1,2-Methylenedioxybenzene
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1,2-Methylenedioxybenzene
1,3-Benzodioxole (1,2-methylenedioxybenzene) is an organic compound with the formula CHOCH. The compound is classified as benzene derivative and a heterocyclic compound containing the methylenedioxy functional group. It is a colorless liquid. Although benzodioxole is not particularly important, many related compounds containing the methylenedioxyphenyl group are bioactive, and thus are found in pesticides and pharmaceuticals. Preparation 1,3-Benzodioxole can be synthesized from catechol with disubstituted halomethanes. See also * 1,4-Benzodioxine * MDMA * Methylenedioxy * Safrole * Piperonal Piperonal, also known as heliotropin, is an organic compound which is commonly found in fragrances and flavors.Karl-Georg Fahlbusch, Franz-Josef Hammerschmidt, Johannes Panten, Wilhelm Pickenhagen, Dietmar Schatkowski, Kurt Bauer, Dorothea Garbe a ... References {{heterocyclic-stub ...
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Functional Group
In organic chemistry, a functional group is any substituent or moiety (chemistry), moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the rest of the molecule's composition. This enables systematic prediction of chemical reactions and behavior of chemical compounds and the design of chemical synthesis. The Reactivity (chemistry), reactivity of a functional group can be modified by other functional groups nearby. Functional group interconversion can be used in retrosynthetic analysis to plan organic synthesis. A functional group is a group of atoms in a molecule with distinctive Chemical property, chemical properties, regardless of the other atoms in the molecule. The atoms in a functional group are linked to each other and to the rest of the molecule by covalent bonds. For repeating units of polymers, functional groups attach to their Chemical polarity, nonp ...
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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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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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Heterocyclic Compound
A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its ring(s). Heterocyclic organic chemistry is the branch of organic chemistry dealing with the synthesis, properties, and applications of organic heterocycles. Examples of heterocyclic compounds include all of the nucleic acids, the majority of drugs, most biomass (cellulose and related materials), and many natural and synthetic dyes. More than half of known compounds are heterocycles. 59% of US FDA-approved drugs contain nitrogen heterocycles. Classification The study of organic heterocyclic chemistry focuses especially on organic unsaturated derivatives, and the preponderance of work and applications involves unstrained organic 5- and 6-membered rings. Included are pyridine, thiophene, pyrrole, and furan. Another large class of organic heterocycles refers to those fused to benzene rings. For example, the fused benzene derivatives of py ...
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Methylenedioxy
Methylenedioxy is the term used in the field of chemistry, particularly in organic chemistry, for a functional group with the structural formula which is connected to the rest of a molecule by two chemical bonds. The methylenedioxy group consists of two oxygen atoms connected to a methylene bridge ( unit). The methylenedioxy group is generally found attached to an aromatic structure such as phenyl where it forms the methylenedioxyphenyl or benzodioxole functional group which is widely found in natural products, including safrole, and drugs and chemicals such as tadalafil, MDMA, paroxetine and piperonyl butoxide. Enzymes within the cytochrome P450 superfamily are able to form methylenedioxy bridges by closure of an open, adjacent phenol and methoxy group. Examples of products formed by this process are canadine and berberine. Similarly, ''ortho''-demethylenation can be carried out by other members of the superfamily to open a bridge; a process which is applied to, as examples, ...
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Catechol
Catechol ( or ), also known as pyrocatechol or 1,2-dihydroxybenzene, is an organic compound with the molecular formula . It is the ''ortho'' isomer of the three isomeric benzenediols. This colorless compound occurs naturally in trace amounts. It was first discovered by destructive distillation of the plant extract catechin. About 20,000 tonnes of catechol are now synthetically produced annually as a commodity organic chemical, mainly as a precursor to pesticides, flavors, and fragrances. Small amounts of catechol occur in fruits and vegetables. Isolation and synthesis Catechol was first isolated in 1839 by Edgar Hugo Emil Reinsch (1809–1884) by distilling it from the solid tannic preparation catechin, which is the residuum of catechu, the boiled or concentrated juice of ''Mimosa catechu'' ('' Acacia catechu''). Upon heating catechin above its decomposition point, a substance that Reinsch first named ''Brenz-Katechusäure'' (burned catechu acid) sublimated as a white efflo ...
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Diiodomethane
Diiodomethane or methylene iodide, commonly abbreviated "MI", is an organoiodine compound. Diiodomethane is a very dense colorless liquid; however, it decomposes upon exposure to light liberating iodine, which colours samples brownish. It is slightly soluble in water, but soluble in organic solvents. It has a very high refractive index of 1.741, and a surface tension of 0.0508 N·m−1.Website of Krüss'' (8.10.2009) Uses Because of its high density, diiodomethane is used in the determination of the density of mineral and other solid samples. It can also be used as an optical contact liquid, in conjunction with the gemmological refractometer, for determining the refractive index of certain gemstones. Diiodomethane is a reagent for installing the CH2 group. In the Simmons–Smith reaction, it is a source of methylene. In fact the Simmons–Smith reaction does not produce free carbene but proceeds via Zn-CH2I intermediates. Diiodomethane is also a source of the equivalent of . ...
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1,4-Benzodioxine
1,4-Benzodioxine, in chemistry, especially organic chemistry, is an aromatic ring. See also * Benzodioxan * 1,3-Benzodioxole 1,3-Benzodioxole (1,2-methylenedioxybenzene) is an organic compound with the formula CHOCH. The compound is classified as benzene derivative and a heterocyclic compound containing the methylenedioxy functional group. It is a colorless liquid. Alt ... * Ethylenedioxy References {{DEFAULTSORT:Benzodioxine, 1,4- Simple aromatic rings Benzodioxins ...
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MDMA
3,4-Methylenedioxymethamphetamine (MDMA), commonly known as ecstasy (tablet form), and molly (crystal form), is an empathogen–entactogenic drug with stimulant and minor Psychedelic drug, psychedelic properties. In studies, it has been used alongside psychotherapy in the treatment of post-traumatic stress disorder (PTSD) and social anxiety in Autism, autism spectrum disorder. The purported pharmacological effects that may be Prosocial behavior, prosocial include altered sensations, increased energy, empathy, and pleasure. When taken by mouth, effects begin in 30 to 45 minutes and last three to six hours. MDMA was first synthesized in 1912 by Merck Group, Merck chemist Anton Köllisch. It was used to enhance psychotherapy beginning in the 1970s and became popular as a street drug in the 1980s. MDMA is commonly associated with dance party, dance parties, raves, and electronic dance music. Tablets sold as ecstasy may be Cutting agent, mixed with other substances such as ephedr ...
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Methylenedioxy
Methylenedioxy is the term used in the field of chemistry, particularly in organic chemistry, for a functional group with the structural formula which is connected to the rest of a molecule by two chemical bonds. The methylenedioxy group consists of two oxygen atoms connected to a methylene bridge ( unit). The methylenedioxy group is generally found attached to an aromatic structure such as phenyl where it forms the methylenedioxyphenyl or benzodioxole functional group which is widely found in natural products, including safrole, and drugs and chemicals such as tadalafil, MDMA, paroxetine and piperonyl butoxide. Enzymes within the cytochrome P450 superfamily are able to form methylenedioxy bridges by closure of an open, adjacent phenol and methoxy group. Examples of products formed by this process are canadine and berberine. Similarly, ''ortho''-demethylenation can be carried out by other members of the superfamily to open a bridge; a process which is applied to, as examples, ...
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Safrole
Safrole is an organic compound with the formula CH2O2C6H3CH2CH=CH2. It is a colorless oily liquid, although impure samples can appear yellow. A member of the phenylpropanoid family of natural products, it is found in sassafras plants, among others. Small amounts are found in a wide variety of plants, where it functions as a natural antifeedant. '' Ocotea pretiosa'', which grows in Brazil, and '' Sassafras albidum'', which grows in eastern North America, are the main natural sources of safrole. It has a characteristic "sweet-shop" aroma. It is a precursor in the synthesis of the insecticide synergist piperonyl butoxide, the fragrance piperonal via isosafrole, and the empathogenic/entactogenic substance MDMA. History Safrole was obtained from a number of plants, but especially from the sassafras tree ('' Sassafras albidum''), which is native to North America, and from Japanese star anise ('' Illicium anisatum'', called ''shikimi'' in Japan). In 1844, the French chemi ...
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Piperonal
Piperonal, also known as heliotropin, is an organic compound which is commonly found in fragrances and flavors.Karl-Georg Fahlbusch, Franz-Josef Hammerschmidt, Johannes Panten, Wilhelm Pickenhagen, Dietmar Schatkowski, Kurt Bauer, Dorothea Garbe and Horst Surburg "Flavors and Fragrances" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2003. The molecule is structurally related to other aromatic aldehydes such as benzaldehyde and vanillin. Natural occurrence Piperonal naturally occurs in various plants. Examples include dill, vanilla, violet flowers, and black pepper. Preparation Piperonal can be prepared by the oxidative cleavage of isosafrole or by using a multistep sequence from catechol or 1,2-methylenedioxybenzene. Synthesis from the latter chemical is accomplished through a condensation reaction with glyoxylic acid followed by cleaving the resulting α-hydroxy acid with an oxidizing agent. Synthesis from catechol requires an additional step, Wi ...
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