Names | |
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Preferred IUPAC name 3-Iodoprop-1-ene | |
Other names Allyl iodide 3-Iodopropene 3-Iodopropylene 3-Iodo-1-propene Iodoallylene 2-Propenyl iodide | |
Identifiers | |
3D model (JSmol) | |
ChemSpider | |
ECHA InfoCard | 100.008.302 |
EC Number |
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PubChem CID | |
UNII | |
UN number | 1723 |
CompTox Dashboard (EPA) | |
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Properties | |
C3H5I | |
Molar mass | 167.977 g·mol−1 |
Appearance | Pale yellow liquid |
Density | 1.837 g/cm3 |
Melting point | −99 °C (−146 °F; 174 K) |
Boiling point | 101 to 103 °C (214 to 217 °F; 374 to 376 K) |
Hazards | |
GHS labelling: | |
Danger | |
H225, H314 | |
P210, P233, P240, P241, P242, P243, P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P370+P378, P403+P235, P405, P501 | |
Flash point | 18 °C (64 °F; 291 K) |
Safety data sheet (SDS) | MSDS at Sigma Aldrich |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Allyl iodide (3-iodopropene) is an organic halide used in synthesis of other organic compounds such as N-alkyl-2-pyrrolidones, [1] [ failed verification ] sorbic acid esters, [1] 5,5-disubstituted barbituric acids, [2] [ failed verification ] and organometallic catalysts. [3] [ failed verification ] Allyl iodide can be synthesized from allyl alcohol and methyl iodide on triphenyl phosphite, [4] Finkelstein reaction on allyl halides, [5] or by the action of elemental phosphorus and iodine on glycerol. [6] [7] Allyl iodide dissolved in hexane can be stored for up to three months in a dark freezer at −5 °C (23 °F) before decomposition into free iodine becomes apparent. [8]
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.
In chemistry, a hydration reaction is a chemical reaction in which a substance combines with water. In organic chemistry, water is added to an unsaturated substrate, which is usually an alkene or an alkyne. This type of reaction is employed industrially to produce ethanol, isopropanol, and butan-2-ol.
Alkylation is a chemical reaction that entails transfer of an alkyl group. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene. Alkylating agents are reagents for effecting alkylation. Alkyl groups can also be removed in a process known as dealkylation. Alkylating agents are often classified according to their nucleophilic or electrophilic character. In oil refining contexts, alkylation refers to a particular alkylation of isobutane with olefins. For upgrading of petroleum, alkylation produces a premium blending stock for gasoline. In medicine, alkylation of DNA is used in chemotherapy to damage the DNA of cancer cells. Alkylation is accomplished with the class of drugs called alkylating antineoplastic agents.
Hydroiodic acid is a colorless and aqueous solution of hydrogen iodide (HI). It is a strong acid, which is ionized completely in an aqueous solution. Concentrated solutions of hydroiodic acid are usually 48% to 57% HI.
In chemistry, halogenation is a chemical reaction that entails the introduction of one or more halogens into a 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. The haloarene 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.
In organic chemistry, an acyl halide is a chemical compound derived from an oxoacid by replacing a hydroxyl group with a halide group.
Acetyl chloride is an acyl chloride derived from acetic acid. It belongs to the class of organic compounds called acid halides. It is a colorless, corrosive, volatile liquid. Its formula is commonly abbreviated to AcCl.
In chemistry, the term phosphonium describes polyatomic cations with the chemical formula PR+
4. These cations have tetrahedral structures. The salts are generally colorless or take the color of the anions.
Trimethylaluminium is one of the simplest examples of an organoaluminium compound. Despite its name it has the formula Al2(CH3)6 (abbreviated as Al2Me6 or TMA), as it exists as a dimer. This colorless liquid is pyrophoric. It is an industrially important compound, closely related to triethylaluminium.
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.
Trimethylsilyl chloride, also known as chlorotrimethylsilane is an organosilicon compound, with the formula (CH3)3SiCl, often abbreviated Me3SiCl or TMSCl. It is a colourless volatile liquid that is stable in the absence of water. It is widely used in organic chemistry.
Benzyl chloride, or α-chlorotoluene, is an organic compound with the formula C6H5CH2Cl. This colorless liquid is a reactive organochlorine compound that is a widely used chemical building block.
Organophosphorus chemistry is the scientific study of the synthesis and properties of organophosphorus compounds, which are organic compounds containing phosphorus. They are used primarily in pest control as an alternative to chlorinated hydrocarbons that persist in the environment. Some organophosphorus compounds are highly effective insecticides, although some are extremely toxic to humans, including sarin and VX nerve agents.
Nickel(II) iodide is an inorganic compound with the formula NiI2. This paramagnetic black solid dissolves readily in water to give bluish-green solutions, from which crystallizes the aquo complex [Ni(H2O)6]I2 (image above). This bluish-green colour is typical of hydrated nickel(II) compounds. Nickel iodides find some applications in homogeneous catalysis.
In inorganic chemistry, sulfonyl halide groups occur when a sulfonyl functional group is singly bonded to a halogen atom. They have the general formula RSO2X, where X is a halogen. The stability of sulfonyl halides decreases in the order fluorides > chlorides > bromides > iodides, all four types being well known. The sulfonyl chlorides and fluorides are of dominant importance in this series.
Allyl bromide (3-bromopropene) is an organic halide. It is an alkylating agent used in synthesis of polymers, pharmaceuticals, synthetic perfumes and other organic compounds. Physically, allyl bromide is a colorless liquid with an irritating and persistent smell, however, commercial samples are yellow or brown. Allyl bromide is more reactive but more expensive than allyl chloride, and these considerations guide its use.
In chemistry, carbonylation refers to reactions that introduce carbon monoxide (CO) into organic and inorganic substrates. Carbon monoxide is abundantly available and conveniently reactive, so it is widely used as a reactant in industrial chemistry. The term carbonylation also refers to oxidation of protein side chains.
An insertion reaction is a chemical reaction where one chemical entity interposes itself into an existing bond of typically a second chemical entity e.g.:
In industrial chemistry, carboalkoxylation is a process for converting alkenes to esters. This reaction is a form of carbonylation. A closely related reaction is hydrocarboxylation, which employs water in place of alcohols
When unsaturated amines are carbonylated in the presence of Co2(CO)8, N-alkyl pyrrolidinones are obtained. Carbonylation of allyl halides in the presence of primary amines and a rhodium compound affords the same products....If allyl derivatives are carbonylated in the presence of acetylene by means of Ni(CO)4 and water or methanol at 20 °C, the acetylene adds onto the allyl halide and 2-cis-5-dienoic acids or esters or sorbic acid esters are obtained.
Disubstitution of barbituric acids at the 5-position is only possible with highly reactive halides, such as allyl halides.
Halogen-containing allyl complexes can often be prepared simply from reactions of allyl halides with metal compounds.