Chlorphenylmagnesium

Phenylmagnesium chloride

HCID 7513CAS 100-59-4

Grundinformationen

Standard-SMILES
[Cl-].[Mg+2].[c-]1ccccc1
InChIKey
IWCVDCOJSPWGRW-UHFFFAOYSA-M
Summenformel
C6H5ClMg
Durchschnittliche Molmasse
136,86 g/mol

Überblick

Phenylmagnesium chloride is an arylmagnesium halide.

Namen und Bezeichner

Bevorzugter Name
Phenylmagnesium chloride
IUPAC
magnesium;benzene;chloride
Lokaler Name
Chlorphenylmagnesium
Englischer Name
PHENYLMAGNESIUM CHLORIDE
Summenformel
C6H5ClMg
Molmasse
136.86

Namen und Synonyme

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

Datenbank-Bezeichner

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

Eigenschaften

Berechnete Struktureigenschaften

Polarare Oberfläche (TPSA)
0 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
0
Schwere Atome
8

Experimentelle und physikochemische Eigenschaften

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 Einträge

Reacts with water

Soluble in tetrahydrofuran

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

Physical Description · 2 Einträge

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.

Physikochemische Eigenschaften

Schmelzpunkt
89 · 89-90℃
Siedepunkt
230 ℃ · 230℃ (8 Torr)
Dichte
0.98 g/mL · 0.98 g/mL at 20 °C
Flammpunkt
1 °F · 1 °F
storage temp.
2 · 2-8°C
Aggregatzustand
solution

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

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.

Gefahrenhinweise

Regulatory Information · 3 Einträge

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 Einträge

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 Eintrag

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

Sicherheit und Schutzausrüstung

Disposal Methods · 1 Eintrag

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.

Toxikologische Informationen

Environmental Fate · 3 Einträge

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 Eintrag

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 Eintrag

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).

Sicherheitsdaten

F
10
wgk
2
tsca
TSCA listed
ridadr
UN 2924 3/PG 2
hs_code
29319090
risk_code
14-19-20/21/22-34-67-65-63-48/20-11-40-37

Chemie und Industrie

Verwendung und Herstellung

Uses · 5 Einträge

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 Einträge

(1979) No Data

(1981) No Data

U.S. Imports · 2 Einträge

(1979) No Data

(1981) No Data

U.S. Production · 3 Einträge

2023: <50,000 lb

(1979) No Data

(1981) No Data

Industry UsesIntermediate
Methods of Manufacturing · 2 Einträge

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).

Anwendungen · 1 Eintrag

VerwendenPhenylmagnesium 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.

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