Isoquinoline
Chemical name	Isoquinoline
Chemical formula	C9H7N
Molecular mass	129.16 g/mol
CAS number	[119-65-3]
Density	1.099 g/cm3
Melting point	26 - 28 °C
Boiling point	242 °C
SMILES	C1(C=NC=C2)=C2C=CC=C1
Disclaimer and references

Isoquinoline (also benzo[c]pyridine)is a heterocyclic aromatic organic compound. It's a structural isomer of quinoline, the other existing benzopyridine (i.e. mononitrogenated analog of naphtalene, fussion of a benzene and a pyridine rings). In a broader sense, the term isoquinolines is used to make reference to isoquinoline derivates. Image File history File links Isoquinoline_chemical_structure. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... The molecular mass (abbreviated MM) of a substance, called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... Density (symbol: ρ - Greek: rho) is a measure of mass per unit of volume. ... The melting point of a solid is the temperature at which it changes state from solid to liquid. ... The boiling point of a substance is the temperature at which it can change its state from a liquid to a gas throughout the bulk of the liquid. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... Heterocyclic compounds are substances which contain a ring structure as found in benzene and the aromatic compounds, or aromatic hydrocarbons, but in which other atoms than carbon, such as sulfur, oxygen or nitrogen are found as part of the ring. ... In chemistry, an aromatic molecule is one in which electrons are free to cycle around circular arrangements of atoms, which are alternately singly and doubly bonded to one another. ... An organic compound is any member of a large class of chemical compounds whose molecules contain carbon, with the exception of carbides, carbonates, carbon oxides and gases containing carbon. ... In chemistry, isomers are molecules with the same chemical formula and often with the same kinds of bonds between atoms, but in which the atoms are arranged differently. ... Quinoline, also known as 1-azanaphthalene, 1-benzazine, or benzo[b]pyridine, is a heterocyclic aromatic organic compound. ... An analog is in chemistry a chemical closely related to another usually sharing the same nucleus. ... Naphthalene (also known as naphthalin, naphthaline, tar camphor, white tar, albocarbon, or naphthene) is a crystalline white solid hydrocarbon with a typical mothball odor. ... Benzene, also known as C6H6, PhH, and benzol, is an organic chemical compound that is a colorless and flammable liquid with a pleasant, sweet smell. ... R-phrases , , , S-phrases , , Flash point 20 °C Supplementary data page Structure and properties n, εr, etc. ... Derivatization is a technique used in Chemistry which transforms a chemical Compound into a Product of similar chemical Structure, called Derivate. ...

It can be found as a structural backbone in natural ocurring alkaloids, of which papaverine, morphine and codeine are the most common ones. An alkaloid is a nitrogenous organic molecule that has a pharmacological effect on humans and other animals. ... Papaverine is an opium alkaloid (opiate) used intravenously in the treatment of erectile dysfunction. ... Morphine (INN), the principal active agent in opium, is a powerful opioid analgesic drug. ... Codeine (INN) or methylmorphine is an opioid used for its analgesic, antitussive and antidiarrheal properties. ...

Chemical properties

Being an analog of pyridine, isoquinoline is a weak base, with a pK_b of 8.6. It protonates to form salts upon treatment with strong acids, such as HCl. It forms adducts with Lewis acids, such as BF₃. An analog is in chemistry a chemical closely related to another usually sharing the same nucleus. ... R-phrases , , , S-phrases , , Flash point 20 °C Supplementary data page Structure and properties n, εr, etc. ... A base is: in mathematics: A number that is raised to a power, or base of an exponential function. ... Państwowy Korpus Bezpieczeństwa (Polish for National Security Corps, short PKB) was a Polish underground police force organized by the Armia Krajowa and Delegates Office under German occupation during World War II. It was trained as the core of the future police forces during the assumed all-national uprising and... For other meanings of the word salt see table salt or salt (disambiguation). ... A strong acid is an acid which is stronger than the hydronium ion. ... Wikipedia does not yet have an article with this exact name. ... In chemistry, a Lewis acid can accept a pair of electrons and form a coordinate covalent bond, after the American chemist Gilbert Lewis. ...

Isolation and Synthesis

Isoquinolone was first isolated from coal tar in 1885 by S. Hooferwerff and W.A. v. Dorp. Coal tar is the liquid by-product of the distillation of coal to make coke. ...

Isoquinolines can be sinthetized by means of several methods:

• Bischler-Napieralski reaction treating a N-acyl-β-phenylethylamine with a dehydrating agent, and then dehydrogenating the product (with palladium for example), thus yielding a 1-alkyl-isoquinoline.

• Pomeranz-Fritsch reaction using acetaldehyde and a glycine acetal, which in an acid medium react to form isoquinoline. Alternatively, benzylamine and a glyoxal acetal can be used, to produce the same result.

• Pictet-Spengler reaction using a β-phenylethylamine and an aldehyde in an acid medium, which produces a 1-alkyl-2,3,4-trihydronquinoline, that can be dehydrogenated to produce the corresponding 1-alkyl-isoquinoline

The Bischler-Napieralski reaction is a chemical reaction that dehydrates an N-acyl β-arylethyl amines into the corresponding heterocycle. ... Phenethylamine is an alkaloid and monoamine. ... Hydrogenation is a chemical reaction in which unsaturated bonds between carbon atoms are reduced by attachment of a hydrogen atom to each carbon. ... General Name, Symbol, Number palladium, Pd, 46 Chemical series transition metals Group, Period, Block 10, 5, d Appearance silvery white metallic Atomic mass 106. ... R-phrases , , S-phrases , , , Flash point −39 °C Autoignition temperature 185 °C RTECS number AB1925000 Supplementary data page Structure and properties n, εr, etc. ... Glycine (Gly, G) is a nonpolar amino acid. ... An acetal is a functional group or molecule containing the functional group of a carbon bonded to two -OR groups. ... It has been suggested that strong acid be merged into this article or section. ... Look up medium in Wiktionary, the free dictionary. ... Glyoxal is an organic compound. ... An acetal is a functional group or molecule containing the functional group of a carbon bonded to two -OR groups. ... The Pictet-Spengler reaction is a chemical reaction in which a β-arylethylamine such as tryptamine is heated in the presence of an aldehyde and acid . The Pictet-Spengler reaction can be considered a special case of the Mannich reaction. ... Phenethylamine is an alkaloid and monoamine. ... An aldehyde is either a functional group consisting of a terminal carbonyl group or a compound containing a terminal carbonyl group. ... It has been suggested that strong acid be merged into this article or section. ... Look up medium in Wiktionary, the free dictionary. ... Hydrogenation is a chemical reaction in which unsaturated bonds between carbon atoms are reduced by attachment of a hydrogen atom to each carbon. ...

See also

• Quinoline, an analog with the nitrogen atom in position 1.
• Pyridine, an analog without the fused benzene ring.
• Naphthalene, an analog without the nitrogen atom.
• Simple aromatic rings

This article incorporates text from the Encyclopædia Britannica Eleventh Edition, a publication now in the public domain. Quinoline, also known as 1-azanaphthalene, 1-benzazine, or benzo[b]pyridine, is a heterocyclic aromatic organic compound. ... R-phrases , , , S-phrases , , Flash point 20 °C Supplementary data page Structure and properties n, εr, etc. ... Benzene, also known as C6H6, PhH, and benzol, is an organic chemical compound that is a colorless and flammable liquid with a pleasant, sweet smell. ... Naphthalene (also known as naphthalin, naphthaline, tar camphor, white tar, albocarbon, or naphthene) is a crystalline, aromatic, white, solid hydrocarbon, best known as the primary ingredient of mothballs. ... Simple aromatic rings are aromatic organic compounds (also known as arenes or aromatics) that consist only of conjugated planar ring systems with delocalized pi electron clouds instead of discrete alternating single and double bonds. ... Encyclopædia Britannica, the 11th edition The Encyclopædia Britannica Eleventh Edition (1910–1911) is perhaps the most famous edition of the Encyclopædia Britannica. ... The public domain comprises the body of all creative works and other knowledge—writing, artwork, music, science, inventions, and others—in which no person or organization has any proprietary interest. ...