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, perfumes [2] and other organic compounds. Allyl bromide is a colorless liquid, although commercial samples appear yellow or brown. It is an irritant and a potentially dangerous alkylating agent. Allyl bromide is more reactive but more expensive than allyl chloride, and these considerations guide its use. [3]
Allyl bromide is produced commercially from allyl alcohol and hydrobromic acid: [3]
It can also be prepared by the halogen-exchange reaction between allyl chloride and hydrobromic acid or by the allylic bromination of propene. [3]
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. [3]
Allyl bromide reacts with magnesium metal in dry ether to form allylmagnesium bromide, a Grignard reagent: [5]
Bromine is a chemical element; it has symbol Br and atomic number 35. It is a volatile red-brown liquid at room temperature that evaporates readily to form a similarly coloured vapour. Its properties are intermediate between those of chlorine and iodine. Isolated independently by two chemists, Carl Jacob Löwig and Antoine Jérôme Balard, its name was derived from the Ancient Greek βρῶμος (bromos) meaning "stench", referring to its sharp and pungent smell.
The haloalkanes are alkanes containing one or more halogen substituents. They are a subset of the general class of halocarbons, although the distinction is not often made. Haloalkanes are widely used commercially. They are used as flame retardants, fire extinguishants, refrigerants, propellants, solvents, and pharmaceuticals. Subsequent to the widespread use in commerce, many halocarbons have also been shown to be serious pollutants and toxins. For example, the chlorofluorocarbons have been shown to lead to ozone depletion. Methyl bromide is a controversial fumigant. Only haloalkanes that contain chlorine, bromine, and iodine are a threat to the ozone layer, but fluorinated volatile haloalkanes in theory may have activity as greenhouse gases. Methyl iodide, a naturally occurring substance, however, does not have ozone-depleting properties and the United States Environmental Protection Agency has designated the compound a non-ozone layer depleter. For more information, see Halomethane. Haloalkane or alkyl halides are the compounds which have the general formula "RX" where R is an alkyl or substituted alkyl group and X is a halogen.
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.
In chemistry, halogenation is a chemical reaction which introduces one or more halogens into a chemical compound. Halide-containing compounds are pervasive, making this type of transformation important, e.g. in the production of polymers, drugs. This kind of conversion is in fact so common that a comprehensive overview is challenging. This article mainly deals with halogenation using elemental halogens. Halides are also commonly introduced using salts of the halides and halogen acids. Many specialized reagents exist for and introducing halogens into diverse substrates, e.g. thionyl chloride.
In organic chemistry, an aryl halide is an aromatic compound in which one or more hydrogen atoms, directly bonded to an aromatic ring are replaced by a halide. Haloarenes are different from haloalkanes because they exhibit many differences in methods of preparation and properties. The most important members are the aryl chlorides, but the class of compounds is so broad that there are many derivatives and applications.
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.
In retrosynthetic analysis, a synthon is a hypothetical unit within a target molecule that represents a potential starting reagent in the retroactive synthesis of that target molecule. The term was coined in 1967 by E. J. Corey. He noted in 1988 that the "word synthon has now come to be used to mean synthetic building block rather than retrosynthetic fragmentation structures". It was noted in 1998 that the phrase did not feature very prominently in Corey's 1981 book The Logic of Chemical Synthesis, as it was not included in the index. Because synthons are charged, when placed into a synthesis an uncharged form is found commercially instead of forming and using the potentially very unstable charged synthons.
n-Butyllithium C4H9Li (abbreviated n-BuLi) is an organolithium reagent. It is widely used as a polymerization initiator in the production of elastomers such as polybutadiene or styrene-butadiene-styrene (SBS). Also, it is broadly employed as a strong base (superbase) in the synthesis of organic compounds as in the pharmaceutical industry.
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.
Lithium bromide (LiBr) is a chemical compound of lithium and bromine. Its extreme hygroscopic character makes LiBr useful as a desiccant in certain air conditioning systems.
Bromoethane, also known as ethyl bromide, is a chemical compound of the haloalkanes group. It is abbreviated by chemists as EtBr. This volatile compound has an ether-like odor.
Allyl alcohol is an organic compound with the structural formula CH2=CHCH2OH. Like many alcohols, it is a water-soluble, colourless liquid. It is more toxic than typical small alcohols. Allyl alcohol is used as a precursor to many specialized compounds such as flame-resistant materials, drying oils, and plasticizers. Allyl alcohol is the smallest representative of the allylic alcohols.
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.
Organobromine chemistry is the study of the synthesis and properties of organobromine compounds, also called organobromides, which are organic compounds that contain carbon bonded to bromine. The most pervasive is the naturally produced bromomethane.
Chloroacetaldehyde is an organic compound with the formula ClCH2CHO. Like some related compounds, it is highly electrophilic reagent and a potentially dangerous alkylating agent. The compound is not normally encountered in the anhydrous form, but rather as the hemiacetal (ClCH2CH(OH))2O.
Propargyl bromide, also known as 3-bromo-prop-1-yne, is an organic compound with the chemical formula HC≡CCH2Br. A colorless liquid, it is a halogenated organic compound consisting of propyne with a bromine substituent on the methyl group. It has a lachrymatory effect, like related compounds. The compound is used as a reagent in organic synthesis.
Transition-metal allyl complexes are coordination complexes with allyl and its derivatives as ligands. Allyl is the radical with the connectivity CH2CHCH2, although as a ligand it is usually viewed as an allyl anion CH2=CH−CH2−, which is usually described as two equivalent resonance structures.
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.
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