MANDELONITRILE

PRODUCT IDENTIFICATION
CAS NO. 532-28-5

MANDELONITRILE

EINECS NO. 208-532-7
FORMULA C6H5CH(OH)CN
MOL WT. 133.15
H.S. CODE  

TOXICITY

  
SYNONYMS alpha-Cyanobenzyl alcohol; Amygdalonitrile;
alpha-Hydroxybenzeneacetonitrile; alpha-Hydroxyphenylacetonitrile; Benzaldehyde cyanohydrin; Hydroxyphenylacetonitrile; Mandelic acid nitrile; Phenylglycolonitrile;

DERIVATION

 

CLASSIFICATION

 

PHYSICAL AND CHEMICAL PROPERTIES
PHYSICAL STATE yellow to brown liquid
MELTING POINT -10 C
BOILING POINT

170 C (Decomposes)

SPECIFIC GRAVITY

1.117

SOLUBILITY IN WATER Decomposes

SOLVENT SOLUBILITY

  
pH

 

VAPOR DENSITY  

AUTOIGNITION

 

REFRACTIVE INDEX

 1.5305 - 1.5335

NFPA RATINGS

 Health: 2; Flammability: 1; Instability: 0
FLASH POINT

97 C

STABILITY Stable under ordinary conditions. Moisture sensitive.

DESCRIPTION AND APPLICATIONS
Nitrile is an organic compounds containing cyano group (-C》N, containing trivalent nitrogen) which is attached to one carbon atom with the general formula RC》N. Their names are corresponding to carboxylic acids by changing '-ic acid' to the suffix, '-onitrile' which denotes only the 》N atom (triply bound) excluding the carbon atom attached to it, or  the suffix, '-carbonitrile' where the carbon atom in the -CN is included, whichever preserves a single letter O. Examples are acetonitrile from acetic acid and benzonitrile from benzoic acid. The prefix,  'cyano-' is used as an alternative naming system to indicate the presence of a nitrile group in a molecule for the compounds of salts and organic derivatives of hydrogen cyanide (HC》N). Isocyanides are salts and hydrocarbyl derivatives from the isomer, HN+》C-. Sodium cyanide, NaCN; potassium cyanide, KCN; calcium cyanide, Ca(CN)2; and hydrocyanic (or prussic) acid, HCN are examples. Chemically, the simple inorganic cyanides resemble chlorides in many ways. Organic nitriles act as solvents and are reacted further for various application including;

  · Extraction solvent for fatty acids, oils and unsaturated hydrocarbons
  · Solvent for spinning and casting and extractive distillation based on its     selective miscibility with organic compounds.
  · Removing agent of colouring matters and aromatic alcohols
  · Non-aqueous solvent for titrations and for inorganic salts
  · Recrystallization of steroids
  · Parent compound for organic synthesis
  · Solvent or chemical intermediate in biochemistry (protein sequencing and DNA synthesis)
  · High-pressure liquid chromatographic analysis
  · Catalyst and component of transition-metal complex catalysts
  · Stabilizer for chlorinated solvents
  · Chemical intermediate and solvent for perfumes and pharmaceuticals

Mandelonitrile is the cyanohydrin from benzaldehyde. Naturally occurring mandelonitrile is found in the millipede Apheloria corrugata as a defense mechanism. when Apheloria is about to be attacked, mandelonitrile decomposes enzymatically  into benzaldehyde and a poison (hydrogen cyanide). Aamygdalin is known as laetrile which has been used as an anti-cancer drug. But it is known that it does not kill cancerous cells selectively.

Mandelic Acid, phenylglycollic acid, is an alpha-hydroxy acid (AHA) which has a hydroxyl group on the carbon atom next to the acid group. If the hydroxy group is on the second carbon next to the acid group, it is called beta-hydroxy acid. Glycolic acid  is the simplest AHA which has dual functionality of alcohol and acid in a low mole weight structure. Because of its small molecular weight and size, it has a better capability to penetrate skin. AHA is used extensively in cosmetics. It is known that it diminishes the lines on the skin and make skins look young by acting as a humectant to absorb moisture in air and by exfoliating action to break the bonds between dead skin cells. Mandelic Acid ( alpha-hydroxybenzeneacetic acid) is the smallest AHA among compounds which have aromatic group. It has an asymmetric carbon atom and thus has two chiral isomers; the dextro-, levo-. The D- and L-mandelic acid are enantiomers (also called enantiomorph; each molecule is asymmetrical and has the mirror image of the other) affect pharmaceutical activity. It is a white crystalline compound; melting at 118 C; partially soluble in water; freely soluble in isopropyl and ethyl alcohol; darkening upon exposure to light. Its structure provide the bacteriostatic property. It is excreted well in the urine. It is used as a antiseptic ingredient particularly against urinary tract infections. Mandelic acid and its derivatives are used to apply the dual activities as an antibacterial agent and as an antiaging agent (AHA activity) similar to glycolic acid. It is used as an intermediate for the synthesis of target molecules for other applications. Naturally occurring mandelic acid is found when amygdalin (a cyanogenetic glycoside found in many plants including bitter almond, apricot, and wild cherry) is spirit by hydrolysis with hydrochloric acid, while amygdalin is broken down into glucose, benzaldehyde, and prussic acid (hydrogen cyanide) in the presence of sulfuric acid.
SALES SPECIFICATION

APPEARANCE

yellow to brown liquid

ASSAY (G.C)

95.0% min

INDIVIDUAL IMPURITY

1.0% max

TRANSPORTATION
PACKING  
HAZARD CLASS 6.1 (Packing group: I)
UN NO. 2810
OTHER INFORMATION
Hazard Symbols: T, Risk Phrases: 23/24/25, Safety Phrases: 24/25-45