532-28-5 Usage
Description
Benzeneacetonitrile, a-hydroxy-, also known as Mandelonitrile, is a reddish-brown to dark red-brown liquid. It is a cyanohydrin derivative of phenylacetonitrile, where one of the methylene hydrogens is replaced by a hydroxy group. Mandelonitrile is a component of the glycoside amygdalin, a precursor of laetrile found in the leaves and seeds of most Prunus species (plum, peach, apricot, etc). It was the first cyanohydrin to be synthesized in 1832 and is commercially prepared from benzaldehyde and hydrogen cyanide.
Uses
1. Used in Chemical Synthesis:
Benzeneacetonitrile, a-hydroxyis used as an intermediate in the synthesis of various organic compounds, particularly for the production of mandeloamide through the action of nitrilase variants.
2. Used in Natural Defense Mechanisms:
In the natural world, Benzeneacetonitrile, a-hydroxyis used by certain insects, such as tiger beetles and an African millipede, as a defense fluid. When these insects expel the fluid, an enzyme catalyzes the conversion of mandelonitrile to benzaldehyde and hydrogen cyanide (HCN), which is usually fatal to the insect's enemy.
3. Used in Pharmaceutical Applications:
Although not explicitly mentioned in the provided materials, Benzeneacetonitrile, a-hydroxycould potentially be used in the pharmaceutical industry as a starting material for the synthesis of various drugs, given its structural properties and reactivity.
4. Used in Extraction Processes:
Benzeneacetonitrile, a-hydroxycan be used in extraction processes to isolate specific compounds, such as mandeloamide, from complex mixtures due to its solubility in alcohol and diethyl ether.
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.
Valmet Chiral Schiff-Base Ligands And Their Copper(II) Complexes as Organo, Homogeneous and Heterogeneous Catalysts for Henry, Cyanosilylation and Aldol Coupling Reactions
Arora, Zinnia,Eftemie, Diana-Ioana,Spinciu, Adela,Maxim, C?t?lin,Hanganu, Ana-Maria,Tudorache, Madalina,Cojocaru, Bogdan,Pavel, Octavian D.,Granger, Pascal,Andruh, Marius,Parvulescu, Vasile I.
, p. 4634 - 4644 (2021/09/08)
Cyanosilylation, aldol coupling and asymmetric Henry reactions were carried out with L- and D-valmet ligands in different configurations: i) coordinated to sodium ions, as organocatalysts, with week base properties, ii) complexes with copper(II), as homogeneous catalysts, and iii) immobilized copper(II) complexes onto graphene oxide (GO) as heterogeneous catalysts. For the reaction of benzaldehyde and nitromethane in water these afforded an asymmetric Henry reaction, with a spectacular increase of the conversion and ee (92.5 and 95.8 %, respectively) after the deposition on GO. Ligand complexed copper was also effective for cyanosilylation and Aldol coupling reaction.
Constructing a triangular metallacycle with salen-Al and its application to a catalytic cyanosilylation reaction
Li, Bo,Li, Yang,Qiu, Huayu,Xu, Jun,Yin, Shouchun,Zhang, Jinjin,Zhang, Pengfei,Zhang, Yueyue
supporting information, p. 10399 - 10402 (2021/10/12)
A triangular metallosalen-based metallacycle was constructed in quantitative yield by the self-assembly of a 180° bis(pyridyl)salen-Al complex and a 60° diplatinum(ii) acceptor in a 1?:?1 stoichiometric ratio. This metallacycle was then successfully used to cyanosilylate a wide range of benzaldehydes with trimethylsilyl cyanide.