chlorophenyl)-phenyl-methane-imine
5606-39-3

(2-amino-5-chlorophenyl)-phenyl-methane-imine

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

Conditions
Conditions Yield
92%
bromobenzene
108-86-1,52753-63-6

bromobenzene

1-methyl-3-fluoro-5,7-dichloro-2,3-dihydro-1H-1,4-benzodiazepin-2-one
60628-69-5

1-methyl-3-fluoro-5,7-dichloro-2,3-dihydro-1H-1,4-benzodiazepin-2-one

3-fluorodiazepam

3-fluorodiazepam

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

Conditions
Conditions Yield
With HF; In tetrahydrofuran;
bromobenzene
108-86-1,52753-63-6

bromobenzene

dimethyl-2,3-O-cyclohexylidene-L-tartrate

dimethyl-2,3-O-cyclohexylidene-L-tartrate

(-)-2,3-O-cyclohexylidene-1,1,4,4-tetra-phenyl-L-threitol

(-)-2,3-O-cyclohexylidene-1,1,4,4-tetra-phenyl-L-threitol

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

Conditions
Conditions Yield
With magnesium; In diethyl ether;
17 g (34%)
bromobenzene
108-86-1,52753-63-6

bromobenzene

(S)-Carbomethoxy oxazolidinone

(S)-Carbomethoxy oxazolidinone

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

Conditions
Conditions Yield
In tetrahydrofuran;

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