フェニルマグネシウムクロリド (27%テトラヒドロフラン溶液, 約2mol/L)

Phenylmagnesium chloride

HCID 7513CAS 100-59-4

基本情報

標準SMILES
[Cl-].[Mg+2].[c-]1ccccc1
InChIKey
IWCVDCOJSPWGRW-UHFFFAOYSA-M
分子式
C6H5ClMg
平均分子量
136.86 g/mol

概要

Phenylmagnesium chloride is an arylmagnesium halide.

名称と識別子

優先名称
Phenylmagnesium chloride
IUPAC
magnesium;benzene;chloride
現地名
フェニルマグネシウムクロリド (27%テトラヒドロフラン溶液, 約2mol/L)
英語名
PHENYLMAGNESIUM CHLORIDE
分子式
C6H5ClMg
分子量
136.86

名称と別名

PHENYLMAGNESIUM CHLORIDE100-59-4Magnesium, chlorophenyl-Chlorophenylmagnesiumchloro(phenyl)magnesiumHSDB 5336EINECS 202-868-8DTXSID8059215CHEBI:51490EC 202-868-8739Y484F5HMagnesium, chlorophenyl
名称をさらに表示
フェニルマグネシウムクロリド (27%テトラヒドロフラン溶液, 約2mol/L)クロロフェニルマグネシウムフェニルマグネシウムクロリドクロロ(フェニル)マグネシウムフェニルクロロマグネシウムフェニルマグネシウム=クロリドフェニルマグネシウムクロリド 溶液(フェニル)(クロロ)マグネシウム(クロロマグネシオ)ベンゼンPhenylmagnesium Chloride 2.0 M In TetrahdyrofuranPhenylmagnesiuChlorphenylmagnesiumchlorophenyl-magnesiuPhenylchloromagnesiumphenylmagnessium chloride
RefChem:861756DTXCID9032456PHENYLMAGNESIUM CHLORIDE [MI]UN3207202-868-8phenyl magnesium chlorideMFCD00000464phenylmagnesiumchloride

データベース識別子

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

物性

構造計算による物性

極性表面積
0 Ų
水素結合供与体数
0
水素結合受容体数
2
回転可能結合数
0
重原子数
8

実験および物理化学的性質

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 件

Reacts with water

Soluble in tetrahydrofuran

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

Physical Description · 2 件

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.

物理化学的性質

融点
89 · 89-90℃
沸点
230 ℃ · 230℃ (8 Torr)
比重(密度)
0.98 g/mL · 0.98 g/mL at 20 °C
闪点
1 °F · 1 °F
貯蔵温度
2 · 2-8°C
外見
solution

化学的性質

化学的特性yellowish-brown to dark brown solution

安全と法規制

GHS分類

GHS Classification · 4 件

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.

危険有害性情報

Regulatory Information · 3 件

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 件

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 件

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

安全と保護具

Disposal Methods · 1 件

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.

毒性情報

Environmental Fate · 3 件

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 件

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 件

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).

安全データ

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

化学と産業

用途と製造

Uses · 5 件

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 件

(1979) No Data

(1981) No Data

U.S. Imports · 2 件

(1979) No Data

(1981) No Data

U.S. Production · 3 件

2023: <50,000 lb

(1979) No Data

(1981) No Data

Industry UsesIntermediate
Methods of Manufacturing · 2 件

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).

応用分野 · 2 件

使用Phenylmagnesium 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.

一般的な説明This product has been enhanced for energy efficiency.

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