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Buy Mandelonitrile | Sarchem Labs USA
CAS: 532-28-5
SKU: S2073
Buy Mandelonitrile | Sarchem Labs USA | SKU: S2073
synonyms: Benzaldehyde cyanohydrin; Mandelic acid nitrile; DL-Mandelonitrile; 2-Hydroxy-2-phenylacetonitrile; α-Hydroxybenzeneacetonitrile
Buy Mandelonitrile | Sarchem Labs USA
Mandelonitrile (benzaldehyde cyanohydrin, 2-hydroxy-2-phenylacetonitrile) is the cyanohydrin of benzaldehyde, C6H5CH(OH)CN (C8H7NO, molecular weight 133.15 g/mol). It is a yellow to brown liquid at room temperature that melts near −10 °C, boils at about 170 °C at 1013 hPa, has a density of 1.121–1.127 g/mL at 20 °C and a closed-cup flash point of 97 °C. The Merck “for synthesis” reference grade is specified at ≥95.0% by argentometric titration. Mandelonitrile has a special place in chemistry and biochemistry. It is the aglycone of the cyanogenic glycosides prunasin and amygdalin found in bitter almonds and stone-fruit kernels, and enzymes called hydroxynitrile lyases (HNLs) split it into benzaldehyde and hydrogen cyanide or, in reverse, build (R)-mandelonitrile from benzaldehyde and cyanide. Industrially it is the precursor of mandelic acid: nitrilase enzymes convert racemic mandelonitrile to (R)-mandelic acid in multi-ton biocatalytic processes, and the same chemistry applied to the ortho-chloro analogue supplies a building block for the antithrombotic clopidogrel. (R)-Mandelic acid is in turn an intermediate in antibiotic, antiobesity and anticancer drug syntheses and a resolving agent for chiral alcohols and amines. Mandelonitrile is acutely toxic by every route of exposure and can release hydrogen cyanide on decomposition, so it is intended for trained users who have cyanide-specific safety procedures in place. Sarchem Labs lists mandelonitrile (SKU S2073) with a Certificate of Analysis and Safety Data Sheet for each lot and can quote laboratory to bulk quantities on request.
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Specifications

Boiling Point102°C
Melting Point−10°C
Density1.121–1.127 g/mL at 20°C
Flash Point97°C (206.6°F), closed cup
ColorYellow to brown
Linear FormulaC6H5CH(OH)CN
Formula Weight133.15
Physical FormClear Liquid at 20°C
Chemical Name or MaterialMandelonitrile (DL-mandelic acid nitrile)
UN Number3276
Molecular Weight133.15 g/mol
SMILES StringOC(C#N)c1ccccc1
Assay≥95.0% (argentometric)
CAS Number532-28-5
EC Number208-532-7
NACRESNA.22
UNSPSC Code12352117
MDL NumberMFCD00004487
InChI1S/C8H7NO/c9-6-8(10)7-4-2-1-3-5-7/h1-5,8,10H
InChI KeyNNICRUQPODTGRU-UHFFFAOYSA-N
PubChem CID10758
FormLiquid
Empirical Formula (Hill Notation)C8H7NO
Identity (IR)IR: passes test

Applications

No Application Found
Clopidogrel-related biocatalysis: mandelonitrile and its ortho-chloro analogue are the benchmark substrates in nitrilase and hydroxynitrile-lyase process development for the (R)-2-chloromandelic acid used to make (S)-clopidogrel.
Hydroxynitrile-lyase and nitrile-enzyme research: the standard substrate for HNLs, which cleave it to benzaldehyde and cyanide or form (R)-mandelonitrile in reverse, and for screening nitrilases, nitrile hydratases and amidases.
Plant and natural-product biochemistry: the aglycone of prunasin and amygdalin, used as a reference compound in cyanogenesis studies in bitter almonds, stone fruits and cyanogenic millipedes.
Organic synthesis: a masked benzaldehyde–cyanide pair and a precursor to α-hydroxy acids and esters by hydrolysis or the Pinner reaction and to 2-amino-1-phenylethanol by reduction of the nitrile.

Product Description

What is Mandelonitrile?

Mandelonitrile forms by addition of cyanide to the carbonyl group of benzaldehyde: the product carries a hydroxyl group and a nitrile on the same benzylic carbon, which is a stereocentre. The material described here is the racemic (DL) mixture; the (R)-enantiomer has its own CAS number. Because cyanohydrin formation is reversible, mandelonitrile is in equilibrium with benzaldehyde and hydrogen cyanide, and decomposition is favoured by bases and by heat. That is why it must be treated as a cyanide-releasing hazard as well as an acutely toxic nitrile.

Uses of Mandelonitrile

Mandelonitrile is mainly a biocatalysis and fine-chemical intermediate. Enzymatic processes that start from racemic mandelonitrile and give (R)-mandelic acid have been operated at multi-ton scale, and (R)-mandelic acid feeds the synthesis of antibiotics, antiobesity agents and anticancer drugs and is used to resolve racemic alcohols and amines. The ortho-chloro analogue follows the same route to an intermediate of the antithrombotic (S)-clopidogrel.

In research, mandelonitrile is the textbook substrate for hydroxynitrile lyases, enzymes that plants, ferns and some millipedes use for cyanide-based chemical defence, and it is the reference compound in studies of the cyanogenic glycosides prunasin and amygdalin.

Buying and Handling Considerations

Order only if your site can handle acutely toxic, cyanide-releasing liquids. Keep the container tightly closed in a cool, well-ventilated, locked area away from bases, strong oxidisers and strong acids, since decomposition can liberate hydrogen cyanide. Check the assay on the Certificate of Analysis, because the equilibrium with benzaldehyde and cyanide means purity can change on storage. Work only in a fume hood, wear chemical-resistant gloves, eye and face protection and protective clothing, and make sure your site’s cyanide emergency and first-aid procedures are in place. Transport follows UN 3276 (nitriles, toxic, liquid, n.o.s.).

Safety Information

Based on Sigma-Aldrich/Merck’s verified classification (819016).

  • Pictograms / Signal Word: GHS06 (skull and crossbones), GHS05 (corrosion) | Danger
  • Hazard Statements: H301 + H311 + H331 (toxic if swallowed, in contact with skin or if inhaled), H318 (causes serious eye damage)
  • Hazard Classification: Acute Tox. 3 Oral, Acute Tox. 3 Dermal, Acute Tox. 3 Inhalation, Eye Dam. 1
  • Precautionary Statements: P261, P280, P301 + P310, P302 + P352 + P312, P304 + P340 + P311, P305 + P351 + P338
  • Storage Class: 6.1C – Combustible acute toxic Cat. 3 / toxic compounds or compounds which cause chronic effects | WGK: 3 | Flash Point: 97°C (206.6°F), closed cup
  • Transport: UN 3276 (nitriles, toxic, liquid, n.o.s.)

May release hydrogen cyanide on decomposition. Avoid all contact and inhalation, keep away from bases and heat, and call a poison centre or doctor immediately after any exposure.

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FAQs: Buy Mandelonitrile

It is used as a precursor of mandelic acid and (R)-mandelic acid, as the benchmark substrate for hydroxynitrile lyases and nitrilases in biocatalysis, as a reference compound in cyanogenic-glycoside research (prunasin, amygdalin), and as a cyanohydrin building block in organic synthesis.

Yes. Mandelonitrile, benzaldehyde cyanohydrin, mandelic acid nitrile and 2-hydroxy-2-phenylacetonitrile are the same compound, CAS 532-28-5, formula C8H7NO.

It can. As a cyanohydrin it is in equilibrium with benzaldehyde and hydrogen cyanide, and decomposition is favoured by bases and heat. Handle it only in a fume hood and follow cyanide-specific safety procedures.

The formula is C8H7NO and the molecular weight is 133.15 g/mol. The liquid has a density of 1.121–1.127 g/mL at 20 °C and a closed-cup flash point of 97 °C, and it melts near −10 °C.

Sigma-Aldrich/Merck classifies it as toxic if swallowed, in contact with skin or if inhaled (H301 + H311 + H331) and as causing serious eye damage (H318). The oral LD50 in rats is 116 mg/kg.

Store it tightly closed, locked up, in a cool and well-ventilated place away from bases, strong oxidisers and strong acids. It ships as UN 3276, nitriles, toxic, liquid, n.o.s.

Yes. Each lot of SKU S2073 ships with a Certificate of Analysis and Safety Data Sheet, and Sarchem Labs quotes laboratory to bulk quantities.