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
Show more names
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
- Formal charge
- 0
- Complexity
- 100
Experimental & physicochemical properties
Density
1.14
Relative density: 1.134 mg/L at 25 °C
Color/Form
A solution in ether
Liquid
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
- color
- Yellow to brown
- Specific Gravity
- 1.14 · 1.14
- Appearance
- Clear to slightly hazy colorless to dark brown liquid.
- Water Solubility
- reacts
- Sensitive
- Air & Moisture Sensitive
- BRN
- 3588849 · 3588849
- InChI
- InChI=1S/C6H5.BrH.Mg/c1-2-4-6-5-3-1;;/h1-5H;1H;/q;;+1/p-1
- InChIKey
- ANRQGKOBLBYXFM-UHFFFAOYSA-M
- SMILES
- C1([Mg]Br)C=CC=CC=1
- CAS DataBase Reference
- 100 · 100-58-3(CAS DataBase Reference)
- EPA Substance Registry System
- Magnesium, bromophenyl- (100-58-3)
- UNSPSC Code
- 12352103 · 12352103
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 2 · GHS02,GHS05,GHS07,GHS08
- Signal word
- Danger
- Hazard statements
- 302 · H302-H314-H371-H372-H351-H335-H225-H260
- Precautionary statements
- 501 · P501-P223-P260-P270-P202-P240-P231+P232-P210-P233-P201-P243-P241-P242-P271-P264-P280-P370+P378-P335+P334-P308+P311-P303+P361+P353-P301+P330+P331-P363-P301+P312+P330-P304+P340+P310-P305+P351+P338+P310-P403+P233-P402+P404-P403+P235-P405
- PPE
- Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
- Hazard Codes
- F+,C,F
- Risk Statements
- 12 · 12-14-22-34-19-11-67-40-37
- Safety Statements
- 16 · 16-26-36/37/39-45-33-29-7/8-6A-43B
- RIDADR
- 3399 · UN 3399 4.3/PG 1
- WGK Germany
- 1 · 1
- F
- 1 · 1-3-10
- TSCA
- TSCA listed
- HazardClass
- 4.3 · 4.3
- PackingGroup
- II
- HS Code
- 29319090 · 29319090
- Storage Class
- 3 · 3 - Flammable liquids
- Hazard Classifications
- 4 OralEye · Acute Tox. 4 OralEye Dam. 1Flam. Liq. 2Skin Corr. 1B
- Hazardous Substances Data
- 100 · 100-58-3(Hazardous Substances Data)
- REACH Registrations
- Active
- Limited Quantities
- 1 L · 1.0 L (0.3 gallon) (liquid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
Safety & regulation
GHS classification
GHS Classification
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
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.
Hazards Summary
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.
Safety & protection
Disposal Methods
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)
1.2 [mg/m3]
13 [mg/m3]
79 [mg/m3]
Toxicology
Antidote and Emergency Treatment
/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
- risk_code
- 12-14-22-34-19-11-67-40-37
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS05,GHS07,GHS08
- hazard_code
- F+,C,F
- safety_code
- 16-26-36/37/39-45-33-29-7/8-6A-43B
- hazard_class
- 4.3
- Storage Class
- 3 - Flammable liquids
- packing_group
- II
- Hazard statements
- H302-H314-H371-H372-H351-H335-H225-H260
- Limited Quantities
- 1.0 L (0.3 gallon) (liquid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 4 OralEye Dam. 1Flam. Liq. 2Skin Corr. 1B
- Precautionary statements
- P501-P223-P260-P270-P202-P240-P231+P232-P210-P233-P201-P243-P241-P242-P271-P264-P280-P370+P378-P335+P334-P308+P311-P303+P361+P353-P301+P330+P331-P363-P301+P312+P330-P304+P340+P310-P305+P351+P338+P310-P403+P233-P402+P404-P403+P235-P405
- Hazardous Substances Data
- 100-58-3(Hazardous Substances Data)
Chemistry & industry
Uses & manufacturing
Uses
Arylating agent in organic synthesis.
Aryl, Chemical Synthesis, Grignard Reagents, Organometallic Reagents
General Manufacturing Information
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
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.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Additional notes
DefinitionChEBI: Phenylmagnesium bromide is an arylmagnesium halide. It has a role as a Grignard reagent.
Related reactions
No reaction records under the current filter.
Linked notes
Loading…