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Benzyl Bromide
Benzyl bromide is an organic compound with the formula . The molecule consists of a benzene ring substituted with a bromomethyl group. It is a colorless liquid with lachrymatory properties. The compound is a reagent for introducing benzyl groups. Synthesis and structure Benzyl bromide can be synthesized by the bromination of toluene under conditions suitable for a free radical halogenation: : The structure has been examined by electron diffraction. Applications Benzyl bromide is used in organic synthesis for the introduction of the benzyl groups when the less expensive benzyl chloride is insufficiently reactive. Benzylations are often achieved in the presence of catalytic amounts of sodium iodide, which generates the more reactive benzyl iodide in situ. In some cases, benzyl serves as protecting group for alcohols and carboxylic acids. Safety Benzyl bromide is a strong lachrymator and is also intensely irritating to skin and mucous membranes. Because of these properties, it ...
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Organic Compound
Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-containing compounds such as alkanes (e.g. methane ) and its derivatives are universally considered organic, but many others are sometimes considered inorganic, such as certain compounds of carbon with nitrogen and oxygen (e.g. cyanide ion , hydrogen cyanide , chloroformic acid , carbon dioxide , and carbonate ion ). Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The study of the properties, reactions, and syntheses of organic compounds comprise the discipline known as organic chemistry. For historical reasons, a few classes of carbon-containing compounds (e.g., carbonate salts and cyanide salts), along with a few other exceptions (e.g., carbon dioxide, and even ...
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Alcohol (chemistry)
In chemistry, an alcohol (), is a type of organic compound that carries at least one hydroxyl () functional group bound to a Saturated and unsaturated compounds, saturated carbon atom. Alcohols range from the simple, like methanol and ethanol, to complex, like sugar alcohols and cholesterol. The presence of an OH group strongly modifies the properties of Hydrocarbon, hydrocarbons, conferring Hydrophile, hydrophilic (water-loving) properties. The OH group provides a site at which many reactions can occur. History The flammable nature of the exhalations of wine was already known to ancient natural philosophers such as Aristotle (384–322 BCE), Theophrastus (–287 BCE), and Pliny the Elder (23/24–79 CE). However, this did not immediately lead to the isolation of alcohol, even despite the development of more advanced distillation techniques in second- and third-century Roman Egypt. An important recognition, first found in one of the writings attributed to Jabir ibn Hayyan, J� ...
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Organobromides
Organobromine chemistry is the study of the synthesis and properties of organobromine compounds, also called organobromides, which are organic compounds that contain carbon Chemical bond, bonded to bromine. The most pervasive is the naturally produced bromomethane. One prominent application of synthetic organobromine compounds is the use of polybrominated diphenyl ethers as fire-retardants, and in fact fire-retardant manufacture is currently the major industrial use of the element bromine. A variety of minor organobromine compounds are found in nature, but none are biosynthesized or required by mammals. Organobromine compounds have fallen under increased scrutiny for their environmental impact. General properties Most organobromine compounds, like most organohalogens, organohalide compounds, are relatively nonpolar. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon–bromine bond is electrophilic, i.e. alkyl bromides are alkylating ...
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Xylyl Bromide
Xylyl-bromide, also known as methylbenzyl bromide or T-stoff ('substance-T'), is any member or a mixture of organic chemical compounds with the molecular formula C6 H4(CH3)(CH2 Br). The mixture was formerly used as a tear gas and has an odor reminiscent of lilac. All members and the mixture are colourless liquids, although commercial or older samples appear yellowish. Use as a weapon Xylyl bromide is an irritant and lachrymatory agent. It has been incorporated in chemical weapons since the early months of World War I. Some commentators say the first use was in August 1914, when the French attacked German soldiers with tear gas grenades, but the agent used in that incident was more likely to be ethyl bromoacetate, which the French had tested before the war. The first extensive use of xylyl bromide was the firing by German forces of 18,000 "T-shells" at Russian positions in the Battle of Bolimów in January 1915. The shells were modified 15 cm (6 inch) artiller ...
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Benzyl Iodide
Benzyl iodide is an organic compound with the chemical formula . The compound consists of a benzene ring with an attached iodidemethyl group. The substance is an alkyl halide and is a constitutional isomer of the iodotoluenes. Synthesis Benzyl iodide can be obtained via the Finkelstein reaction from benzyl chloride and sodium iodide in acetone. Properties Benzyl iodide forms colorless to yellow needles, melting at 24.5 °C.''CRC Handbook of Chemistry and Physics'', 90. Edition, CRC Press, Boca Raton, Florida, 2009, , Section 3, ''Physical Constants of Organic Compounds'', p. 3-306. As a liquid, the compound has the high refractive index of 1.6334. Benzyl iodide is also a powerful lachrymator. See also * Benzyl bromide * Benzyl chloride * Benzyl fluoride References

{{Chemical agents Organoiodides Benzyl compounds Lachrymatory agents ...
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Benzyl Fluoride
Benzyl fluoride is an organic compound consisting of a benzene ring substituted with a fluoromethyl group. See also * Benzyl chloride * Benzyl bromide * Benzyl iodide Benzyl iodide is an organic compound with the chemical formula . The compound consists of a benzene ring with an attached iodidemethyl group. The substance is an alkyl halide and is a constitutional isomer of the iodotoluenes. Synthesis Benzyl i ... References Organofluorides Benzyl compounds {{organic-compound-stub ...
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Benzyl Chloride
Benzyl chloride, or α-chlorotoluene, is an organic compound with the formula . This colorless liquid is a reactive organochlorine compound that is a widely used chemical building block. Preparation Benzyl chloride is prepared industrially by the gas-phase photochemical reaction of toluene with chlorine: : In this way, approximately 100,000 tonnes are produced annually. The reaction proceeds by the free radical process, involving the intermediacy of free chlorine atoms. Side products of the reaction include benzal chloride and benzotrichloride. Other methods of production exist, such as the Blanc chloromethylation of benzene. Benzyl chloride was first prepared from treatment of benzyl alcohol with hydrochloric acid. Uses and reactions Industrially, benzyl chloride is the precursor to benzyl esters, which are used as plasticizers, flavorants, and perfumes. Phenylacetic acid, a precursor to pharmaceuticals, is produced from benzyl cyanide, which in turn is generated b ...
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Lachrymatory Agent
Tear gas, also known as a lachrymatory agent or lachrymator (), sometimes colloquially known as "mace" after the early commercial self-defense spray, is a chemical weapon that stimulates the nerves of the lacrimal gland in the eye to produce tears. In addition, it can cause severe eye and respiratory pain, skin irritation, bleeding, and blindness. Common lachrymators both currently and formerly used as tear gas include pepper spray (OC gas), PAVA spray ( nonivamide), CS gas, CR gas, CN gas (phenacyl chloride), bromoacetone, xylyl bromide, chloropicrin (PS gas) and Mace (a branded mixture). While lachrymatory agents are commonly deployed for riot control by law enforcement and military personnel, its use in warfare is prohibited by various international treaties.E.g. the Geneva Protocol of 1925 prohibited the use of "asphyxiating gas, or any other kind of gas, liquids, substances or similar materials". During World War I, increasingly toxic and deadly lachrymatory age ...
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Carboxylic Acid
In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an Substituent, R-group. The general formula of a carboxylic acid is often written as or , sometimes as with R referring to an organyl group (e.g., alkyl, alkenyl, aryl), or hydrogen, or other groups. Carboxylic acids occur widely. Important examples include the amino acids and fatty acids. Deprotonation of a carboxylic acid gives a carboxylate anion. Examples and nomenclature Carboxylic acids are commonly identified by their trivial names. They often have the suffix ''-ic acid''. IUPAC-recommended names also exist; in this system, carboxylic acids have an ''-oic acid'' suffix. For example, butyric acid () is butanoic acid by IUPAC guidelines. For nomenclature of complex molecules containing a carboxylic acid, the carboxyl can be considered position one of the parent chain even if there are other substituents, such as 3-chloropropanoic acid. Alternately, it can be named ...
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Protecting Group
A protecting group or protective group is introduced into a molecule by chemical modification of a functional group to obtain chemoselectivity in a subsequent chemical reaction. It plays an important role in multistep organic synthesis. In many preparations of delicate organic compounds, specific parts of the molecules cannot survive the required reagents or chemical environments. These parts (functional groups) must be protected. For example, lithium aluminium hydride is a highly reactive reagent that usefully reduces esters to alcohols. It always reacts with carbonyl groups, and cannot be discouraged by any means. When an ester must be reduced in the presence of a carbonyl, hydride attack on the carbonyl must be prevented. One way to do so converts the carbonyl into an acetal, which does not react with hydrides. The acetal is then called a protecting group for the carbonyl. After the hydride step is complete, aqueous acid removes the acetal, restoring the carbonyl. This step ...
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Benzene
Benzene is an Organic compound, organic chemical compound with the Chemical formula#Molecular formula, molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar hexagonal Ring (chemistry), ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms, benzene is classed as a hydrocarbon. Benzene is a natural constituent of petroleum and is one of the elementary petrochemicals. Due to the cyclic continuous pi bonds between the carbon atoms, benzene is classed as an aromatic hydrocarbon. Benzene is a colorless and highly Combustibility and flammability, flammable liquid with a sweet smell, and is partially responsible for the aroma of gasoline. It is used primarily as a Precursor (chemistry), precursor to the manufacture of chemicals with more complex structures, such as ethylbenzene and cumene, of which billions of kilograms are produced annually. Although benzene is a major Chemical industry, industrial che ...
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