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Methylmagnesium bromide

Methylmagnesium bromide structure

Methylmagnesium bromide 

structure
  • CAS No:

    75-16-1

  • Formula:

    CH3BrMg

  • Chemical Name:

    Methylmagnesium bromide

  • Synonyms:

    Magnesium,bromomethyl-;Methylmagnesium bromide;Bromomethylmagnesium

  • Categories:

    Organic Chemistry  >  Organometallic Compounds

Description

Clear brown solution when properly stored


Methylmagnesium chloride is an organometallic compound with the general formula CH3MgCl. This highly flammable and moisture sensitive material is the simplest Grignard reagent and is commercially available, usually as a solution in tetrahydrofuran. Like methyllithium, it is the synthetic equivalent to the methyl carbanion synthon.


Methyl magnesium bromide in ethyl ether appears as a colorless cloudy solution in diethyl ether. Vapors heavier than air.


Methyl magnesium bromide in ethyl ether appears as a colorless cloudy solution in diethyl ether. Vapors heavier than air.

Methylmagnesium bromide Basic Attributes

119.24

117.92700

200-844-1

1928

DTXSID7052496

2931900090

Characteristics

0

1.42940

Pale brown Solution, may develop some turbidity precipitate

1.035 g/mL at 25 °C

0ºC

78-80℃

77 °F

Reacts with water.soluble in ether and tetrahydrofuran; insoluble in hydrocarbons

water-free area

Prone to spontaneous combustion when there is no ether immersion; ether is flammable

EXPLOSION RISK.

Moisture sensitive|... May react violently with water. /Methyl magnesium bromide in ethyl ether/

Highly flammable. The solution reacts with water or moisture in the air to form flammable methane gas. The heat from this reaction may be sufficient to ignite the produced methane. Unstable peroxides may form with exposure of the ether to air. This is a slow process.

Ethers

Highly Flammable

Organometallics, such as METHYL MAGNESIUM BROMIDE, are reactive with many other groups. Incompatible with acids and bases. Organometallics are good reducing agents and therefore incompatible with oxidizing agents. Often reactive with water to generate toxic or flammable gases.

Safety Information

I

4.3

UN 3399 4.3/PG 1

2

12-14-19-22-34-66-67-52/53-10-65-63-48/20-14/15-11-37

9-16-26-45-61-36/37/39-62-43-36/37-23

OM3700000

C,F+,F

Treasury is ventilated, low temperature and dry; stored separately from oxidant

Ether is explosive

P210-P223-P231 + P232-P261-P370 + P378-P422

H225-H260-H302-H314-H336

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

...CAN REACT VIGOROUSLY WITH OXIDIZING MATERIALS. /ETHERS/

UN 3399 4

P210; P231 + P232; P280; P370 + P378; P402 + P404; P403 + P235

Excerpt from ERG Guide 135 [Substances - Spontaneously Combustible]: Flammable/combustible material. May ignite on contact with moist air or moisture. May burn rapidly with flare-burning effect. Some react vigorously or explosively on contact with water. Some may decompose explosively when heated or involved in a fire. May re-ignite after fire is extinguished. Runoff may create fire or explosion hazard. Containers may explode when heated. (ERG, 2016)

|Danger|H225 (38.57%): Highly Flammable liquid and vapor [Danger Flammable liquids]|P210, P223, P231+P232, P233, P240, P241, P242, P243, P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P335+P334, P363, P370+P378, P402+P404, P403+P235, P405, and P501|Aggregated GHS information provided by 70 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Excerpt from ERG Guide 135 [Substances - Spontaneously Combustible]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

Excerpt from ERG Guide 135 [Substances - Spontaneously Combustible]: Fully encapsulating, vapor-protective clothing should be worn for spills and leaks with no fire. ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). Do not touch or walk through spilled material. Stop leak if you can do it without risk. SMALL SPILL: EXCEPTION: For spills of Xanthates, UN3342 and for Dithionite (Hydrosulfite/Hydrosulphite), UN1384, UN1923 and UN1929, dissolve in 5 parts water and collect for proper disposal. CAUTION: UN3342 when flooded with water will continue to evolve flammable Carbon disulfide/Carbon disulphide vapors. Cover with DRY earth, DRY sand or other non-combustible material followed with plastic sheet to minimize spreading or contact with rain. Use clean, non-sparking tools to collect material and place it into loosely covered plastic containers for later disposal. Prevent entry into waterways, sewers, basements or confined areas. (ERG, 2016)

Excerpt from ERG Guide 135 [Substances - Spontaneously Combustible]: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing will only provide limited protection. (ERG, 2016)|Personnel protection: ... Wear appropriate chemical protective gloves, boots and goggles. ... /Methyl magnesium bromide in ethyl ether/

SEE ETHERS. ...ETHERS...ARE...DANGEROUS FIRE HAZARDS. ...EASILY IGNITED & HAVE LOW FLASH POINTS. IT IS NECESSARY TO CONTROL SMOKING, OPEN FLAMES...HOT PLATES...WHERE LOW MOLECULAR WT ETHERS ARE APT TO REACH 1% CONCN OR MORE IN AIR. /ETHERS/|FLAMMABLE, DANGEROUS FIRE...RISK

... DANGEROUS FIRE AND EXPLOSION HAZARDS WHEN EXPOSED TO HEAT, FLAME OR SPARKS. ...ETHERS TEND TO FORM PEROXIDES UPON STANDING. ...WHEN ETHERS CONTAINING PEROXIDES ARE HEATED THEY CAN DETONATE. /ETHERS/|...EXPLOSION RISK.

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use "alcohol" foam, dry chemical or carbon dioxide. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Do not use water on material itself. /Methyl magnesium bromide in ethyl ether/|Evacuation: If fire becomes uncontrollable or container is exposed to direct flame - consider evacuation of one-third (1/3) mile radius. /Methyl magnesium bromide in ethyl ether/

The solution /methyl magnesium bromide in ethyl ether/ reacts with water to give methane, a flammable gas. The heat of this reaction may be sufficient to ignite the methane. /Methyl magnesium bromide in ethyl ether/

If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Build dikes to contain flow as necessary. Use water spray to knock-down vapors. Do not use water on material itself. /Methyl magnesium bromide in ethyl ether/|Personnel protection: Avoid breathing vapors. Keep upwind. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. /Methyl magnesium bromide in ethyl ether/|If material leaking (not on fire) consider evacuation from downwind area based on amount of material spilled, location and weather conditions. /Methyl magnesium bromide in ethyl ether/

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

Drug Information

Excerpt from ERG Guide 135 [Substances - Spontaneously Combustible]: Fire will produce irritating, corrosive and/or toxic gases. Inhalation of decomposition products may cause severe injury or death. Contact with substance may cause severe burns to skin and eyes. Runoff from fire control may cause pollution. (ERG, 2016)

Excerpt from ERG Guide 135 [Substances - Spontaneously Combustible]: Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. Keep victim calm and warm. (ERG, 2016)

Methylmagnesium bromide Use and Manufacturing

Methods of Manufacturing

REACTION OF MAGNESIUM AND METHYLBROMIDE.

Uses

Grignard reagent in greener solvent, 2-methyltetrahydrofuran (2-MeTHF)

Available in soln in ether

Magnesium, bromomethyl-: ACTIVE

Computed Properties

Molecular Weight:119.24
Hydrogen Bond Acceptor Count:2
Exact Mass:117.92685
Monoisotopic Mass:117.92685
Heavy Atom Count:3
Complexity:4.8
Covalently-Bonded Unit Count:3
Compound Is Canonicalized:Yes

Material

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