Names | |
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Preferred IUPAC name 3-Bromoprop-1-ene | |
Other names Allyl bromide 3-Bromopropene 3-Bromopropylene 3-Bromo-1-propene Bromoallylene 2-Propenyl bromide | |
Identifiers | |
3D model (JSmol) | |
ChemSpider | |
ECHA InfoCard | 100.003.134 |
EC Number |
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PubChem CID | |
RTECS number |
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UNII | |
UN number | 1099 |
CompTox Dashboard (EPA) | |
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Properties | |
C3H5Br | |
Molar mass | 120.977 g·mol−1 |
Appearance | Clear to light yellow liquid |
Odor | Unpleasant, irritating, pungent |
Density | 1.398 g/cm3 |
Melting point | −119 °C (−182 °F; 154 K) |
Boiling point | 71 °C (160 °F; 344 K) |
0.38 g/100 g H2O [1] | |
log P | 1.79 [1] |
Vapor pressure | 18.6 kPa |
−58.6·10−6 cm3·mol−1 [1] | |
Refractive index (nD) | 1.4697 (20 °C, 589.2 nm) |
Viscosity | 0.471 cP [1] |
≈1.9 D [1] | |
Thermochemistry | |
Std enthalpy of formation (ΔfH⦵298) | 12.2 kJ·mol−1 (liquid) 45.2 kJ·mol−1 (gas) [1] |
Enthalpy of vaporization (ΔfHvap) | 32.73 kJ·mol−1 [1] |
Hazards | |
GHS labelling: | |
Danger | |
H225, H301, H314, H330, H331, H340, H350, H400 | |
P201, P202, P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P273, P280, P281, P284, P301+P310, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P308+P313, P310, P311, P320, P321, P330, P363, P370+P378, P391, P403+P233, P403+P235, P405, P501 | |
NFPA 704 (fire diamond) | |
Flash point | −2 to −1 °C |
280 °C (536 °F; 553 K) | |
Explosive limits | 4.3–7.3 % |
Threshold limit value (TLV) | 0.1 ppm [1] (TWA), 0.2 ppm [1] (STEL) |
Safety data sheet (SDS) | MSDS at Oxford University |
Related compounds | |
Related compounds | Allyl chloride Allyl iodide |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Allyl bromide (3-bromopropene) is an organic halide. It is an alkylating agent used in synthesis of polymers, pharmaceuticals, [2] synthetic perfumes [3] and other organic compounds. Physically, allyl bromide is a colorless liquid with an irritating and persistent smell, however, commercial samples are yellow or brown. [4] Allyl bromide is more reactive but more expensive than allyl chloride, and these considerations guide its use. [5]
Allyl bromide is produced commercially from allyl alcohol and hydrobromic acid: [5]
It can also be prepared by the halogen-exchange reaction between allyl chloride and hydrobromic acid or by the allylic bromination of propene. [5]
Allyl bromide is an electrophilic alkylating agent. [4] It reacts with nucleophiles, such as amines, carbanions, alkoxides, etc., to introduce the allyl group:
It is used in the synthesis of compounds containing the allyl functionality, such as the pharmaceuticals methohexital, secobarbital and thiamylal. [2]
Allyl bromide reacts with magnesium metal in dry ether to form allylmagnesium bromide, a Grignard reagent: [6]
1,2-Dibromoethane, also known as ethylene dibromide (EDB), is an organobromine compound with the chemical formula C
2H
4Br
2. Although trace amounts occur naturally in the ocean, where it is probably formed by algae and kelp, it is mainly synthetic. It is a dense colorless liquid with a faint, sweet odor, detectable at 10 ppm, and is a widely used and sometimes-controversial fumigant. The combustion of 1,2-dibromoethane produces hydrogen bromide gas that is significantly corrosive.
Hydrobromic acid is an aqueous solution of hydrogen bromide. It is a strong acid formed by dissolving the diatomic molecule hydrogen bromide (HBr) in water. "Constant boiling" hydrobromic acid is an aqueous solution that distills at 124.3 °C (255.7 °F) and contains 47.6% HBr by mass, which is 8.77 mol/L. Hydrobromic acid is one of the strongest mineral acids known.
Allyl chloride is the organic compound with the formula CH2=CHCH2Cl. This colorless liquid is insoluble in water but soluble in common organic solvents. It is mainly converted to epichlorohydrin, used in the production of plastics. It is a chlorinated derivative of propylene. It is an alkylating agent, which makes it both useful and hazardous to handle.
Hydrogen bromide is the inorganic compound with the formula HBr. It is a hydrogen halide consisting of hydrogen and bromine. A colorless gas, it dissolves in water, forming hydrobromic acid, which is saturated at 68.85% HBr by weight at room temperature. Aqueous solutions that are 47.6% HBr by mass form a constant-boiling azeotrope mixture that boils at 124.3 °C (255.7 °F). Boiling less concentrated solutions releases H2O until the constant-boiling mixture composition is reached.
Sodium bromide is an inorganic compound with the formula NaBr. It is a high-melting white, crystalline solid that resembles sodium chloride. It is a widely used source of the bromide ion and has many applications.
A hydrohalogenation reaction is the electrophilic addition of hydrogen halides like hydrogen chloride or hydrogen bromide to alkenes to yield the corresponding haloalkanes.
1-Bromobutane is the organobromine compound with the formula CH3(CH2)3Br. It is a colorless liquid, although impure samples appear yellowish. It is insoluble in water, but soluble in organic solvents. It is primarily used as a source of the butyl group in organic synthesis. It is one of several isomers of butyl bromide.
Calcium bromide is the name for compounds with the chemical formula CaBr2(H2O)x. Individual compounds include the anhydrous material (x = 0), the hexahydrate (x = 6), and the rare dihydrate (x = 2). All are white powders that dissolve in water, and from these solutions crystallizes the hexahydrate. The hydrated form is mainly used in some drilling fluids.
1-Bromohexane is organobromine compound with formula Br(CH2)5CH3. It is a colorless liquid.
Dibromomethane or methylene bromide, or methylene dibromide is a halomethane with the formula CH2Br2. It is slightly soluble in water but very soluble in organic solvents. It is a colorless liquid.
Bromochloromethane or methylene bromochloride and Halon 1011 is a mixed halomethane. It is a heavy low-viscosity liquid with refractive index 1.4808.
Bromoacetic acid is the chemical compound with the formula CH2BrCO2H. This colorless solid is a relatively strong alkylating agent. Bromoacetic acid and its esters are widely used building blocks in organic synthesis, for example, in pharmaceutical chemistry.
Vinyl bromide is the organobromine compound with the formula CH2=CHBr. Classified as a vinyl halide, it is a colorless gas at room temperature. It is used as a reagent and a comonomer.
1,1,2,2-Tetrabromoethane, or simply tetrabromoethane (TBE), is a halogenated hydrocarbon, chemical formula C2H2Br4. Although three bromine atoms may bind to one of the carbon atoms creating 1,1,1,2-tetrabromoethane this is not thermodynamically favorable, so in practice tetrabromoethane is equal to 1,1,2,2-tetrabromoethane, where each carbon atom binds two bromine atoms.
2-Bromohexane is the organobromine compound with the formula CH3CH(Br)(CH2)3CH3. It is a colorless liquid. The compound is chiral. Most 2-bromoalkanes are prepared by addition of hydrogen bromide to the 1-alkene. Markovnikov addition proceeds in the absence of free-radicals, i.e. give the 2-bromo derivatives.
2-Phenylethyl bromide is an organobromide with the formula C6H5CH2CH2Br. It is a colorless liquid, although older samples appear yellow. Analogous to the preparation of most 1-bromoalkanes, it is prepared by free-radical addition of hydrogen bromide to styrene. These conditions lead to anti-Markovnikov addition, giving the 1-bromo derivatives.
In chemistry, a fatty amine is loosely defined as any amine possessing a mostly linear hydrocarbon chain of eight or more carbon atoms. They are typically prepared from the more abundant fatty acids, with vegetable or seed-oils being the ultimate starting material. As such they are often mixtures of chain lengths, ranging up to about C22. They can be classified as oleochemicals. Commercially important members include coco amine, oleylamine, tallow amine, and soya amine. These compounds and their derivatives are used as fabric softeners, froth flotation agents, corrosion inhibitors, lubricants and friction modifiers. They are also the basis for a variety of cosmetic formulations.
1-Bromo-3-chloropropane is an organohalogen compound with the formula Br(CH2)3Cl. It is a colorless liquid, produced by free-radical addition of hydrogen bromide to allyl chloride. It is used as an alkylating agent to install the –(CH2)3Cl and –(CH2)3– groups. For example, it is a precursor to 4-chlorobutyronitrile.
1-Bromododecane is a bromoalkane with the formula Br(CH2)11CH3. It is a colorless liquid. It is used as a long chain alkylating agent to improve the lipophilicity and hydrophobicity of organic molecules for biological applications.
1-Bromopentane or amyl bromide is an isomer of bromopentane. It is a colorless liquid. It is found as a natural product in Fucus vesiculosus.
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