106-95-6 Usage
Chemical Description
Different sources of media describe the Chemical Description of 106-95-6 differently. You can refer to the following data:
1. Allyl bromide is used in the alkylation step to introduce a substituent onto the oxazinone ring.
2. Allyl bromide is used in the synthesis of compound 8.
Chemical Properties
Different sources of media describe the Chemical Properties of 106-95-6 differently. You can refer to the following data:
1. Colorless liquid
2. Allyl bromide is a clear to light yellow liquid. As an alkylating agent, allyl bromide is used
extensively in the synthesis of polymers, pharmaceuticals, allyls, and other organic compounds.
Allyl bromide is a clear liquid with an intense, acrid, persistent smell and is flammable.
It is insoluble in water, but soluble in alcohol, aether, acetone, carbon tetrachloride,
and chloroform. In fact, allyl bromide is used in the synthesis of other allyl compounds, to
synthesize dyestuff, spice, and as a curative in the medicine industry. Allyl bromide has a
very high mobility in soil. It is also used as a soil fumigant and as a contact poison. Allyl
bromide induces unscheduled DNA synthesis in HeLa cells.
3. Allyl bromide is a highly flammable, colorless to light yellow liquid with an unpleasant, pungent odor.
Uses
Different sources of media describe the Uses of 106-95-6 differently. You can refer to the following data:
1. Allyl Bromide is used as a reagent in the synthesis of Resveratrol derivatives. Resveratrol (R150000) is a minor constituent of wine, correlated with serum lipid reduction and inhibition of platelet a
ggregation. Resveratrol is a specific inhibitor of COX-1, and it also inhibits the hydroperoxidase activity of COX-1. It has been shown to inhibit events associated with tumor initiation, promotion a
nd progression.
2. manufacture of synthetic perfumes, other allyl compounds.
3. Allyl bromide is used as an alkylating agent in the synthesis of pharmaceuticals, polymers, adhesives, perfumes, biochemicals and other allylic compounds. It is used as precursor for the preparation of allyliczinc bromide by reacting it with zinc. It is also used in the preparation of allylethers like allyl decyl ether, allyl benzyl ether and allyl geranyl ether. It 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.
General Description
A clear colorless to light yellow liquid with an irritating unpleasant odor. Flash point 30°F. Irritates eyes, skin, and respiratory system. Toxic by skin absorption. Denser than water and slightly soluble in water.
Air & Water Reactions
Highly flammable. Slightly soluble in water.
Reactivity Profile
Allyl bromide 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.
Hazard
Strong irritant to skin and eyes, flammable,
high fire risk. Upper respiratory tract irritant. Ques-
tionable carcinogen.
Health Hazard
Different sources of media describe the Health Hazard of 106-95-6 differently. You can refer to the following data:
1. Inhalation of vapor irritates mucous membranes and causes dizziness, headache, and lung irritation. Contact with liquid irritates eyes and skin. Ingestion causes irritation of mouth and stomach.
2. Exposures to allyl bromide cause severe eye and skin burns, irritation to the eyes, skin,
and respiratory system. It 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 allyl bromide may cause dizziness or suffocation, headache, coughing,
and distressed breathing.
Flammability and Explosibility
Highlyflammable
Safety Profile
Poison by ingestion and intraperitoneal routes. Mdly toxic by inhalation. Human mutation data reported. See also ALLYL CHLORIDE and ALLYL COMPOUNDS. 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
Synthesis
Allyl alcohol 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 allyl bromide distilled as per the conventional method. It was then redistilled with 3A molecular sieves drying agent to yield the final product which is stored over additional 3A molecular sieves.
Potential Exposure
Used as an insecticide; in the manufacture of resins, fragrances, and other chemicals
storage
Allyl bromide should be stored separate from oxidizing materials and alkalis in a cool,
dry, well-ventilated location in tightly closed containers.
Shipping
UN1099 Allyl bromide, Hazard Class: 3; Labels: 3-Flammable liquid, 6.1-Poisonous materials
Purification Methods
Wash the bromide with NaHCO3 solution then distilled water, dry (CaCl2 or MgSO4), and fractionally distil. Protect it from strong light. [Beilstein 1 IV 754.] LACHRYMATORY, HIGHLY TOXIC and FLAMMABLE.
Incompatibilities
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.
Waste Disposal
In accordance with 40CFR 165 recommendations for the disposal of pesticides and pesticide containers. Must be disposed properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office.
Precautions
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 allyl bromide reacts with oxidizing materials and alkalis.
Check Digit Verification of cas no
The CAS Registry Mumber 106-95-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 6 respectively; the second part has 2 digits, 9 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 106-95:
(5*1)+(4*0)+(3*6)+(2*9)+(1*5)=46
46 % 10 = 6
So 106-95-6 is a valid CAS Registry Number.
InChI:InChI=1/C3H5Br/c1-2-3-4/h2H,1,3H2
106-95-6Relevant articles and documents
Kinetics of free radicals produced by infrared multiphoton-induced decompositions. 1. Reactions of allyl radicals with nitrogen dioxide and bromine
Slagle, Irene R.,Yamada, Fumiaki,Gutman, David
, p. 149 - 153 (1981)
A new versatile technique to study quantitatively the gaseous reactions of polyatomic free radicals is described in detail. Free radicals are generated homogeneously in a tubular reactor by the infrared multiphoton-induced decomposition (MPD) of suitable radical precursors. The concentrations of reactants and products (both stable and labile) are monitored by using photoionization mass spectrometry. Reactions of the allyl radical, generated by the MPD of allyl bromide, with nitrogen dioxide and bromine have been studied at 300 K. The measured rate constants are 3.9(±0.8) × 10-11 cm3 s-1 for the C3H5 + NO2 reaction and 9.0(±1.8) × 10-12 cm3 s-1 for the C3H5 + Br2 reaction. The potential of the experimental facility for other kinds of studies is discussed.
-
Frazer,Gerrard
, p. 3624,3626, 3627 (1955)
-
Kinetics of the Reactions of Unsaturated Hydrocarbon Free Radicals (Vinyl, Propargyl, and Allyl) with Molecular Bromine
Timonen, R. S.,Seetula, J. A.,Gutman, D.
, p. 8217 - 8221 (1993)
The kinetics of the reactions of three unsaturated free radicals (vinyl, propargyl, and allyl) with molecular bromine have been studied by using a tubular reactor coupled to a photoionization mass spectrometer.The radicals were homogeneously generated by the pulsed photolysis of precursor molecules at 193 nm.The subsequent decays of the radical concentrations were monitored in time-resolved experiments as a function of Br2 concentration to obtain the rate constants of these Br-atom metathesis reactions.Rate constants were measured as a function of temperature to obtain Arrhenius parameters.The following rate constant expressions were obtained (units of the preexponential factor are cm3 molecule-1 s-1 and activation energies are kJ mol-1; the temperature range covered in each study is also indicated): C2H3 + Br2 , C3H3 + Br2 , and C3H5 +/- Br2 .The kinetics of R + Br2 reactions is reviewed, and the factors governing the reactivity of polyatomic free radicals in R + Br2 reactions are discussed.
Generalized route to metal nanoparticles with liquid behavior
Warren, Scott C.,Banholzer, Matthew J.,Slaughter, Liane S.,Giannelis, Emmanuel P.,DiSalvo, Francis J.,Wiesner, Ulrich B.
, p. 12074 - 12075 (2006)
We report the generalized synthesis of metal nanoparticles with liquid-like behavior. We introduce a thiol-containing ionic liquid, N,N-dioctyl-N-(3-mercaptopropyl)-N-methylammonium bromide, which serves as a ligand for platinum, gold, palladium, and rhodium nanoparticles. A rapid reduction using THF-soluble metal salts in the presence of the thiol generates nanoparticles with tunable sizes and size distributions. The as-synthesized nanoparticles are a solid and decompose before melting. Upon exchange of the halide anion for an amphiphilic sulfonate anion, however, the nanoparticles exhibit liquid-like properties at room temperature. The liquids have high metal loadings; for example, the 2.7 nm platinum nanoparticle liquid is 36% platinum by mass. Copyright
Synthesis and characterization of ferroelectric liquid crystalline siloxanes containing 4-hydroxyphenyl(2S,3S)-2-chloro-3-methylvalerate
Lin, Chih-Hung
, p. 33 - 42 (2012)
New series of organosiloxane ferroelectric liquid crystalline materials have been synthesized, and their mesomorphic and physical properties have been characterized. These new series contain bis-siloxane or tris-siloxane unit attached to the flexible alkyl chain end of (2S,3S)-2-chloro-3-methylvalerate. The siloxane molecule induction is helpful to the chiral smectic C (S C) formation and chiral SC* stabilization, and it simultaneously causes the liquid crystal temperature range of chiral S C* to be broader. The siloxane member is helpful in reducing the smectic C (SC) transation shift temperature, and the molecule containing tris-siloxane units shows better effect than the bis-siloxane one. The synthesis and characterization of the new FLCs materials which exhibit SC* phase at room temperature and higher spontaneous polarization are presented.
-
Philippi
, p. 277 (1929)
-
-
Asahara,T. et al.
, p. 1130 - 1133 (1971)
-
Enantioselective synthesis of ammonium cations
Walsh, Mark P.,Phelps, Joseph M.,Lennon, Marc E.,Yufit, Dmitry S.,Kitching, Matthew O.
, p. 70 - 76 (2021/09/06)
Control of molecular chirality is a fundamental challenge in organic synthesis. Whereas methods to construct carbon stereocentres enantioselectively are well established, routes to synthesize enriched heteroatomic stereocentres have garnered less attention1–5. Of those atoms commonly present in organic molecules, nitrogen is the most difficult to control stereochemically. Although a limited number of resolution processes have been demonstrated6–8, no general methodology exists to enantioselectively prepare a nitrogen stereocentre. Here we show that control of the chirality of ammonium cations is easily achieved through a supramolecular recognition process. By combining enantioselective ammonium recognition mediated by 1,1′-bi-2-naphthol scaffolds with conditions that allow the nitrogen stereocentre to racemize, chiral ammonium cations can be produced in excellent yields and selectivities. Mechanistic investigations demonstrate that, through a combination of solution and solid-phase recognition, a thermodynamically driven adductive crystallization process is responsible for the observed selectivity. Distinct from processes based on dynamic and kinetic resolution, which are under kinetic control, this allows for increased selectivity over time by a self-corrective process. The importance of nitrogen stereocentres can be revealed through a stereoselective supramolecular recognition, which is not possible with naturally occurring pseudoenantiomeric Cinchona alkaloids. With practical access to the enantiomeric forms of ammonium cations, this previously ignored stereocentre is now available to be explored.
Nickel-Catalyzed Asymmetric Reductive 1,2-Carboamination of Unactivated Alkenes
He, Jun,Xue, Yuhang,Han, Bo,Zhang, Chunzhu,Wang, You,Zhu, Shaolin
supporting information, p. 2328 - 2332 (2020/01/08)
Starting from diverse alkene-tethered aryl iodides and O-benzoyl-hydroxylamines, the enantioselective reductive cross-electrophilic 1,2-carboamination of unactivated alkenes was achieved using a chiral pyrox/nickel complex as the catalyst. This mild, modular, and practical protocol provides rapid access to a variety of β-chiral amines with an enantioenriched aryl-substituted quaternary carbon center in good yields and with excellent enantioselectivities. This process reveals a complementary regioselectivity when compared to Pd and Cu catalysis.
