PHENYLMAGNESIUM BROMIDE
phenylmagnesium bromide solution
CAS: 100-58-3
Molecular Formula: C6H5BrMg
PHENYLMAGNESIUM BROMIDE - Names and Identifiers
| Name | phenylmagnesium bromide solution |
| Synonyms | bromo(phenyl)magnesium Phenylmagnesium bromide phenylmagnesium bromide solution |
| CAS | 100-58-3 |
| EINECS | 202-867-2 |
| InChI | InChI=1/C6H5.BrH.Mg/c1-2-4-6-5-3-1;;/h1-5H;1H;/q;;+1/p-1/rC6H5BrMg/c7-8-6-4-2-1-3-5-6/h1-5H |
| InChIKey | ANRQGKOBLBYXFM-UHFFFAOYSA-M |
PHENYLMAGNESIUM BROMIDE - Physico-chemical Properties
| Molecular Formula | C6H5BrMg |
| Molar Mass | 181.313 |
| Density | 1.134 g/mL at 25 °C |
| Melting Point | 153-154 °C |
| Flash Point | −40 °F |
| Water Solubility | reacts |
| Appearance | Yellow to brown Liquid |
| Storage Condition | water-free area |
| Stability | Air & Moisture Sensitive |
PHENYLMAGNESIUM BROMIDE - Risk and Safety
| Hazard Symbols | F - Flammable C - Corrosive  |
| Risk Codes | R11 - Highly Flammable R14 - Reacts violently with water R19 - May form explosive peroxides R34 - Causes burns |
| Safety Description | S16 - Keep away from sources of ignition. S33 - Take precautionary measures against static discharges. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) |
| UN IDs | UN 3399 |
| WGK Germany | 1 |
| FLUKA BRAND F CODES | 1-3-10 |
| TSCA | Yes |
| HS Code | 29319090 |
| Hazard Class | 4.3 |
| Packing Group | II |
PHENYLMAGNESIUM BROMIDE - Upstream Downstream Industry
PHENYLMAGNESIUM BROMIDE - Preparation
Synthesis of Grignard reagent for phenylmagnesium bromide:
in a 500mL round bottom flask equipped with mechanical stirring, reflux condenser tube, dropping funnel and thermometer, 9.95g(0.41mol) of magnesium chips, 1.47g(0.008mol) of 1,2-dibromoethane, 65mL of anhydrous 2-methyltetrahydrofuran are added, nitrogen is applied, the device is sealed, the temperature is increased to initiate a reaction, and 2-methyltetrahydrofuran solution containing 61.23g, anhydrous 2-methyl tetrahydrofuran 60mL), drop the temperature to 60 ℃, reaction 4h. 1mL of reaction solution was diluted with 3mL of methanol as a sample, and GC was used to detect bromobenzene 0.9%, benzene 98.7% and biphenyl 0.2%. GC detection conditions: gas phase column: SE-54(50m), sample inlet temperature: 280 ℃, detector temperature: 280 ℃, carrier gas N2 flow rate: 2 mL/min, column box programmed temperature rise: 100 ℃ for 3min, then 20 ℃/min to 260 ℃ for 6min.
Last Update：2024-04-09 19:55:45
PHENYLMAGNESIUM BROMIDE - Reducing agents for the preparation of metal carbonylates
In 1890, L.Mond discovered that when carbon monoxide burns after passing through the active metal nickel powder, it emits a bright green flame, and cools the obtained gas to obtain a colorless liquid (melting point 298K, boiling point 316K); If this gas flows through a heated glass tube, metal nickel is deposited on the tube wall. This gas is nickel tetracarbonyl Ni(CO)4. Since the 2060s, people have synthesized more than one hundred such carbonyl compounds and their derivatives, and almost all transition metals can form such compounds. This kind of special complex formed by transition metals and carbon monoxide ligands is called metal carbonyl compounds, or carbonyl complexes. Metal carbonyl compounds play an important role in modern inorganic chemistry, both in theoretical research and practical application.
The preparation of metal carbonyl compounds usually has the following methods:
(1) Direct synthesis. Most carbonyl complexes are made by the direct combination of metal and carbon monoxide, but the metal must be a new reduced product and be in a very activated state.
(2) Reductive carbonylation under high pressure. Using a reducing agent under high pressure, the metal and the carbonyl group undergo a carbonylation reaction. The reducing agents used are mainly hydrogen, active metals, phenyl magnesium bromide (C6H5MgBr), etc.
(3) Some polynuclear carbonyl compounds can be prepared by thermal decomposition or ultraviolet light decomposition.
(4) Two different metal carbonyl compounds interact to produce heteronuclear carbonyl compounds.
Last Update：2024-04-09 19:55:45
PHENYLMAGNESIUM BROMIDE - Related chemical reactions
Phenylmagnesium bromide is an organometallic compound, also known as Grignard reagent. It is obtained by reacting brominated alkyl groups with magnesium. Phenylmagnesium bromide has a wide range of applications in organic synthesis and can be used to achieve a series of important chemical reactions.
1. Grieg reagent reacts with aldehydes and ketones: Phenylmagnesium bromide can react with aldehydes or ketones to produce corresponding alcohols or alcohol ethers. This reaction is a nucleophilic addition reaction, usually carried out in a dry and anhydrous environment.
2. Grieg reagent and ester reaction: The reaction of phenyl magnesium bromide with ester can also achieve the synthesis of alcohols. It can convert esters into alcohols and generate corresponding brominated alkyl groups, with a typical reaction being the conversion of esters into alcohol ethers.
3. Grieg reagent reacts with acid anhydrides: Phenylmagnesium bromide can react with acid anhydrides to generate corresponding carboxylic acids. This reaction is called the Grieg reaction and is an important method for synthesizing carboxylic acids.
In addition to the above reactions, phenylmagnesium bromide can also be used for some other important reactions, such as nucleophilic aromatic substitution reactions, reduction reactions, etc. These reactions have important application value for organic synthesis. It should be noted that phenylmagnesium bromide is easily decomposed in air and water, so it is necessary to maintain dry and anhydrous conditions in the experiment.
Last Update：2024-04-09 19:55:45
PHENYLMAGNESIUM BROMIDE - Application
Phenylmagnesium bromide is an organometallic compound with the molecular formula C6H5BrMg. It is an important reagent with extensive applications in organic synthesis.
Firstly, phenylmagnesium bromide is commonly used to construct carbon carbon bonds. It can react with compounds such as aldehydes, ketones, or carboxylic esters to form organic compounds such as alkylbenzyl alcohols, aldehydes, ketones, or acids, thereby achieving the formation of carbon carbon bonds.
In addition, phenylmagnesium bromide is widely used in phenylation reactions. It can react with halogenated alkanes or halogenated aromatic hydrocarbons to introduce phenyl groups into organic compounds.
Phenylmagnesium bromide can also be used to synthesize aromatic compounds. It can react with aromatic aldehydes or ketones to form corresponding aromatic alcohols or ketones.
Finally, phenylmagnesium bromide is also commonly used to construct heterocyclic compounds. It can react with compounds containing double or multiple bonds to form various heterocyclic compounds.
Last Update：2024-04-09 19:55:45
PHENYLMAGNESIUM BROMIDE - Production method
The production method of phenyl magnesium bromide generally includes the following steps:
1. Preparation: First, the raw materials for benzene and magnesium bromide need to be prepared. Benzene can be obtained through the alkylation reaction of benzene, while magnesium bromide can be prepared through the reaction of magnesium bromide and ethanol.
2. Reaction: Mix benzene and magnesium bromide, and heat and stir at appropriate reaction temperature and time for substitution reaction. In this reaction, bromine ions replace the hydrogen atom in the benzene ring, forming phenyl magnesium bromide.
3. Termination of reaction: After the reaction is completed, an appropriate termination agent can be added to neutralize the remaining magnesium bromide or phenyl magnesium bromide to ensure a complete cessation of the reaction.
4. Separation and purification: After the reaction is completed, the solid product of phenylmagnesium bromide can be separated by filtration or extraction.
It should be noted that in actual production, it is also necessary to control the reaction conditions and operating methods to ensure the selectivity and yield of the reaction. In addition, phenylmagnesium bromide is generally used as an important intermediate in organic synthesis, which can further react to prepare more complex organic compounds.
Last Update：2024-04-09 19:55:45
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View History
Downstream Products for PHENYLMAGNESIUM BROMIDE
2-(Methanesulfonylamino)phenylboronic acid
(S)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole
2-Phenylquinoline
(S)-(+)-α,α-Diphenyl-2-pyrrolidinemethanol
Benzhydrol
2,7-Dibromo-9,9'-spiro-bifluorene
2-Bromo-9,9-diphenylfluorene
1-BROMO-8-PHENYLOCTANE
3-HYDROXY-3-PHENYL-PIPERIDINE
(S)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole
2-Phenylquinoline
(S)-(+)-α,α-Diphenyl-2-pyrrolidinemethanol
Benzhydrol
2,7-Dibromo-9,9'-spiro-bifluorene
2-Bromo-9,9-diphenylfluorene
1-BROMO-8-PHENYLOCTANE
3-HYDROXY-3-PHENYL-PIPERIDINE