(R)-1-Hydroxy-1-phenylacetone

Base Information

• Chemical Name: (R)-1-Hydroxy-1-phenylacetone
• CAS No.: 1798-60-3
• Molecular Formula: C9H10O2
• Molecular Weight: 150.177
• Hs Code.: 2914400090
• European Community (EC) Number: 217-285-4
• UNII: 7V3493I8FQ
• DSSTox Substance ID: DTXSID601313240
• Nikkaji Number: J53.527C
• Wikidata: Q27268887
• Mol file: 1798-60-3.mol

Synonyms:1798-60-3;(R)-1-Hydroxy-1-phenylacetone;(r)-phenylacetylcarbinol;(1R)-1-hydroxy-1-phenylpropan-2-one;Phenylacetylcarbinol, (-)-;(R)-PAC;(R)-1-Hydroxy-1-phenyl-2-propanone;(R)-1-Hydroxy-1-phenylpropan-2-one;L-PAC;(-)-phenylacetylcarbinol;UNII-7V3493I8FQ;(r)-1-hydroxy-1-phenylpropanone;7V3493I8FQ;EINECS 217-285-4;(1R)-1-Hydroxy-1-phenyl-2-propanone;EC 217-285-4;l-phenylacetylcarbinol;rel-(1R)-1-hydroxy-1-phenylpropan-2-one;R-PAC;(R)-Acetylphenylcarbinol;(1r)-phenylacetylcarbinol;SCHEMBL890219;(r)-(-)-phenylacetylcarbinol;CHEBI:149671;ZBFFNPODXBJBPW-VIFPVBQESA-N;DTXSID601313240;D-(-)-PHENYLACETYLCARBINOL;MFCD22414394;AKOS027384464;D-(-)-1-HYDROXY-1-PHENYLPROPANONE;2-Propanone, 1-hydroxy-1-phenyl-, (1R)-;(1R)-1-PHENYL-1-HYDROXYPROPAN-2-ONE;D-(-)-1-PHENYL-1-HYDROXY-2-PROPANONE;EN300-1268487;EN300-6735033;(-)-(1R)-1-HYDROXY-1-PHENYL-2-PROPANONE;(-)-(1R)-1-HYDROXY-1-PHENYLPROPAN-2-ONE;.ALPHA.-ACETYLBENZYL ALCOHOL [USP IMPURITY];Q27268887;EPHEDRINE HYDROCHLORIDE IMPURITY A [EP IMPURITY]

Chemical Property of (R)-1-Hydroxy-1-phenylacetone

Chemical Property:

• Vapor Pressure: 0.01mmHg at 25°C
• Refractive Index: 1.539
• Boiling Point: 253.343 °C at 760 mmHg
• PKA: 12.33±0.20(Predicted)
• Flash Point: 104.584 °C
• PSA: 37.30000
• Density: 1.12 g/cm³
• LogP: 1.30900
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Ethanol (Sparingly), Ethyl Acetate (Slightly), Methanol (
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 150.068079557
• Heavy Atom Count: 11
• Complexity: 137

Purity/Quality:

99.9% ^*data from raw suppliers

(R)-1-Hydroxy-1-phenylpropanone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C(C1=CC=CC=C1)O
• Isomeric SMILES: CC(=O)[C@@H](C1=CC=CC=C1)O
• Uses: (R)-1-Hydroxy-1-phenylpropanone is used as a reagent in the preparation of chiral (amino)alkanol derivatives and determination of their activity as antibacterial agents and antifungal agents. It is also an intermediate used in the synthesis of Pseudoephedrine and Ephedrine.

Technology Process of (R)-1-Hydroxy-1-phenylacetone

There total 60 articles about (R)-1-Hydroxy-1-phenylacetone 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: 80.6%

benzaldehyde (100-52-7) + 2-oxo-propionic acid (127-17-3) → (R)-1-hydroxy-1-phenyl-2-propanone (1798-60-3)

Guidance literature:

With glutathione S-transferase fused with Escherichia coli acetohydroxy acid synthase I; thiamine pyrophosphate; magnesium chloride; D,L-dithiothreitol; In aq. phosphate buffer; dimethyl sulfoxide; at 30 ℃; for 1.33333h; pH=7; pH-value; Temperature; Solvent; enantioselective reaction; Catalytic behavior; Enzymatic reaction;

DOI:10.1039/c7ra04641c

Reference yield: 62.0%

sodium pyruvate (113-24-6) + benzaldehyde (100-52-7) → (R)-1-hydroxy-1-phenyl-2-propanone (1798-60-3)

Guidance literature:

With thiamine diphosphate; In phosphate buffer; at 30 ℃; pH=6.0;

DOI:10.1016/j.bioorg.2006.09.006

Reference yield: 46.0%

1-Phenylpropane-1,2-dione (579-07-7) → (1R,2S)-1-phenylpropane-1,2-diol (40421-52-1) + (R)-1-hydroxy-1-phenyl-2-propanone (1798-60-3) + (S)-2-hydroxypropiophenone (5650-40-8,65646-06-2,91840-95-8,65646-07-3)

Guidance literature:

With baker'syeast; In water; at 5 ℃; for 9h;

upstream raw materials:

acetylphosphoric acid

benzaldehyde

2-oxo-propionic acid

Sucrose

Downstream raw materials:

2-(ethylamino)-1-phenyl-1-propanol

(R)-1-methoxy-1-phenyl-acetone

u-2-amino-1-phenylpropan-1-ol

(RS)-1-hydroxy-1-phenylpropan-2-one

Refernces

• 1、 Urbina, Claudia,Campos, Cristian,Pecchi, Gina,Claver, Carmen,Reyes, Patricio. "Chiral Pt/ZrO2 catalysts. enantioselective hydrogenation of 1-phenyl-1,2-propanedione". . p. 3428 - 3440. Retrieved 2010.
• 2、 Campos, Cristian H.,Torres, Cecilia,Fierro, José L.G.,Reyes, Patricio. "Enantioselective hydrogenation of 1-phenyl-1,2-propanedione over Pt on immobilized cinchonidine on γ-Al2O3 catalysts". . p. 198 - 207. Retrieved 2013.
• 3、 Campos, Cristian H.,Torres, Cecilia C.,Dongil, Ana B.,Ruiz, Doris,Fierro, José L.G.,Reyes, Patricio. "Enantioselective hydrogenation of 1-phenyl-1,2-propanedione on immobilised cinchonidine-TiO2 catalysts". . p. 226 - 236. Retrieved 2014.
• 4、 Campos, Cristian H.,Oportus, Marcelo,Torres, Cecilia,Urbina, Claudia,Fierro, José L.G.,Reyes, Patricio. "Enantioselective hydrogenation of 1-phenyl-propane-1,2-dione on immobilised cinchonidine Pt/SiO2 catalysts". . p. 30 - 41. Retrieved 2011.
• 5、 Gocke, Doerte,Nguyen, Cong Luan,Pohl, Martina,Stillger, Thomas,Walter, Lydia,Mueller, Michael. "Branched-chain keto acid decarboxylase from Lactococcus lactis (KdcA), a valuable thiamine diphosphate-dependent enzyme for asymmetric C - C bond formation". . p. 1425 - 1435. Retrieved 2007.
• 6、 Toukoniitty, Esa,Nieminen, Ville,Taskinen, Antti,Paeivaerinta, Juha,Hotokka, Matti,Murzin, Dmitry Yu.. "A combined experimental and theoretical study of 1-phenylpropane-1,2-dione hydrogenation over heterogeneous cinchonidine-modified Pt catalyst". . p. 326 - 339. Retrieved 2004.
• 7、 Maurer, Dirk,Enugala, Thilak Reddy,Hamnevik, Emil,Bauer, Paul,Lüking, Malin,Petrovi?, Du?an,Hillier, Heidi,Kamerlin, Shina C. L.,Dobritzsch, Doreen,Widersten, Mikael. "Stereo- and Regioselectivity in Catalyzed Transformation of a 1,2-Disubstituted Vicinal Diol and the Corresponding Diketone by Wild Type and Laboratory Evolved Alcohol Dehydrogenases". . p. 7526 - 7538. Retrieved 2018.
• 8、 Davis, Franklin A.,Sheppard, Aurelia C.,Lal, G. Sankar. "INFLUENCE OF ENOLATE GEOMETRY AND STRUCTURE ON THE STEREOCHEMISTRY OF THE ASYMMETRIC OXIDATION OF PROCHIRAL KETONE ENOLATES TO OPTICALLY ACTIVE α-HYDROXY KETONES". . p. 779 - 782. Retrieved 1989.
• 9、 Campos, Cristian H.,Torres, Cecilia C.,Osorio-Vargas, Paula,Mella, Claudio,Belmar, Julio,Ruiz, Doris,Fierro, José L.G.,Reyes, Patricio. "Immobilised chiral inducer on Pt-based mesoporous titanate nanotubes as heterogeneous catalysts for enantioselective hydrogenation". . p. 190 - 202. Retrieved 2015.
• 10、 Kren, Vladimir,Crout, David H. G.,Dalton, Howard,Hutchinson, David W.,Koenig, Wilfred,et al.. "Pyruvate Decarboxylase: a New Enzyme for the Production of Acyloins by Biotransformation". . p. 341 - 343. Retrieved 1993.