92418-71-8

Basic information

• Product Name: (2R,3R)-(+)-3-PROPYLOXIRANEMETHANOL, 97% (94% EE/GLC)
• Synonyms: (2R,3R)-(+)-3-PROPYLOXIRANEMETHANOL, 97% (94% EE/GLC);(2R,3R)-(+)-3-propyloxiranemethanol;Oxiranemethanol,3-propyl-,(2R,3R)-(9CI);propyloxiranemethanol
• CAS NO: 92418-71-8
• Molecular Formula: C₆H₁₂O₂
• Molecular Weight: 116.15828
• Product Categories: EPOXYDE
• Mol File: 92418-71-8.mol
• Article Data: 57

Chemical Properties

• Melting Point: 19 °C(lit.)
• Boiling Point: 31-33 °C0.35 mm Hg(lit.)
• Flash Point: 188 °F
• Appearance: /
• Density: 0.96 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.179mmHg at 25°C
• Refractive Index: n20/D 1.434(lit.)
• CAS DataBase Reference: (2R,3R)-(+)-3-PROPYLOXIRANEMETHANOL, 97% (94% EE/GLC)(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R)-(+)-3-PROPYLOXIRANEMETHANOL, 97% (94% EE/GLC)(92418-71-8)
• EPA Substance Registry System: (2R,3R)-(+)-3-PROPYLOXIRANEMETHANOL, 97% (94% EE/GLC)(92418-71-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 92418-71-8(Hazardous Substances Data)

Usage

Description

(2R,3R)-(+)-3-PROPYLOXIRANEMETHANOL, 97% (94% EE/GLC) is a chiral chemical compound with a high purity level of 97% and an enantiomeric excess of 94%. It has two stereocenters with the (2R,3R) configuration, indicating the absolute configuration of the molecule. (2R,3R)-(+)-3-PROPYLOXIRANEMETHANOL, 97% (94% EE/GLC) features a propyloxirane functional group, making it versatile for use in various organic synthesis processes.

Uses

Used in Organic Synthesis:
(2R,3R)-(+)-3-PROPYLOXIRANEMETHANOL, 97% (94% EE/GLC) is used as a chiral building block in organic synthesis for the creation of complex organic molecules. Its high purity and enantiomeric excess make it suitable for enantioselective reactions where the stereochemistry of the compound is crucial for the desired outcome.
Used in Asymmetric Synthesis:
(2R,3R)-(+)-3-PROPYLOXIRANEMETHANOL, 97% (94% EE/GLC) is used as a reagent in asymmetric synthesis, a technique that allows for the selective formation of one enantiomer over another. The high enantiomeric excess and GLC purity of the compound contribute to the success of these reactions, enabling the production of enantiomerically pure products.
Used in Pharmaceutical Industry:
(2R,3R)-(+)-3-PROPYLOXIRANEMETHANOL, 97% (94% EE/GLC) is used as an intermediate in the synthesis of pharmaceutical compounds. Its chiral nature and high purity make it an ideal candidate for the development of enantiomerically pure drugs, which can have significant implications for the efficacy and safety of medications.
Used in Agrochemical Industry:
(2R,3R)-(+)-3-PROPYLOXIRANEMETHANOL, 97% (94% EE/GLC) is used as a building block in the synthesis of agrochemicals, such as pesticides and herbicides. (2R,3R)-(+)-3-PROPYLOXIRANEMETHANOL, 97% (94% EE/GLC)'s chiral properties allow for the development of enantiomerically pure active ingredients, which can improve the effectiveness and reduce the environmental impact of these chemicals.
Used in Fragrance Industry:
(2R,3R)-(+)-3-PROPYLOXIRANEMETHANOL, 97% (94% EE/GLC) is used as a starting material in the synthesis of chiral fragrances and flavor compounds. The high purity and enantiomeric excess of the compound ensure that the resulting products have the desired scent and taste profiles, contributing to the overall quality of the final products.

InChI:InChI=1/C6H12O2/c1-2-3-5-6(4-7)8-5/h5-7H,2-4H2,1H3/t5-,6-/m1/s1

Upstream product

• 928-95-0 (E)-2-Hexen-1-ol 
• 139164-92-4 (3R)-1-hexen-3-ol 
• 113566-32-8 (2S,3R)-3-Chlorotridecane-1,2-diol 
• 475056-69-0 (2S,3R)-3-propyloxirane-2-carbaldehyde 
• 6728-26-3 (E)-2-Hexenal 
• 113524-86-0 ethyl 3-chloro-2-oxotridecanoate 
• 113566-29-3 Ethyl (2S,3R)-3-chloro-2-hydroxytridecanoate 
• 89321-71-1 (2S,3S)-3-propyl-2-oxiranemethanol 
• 142204-61-3 (-)-(R)-hex-1-en-3-yl benzoate 
• 142204-60-2 (2S,3R)-3-benzoyloxy-1,2-hexanediol 
• 220038-45-9 DIPT 
• 87-69-4 tartaric acid 
• 2305-21-7 2-hexen-1-ol 
• 75-91-2 tert.-butylhydroperoxide 

Downstream Products

• 107796-99-6 Methyl (2S,3R)-(+)-3-propyloxirane-2-carboxylate 
• 100992-81-2 Methyl (2R,3S)-(-)-3-propyloxirane-2-carboxylate 
• 145841-94-7 (2S,3R)-2-Methylsulfanylmethyl-3-propyl-oxirane 
• 21531-91-9 1,3-hexanediol 
• 6920-22-5 (2S)-hexane-1,2-diol 
• 92693-35-1 (2S,3S)-2,3-epithio-1-hexanol 
• 125414-19-9 2,2,2-Trichloro-acetimidic acid (2S,3R)-3-propyl-oxiranylmethyl ester 
• 145841-97-0 (2S,3R)-2-<(S)-(phenylsulfinyl)methyl>-3-propyloxirane 
• 145841-93-6 (2S,3R)-2-<(S)-(phenylsulfanyl)methyl>-3-propyloxirane 
• 220515-17-3 (2S,3S)-3-Azido-hexane-1,2-diol 
• 94992-81-1 (2R,3R)-3-Methyl-hexane-1,2-diol 
• 608520-05-4 (3R,2S)-3-propyloxirane-2-carboxylic acid 
• 84314-30-7 (R)-(-)-hexane-1,3-diol 
• 130855-55-9 (2R,3S)-hexane-1,2,3-triol 

Relevant articles and documents

Solid-Phase Total Synthesis of Dehydrotryptophan-Bearing Cyclic Peptides Tunicyclin B, Sclerotide A, CDA3a, and CDA4a using a Protected β-Hydroxytryptophan Building Block

A new approach to the synthesis of Z-dehydrotryptophan (ΔTrp) peptides is described. This approach uses Fmoc-β-HOTrp(Boc)(TBS)-OH as a building block, which is readily prepared in high yield and incorporated into peptides using solid-phase Fmoc chemistry. The tert-butyldimethylsilyl-protected indolic alcohol is eliminated during global deprotection/resin cleavage to give ΔTrp peptides exclusively as the thermodynamically favored Z isomer. This approach was applied to the solid-phase synthesis of tunicyclin B, sclerotide A, CDA3a, and CDA4a.

Kinetic resolution of epoxy alcohols with the Sharpless Ti-isopropoxide/tartaric ester complex

When investigating the Sharpless epoxidation of enol-protected 4-hydroxy-1,2-cyclopentanediones, the ability of the asymmetric Ti(OiPr)4/tartaric ester complex to discriminate between enantiomeric epoxides formed in situ was discovered, leading to the epoxide opening reaction of only one enantiomer. This observation was used in the kinetic resolution of racemic substituted 2,3-epoxy-4-hydroxy-cyclopentanol, to afford enantiomerically enriched epoxyalcohols in good yields and with ees up to 96%.

Pore size matters! Helical heterogeneous catalysts in olefin oxidation

Helical mesoporous materials of the MCM-41 type with different pore sizes were prepared, choosing as templates myristyl (C14) or cetyl (C16) trimethyl ammonium salts, and functionalized with Mo(II) active sites based on MoI2(CO)3 (1) and MoBr(η3-C3H5)(CO)2 (2) fragments, respectively, using a pyridine-2-carbaldehyde ligand as anchor. The new materials were tested as the catalytic precursors in the epoxidation of cis-cyclooctene, styrene, R-(+)-limonene, trans-hex-2-en-1-ol, cis-3-hex-1-ol, and geraniol using tert-butylhydroperoxide (tbhp) as oxidant. All catalysts were moderately to highly selective toward the epoxide products. The materials with larger pores (C16 template) displayed a better catalytic activity, leading in general to higher conversions and selectivities, as well as faster kinetics. For instance, geraniol is epoxidized (more than 90%) with conversions above 90%. The major achievement of these catalysts, however, is the excellent product selectivity control, which is boosted when the allyl complex 1 is used, reaching 100% of the 2S, 3R species in the epoxidation of trans-hex-2-en-1-ol. The catalysts were also found to be stable through recycling experiments and truly heterogeneous with little or no leaching.