Phenylhydrazine
Encyclopedia
Phenylhydrazine is the chemical compound
with the formula C6H5NHNH2. Organic chemists abbreviate the compound as PhNHNH2.
, diethyl ether
, chloroform
, and benzene
. It is sparingly soluble in water.
with sodium nitrite
in the presence of hydrogen chloride
to form the diazonium salt, which is subsequently reduced using sodium sulfite
in the presence of sodium hydroxide to form the final product.
derivative characterized, reported by Emil Fischer
in 1875. He prepared it by reduction of a phenyl diazonium salt using sulfite
salts. Fischer used phenylhydrazine to characterize sugar
s via formation of hydrazone
s with the sugar aldehyde
. He also demonstrated in this first paper many of the key properties recognized for hydrazines.
s which are intermediates in the synthesis of various dyes and pharmaceuticals.
Phenylhydrazine is used to form phenylhydrazones of natural mixtures of simple sugar
s in order to render the differing sugars easily separable from each other.
The compound is also used to induce acute hemolytic anemia in studies examining the hematopoietic system.
, hemolytic anemia
, and liver and kidney injury.
Chemical compound
A chemical compound is a pure chemical substance consisting of two or more different chemical elements that can be separated into simpler substances by chemical reactions. Chemical compounds have a unique and defined chemical structure; they consist of a fixed ratio of atoms that are held together...
with the formula C6H5NHNH2. Organic chemists abbreviate the compound as PhNHNH2.
Chemical properties
Phenylhydrazine forms monoclinic prisms that melt to an oil around room temperature which may turn yellow to dark red upon exposure to air. Phenylhydrazine is miscible with ethanolEthanol
Ethanol, also called ethyl alcohol, pure alcohol, grain alcohol, or drinking alcohol, is a volatile, flammable, colorless liquid. It is a psychoactive drug and one of the oldest recreational drugs. Best known as the type of alcohol found in alcoholic beverages, it is also used in thermometers, as a...
, diethyl ether
Diethyl ether
Diethyl ether, also known as ethyl ether, simply ether, or ethoxyethane, is an organic compound in the ether class with the formula . It is a colorless, highly volatile flammable liquid with a characteristic odor...
, chloroform
Chloroform
Chloroform is an organic compound with formula CHCl3. It is one of the four chloromethanes. The colorless, sweet-smelling, dense liquid is a trihalomethane, and is considered somewhat hazardous...
, and benzene
Benzene
Benzene is an organic chemical compound. It is composed of 6 carbon atoms in a ring, with 1 hydrogen atom attached to each carbon atom, with the molecular formula C6H6....
. It is sparingly soluble in water.
Preparation
Phenylhydrazine is prepared by oxidizing anilineAniline
Aniline, phenylamine or aminobenzene is an organic compound with the formula C6H5NH2. Consisting of a phenyl group attached to an amino group, aniline is the prototypical aromatic amine. Being a precursor to many industrial chemicals, its main use is in the manufacture of precursors to polyurethane...
with sodium nitrite
Sodium nitrite
Sodium nitrite is the inorganic compound with the chemical formula NaNO2. It is a white to slight yellowish crystalline powder that is very soluble in water and is hygroscopic...
in the presence of hydrogen chloride
Hydrogen chloride
The compound hydrogen chloride has the formula HCl. At room temperature, it is a colorless gas, which forms white fumes of hydrochloric acid upon contact with atmospheric humidity. Hydrogen chloride gas and hydrochloric acid are important in technology and industry...
to form the diazonium salt, which is subsequently reduced using sodium sulfite
Sodium sulfite
Sodium sulfite is a soluble sodium salt of sulfurous acid. It is a product of sulfur dioxide scrubbing, a part of the flue gas desulfurization process...
in the presence of sodium hydroxide to form the final product.
History
Phenylhydrazine was the first hydrazineHydrazine
Hydrazine is an inorganic compound with the formula N2H4. It is a colourless flammable liquid with an ammonia-like odor. Hydrazine is highly toxic and dangerously unstable unless handled in solution. Approximately 260,000 tons are manufactured annually...
derivative characterized, reported by Emil Fischer
Emil Fischer
Emil Fischer may refer to:* Emil Fischer , German dramatic basso* Franz Joseph Emil Fischer , German chemist, worked with oil and coal* Hermann Emil Fischer , German Nobel laureate in chemistry...
in 1875. He prepared it by reduction of a phenyl diazonium salt using sulfite
Sulfite
Sulfites are compounds that contain the sulfite ion SO. The sulfite ion is the conjugate base of bisulfite. Although the acid itself is elusive, its salts are widely used.-Structure:...
salts. Fischer used phenylhydrazine to characterize sugar
Sugar
Sugar is a class of edible crystalline carbohydrates, mainly sucrose, lactose, and fructose, characterized by a sweet flavor.Sucrose in its refined form primarily comes from sugar cane and sugar beet...
s via formation of hydrazone
Hydrazone
Hydrazones are a class of organic compounds with the structure R1R2C=NNH2. They are related to ketones and aldehydes by the replacement of the oxygen with the NNH2 functional group...
s with the sugar aldehyde
Aldehyde
An aldehyde is an organic compound containing a formyl group. This functional group, with the structure R-CHO, consists of a carbonyl center bonded to hydrogen and an R group....
. He also demonstrated in this first paper many of the key properties recognized for hydrazines.
Uses
Phenylhydrazine is used in preparation of indoleIndole
Indole is an aromatic heterocyclic organic compound. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. Indole is a popular component of fragrances and the precursor to many pharmaceuticals. Compounds that contain an...
s which are intermediates in the synthesis of various dyes and pharmaceuticals.
Phenylhydrazine is used to form phenylhydrazones of natural mixtures of simple sugar
Sugar
Sugar is a class of edible crystalline carbohydrates, mainly sucrose, lactose, and fructose, characterized by a sweet flavor.Sucrose in its refined form primarily comes from sugar cane and sugar beet...
s in order to render the differing sugars easily separable from each other.
The compound is also used to induce acute hemolytic anemia in studies examining the hematopoietic system.
Safety
Exposure to phenylhydrazine may cause contact dermatitisContact dermatitis
Contact dermatitis is a term for a skin reaction resulting from exposure to allergens or irritants . Phototoxic dermatitis occurs when the allergen or irritant is activated by sunlight....
, hemolytic anemia
Hemolytic anemia
Hemolytic anemia is a form of anemia due to hemolysis, the abnormal breakdown of red blood cells , either in the blood vessels or elsewhere in the human body . It has numerous possible causes, ranging from relatively harmless to life-threatening...
, and liver and kidney injury.