ALLYLBROMID

Allylbromid is a flammable liquid with an intense, acrid, persistent smell. 
Allylbromid is insoluble in water but in alcohol, aether, acetone, carbon tetrachloride, and chloroform.
Allylbromid is used to synthesize other allyl compounds, to synthesize dyestuff and spice, and as a curative in the medicine industry. 

CAS Number: 106-95-6
Molecular Formula: C3H5Br
Molecular Weight: 120.98
EINECS Number: 203-446-6

Synonyms: Allylbromid, 106-95-6, 3-Bromopropene, 3-Bromo-1-propene, 3-Bromopropylene, Bromallylene, 2-Propenyl bromide, 1-Bromo-2-propene, Propene, 3-bromo-, NSC 7596, CCRIS 9049, HSDB 622, UNII-FXQ8X2F74Z, EINECS 203-446-6, FXQ8X2F74Z, BRN 0605308, DTXSID8024442, AI3-52208, NSC-7596, DTXCID204442, EC 203-446-6, 203-446-6, 3-bromoprop-1-ene, 1-Propene, 3-bromo-, Allylbromid, MFCD00000244, Allylbromid (Stabilized with Propylene Oxide), UN1099, allylbromid, allyl bromine, allyl-bromide, 3-bromo-propene, 1-brom-2-propene, 3-bromo-1-propen, UN 1099, 3-bromo-prop-1-ene, CH2=CHCH2Br, SCHEMBL411, Allylbromid [MI], 3-Bromopropene Allylbromid, SCHEMBL26132, Allylbromid [HSDB], WLN: E2U1, SCHEMBL299368, SCHEMBL887973, SCHEMBL5494851, CHEMBL1429506, NSC7596, STR00178, Tox21_200801, BR1119, SBB059929, STL199163, AKOS000118756, NCGC00091515-01, NCGC00091515-02, NCGC00258355-01, Allylbromid, purum, >=98.0% (GC), BP-13477, CAS-106-95-6, Allylbromid, puriss., >=99.0% (GC), B0643, NS00008702, ST51046196, Allylbromid [UN1099] [Flammable liquid], EN300-19278, InChI=1/C3H5Br/c1-2-3-4/h2H,1,3H, Q223062, F2190-0178, Allylbromid, 99%, stab. with 300-1000ppm Propylene oxide, Allylbromid, reagent grade, 97%, contains <=1000 ppm propylene oxide as stabilizer, Allylbromid, ReagentPlus(R), 99%, contains <=1000 ppm propylene oxide as stabilizer, BROMALLYLENE, 2-PROPENYL BROMIDE, Allylbromid, 3-BROMOPROPYLENE, 3-BROMOPROPENE, 3-BROMO-1-PROPENE, CH2=CHCH2Br, Propene, 3-bromo-

Allylbromid has a very high mobility in soil. 
Allylbromid is also used as a soil fumigant and as a contact poison. 
Allylbromid induces unscheduled DNA synthesis in HeLa cells.

Allylbromid, is a colorless to pale yellow liquid with a sharp, pungent odor that is chemically classified as an organic halide and specifically as an alkyl bromide. 
Its molecular formula is C3H5Br, and structurally, it consists of a three-carbon chain with a carbon-carbon double bond (alkene group) between the first and second carbon atoms and a bromine atom attached to the terminal carbon, making it a reactive molecule with both alkene and alkyl halide functionalities.

Allylbromid is frequently employed in the manufacture of allyl derivatives, which are important building blocks in the production of polymers, resins, and plasticizers. 
Its ability to undergo polymerization and crosslinking reactions is exploited to modify material properties, such as flexibility and durability, in industrial applications.
Allylbromid is an organic halide. 

Allylbromid is an alkylating agent used in synthesis of polymers, pharmaceuticals, perfumes and other organic compounds. 
Allylbromid is a colorless liquid, although commercial samples appear yellow or brown. 
Allylbromid is an irritant and a potentially dangerous alkylating agent. 

Allylbromid is more reactive but more expensive than allyl chloride, and these considerations guide its use.
Allylbromid appears as a clear colorless to light yellow liquid with an irritating unpleasant odor.
Irritates eyes, skin, and respiratory system. 

Toxic by skin absorption denser than water and slightly soluble in water.
Because of the presence of both the allylic double bond and the bromine substituent, Allylbromid is highly reactive and serves as a valuable intermediate in organic synthesis.
Allylbromid readily undergoes nucleophilic substitution reactions where the bromine atom can be replaced by various nucleophiles such as amines, thiols, or cyanides, enabling the synthesis of a wide variety of compounds including pharmaceuticals, agrochemicals, and specialty chemicals.

Allylbromid decomposes upon heating and exposure to light, forming HBr (a strong reducing agent). 
Reacts violently with oxidizing agents. Can react exothermically with reducing agents to release hydrogen gas. 
In the presence of various catalysts (such as acids) or initiators, may undergo exothermic addition polymerization reactions.

Allylbromid is produced commercially from allyl alcohol and hydrobromic acid: CH2=CHCH2OH + HBr → CH2=CHCH2Br + H2O
Allylbromid can also be prepared by the halogen-exchange reaction between allyl chloride and hydrobromic acid or by the allylic bromination of propene.
Allylbromid is an electrophilic alkylating agent.

Allylbromid reacts with nucleophiles, such as amines, carbanions, alkoxides, etc., to introduce the allyl group: CH2=CHCH2Br + Nu− → CH2=CHCH2Nu + Br− (Nu− is a nucleophile)
It is used in the synthesis of compounds containing the allyl functionality, such as the pharmaceuticals methohexital, secobarbital and thiamylal.
Allylbromid reacts with magnesium metal in dry ether to form allylmagnesium bromide, a Grignard reagent: CH2=CHCH2Br + Mg → CH2=CHCH2MgBr

Allylbromid is a highly reactive, multifunctional chemical intermediate with critical applications in organic synthesis and materials science, but it demands careful handling due to its hazardous nature. 
Its dual functionality as both an alkyl halide and an alkene allows chemists to use it as a versatile tool for creating a wide array of industrially and pharmaceutically important compounds.

Environmental concerns also arise due to its toxicity; accidental releases of Allylbromid require immediate containment and remediation to prevent harm to aquatic and terrestrial ecosystems. 
Disposal and waste management practices are tightly regulated to minimize environmental impact.

Melting point: -119 °C  
Boiling point: 70–71 °C (lit.)  
Density: 1.398 g/mL at 25 °C (lit.)  
Vapor density: 4.2 (vs air)  
Vapor pressure: 18.66 kPa at 25 °C  
Refractive index: n20/D 1.469 (lit.)  
Flash point: 28 °F  
Storage temp.: 2–8 °C  
Solubility: Chloroform (Soluble)  
Form: Liquid  
Color: Clear colorless to slightly colored  
Specific Gravity: 1.398  
Odor: Unpleasant  
Explosive limit: 4.3–7.3% (V)  
Water Solubility: Insoluble  
Sensitive: Light Sensitive  
Merck: 14,288  
BRN: 605308  
Exposure limits: ACGIH: TWA 0.1 ppm, STEL 0.2 ppm (Skin)  
Dielectric constant: 7.0  
Stability: Stable. Flammable. Incompatible with strong oxidizing agents.  
InChIKey: BHELZAPQIKSEDF-UHFFFAOYSA-N  
LogP: 1.79  

Allylbromid, also known as Allylbromid, is an organobromine compound that belongs to the family of allylic halides, characterized by a bromine atom attached to an allylic carbon—meaning the carbon atom adjacent to a carbon-carbon double bond. 
This unique positioning of the bromine atom gives Allylbromid distinct chemical properties, including a higher reactivity than typical alkyl bromides because the adjacent double bond can stabilize reaction intermediates such as carbocations or radicals. 

This stabilization facilitates various nucleophilic substitution and addition reactions, making Allylbromid a highly valuable reagent in organic synthesis.
Allylbromid was synthesized from glycerol and formic acid under inert atmosphere, hydrolysed with NaOH and fractionally distilled to yield the 73% allyl alcohol water azeotrope. 
This was then reacted with 48% hydrobromic acid and sulfuric acid and the Allylbromid distilled as per the conventional method. 

Allylbromid was then redistilled with 3A molecular sieves drying agent to yield the final product which is stored over additional 3A molecular sieves.
Because of its volatility and flammability, Allylbromid must be handled with care under controlled conditions, usually in well-ventilated laboratories or industrial plants equipped with explosion-proof equipment. 
Additionally, it is toxic and irritating to the skin, eyes, and respiratory system, so appropriate personal protective equipment is essential during its use.

In summary, allylbromid is a versatile and reactive chemical intermediate with broad utility in chemical synthesis and industrial manufacturing, valued particularly for its dual reactive sites that allow for diverse chemical transformations.
Vapor may form explosive mixture with air. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.),  contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. Heat or light exposure may cause decomposition and corrosive vapors.

Workers should wear positive pressure self-contained breathing apparatus (SCBA), goggles and a face shield, protective clothing for high concentrations of vapor, chemical protective clothing that is specifi cally recommended by the manufacturer to avoid poisoning. 
Workers should be careful as Allylbromid reacts with oxidizing materials and alkalis.
In industrial and laboratory settings, Allylbromid is widely used as a building block for synthesizing more complex organic molecules, such as allyl ethers, allyl amines, and other functionalized compounds. 

These derivatives find applications in pharmaceuticals, agrochemicals, and the production of specialty polymers and resins. 
For example, Allylbromid can be used to introduce an allyl group into molecules, thereby imparting sites for further chemical modifications like crosslinking or polymerization, which are critical in the manufacture of materials with enhanced mechanical or chemical resistance.

Moreover, Allylbromid’s ability to participate in radical polymerization reactions makes it important in the creation of advanced materials such as adhesives, coatings, and plasticizers. 
In particular, its role in forming copolymers with other vinyl monomers enables the tailoring of polymer properties, including flexibility, thermal stability, and adhesion characteristics, which are essential for a wide range of industrial applications.

From a safety perspective, Allylbromid is known to be highly volatile, flammable, and toxic. 
Allylbromid can readily vaporize at room temperature, posing inhalation hazards, and it is also corrosive to skin and mucous membranes. 

Exposure to Allylbromid vapors can cause respiratory irritation, headaches, dizziness, and even more severe neurological effects with prolonged exposure. 
Therefore, it must be handled using stringent safety protocols, including the use of proper personal protective equipment, adequate ventilation, and storage in tightly sealed containers away from sources of ignition.

Uses Of Allylbromid:
Allylbromid is used as an alkylating agent in the synthesis of pharmaceuticals, polymers, adhesives, perfumes, biochemicals and other allylic compounds. 
Allylbromid is used as precursor for the preparation of allyliczinc bromide by reacting it with zinc. 
Allylbromid is also used in the preparation of allylethers like allyl decyl ether, allyl benzyl ether and allyl geranyl ether. 

Allylbromid is also used in the preparation of R enantiomer of allyl phenyl carbinol (APC) such as 1-phenyl-3-butene, which is a valuable intermediate for drugs and agro-chemicals.
Allylbromid can be used: For the synthesis of stereodefined allylated arenes via Suzuki-type coupling reaction.
In Barbier-type allylation reactions of aldehydes and ketones.

To synthesize a monomer, 1-1-(allyloxy)-4-nitrobenzene while synthesizing nanostructured molecularly imprinted polymer for selective tryptophan assay in biological and pharmaceutical samples.
Allylbromid is widely utilized in organic synthesis as a versatile intermediate due to its high reactivity stemming from the combination of a bromine atom bonded to an allylic carbon, which facilitates a range of chemical transformations including nucleophilic substitutions and polymerization reactions.

One of its primary industrial applications is in the synthesis of allyl compounds, such as allyl ethers and allyl amines, which serve as key building blocks for the manufacture of pharmaceuticals, agrochemicals, and fine chemicals, where the allyl group often imparts unique biological activity or chemical functionality essential for drug design and crop protection agents.
In addition to its role as a synthetic precursor, allylbromid is extensively employed in the production of specialty polymers and resins, where its ability to participate in radical polymerization and crosslinking reactions allows for the modification of polymer properties, such as enhancing flexibility, adhesion, and chemical resistance.
 
These polymers are commonly used in coatings, adhesives, sealants, and plasticizers, playing critical roles in industries ranging from automotive and construction to electronics and consumer goods, where durable and high-performance materials are required.
Moreover, Allylbromid is used as an alkylating agent in various organic reactions, enabling the introduction of allyl groups into molecules, which can subsequently undergo further chemical modifications to produce compounds with tailored physical and chemical properties. 

This capacity is particularly valuable in the synthesis of complex molecules in the pharmaceutical and materials science fields, where allyl-functionalized intermediates serve as precursors to biologically active molecules or advanced materials with specific mechanical or thermal characteristics.
Furthermore, in the realm of research and development, allylbromid serves as a reagent for the preparation of crosslinking agents and surface modifiers, facilitating the formation of chemical bonds between polymer chains or between polymers and substrates, which improves the performance of coatings and composite materials. 

This application extends to the manufacture of photoresists and specialty chemicals used in microelectronics and nanotechnology, where precise molecular architecture and surface properties are essential.
Due to its volatility and hazardous nature, allylbromid’s handling and use require stringent safety measures, yet despite these challenges, it remains indispensable in chemical industries that rely on the allyl functionality to build complex molecules and engineer materials with enhanced properties.

Allylbromid is a highly reactive compound extensively employed in organic chemistry as a fundamental building block for synthesizing a wide variety of chemically and biologically significant molecules. 
Its unique molecular structure, featuring a bromine atom bonded to an allylic carbon adjacent to a carbon-carbon double bond, enables it to readily participate in nucleophilic substitution and addition reactions, making it invaluable in the preparation of numerous intermediates used across the pharmaceutical, agricultural, and materials industries.

In the pharmaceutical sector, Allylbromid serves as a key reagent for the synthesis of allyl-containing drugs and bioactive molecules, where the allyl group can enhance biological activity or act as a handle for further molecular modifications. 
Its ability to introduce reactive allylic substituents facilitates the design of complex molecules, including enzyme inhibitors, anticancer agents, and other therapeutics that require precise chemical functionality and stereochemistry for efficacy.

Allylbromid plays a pivotal role in the production of specialty polymers and copolymers, where it is utilized to incorporate allyl groups into polymer backbones or side chains, providing sites for crosslinking and functionalization. 
This functionalization improves the physical and chemical properties of polymers, such as elasticity, adhesion, thermal stability, and chemical resistance, which are critical attributes in high-performance materials for coatings, adhesives, and elastomers used in automotive, aerospace, and electronics applications.

Health Hazard Of Allylbromid:
Exposures to Allylbromid cause severe eye and skin burns, irritation to the eyes, skin, and respiratory system. 
Allylbromid is harmful when absorbed through the skin or inhaled in the workplace. 

Laboratory rats exposed for a prolonged period of time developed symptoms of poisoning, such as excessive salivation in a small number of animals, and severe gastric irritation. 
Vapors of Allylbromid may cause dizziness or suffocation, headache, coughing, and distressed breathing.

Safety Profile Of Allylbromid:
Poison by ingestion and intraperitoneal routes. 
Human mutation data reported. 
Dangerous fire and explosion hazard when exposed to heat, flame, or oxidizers. 

When heated to decomposition it emits toxic fumes of Br-. 
To fight fire, use alcohol foam, water spray or mist, CO2, dry chemical.
Allylbromid is classified as a highly hazardous chemical due to its toxicity, flammability, and irritant properties, which pose significant risks to human health and safety if not handled properly. 

Allylbromid is a volatile liquid with a strong, irritating odor, and exposure to its vapors can cause severe respiratory tract irritation, leading to symptoms such as coughing, wheezing, shortness of breath, and inflammation of the mucous membranes. 
Prolonged or high-level inhalation may result in more serious respiratory effects, including pulmonary edema and chemical pneumonitis, which require immediate medical attention.

In addition to respiratory hazards, allylbromid is a corrosive substance that can cause severe burns upon contact with skin or eyes, resulting in redness, pain, blistering, and potentially permanent tissue damage or loss of vision if not promptly and adequately treated. 
Allylbromid also has sensitizing properties, meaning repeated or prolonged skin contact may lead to allergic dermatitis or other hypersensitivity reactions, increasing vulnerability upon subsequent exposures.

Allylbromid is highly flammable and volatile, with a low flash point that enables it to ignite easily in the presence of heat, sparks, or open flames. 
Therefore, it must be stored and used away from ignition sources, in well-ventilated areas, and with appropriate explosion-proof equipment to prevent fires or explosions, which could cause severe injury, property damage, or environmental contamination.