Phenylmagnesium chloride

HCID 7513CAS 100-59-4

Basic information

Standard SMILES
[Cl-].[Mg+2].[c-]1ccccc1
InChIKey
IWCVDCOJSPWGRW-UHFFFAOYSA-M
Molecular formula
C6H5ClMg
Average molar mass
136.86 g/mol

Overview

Phenylmagnesium chloride is an arylmagnesium halide.

Names & identifiers

Preferred name
Phenylmagnesium chloride
IUPAC
magnesium;benzene;chloride
English name
PHENYLMAGNESIUM CHLORIDE
Molecular formula
C6H5ClMg
Molecular weight
136.86

Names & synonyms

PHENYLMAGNESIUM CHLORIDE100-59-4Magnesium, chlorophenyl-Chlorophenylmagnesiumchloro(phenyl)magnesiumHSDB 5336EINECS 202-868-8DTXSID8059215CHEBI:51490EC 202-868-8739Y484F5HMagnesium, chlorophenyl
Show more names
Phenylmagnesium Chloride 2.0 M In TetrahdyrofuranPhenylmagnesiuChlorphenylmagnesiumchlorophenyl-magnesiuPhenylchloromagnesiumphenylmagnessium chloride
RefChem:861756DTXCID9032456PHENYLMAGNESIUM CHLORIDE [MI]UN3207202-868-8phenyl magnesium chlorideMFCD00000464phenylmagnesiumchloride

Database identifiers

CAS
100-59-4
PubChem CID
7513
DTXSID
DTXSID8059215
ChEBI
CHEBI:51490
EC Number
202-868-8

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
DensityA solution which is about 3 molar has an approximate strength of 48%, and a density (20/4 °C) of about 1.15
Color/FormCrystals
Solubility · 3 items

Reacts with water

Soluble in tetrahydrofuran

Soluble in ether (ethyl ether, other ethers may be used as solvents)

Physical Description · 2 items

Liquid

Solution in 73% tetrahydrofuran: Dark liquid; [MSDSonline]

Other Experimental PropertiesReacts with water, steam or acids to produce toxic and flammable vapors with evolution of heat.

Physicochemical properties

Melting point
89 · 89-90℃
Boiling point
230 ℃ · 230℃ (8 Torr)
Density
0.98 g/mL · 0.98 g/mL at 20 °C
Flash point
1 °F · 1 °F
storage temp.
2 · 2-8°C
form
solution

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H225 (77.4%): Highly Flammable liquid and vapor [Danger Flammable liquids]

P210, P233, P240, P241, P242, P243, P260, P264, P264+P265, P280, P301+P330+P331, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P321, P363, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 177 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 3 items

Chemical: Magnesium, chlorophenyl-

Magnesium, chlorophenyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Magnesium, chlorophenyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 14-06-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/10694

Fire Potential · 2 items

Reacts with water, steam or acids to produce toxic and flammable vapors with evolution of heat.

Dangerous fire risk, solution highly flammable.

Hazards Summary · 1 item

Reacts with water evolving toxic and flammable gases and heat; [Merck Index] Reacts violently with water; Extremely flammable; An irritant; May cause serious eye injury; May cause liver injury; Can be absorbed through skin; [MSDSonline] See Cyclohexylmagnesium chloride and Methylmagnesium chloride.

Hazard Classes and CategoriesFlam. Liq. 2 (77.4%)
Hazardous Reactivities and IncompatibilitiesReacts with water, steam or acids to produce toxic and flammable vapors with evolution of heat

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.

Toxicology

Environmental Fate · 3 items

TERRESTRIAL FATE: Phenylmagnesium chloride reacts violently with water(1) and, therefore, leaching or volatilization in moist soil are not expected to be important fate processes(SRC). Reaction with water will be the dominant fate mechanism(SRC).

AQUATIC FATE: Phenylmagnesium chloride reacts violently with water(1) and, therefore, hydrolysis will be the only important fate mechanism in the aquatic environment(SRC).

ATMOSPHERIC FATE: Relevant vapor pressure data were not available for phenylmagnesium chloride(SRC, 2017). However, phenylmagnesium chloride reacts violently with water(1) and, therefore, both particulate phase and vapor phase phenylmagnesium chloride are expected to react with precipitation, cloud water, fog and possibly water vapor in the atmosphere(SRC).

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Toxicity Summary · 1 item

IDENTIFICATION AND USE: Phenylmagnesium chloride is used as a Grignard reagent in organic synthesis, especially in the production of hydrocarbons, alcohols, ketones, organic acids, amines, silicones, boranes. HUMAN STUDIES: There are no data available. ANIMAL STUDIES: There are no data available.

Soil Adsorption/MobilityPhenylmagnesium chloride reacts violently with water(1); therefore, leaching in moist soil is not expected to be an important fate process(SRC).
Artificial Pollution Sources · 1 item

Phenylmagnesium chloride's production and use in organic synthesis and as a Grignard reagent(1,2) may result in its release to the environment through various waste streams(SRC). Phenylmagnesium chloride is on the US DEA (Drug Enforcement Administration) list of special surveillance chemicals used in clandestine drug manufacture(3).

Environmental BioconcentrationPhenylmagnesium chloride reacts violently with water(1); therefore, the potential for bioconcentration in aquatic organisms low or non-existent(SRC).

Safety data

F
10
PPE
Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
wgk
2
tsca
TSCA listed
ridadr
UN 2924 3/PG 2
hs_code
29319090

Chemistry & industry

Uses & manufacturing

Uses · 5 items

Used as a Grignard reagent and in organic synthesis (hydrocarbons, alcohols, ketones, organic acids, amines, silicones, boranes, pesticides, and organotin compounds); [HSDB]

One of the Grignard reagents. ... In organic synthesis, especially in the production of hydrocarbons, alcohols, ketones, organic acids, amines, silicones, boranes.

CHEM INT FOR PESTICIDES, EG, FENTIN HYDROXIDE

CHEM INT FOR SILICONE INTS, EG, PHENYLTRICHLOROSILANE

CHEM INT FOR ORGANOTIN COMPDS, EG, TETRAPHENYLTIN

U.S. Exports · 2 items

(1979) No Data

(1981) No Data

U.S. Imports · 2 items

(1979) No Data

(1981) No Data

U.S. Production · 3 items

2023: <50,000 lb

(1979) No Data

(1981) No Data

Industry UsesIntermediate
Methods of Manufacturing · 2 items

Prepared by reacting chlorobenzene with magnesium at reflux temperatures in the presence of catalytic amounts of an organic nitrate.

Chloro-, bromo-, or iodobenzene will react with magnesium metal in ethereal solvents to produce phenylmagnesium chloride, bromide, or iodide (Grignard reagents).

Applications · 4 items

UsesGrignard reagent in greener solvent, 2-methyltetrahydrofuran (2-MeTHF)2-Methyltetrahydrofuran (2-MeTHF): A Biomass-Derived Solvent with Broad Application in Organic Chemistry

UsesIn organic synthesis, especially in the production of hydrocarbons, alcohols, ketones, organic acids, amines, silicones, boranes.

UsesPhenylmagnesium chloride (PhMgCl) solution is a common Grignard reagent used in the synthesis of ()-phenserine and stephacidin B. It is employed in a variety of cross-coupling reactions. It can also be used as an electrolyte solution along with aluminium chloride (AlCl3) in the rechargeable magnesium batteries.

General DescriptionThis product has been enhanced for energy efficiency.

Suppliers50 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
湖北永阔科技有限公司027-59223108 15972152991 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
湖北万得化工有限公司15377098680 15377098680 · [email protected]
Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]

Additional notes

DefinitionChEBI: Phenylmagnesium chloride is an arylmagnesium halide.

Related reactions

0 records

No reaction records under the current filter.

Linked notes

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