(R)-mandelonitrile

Base Information

• Chemical Name: (R)-mandelonitrile
• CAS No.: 10020-96-9
• Molecular Formula: C8H7NO
• Molecular Weight: 133.15
• Hs Code.: 29269090
• European Community (EC) Number: 624-802-0
• UNII: B46TK780ZC
• DSSTox Substance ID: DTXSID50429525
• Nikkaji Number: J74.252J
• Wikidata: Q27109028
• Metabolomics Workbench ID: 53633
• Mol file: 10020-96-9.mol

Synonyms:10020-96-9;(R)-2-Hydroxy-2-phenylacetonitrile;(R)-mandelonitrile;(R)-(+)-mandelonitrile;(+)-mandelonitrile;d-mandelonitrile;Mandelonitrile, (+)-;Mandelonitrile D-form [MI];(2R)-2-hydroxy-2-phenylacetonitrile;Benzeneacetonitrile, alpha-hydroxy-, (alphaR)-;(R)-Hydroxy(phenyl)acetonitrile;(2R)-hydroxy(phenyl)acetonitrile;(+)-alpha-Mandelonitrile;UNII-B46TK780ZC;B46TK780ZC;(2r)-Hydroxy(Phenyl)ethanenitrile;MFCD01320485;Benzeneacetonitrile, a-hydroxy-, (aR)-;(R)-(+)-alpha-Hydroxybenzeneacetonitrile;(+)-(alphaR)-alpha-Hydroxybenzeneacetonitrile;(R)-(+)-ALPHA-HYDROXYBENZENE-ACETONITRILE;(2R)-2-Hydroxy-2-phenyl-acetonitrile;MXN;MANDELONITRILE, D-;SCHEMBL6061809;CHEBI:18450;DTXSID50429525;NNICRUQPODTGRU-QMMMGPOBSA-N;(R)-(+)-Mandelonitrile, 97%;(+)-.ALPHA.-MANDELONITRILE;(R)-(+)-alpha-cyanobenzyl alcohol;AKOS016842280;C00561;A897547;J-000064;Q27109028;(+)-(.ALPHA.R)-.ALPHA.-HYDROXYBENZENEACETONITRILE;BENZENEACETONITRILE, .ALPHA.-HYDROXY-, (.ALPHA.R)-

Chemical Property of (R)-mandelonitrile

Chemical Property:

• Vapor Pressure: 0.002mmHg at 25°C
• Melting Point: 28-30 °C(lit.)
• Refractive Index: n20/D 1.532(lit.)
• Boiling Point: 282.696 °C at 760 mmHg
• PKA: 10.50±0.20(Predicted)
• Flash Point: 97.222 °C
• PSA: 44.02000
• Density: 1.169 g/cm³
• LogP: 1.24358
• Storage Temp.: ?20°C
• Sensitive.: Moisture Sensitive
• Water Solubility.: Slightly soluble in water.
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 133.052763847
• Heavy Atom Count: 10
• Complexity: 141

Purity/Quality:

99% ^*data from raw suppliers

(R)-(+)-Mandelonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 23/24/25-36/37/38-41
• Safety Statements: 22-26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(C#N)O
• Isomeric SMILES: C1=CC=C(C=C1)[C@H](C#N)O
• Uses: It is a useful intermediate in the preparation of optically active α-hydroxyl carboxylic acids, α-hydroxyl aldehydes, α-hydroxy ketones, and 2-amino alcohols.

Technology Process of (R)-mandelonitrile

There total 59 articles about (R)-mandelonitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

hydrogen cyanide (74-90-8) + benzaldehyde (100-52-7) → (R)-Mandelonitrile (10020-96-9)

Guidance literature:

With (R)-oxynitrilase (almond meal); citric buffer pH 5.5; In ethyl acetate; at 4 ℃; for 48h; Product distribution; other aldehydes and methyl ketones, also in micro-aqueous phase, var temp. and solvents;

DOI:10.1016/S0957-4166(98)00177-3

Reference yield: 99.0%

trimethylsilyl cyanide (7677-24-9) + benzaldehyde (100-52-7) → (R)-Mandelonitrile (10020-96-9)

Guidance literature:

With 4 A molecular sieve; dimethylaluminum chloride; Triphenylphosphine oxide; (S)-3,3'-bis[(diethylamino)methyl]-2,2'-dihydroxy-1,1'-binaphthalene; In toluene; at -20 ℃; for 6h;

DOI:10.1021/ol0262338

Reference yield: 95.0%

(R)-2-phenyl-2-(trimethylsiloxy)acetonitrile (120443-82-5) → (R)-Mandelonitrile (10020-96-9)

Guidance literature:

With hydrogenchloride; In ethyl acetate; at 27 ℃;

DOI:10.1021/jo971868j

upstream raw materials:

hydrogen cyanide

benzaldehyde

amygdalin

vinyl acetate

Downstream raw materials:

(S)-α-(4-methoxyphenylacetoxy)benzeneacetonitrile

R-(-)-1-(4-chlorophenyl)-2-hydroxy-2-phenylethanone

(R)-2-(diethylphosphoryloxy)-2-phenylacetonitrile

(R)-cyano(phenyl)methyl acetate

Refernces

• 1、 Niemeyer, Jochen,Cloppenburg, Jeannine,Fr?hlich, Roland,Kehr, Gerald,Erker, Gerhard. "Salen-ligands based on a planar-chiral hydroxyferrocene moiety: Synthesis, coordination chemistry and use in asymmetric silylcyanation". . p. 1801 - 1812. Retrieved 2010.
• 2、 Jiang,Zhou,Hu,Li,Mi. "Asymmetric synthesis XXVII: Asymmetric catalytic trimethylsilylcyanation of aldehydes by novel Ti-chiral Schiff base complexes". . p. 2915 - 2916. Retrieved 1995.
• 3、 Iovel, Irina,Popelis, Yuris,Fleisher, Mendel,Lukevics, Edmunds. "Trimethylsilylcyanation of aromatic aldehydes catalyzed by Pybox-AlCl3 complex". . p. 1279 - 1285. Retrieved 1997.
• 4、 Rowlands, Gareth J.. "Chiral sulfoxide ligands in catalytic asymmetric cyanohydrin synthesis". . p. 236 - 240. Retrieved 2003.
• 5、 Purkarthofer, Thomas,Skranc, Wolfgang,Weber, Hansj?rg,Griengl, Herfried,Wubbolts, Marcel,Scholz, Gerald,P?chlauer, Peter. "One-pot chemoenzymatic synthesis of protected cyanohydrins". . p. 735 - 739. Retrieved 2004.
• 6、 Go, Mi-Ran,Kim, Hyeon-Jin,Yu, Jin,Choi, Soo-Jin. "Toxicity and Toxicokinetics of Amygdalin in Maesil (Prunus mume) Syrup: Protective Effect of Maesil against Amygdalin Toxicity". . p. 11432 - 11440. Retrieved 2018.
• 7、 Ribeiro, Sandra S.,De Oliveira, Julieta R.,Porto, Andre? L. M.. "Lipase-catalyzed kinetic resolution of (±)-mandelonitrile under conventional condition and microwave irradiation". . p. 1395 - 1399. Retrieved 2012.
• 8、 Abiko, Atsushi,Wang, Guo-Qiang. "A BMPD-yttrium isopropoxide complex: Highly efficient chiral Lewis acid catalyst for asymmetric silylcyanation". . p. 2264 - 2265. Retrieved 1996.
• 9、 Callant, Dominique,Stanssens, Dirk,Vries, Johannes G. de. "(S)-3,3-Dimethyl-1,2,4-butanetriol as Ligand for Titanium Catalysed Asymmetric Silylcyanation". . p. 185 - 188. Retrieved 1993.
• 10、 Zhu, Wenting,Wu, Xiao,He, Cheng,Duan, Chunying. "Proline adducts of metallo-organic, sextuply-stranded lanterns as homogeneous catalysts for asymmetric catalysis". . p. 10477 - 10481. Retrieved 2013.