Phenylmagnesium bromide

HCID 66852CAS 100-58-3

Basic information

Standard SMILES
[Br-].[Mg+2].[c-]1ccccc1
InChIKey
ANRQGKOBLBYXFM-UHFFFAOYSA-M
Molecular formula
C6.H5.Mg.Br
Average molar mass
181.31 g/mol

Overview

Phenylmagnesium bromide is an arylmagnesium halide. It has a role as a Grignard reagent.

Names & identifiers

Preferred name
Phenylmagnesium bromide
IUPAC
magnesium;benzene;bromide
English name
Phenylmagnesium bromide
Molecular formula
C6H5BrMg
Molecular weight
181.31

Names & synonyms

phenylmagnesium bromide100-58-3BromophenylmagnesiumMagnesium, bromophenyl-bromo(phenyl)magnesiumBromomagnesiobenzeneEINECS 202-867-2DTXSID3059214CHEBI:51238HSDB 8383Magnesium, bromophenylRefChem:861755
Show more names
Phenylmagnesium bromide, 2.8M solution in Diethyl etherPhenylmagnesinesium bromidePhenylbromomagnesiumbromophenyl-magnesiu(Bromomagnesio)benzenePhenylMagnesiuM BroMid
DTXCID4032455202-867-2phenyl magnesium bromidemagnesium;benzene;bromidePhMgBrMFCD00000038Bromidophenylmagnesiumphenyhnagnesium bromide

Database identifiers

CAS
100-58-3
PubChem CID
66852
DTXSID
DTXSID3059214
ChEBI
CHEBI:51238
EC Number
202-867-2

Properties

Computed structural properties

Topological polar surface area
0 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
0
Heavy atoms
8

Experimental & physicochemical properties

Chemical ClassesMetals -> Metals, Organic Compounds
Density · 2 items

1.14

Relative density: 1.134 mg/L at 25 °C

Color/Form · 2 items

A solution in ether

Liquid

Physical Description3 molar (76%) solution in diethyl ether: Yellow to brown liquid; [Alfa Aesar MSDS]
Other Experimental PropertiesSubstances and mixtures, which In contact with water, emit flammable gases

Physicochemical properties

Melting point
153 · 153-154 °C
Density
1.134 g/mL · 1.134 g/mL at 25 °C
Flash point
40 °F · −40 °F
storage temp.
water-free area
solubility
Miscible with tetrahydrofuran.
form
Liquid

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H225 (39.2%): Highly Flammable liquid and vapor [Danger Flammable liquids]

P210, P233, P240, P241, P242, P243, P260, P264, P280, P301+P330+P331, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P321, P363, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 74 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 2 items

REACH registered substance: Bromophenylmagnesium (EC: 202-867-2)

Magnesium, bromophenyl-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Fire PotentialDangerous fire risk, solution highly flammable.
Hazards Summary · 1 item

3 molar solution in diethyl ether (CAS# 60-29-7): Reacts violently with water evolving flammable gases; May form explosive peroxides; Causes burns; [Alfa Aesar MSDS] See Methyl magnesium bromide, Cyclohexylmagnesium chloride, Phenylmagnesium chloride, and Ethyl magnesium bromide.

Hazard Classes and CategoriesFlam. Liq. 2 (39.2%)

Safety & protection

Disposal Methods · 1 item

SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.

Protective Action Criteria (PAC) · 3 items

1.2 [mg/m3]

13 [mg/m3]

79 [mg/m3]

Toxicology

Adverse EffectsDermatotoxin - Skin burns.
Toxicity SummaryIDENTIFICATION AND USE: Phenylmagnesium bromide is used for chemical Synthesis as Grignard reagent. HUMAN STUDIES: There are no data available. ANIMAL STUDIES: There are no data available.
Antidote and Emergency Treatment · 3 items

/SRP:/ 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 if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the 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. /Poisons A and B/

/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/

/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W TKO /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

Safety data

F
1-3-10
PPE
Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
wgk
1
tsca
TSCA listed
ridadr
UN 3399 4.3/PG 1
hs_code
29319090

Chemistry & industry

Uses & manufacturing

Uses · 2 items

Arylating agent in organic synthesis.

Aryl, Chemical Synthesis, Grignard Reagents, Organometallic Reagents

Methods of ManufacturingFrom magnesium and bromobenzene.
Formulations/PreparationsA Grignard reagent available as a solution in ether.
General Manufacturing Information · 2 items

Magnesium, bromophenyl-: ACTIVE

Grignard reagents is basically an organomagnesium halide having a formula of RMgX where X is a halogen, and R is an alkyl or aryl (based on a benzene ring) group. On the event of Grignard Reaction, Grignard reagent is added to a ketone or aldehyde, to form a tertiary or secondary alcohol, respectively. The reaction with formaldehyde leads to a primary alcohol. Grignard reagent can be used for determining the number of halogen atoms present in a halogen compound. ... Used for the chemical analysis of certain triacylglycerols. /Grignard reagents/

Applications · 2 items

UsesThese compounds can be obtained as a formula ``RMgX'' by the reaction of halogenated hydrocarbons with magnesium metal in anhydrous solvents such as diethyl ether, and have been widely used in organic synthesis.Grignard reagent in greener solvent, 2-Methyltetrahydrofuran (2-MeTHF): A Biomass-Derived Solvent with Broad Application in Organic Chemistry

UsesPhenylmagnesium Bromide is a reagent used in the preparation of arylcarbonimidic dichlorides via dichloroiodobenzene-mediated gem-dichlorination of aryl isonitriles.

Preparation methods

PreparationPhenylmagnesium bromide was prepared by the action of phenyl bromide and magnesium in diethyl ether.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
阿诺西(上海)生物技术有限公司400-1107768 15058188853 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
宁波君龙新材料有限公司0574 88552216 19032109277 · [email protected]

Additional notes

DefinitionChEBI: Phenylmagnesium bromide is an arylmagnesium halide. It has a role as a Grignard reagent.

Related reactions

0 records

No reaction records under the current filter.

Linked notes

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