40560-98-3

Basic information

• Product Name: (1R,2S)-1-phenylpropane-1,2-diol
• Synonyms: 1,2-propanediol, 1-phenyl-, (1R,2S)-
• CAS NO: 40560-98-3
• Molecular Formula: C₉H₁₂O₂
• Molecular Weight: 152.1904
• Mol File: 40560-98-3.mol
• Article Data: 32

Chemical Properties

• Boiling Point: 294.611°C at 760 mmHg
• Flash Point: 144.021°C
• Density: 1.128g/cm³
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.558
• CAS DataBase Reference: (1R,2S)-1-phenylpropane-1,2-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2S)-1-phenylpropane-1,2-diol(40560-98-3)
• EPA Substance Registry System: (1R,2S)-1-phenylpropane-1,2-diol(40560-98-3)

Safety Data

• Hazardous Substances Data: 40560-98-3(Hazardous Substances Data)

Upstream product

• 40421-52-1 (1RS,2SR)-1-phenylpropane-1,2-diol 
• 14212-54-5 (+)-(R,R)-β-methylstyrene oxide 
• 766-90-5 cis-1-phenyl-1-propylene 
• 1855-09-0 1-phenyl-1,2-propandiol 
• 1798-60-3 (R)-1-hydroxy-1-phenyl-2-propanone 
• 98819-68-2 3-phenyl-(2R,3R)-oxiran-2-ylmethanol 
• 5650-40-8 (S)-2-hydroxypropiophenone 
• 37580-42-0 (E)-2-methyl-1-phenyl-1,3-butadiene 
• 1333259-97-4 (S,Z)-2-methyl-1-phenylbut-2-ene-1,4-diol 
• 827608-92-4 (S)-4,4,5,5-tetramethyl-2-(1-phenyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-en-2-yl)-1,3,2-dioxaborolane 
• 2327-99-3 1-phenylpropadiene 
• 873-66-5 1-propenylbenzene 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 100-52-7 benzaldehyde 

Downstream Products

• 132538-09-1 (1S,2R)-(-)-1-cyclohexyl-1,2-propanediol 
• 492-39-7 (1S,2S)-2-amino-1-phenylpropanol 
• 37577-07-4 Norpseudoephedrine 
• 37577-28-9 (1S,2R)-(+)-norphedrine 
• 40421-51-0 (1R,2R)-1-phenylpropane-1,2-diol 
• 40421-52-1 (1R,2S)-1-phenylpropane-1,2-diol 
• 1572-95-8 (R)-1-phenyl-propan-2-ol 
• 159992-91-3 2,2,4-trimethyl-5-phenyldioxolan 
• 159992-92-4 2,2,4-trimethyl-5-phenyldioxolan 
• 123485-24-5 (1R,2S)-1,2-diacetoxy-1-phenylpropane 
• 123485-26-7 (1S,2R)-1,2-diacetoxy-1-phenylpropane 
• 123485-25-6 (1R,2R)-1,2-diacetoxy-1-phenylpropane 
• 88196-06-9 (1S,2S)-1-phenyl-1,2-propanediol 

Relevant articles and documents

Regio- and stereoselective multi-enzymatic aminohydroxylation of β-methylstyrene using dioxygen, ammonia and formate

We report an enzymatic route for the formal regio- and stereoselective aminohydroxylation of β-methylstyrene that consumes only dioxygen, ammonia and formate; carbonate is the by-product. The biocascade entails highly selective epoxidation, hydrolysis and hydrogen-borrowing alcohol amination. Thus, β-methylstyrene was converted into 1R,2R and 1S,2R-phenylpropanolamine in 59-63% isolated yields, and up to >99.5 : 0.5 dr and er.

Highly Enantioselective Iron-Catalyzed cis-Dihydroxylation of Alkenes with Hydrogen Peroxide Oxidant via an FeIII-OOH Reactive Intermediate

The development of environmentally benign catalysts for highly enantioselective asymmetric cis-dihydroxylation (AD) of alkenes with broad substrate scope remains a challenge. By employing [FeII(L)(OTf)2] (L=N,N′-dimethyl-N,N′-bis(2-methyl-8-quinolyl)-cyclohexane-1,2-diamine) as a catalyst, cis-diols in up to 99.8 % ee with 85 % isolated yield have been achieved in AD of alkenes with H2O2as an oxidant and alkenes in a limiting amount. This “[FeII(L)(OTf)2]+H2O2” method is applicable to both (E)-alkenes and terminal alkenes (24 examples >80 % ee, up to 1 g scale). Mechanistic studies, including18O-labeling, UV/Vis, EPR, ESI-MS analyses, and DFT calculations lend evidence for the involvement of chiral FeIII-OOH active species in enantioselective formation of the two C?O bonds.

Stereoselective Two-Step Biocatalysis in Organic Solvent: Toward All Stereoisomers of a 1,2-Diol at High Product Concentrations

Biotransformations on larger scale are mostly limited to cases in which alternative chemical routes lack sufficient chemo-, regio-, or stereoselectivity. Here, we expand the applicability of biocatalysis by combining cheap whole cell catalysts with a microaqueous solvent system. Compared to aqueous systems, this permits manifoldly higher concentrations of hydrophobic substrates while maintaining stereoselectivity. We apply these methods to four different two-step reactions of carboligation and oxidoreduction to obtain 1-phenylpropane-1,2-diol (PPD), a versatile building block for pharmaceuticals, starting from inexpensive aldehyde substrates. By a modular combination of two carboligases and two alcohol dehydrogenases, all four stereoisomers of PPD can be produced in a flexible way. After thorough optimization of each two-step reaction, the resulting processes enabled up to 63 g L-1 product concentration (98% yield), space-time-yields up to 144 g L-1 d-1, and a target isomer content of at least 95%. Despite the use of whole cell catalysts, we did not observe any side product formation of note. In addition, we prove that, by using 1,5-pentandiol as a smart cosubstrate, a very advantageous cofactor regeneration system could be applied.