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532-28-5

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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

532-28-5 Well-known Company Product Price

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  • (Code)Product description
  • CAS number
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  • Alfa Aesar

  • (L08698)  Mandelonitrile, tech. 80%   

  • 532-28-5

  • 25g

  • 238.0CNY

  • Detail
  • Alfa Aesar

  • (L08698)  Mandelonitrile, tech. 80%   

  • 532-28-5

  • 100g

  • 370.0CNY

  • Detail
  • Alfa Aesar

  • (L08698)  Mandelonitrile, tech. 80%   

  • 532-28-5

  • 500g

  • 1216.0CNY

  • Detail

532-28-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name mandelonitrile

1.2 Other means of identification

Product number -
Other names 2-hydroxy-2-phenylacetonitrile

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:532-28-5 SDS

532-28-5Relevant articles and documents

-

Walker,Krieble

, p. 1371 (1909)

-

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.

-

Auld

, p. 929 (1909)

-

High-yield DL-mandelic acid synthesis process

-

Paragraph 0021-0025, (2021/09/04)

The invention provides a high-yield DL-mandelic acid synthesis process. The synthesis process specifically comprises the following steps: 1, treating benzaldehyde by using sodium hydrogen sulfite to obtain benzaldehyde sodium hydrogen sulfite; 2, extracting the benzaldehyde sodium hydrogen sulfite by using an organic solvent, recovering unreacted benzaldehyde in the benzaldehyde sodium hydrogen sulfite, and adding sodium cyanide after the extraction is completed to prepare mandelonitrile; 3, adding an inorganic acid, and then carrying out heating and pressure maintaining treatment to hydrolyze the mandelonitrile so as to obtain mandelic acid; and 4, purifying the mandelic acid. According to the method, the step of extracting the p-benzaldehyde sodium hydrogen sulfite salt is added, so that the probability that the product purity is reduced due to benzoin condensation is reduced, the recycled benzaldehyde can be returned to the raw material for use, and the yield can be increased in multiple rounds of reactions; and the hydrolysis process of the mandelonitrile adopts heating and pressure maintaining treatment, so that consumption of inorganic acid can be reduced, and the hydrolysis efficiency is improved.

Designing of amino functionalized imprinted polymeric resin for enantio-separation of (±)-mandelic acid racemate

Alhawiti, Aliyah S.,Monier,Elsayed, Nadia H.

, (2021/02/12)

S-Mandelic acid (MA) enantio-selective resinous material functionalized with –NH2 groups has been developed and effectively utilized in chiral separation of (±)-MA racemate solution. S-MA has first combined with the polymerizable p-aminophenol and form the corresponding amide derivative, which was then polymerized with phenol/formalin using HCl as a catalyst. The stereo-selective –NH2 functionalized binding sites were then generated within the resin upon the alkaline degradation of the amide linkages followed by acidic treatments that will expel the resin incorporated S-MA out of the polymeric material to get the S-MA imprinted polymer (S-MAPR). The synthesized S-MA chiral amide derivative along with the developed polymeric resin was investigated by various techniques including FTIR and NMR spectra that confirmed the executed chemical modifications. In addition, the morphological appearance of the obtained resins were observed using SEM images. Moreover, the S-MAPR resin was examined to optimize the enantio-selective separation conditions and the studies indicated that the adsorption reached the highest value at pH 7 and the maximum capacity was 243 ± 1 mg/g. In addition, the chiral separation of (±)-MA racemic solution was successfully executed by the S-MAPR separation column with 55% and 82% enantiomeric excess of R- and S-MA within both the initial loading and recovery eluant solutions, respectively.

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