1075-04-3

Basic information

• Product Name: 1,2-Propanediol, 1-phenyl-, (1R,2S)-rel-
• CAS NO: 1075-04-3
• Molecular Formula: C9H12O2
• Molecular Weight: 152.193
• Mol File: 1075-04-3.mol
• Article Data: 13

Chemical Properties

• CAS DataBase Reference: 1,2-Propanediol, 1-phenyl-, (1R,2S)-rel-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Propanediol, 1-phenyl-, (1R,2S)-rel-(1075-04-3)
• EPA Substance Registry System: 1,2-Propanediol, 1-phenyl-, (1R,2S)-rel-(1075-04-3)

Safety Data

• Hazardous Substances Data: 1075-04-3(Hazardous Substances Data)

Usage

General Description

1,2-Propanediol, 1-phenyl-, (1R,2S)-rel- is a chemical compound with the molecular formula C9H12O2. It is a chiral molecule with a stereo center and is commonly referred to as (R,R)-tartaric acid. This chemical is often used as a chiral resolving agent in organic synthesis, as well as a component in the production of pharmaceuticals, fragrances, and flavors. It has been used as a resolving agent for amino acids, and it plays a role in the production of certain food additives and pharmaceuticals. Additionally, (R,R)-tartaric acid can be used as a chiral additive in electrochemical studies and as an agent for separating enantiomers in chromatography. Overall, it is a versatile chemical compound that has various applications in both the laboratory and industry.

Upstream product

• 93-54-9 1-Phenyl-1-propanol 
• 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 
• 98819-68-2 3-phenyl-(2R,3R)-oxiran-2-ylmethanol 
• 1798-60-3 (R)-1-hydroxy-1-phenyl-2-propanone 
• 676-58-4 methylmagnesium chloride 
• 4436-22-0 1-phenylpropylene oxide 
• 25438-37-3 phenyl(trimethylsiloxy)acetonitrile 
• 14212-54-5 (+)-(R,R)-β-methylstyrene oxide 
• 579-07-7 1-Phenylpropane-1,2-dione 
• 103687-21-4 ((CH₃)3C₆H₂)2BCHLiCH₃ 

Downstream Products

• 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 
• 88196-06-9 (1S,2S)-1-phenyl-1,2-propanediol 
• 40421-52-1 (1R,2S)-1-phenylpropane-1,2-diol 
• 40421-51-0 (1R,2R)-1-phenylpropane-1,2-diol 
• 123485-25-6 (1R,2R)-1,2-diacetoxy-1-phenylpropane 

Relevant articles and documents

Highly stereoselective syn-ring opening of enantiopure epoxides with nitric oxide

Reaction of enantiopure epoxides (1) with NO occurred highly stereoselectively, affording syn-ring opened products, nitrates (2). The configuration of 2 was confirmed to be retained by determining the configuration of reduced products 1,2-glycols (4) from 2. A possible mechanism is suggested to trace out the syn-ring opening pathway.

Stereospecific metabolic reduction of ketones

The stereospecificity of the metabolic reduction of arylalkylketones was investigated. The ketones, propiophenone (I), phenylacetone (III), and 1-phenyl-1,2-propanedione (V) were reduced in vitro and in vivo in rats and rabbits to the corresponding alcohols, 1-phenyl-1-propanol (II), 1-phenyl-2-propanol (IV), and 1-phenyl-1,2-propanediol (VIII), respectively. For the analysis, a capillary GLC method employing chiral derivatizing reagents for the resolution the these optically active alcohols were utilized. This study revealed that the metabolic reduction of each ketone produced the corresponding alcohol as a mixture of its enantiomers. With one exception, the mixtures obtained from all in vivo and in vitro reactions were shown to contain at least 70% of one isomer [S(-)-II,S(+)-IV, and erythro-VIII, respectively, with in vitro reduction showing the highest degree of stereospecificity (90-98%). The in vivo reduction of I by the rat was exceptional in that both optical isomers of II were recovered in equal proportions.

A sequential o-nitrosoaldol and grignard addition process: an enantio- and diastereoselective entry to chiral 1,2-diols

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Concatenated catalytic asymmetric allene diboration/allylation/ functionalization

(Chemical Equation Presented) Palladium-catalyzed enantioselective diboration of prochiral allenes generates a reactive chiral allylboron intermediate which is a versatile reagent for the allylation of carbonyls. Experiments that improve the enantioselectivity of this process, examine the substrate scope, and are directed toward functionalization of the allylation intermediate are described.