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3,3'-Dichlorobenzidine
3,3'-Dichlorobenzidine is an organic compound with the formula (C6H3Cl(NH2))2. The pure compound is pale yellow, but commercial samples are often colored. It is barely soluble in water and is often supplied as a wet paste. It is widely used in the production of diarylide yellow pigments used in the production of printing inks. Its use in the production of dyes has been largely discontinued because of concerns about carcinogenicity. Preparation and reactions 3,3'-Dichlorobenzidine is prepared in two steps from 2-nitrochlorobenzene. The first step involves reduction with zinc in base to afford 2,2'-dichlorodiphenylhydrazine. This intermediate undergoes the benzidine rearrangement to afford 3,3'-dichlorobenzidine. Aqueous solutions of 3,3'-dichlorobenzidine degrade in light to monochloro derivative. It undergoes chlorination (for example in water treatment plants) to give the tetrachloro derivative. The most widely practiced reaction of 3,3'-dichlorobenzidine is its double diazot ...
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Pigment Yellow 13
Pigment Yellow 13 is an organic compound and an azo compound. It is a widely used yellow pigment. It is also classified as a diarylide pigment, being derived from 3,3'-dichlorobenzidine. It is closely related to Pigment Yellow 12 Pigment Yellow 12 is an organic compound and an azo compound. It is a widely used yellow pigment. It is also classified as a diarylide pigment, being derived from 3,3'-dichlorobenzidine. It is closely related to Pigment Yellow 13, wherein the t ..., wherein the two xylyl groups are replaced by phenyl.{{cite encyclopedia, authors=K. Hunger. W. Herbst , title=Pigments, Organic, encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry, publisher=Wiley-VCH, place=Weinheim, year=2012, doi=10.1002/14356007.a20_371, isbn=978-3527306732 References Pigments Organic pigments Shades of yellow Diarylide pigments ...
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Diarylide Yellow
Diarylide pigments are organic compounds that are used as pigments in inks and related materials. They often are yellow or yellow-green. To some extent, these organic compounds have displaced cadmium sulfide from the market. They exist as yellow powders of low solubility in water.K. Hunger. W. Herbst "Pigments, Organic" in ''Ullmann's Encyclopedia of Industrial Chemistry'', Wiley-VCH, Weinheim, 2012. Production The formation of these pigments involves the reaction of diazotized aromatic diamines (derivatives of benzidine) with coupling components, typically derivatives of acetoacetanilide. By varying both of these components, a wide variety of pigments have been produced. A related family of organic pigments are the simpler arylides, which arise from the coupling of monodiazonium salts with the same coupling partners. The molecular structures of these molecules is more conjugated than represented in the images shown below. The pigments' colors can range from yellow to g ...
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Benzidine Rearrangement
Benzidine (trivial name), also called 1,1'-biphenyl-4,4'-diamine (systematic name), is an organic compound with the formula (C6H4NH2)2. It is an aromatic amine. It is a component of a test for cyanide. Related derivatives are used in the production of dyes. Benzidine has been linked to bladder and pancreatic cancer. Synthesis and properties Benzidine is prepared in a two step process from nitrobenzene. First, the nitrobenzene is converted to 1,2-diphenylhydrazine, usually using iron powder as the reducing agent. Treatment of this hydrazine with mineral acids induces a rearrangement reaction to 4,4'-benzidine. Smaller amounts of other isomers are also formed. The benzidine rearrangement, which proceeds intramolecularly, is a classic mechanistic puzzle in organic chemistry. : The conversion is described as a ,5 igmatropic reaction. : In terms of its physical properties, 4,4'-benzidine is poorly soluble in cold water but can be recrystallized from hot water, where it cry ...
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Pigment Yellow 12
Pigment Yellow 12 is an organic compound and an azo compound. It is a widely used yellow pigment. It is also classified as a diarylide pigment, being derived from 3,3'-dichlorobenzidine. It is closely related to Pigment Yellow 13, wherein the two phenyl groups are replaced by 2,4-xylyl In organic chemistry, xylene or xylol (; IUPAC name: dimethylbenzene) are any of three organic compounds with the formula . They are derived from the substitution of two hydrogen atoms with methyl groups in a benzene ring; which hydrogens are sub ....{{cite encyclopedia, authors=K. Hunger. W. Herbst , title=Pigments, Organic, encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry, publisher=Wiley-VCH, place=Weinheim, year=2012, doi=10.1002/14356007.a20_371, isbn=978-3527306732 References Pigments Organic pigments Shades of yellow Diarylide pigments ...
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Pigment Yellow 13
Pigment Yellow 13 is an organic compound and an azo compound. It is a widely used yellow pigment. It is also classified as a diarylide pigment, being derived from 3,3'-dichlorobenzidine. It is closely related to Pigment Yellow 12 Pigment Yellow 12 is an organic compound and an azo compound. It is a widely used yellow pigment. It is also classified as a diarylide pigment, being derived from 3,3'-dichlorobenzidine. It is closely related to Pigment Yellow 13, wherein the t ..., wherein the two xylyl groups are replaced by phenyl.{{cite encyclopedia, authors=K. Hunger. W. Herbst , title=Pigments, Organic, encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry, publisher=Wiley-VCH, place=Weinheim, year=2012, doi=10.1002/14356007.a20_371, isbn=978-3527306732 References Pigments Organic pigments Shades of yellow Diarylide pigments ...
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Benzidine
Benzidine (trivial name), also called 1,1'-biphenyl-4,4'-diamine (systematic name), is an organic compound with the formula (C6H4NH2)2. It is an aromatic amine. It is a component of a test for cyanide. Related derivatives are used in the production of dyes. Benzidine has been linked to bladder and pancreatic cancer. Synthesis and properties Benzidine is prepared in a two step process from nitrobenzene. First, the nitrobenzene is converted to 1,2-diphenylhydrazine, usually using iron powder as the reducing agent. Treatment of this hydrazine with mineral acids induces a rearrangement reaction to 4,4'-benzidine. Smaller amounts of other isomers are also formed. The benzidine rearrangement, which proceeds intramolecularly, is a classic mechanistic puzzle in organic chemistry. : The conversion is described as a ,5 igmatropic reaction. : In terms of its physical properties, 4,4'-benzidine is poorly soluble in cold water but can be recrystallized from hot water, where it cryst ...
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PubChem
PubChem is a database of chemical molecules and their activities against biological assays. The system is maintained by the National Center for Biotechnology Information (NCBI), a component of the National Library of Medicine, which is part of the United States National Institutes of Health (NIH). PubChem can be accessed for free through a web user interface. Millions of compound structures and descriptive datasets can be freely downloaded via FTP. PubChem contains multiple substance descriptions and small molecules with fewer than 100 atoms and 1,000 bonds. More than 80 database vendors contribute to the growing PubChem database. History PubChem was released in 2004 as a component of the Molecular Libraries Program (MLP) of the NIH. As of November 2015, PubChem contains more than 150 million depositor-provided substance descriptions, 60 million unique chemical structures, and 225 million biological activity test results (from over 1 million assay experiments performed on more t ...
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Chlorobenzenes
Chlorobenzene is an aromatic organic compound with the chemical formula C6H5Cl. This colorless, flammable liquid is a common solvent and a widely used intermediate in the manufacture of other chemicals. Uses Historical The major use of chlorobenzene is as an intermediate in the production of herbicides, dyestuffs, and rubber. Chlorobenzene is also used as a high-boiling solvent in industrial applications as well as in the laboratory. Chlorobenzene is nitrated on a large scale to give a mixture of 2-nitrochlorobenzene and 4-nitrochlorobenzene, which are separated. These mononitrochlorobenzenes are converted to related 2-nitrophenol, 2-nitroanisole, bis(2-nitrophenyl)disulfide, and 2-nitroaniline by nucleophilic displacement of the chloride, with respectively sodium hydroxide, sodium methoxide, sodium disulfide, and ammonia. The conversions of the 4-nitro derivative are similar. Chlorobenzene once was used in the manufacture of pesticides, most notably DDT, by reaction with ...
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Bladder Cancer
Bladder cancer is any of several types of cancer arising from the tissues of the urinary bladder. Symptoms include blood in the urine, pain with urination, and low back pain. It is caused when epithelial cells that line the bladder become malignant. Risk factors for bladder cancer include smoking, family history, prior radiation therapy, frequent bladder infections, and exposure to certain chemicals. The most common type is transitional cell carcinoma. Other types include squamous cell carcinoma and adenocarcinoma. Diagnosis is typically by cystoscopy with tissue biopsies. Staging of the cancer is determined by transurethral resection and medical imaging. Treatment depends on the stage of the cancer. It may include some combination of surgery, radiation therapy, chemotherapy, or immunotherapy. Surgical options may include transurethral resection, partial or complete removal of the bladder, or urinary diversion. The typical five-year survival rates in the United States i ...
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Carcinogen
A carcinogen is any substance, radionuclide, or radiation that promotes carcinogenesis (the formation of cancer). This may be due to the ability to damage the genome or to the disruption of cellular metabolic processes. Several radioactive substances are considered carcinogens, but their carcinogenic activity is attributed to the radiation, for example gamma rays and alpha particles, which they emit. Common examples of non-radioactive carcinogens are inhaled asbestos, certain dioxins, and tobacco smoke. Although the public generally associates carcinogenicity with synthetic chemicals, it is equally likely to arise from both natural and synthetic substances. Carcinogens are not necessarily immediately toxic; thus, their effect can be insidious. Carcinogens, as mentioned, are agents in the environment capable of contributing to cancer growth. Carcinogens can be categorized into two different types: activation-dependent and activation-independent, and each nature impacts their level ...
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Pigment Yellow 14
A pigment is a colored material that is completely or nearly insoluble in water. In contrast, dyes are typically soluble, at least at some stage in their use. Generally dyes are often organic compounds whereas pigments are often inorganic compounds. Pigments of prehistoric and historic value include ochre, charcoal, and lapis lazuli. Economic impact In 2006, around 7.4 million tons of inorganic, organic, and special pigments were marketed worldwide. Estimated at around US$14.86 billion in 2018 and will rise at over 4.9% CAGR from 2019 to 2026. The global demand for pigments was roughly US$20.5 billion in 2009. According to an April 2018 report by ''Bloomberg Businessweek'', the estimated value of the pigment industry globally is $30 billion. The value of titanium dioxide – used to enhance the white brightness of many products – was placed at $13.2 billion per year, while the color Ferrari red is valued at $300 million each year. Physical principles Like ...
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