HuagongsheHuagongshe Chemistry Print Report · For research reference only
Phenylmagnesium chloride
Phenylmagnesium Chloride 2.0 M In Tetrahdyrofuran · Phenylmagnesiu · Chlorphenylmagnesium · chlorophenyl-magnesiu · Phenylchloromagnesium · chlorophenylmagnesium · Magnesium, chlorophenyl- · PHENYLMAGNESIUM CHLORIDE
Identifiers & Physical Properties
| CAS No. | 100-59-4 |
|---|---|
| Molecular formula | C6H5ClMg |
| Average molar mass | 136.86 g/mol |
| SMILES | [Cl-].[Mg+2].[c-]1ccccc1 |
| InChIKey | IWCVDCOJSPWGRW-UHFFFAOYSA-M |
| PubChem CID | 7513 |
| ChEBI | CHEBI:51490 |
| EC No. | 202-868-8 |
| DTXSID | DTXSID8059215 |
Chemical & Physical Properties
| Topological polar surface area | 0 |
|---|---|
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 2 |
| Rotatable bonds | 0 |
| Heavy atoms | 8 |
| Formal charge | 0 |
| Complexity | 100 |
| Chemical classes | Metals -> Metals, Organic Compounds |
| Density | A solution which is about 3 molar has an approximate strength of 48%, and a density (20/4 °C) of about 1.150.98 g/mL at 20 °C |
| Color/Form | Crystals |
| Solubility | Reacts with waterSoluble in tetrahydrofuranSoluble in ether (ethyl ether, other ethers may be used as solvents)It reacts violently with water. |
| Physical Description | LiquidSolution in 73% tetrahydrofuran: Dark liquid[MSDSonline] |
| Other Experimental Properties | Reacts with water, steam or acids to produce toxic and flammable vapors with evolution of heat. |
| Melting point | 89-90℃ |
| Boiling point | 230℃ (8 Torr) |
| Flash point | 1 °F |
| Storage conditions | 2-8°C |
| Physical state | solution |
| Sensitivity | Air & Moisture Sensitive |
| Merck | 14,7298 |
| BRN | 3587900 |
| InChI | InChI=1S/C6H5.ClH.Mg/c1-2-4-6-5-3-1/h1-5H1H/q+1/p-1 |
| InChIKey | GQONLASZRVFGHI-UHFFFAOYSA-M |
| SMILES | C1([Mg]Cl)C=CC=CC=1 |
| CAS DataBase Reference | 100-59-4(CAS DataBase Reference) |
| FDA UNII | 739Y484F5H |
| EPA Substance Registry System | Magnesium, chlorophenyl- (100-59-4) |
| UNSPSC Code | 12352103 |
| NACRES | NA.22 |
| GHS pictogram | GHS02,GHS05,GHS07,GHS08 |
| Signal word | Danger |
| GHS hazard statements | H371-H372-H261-H312-H318-H333-H225-H302-H314-H335-H351 |
| GHS precautionary statements | P223-P303+P361+P353-P501a-P210-P260-P280-P305+P351+P338-P370+P378-P403+P235-P233-P240-P241+P242+P243-P264-P270-P271-P301+P330+P331+P310-P303+P361+P353+P310+P363-P304+P340+P310-P305+P351+P338+P310-P308+P311-P403+P233-P405-P501 |
| Target organs | Central nervous system, Respiratory system |
| Personal protective equipment (PPE) | Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter |
| Hazard symbols | F,C |
| Risk statements (R) | 14-19-20/21/22-34-67-65-63-48/20-11-40-37 |
| Safety statements (S) | 26-36/37/39-45-62-33-16 |
| UN transport number | UN 2924 3/PG 2 |
| Water hazard class (WGK) | 2 |
| F | 10 |
| TSCA inventory status | TSCA listed |
| Hazard class | 8Carc. 2Eye Dam. 1Flam. Liq. 2Skin Corr. 1BSTOT SE 3 |
| Packing group | II |
| Customs code | 29319090 |
| Storage class | 3 - Flammable liquids |
| Hazardous substances data | 100-59-4(Hazardous Substances Data) |
| REACH registrations | Active |
Safety & Regulations
| GHS classification | DangerH225 (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. |
|---|---|
| Regulatory information | 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 | Reacts with water, steam or acids to produce toxic and flammable vapors with evolution of heat.Dangerous fire risk, solution highly flammable. |
| Hazards summary | Reacts with water evolving toxic and flammable gases and heat[Merck Index] Reacts violently with waterExtremely flammableAn irritantMay cause serious eye injuryMay cause liver injuryCan be absorbed through skin[MSDSonline] See Cyclohexylmagnesium chloride and Methylmagnesium chloride. |
| Hazard Classes and Categories | Flam. Liq. 2 (77.4%) |
| Hazardous Reactivities and Incompatibilities | Reacts with water, steam or acids to produce toxic and flammable vapors with evolution of heat |
| 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 qualitypotential migration in air, soil or watereffects on animal, aquatic and plant lifeand 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. |
| Environmental fate | 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 effects | Occupational 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 | 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/Mobility | Phenylmagnesium chloride reacts violently with water(1)therefore, leaching in moist soil is not expected to be an important fate process(SRC). |
| Artificial Pollution Sources | 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 Bioconcentration | Phenylmagnesium chloride reacts violently with water(1)therefore, the potential for bioconcentration in aquatic organisms low or non-existent(SRC). |
| Volatilization from Water/Soil | Phenylmagnesium chloride reacts violently with water(1)therefore, volatilization from water surfaces or moist soil is not expected to be an important fate process(SRC). |
| Environmental Abiotic Degradation | Phenylmagnesium chloride reacts violently with water(1). Phenylmagnesium chloride reacts with water, steam or acids to produce toxic and flammable vapors(2). Hydrolysis of a phenylmagnesium halide produces benzene with a potential release of hydrogen halide vapors such as hydrochloric acid (HCl) vapors(3). Phenylmagnesium chloride is sensitive to light and exposure to sunlight may cause explosive peroxides to form in the commercially sold tetrahydrofuran solutions of phenylmagnesium chloride(4). |
| Probable Routes of Human Exposure | Occupational exposure to phenylmagnesium chloride may occur through dermal contact with this compound at workplaces where phenylmagnesium chloride is produced or used(SRC). The general population is not expected to be exposed to phenylmagnesium chloride(SRC). A possible rare exposure to the general population may be possible in the vicinity of its use as a reagent during illicit drug manufacture. Phenylmagnesium chloride is on the US DEA (Drug Enforcement Administration) list of special surveillance chemicals used in clandestine drug manufacture(1). |
| Environmental Fate/Exposure Summary | Phenylmagnesium chloride's production and use in organic synthesis and as a Grignard reagent may result in its release to the environment through various waste streams. Phenylmagnesium chloride is on the US DEA (Drug Enforcement Administration) list of special surveillance chemicals used in clandestine drug manufacture. Phenylmagnesium chloride reacts violently with water, therefore, hydrolysis will be the dominant fate process in air, soil and water. Occupational exposure to phenylmagnesium chloride may occur through dermal contact with this compound at workplaces where phenylmagnesium chloride is produced or used. The general population is not expected to be exposed to phenylmagnesium chloride. A possible rare exposure to the general population may be possible in the vicinity of its use as a reagent during illicit drug manufacture. (SRC) |
| 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/ |
| F | 10 |
| Personal protective equipment (PPE) | Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter |
| Water hazard class (WGK) | 2 |
| TSCA inventory status | TSCA listed |
| UN transport number | UN 2924 3/PG 2 |
| Customs code | 29319090 |
| Risk statements (R) | 14-19-20/21/22-34-67-65-63-48/20-11-40-37 |
| Signal word | Danger |
| GHS pictogram | GHS02,GHS05,GHS07,GHS08 |
| Hazard symbols | F,C |
| Safety statements (S) | 26-36/37/39-45-62-33-16 |
| Hazard class | 8Carc. 2Eye Dam. 1Flam. Liq. 2Skin Corr. 1BSTOT SE 3 |
| Storage class | 3 - Flammable liquids |
| Packing group | II |
| Target organs | Central nervous system, Respiratory system |
| GHS hazard statements | H371-H372-H261-H312-H318-H333-H225-H302-H314-H335-H351 |
| REACH registrations | Active |
| GHS precautionary statements | P223-P303+P361+P353-P501a-P210-P260-P280-P305+P351+P338-P370+P378-P403+P235-P233-P240-P241+P242+P243-P264-P270-P271-P301+P330+P331+P310-P303+P361+P353+P310+P363-P304+P340+P310-P305+P351+P338+P310-P308+P311-P403+P233-P405-P501 |
| Hazardous substances data | 100-59-4(Hazardous Substances Data) |
Applications & Uses
Uses
Grignard reagent in greener solvent, 2-methyltetrahydrofuran (2-MeTHF)2-Methyltetrahydrofuran (2-MeTHF): A Biomass-Derived Solvent with Broad Application in Organic Chemistry
Uses
In organic synthesis, especially in the production of hydrocarbons, alcohols, ketones, organic acids, amines, silicones, boranes.
Uses
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.
General Description
This product has been enhanced for energy efficiency.