13093-65-7

Basic information

• Product Name: P-Hydroxymandelonitrile
• Synonyms: P-Hydroxymandelonitrile;(S)-2-(4-Hydroxyphenyl)-2-hydroxyacetonitrile;(S)-α,p-Dihydroxybenzeneacetonitrile;(αS)-α,4-Dihydroxybenzeneacetonitrile;DL-4-Hydroxymandelonitrile
• CAS NO: 13093-65-7
• Molecular Formula: C₈H₇NO₂
• Molecular Weight: 149.14668
• Mol File: 13093-65-7.mol
• Article Data: 11

Chemical Properties

• Melting Point: 96.0 to 99.0 °C
• Boiling Point: 366°Cat760mmHg
• Flash Point: 175.1°C
• Appearance: /
• Density: 1.327g/cm³
• Vapor Pressure: 5.32E-06mmHg at 25°C
• Refractive Index: 1.613
• Solubility: soluble in Methanol
• PKA: 9.35±0.26(Predicted)
• CAS DataBase Reference: P-Hydroxymandelonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: P-Hydroxymandelonitrile(13093-65-7)
• EPA Substance Registry System: P-Hydroxymandelonitrile(13093-65-7)

Safety Data

• Hazardous Substances Data: 13093-65-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H7NO2/c9-5-8(11)6-1-3-7(10)4-2-6/h1-4,8,10-11H/t8-/m1/s1

Upstream product

• 123-08-0 4-hydroxy-benzaldehyde 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 7677-24-9 trimethylsilyl cyanide 
• 74-90-8 hydrogen cyanide 
• 151-50-8 potassium cyanide 
• 613-90-1 benzoyl cyanide 

Downstream Products

• 93717-58-9 bis(4-hydroxyphenyl)-cyanomethane 
• 125237-25-4 p,p'-bis(α-cyano(4-hydroxyphenyl)methylhydrazinocarbonylmethoxy)diphenyl sulphone 
• 123-08-0 4-hydroxy-benzaldehyde 
• 92245-42-6 4.4'-Dihydroxy-diphenyl-acetamidin 
• 115353-16-7 (1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-ylamino)-(4-hydroxy-phenyl)-acetonitrile 

Relevant articles and documents

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Immobilized Baliospermum montanum hydroxynitrile lyase catalyzed synthesis of chiral cyanohydrins

Hydroxynitrile lyase (HNL) catalyzed enantioselective C–C bond formation is an efficient approach to synthesize chiral cyanohydrins which are important building blocks in the synthesis of a number of fine chemicals, agrochemicals and pharmaceuticals. Immobilization of HNL is known to provide robustness, reusability and in some cases also enhances activity and selectivity. We optimized the preparation of immobilization of Baliospermium montanum HNL (BmHNL) by cross linking enzyme aggregate (CLEA) method and characterized it by SEM. Optimization of biocatalytic parameters was performed to obtain highest % conversion and ee of (S)-mandelonitrile from benzaldehyde using CLEA-BmHNL. The optimized reaction parameters were: 20 min of reaction time, 7 U of CLEA-BmHNL, 1.2 mM substrate, and 300 mM citrate buffer pH 4.2, that synthesized (S)-mandelonitrile in ～99% ee and ～60% conversion. Addition of organic solvent in CLEA-BmHNL biocatalysis did not improve in % ee or conversion of product unlike other CLEA-HNLs. CLEA-BmHNL could be successfully reused for eight consecutive cycles without loss of conversion or product formation and five cycles with a little loss in enantioselectivity. Eleven different chiral cyanohydrins were synthesized under optimal biocatalytic conditions in up to 99% ee and 59% conversion, however the % conversion and ee varied for different products. CLEA-BmHNL has improved the enantioselectivity of (S)-mandelonitrile synthesis compared to the use of purified BmHNL. Nine aldehydes not tested earlier with BmHNL were converted into their corresponding (S)-cyanohydrins for the first time using CLEA-BmHNL. Among the eleven (S)-cyanohydrins syntheses reported here, eight of them have not been synthesized by any CLEA-HNL. Overall, this study showed preparation, characterization of a stable, robust and recyclable biocatalyst i.e. CLEA-BmHNL and its biocatalytic application in the synthesis of different (S)-aromatic cyanohydrins.

Application of crude preparations of leaves from food plants for the formation of cyanohydrins with high enantiomeric excesses

Crude preparations obtained from mamey (Pouteria sapota), capulin (Prunus serotina var. capulli) and peach (Prunus persica) leaves were used to catalyze the enantioselective addition of HCN to a variety of aldehydes. The corresponding cyanohydrins were obtained with high levels of enantioselectivity, comparable with those obtained with other catalysts used for the same purpose.