532-28-5 Usage
Occurrence
Mandelonitrile, is a yellow, oily liquid, insoluble in water, but soluble in alcohol and diethyl ether. Mandelonitrile is a component of the glycoside amygdalin, a precursor of laetrile found in the leaves and seeds on most Prunus species (plum, peach, apricot, etc). In 1832, mandelonitrile was the first cyanohydrin to be synthesized. It is commercially prepared from benzaldehyde and hydrogen cyanide. Mandelonitrile is used by certain insects (tiger beetles, an African millipede) as a defense fluid. After expelling the fluid an enzyme catalyzes the conversion of mandelonitrile to benzaldehyde and HCN, which is usually fatal to the insect’s enemy.
Uses
Mandelonitrile has been used to extract mandeloamide by the nitrilase variants.
Definition
ChEBI: A cyanohydrin that is phenylacetonitrile in which one of the methylene hydrogens is replaced by a hydroxy group.
General Description
Reddish-brown to dark red-brown liquid.
Air & Water Reactions
Mandelonitrile is sensitive to moisture. . Insoluble in water.
Reactivity Profile
Nitriles, such as Mandelonitrile, may polymerize in the presence of metals and some metal compounds. They are incompatible with acids; mixing nitriles with strong oxidizing acids can lead to extremely violent reactions. Nitriles are generally incompatible with other oxidizing agents such as peroxides and epoxides. The combination of bases and nitriles can produce hydrogen cyanide. Nitriles are hydrolyzed in both aqueous acid and base to give carboxylic acids (or salts of carboxylic acids). These reactions generate heat. Peroxides convert nitriles to amides. Nitriles can react vigorously with reducing agents. Acetonitrile and propionitrile are soluble in water, but nitriles higher than propionitrile have low aqueous solubility. They are also insoluble in aqueous acids.
Health Hazard
TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.
Fire Hazard
Mandelonitrile is combustible.
Safety Profile
Poison by intravenous
and subcutaneous routes. Mutation data
reported. A severe eye irritant. When heated
to decomposition it emits toxic fumes of
NOx and CN-. See also NITRILES.
Check Digit Verification of cas no
The CAS Registry Mumber 532-28-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,3 and 2 respectively; the second part has 2 digits, 2 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 532-28:
(5*5)+(4*3)+(3*2)+(2*2)+(1*8)=55
55 % 10 = 5
So 532-28-5 is a valid CAS Registry Number.
InChI:InChI=1/C8H7NO/c9-6-8(10)7-4-2-1-3-5-7/h1-5,8,10H/t8-/m1/s1
532-28-5Relevant articles and documents
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Walker,Krieble
, p. 1371 (1909)
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Determination of the time course of an enzymatic reaction by 1H NMR spectroscopy: Hydroxynitrile lyase catalysed transhydrocyanation
Hickel,Gradnig,Griengl,Schall,Sterk
, p. 93 - 96 (1996)
The time course of the enzyme catalysed transhydrocyanation of benzaldehyde to give (S)-mandelonitrile was investigated using a hydroxynitrile lyase from Hevea brasiliensis as catalyst and acetone cyanohydrin as cyanide donor. Employing special techniques it was possible to apply 1H NMR spectroscopy in aqueous medium to monitor the concentration changes of all substrates and products. By this technique strong evidence for inhibition of the enzyme at higher substrate concentrations was obtained.
CO2-Enabled Cyanohydrin Synthesis and Facile Iterative Homologation Reactions**
Juhl, Martin,Petersen, Allan R.,Lee, Ji-Woong
supporting information, p. 228 - 232 (2020/11/30)
Thermodynamic and kinetic control of a chemical process is the key to access desired products and states. Changes are made when a desired product is not accessible; one may manipulate the reaction with additional reagents, catalysts and/or protecting groups. Here we report the use of carbon dioxide to accelerate cyanohydrin synthesis under neutral conditions with an insoluble cyanide source (KCN) without generating toxic HCN. Under inert atmosphere, the reaction is essentially not operative due to the unfavored equilibrium. The utility of CO2-mediated selective cyanohydrin synthesis was further showcased by broadening Kiliani–Fischer synthesis under neutral conditions. This protocol offers an easy access to a variety of polyols, cyanohydrins, linear alkylnitriles, by simply starting from alkyl- and arylaldehydes, KCN and an atmospheric pressure of CO2.
CO2-Mediated Non-Destructive Cyanide Wastewater Treatment
Juhl, Martin,Lee, Ji-Woong,Petersen, Allan R.,Petrovic, Aleksa
supporting information, p. 5003 - 5007 (2021/09/30)
The facile removal of cyanide anions from cyanide-containing water was achieved using CO2 in conjunction with aldehydes which can be recycled from the process. The conversion of the cyanide ion into an insoluble cyanohydrin in water allowed the removal of cyanide and could be used as a method for treating cyanide contaminated wastewater and for recovering cyanide or cyanohydrins for further applications.
T:Toxic;
