(S)-(−)-Glycidol
(S)-(−)-Glycidol (CAS: 60456-23-7), a chiral epoxide with the formula C3H6O2 and a molecular weight of 74.08 g/mol, is a valuable building block. It serves as a key intermediate in asymmetric synthesis, particularly for introducing chiral allylic alcohol side-chains into complex molecules like prostacyclin and prostaglandin frameworks. Its defined stereochemistry makes it essential for stereoselective synthetic routes.
- IUPAC
- (S)-(−)-2,3-Epoxy-1-propanol,(S)-(−)-Oxirane-2-methanol
- Synonyms
- (S)-(−)-2,3-Epoxy-1-propanol(S)-(−)-Oxirane-2-methanol
Chiral Synthesis of Prostacyclin Analogues
Employed in the stereoselective synthesis of allylic alcohol side-chains for prostacyclin and prostaglandin derivatives via cross-metathesis. This application leverages the chiral nature of glycidol to build complex bioactive molecules with defined stereochemistry.
Chiral Building Block for Organic Synthesis
As a versatile chiral epoxide, (S)-(−)-Glycidol functions as a fundamental building block in various organic synthesis pathways. It enables the introduction of a chiral three-carbon unit with an epoxide and primary alcohol functionality.
Epoxide Chemistry
Undergoes ring-opening reactions characteristic of epoxides, allowing for regioselective and stereoselective functionalization. This reactivity is crucial for constructing more complex chiral molecules.
| Molecular weight | 74.08 |
|---|---|
| Empirical formula | C3H6O2 |
| Assay | 97% |
| Boiling point | 66-67 °C/19 mmHg(lit.) |
| Density | 1.116 g/mL at 20 °C(lit.) |
| Refractive index | n20/D 1.433(lit.) |
| Optical activity | [α]20/D −15°, neat |
| Optical purity | ee: 98% (GLC) |
| Storage temperature | −20°C |
| Application | Employed in the synthesis of chiral (E)-allylic alcohol side-chains for introduction into prostacyclin and prostaglandin frameworks by cross-metathesis.1 |
Hazard statements
- H302Harmful if swallowed
- H312Harmful in contact with skin
- H315Causes skin irritation
- H318Causes serious eye damage
- H331Toxic if inhaled
- H335May cause respiratory irritation
- H350May cause cancer
- H360May damage fertility or the unborn child
Precautionary statements
- P201Obtain special instructions before use
- P261Avoid breathing dust, fume, gas or vapours
- P280Wear protective gloves, clothing and eye/face protection
- P305IF IN EYES
- P311Call a POISON CENTER or doctor
| Protective equipment | Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter |
|---|---|
| Flash point | 66 °C / 150.8 °F |
| Transport (UN / ADR) | UN 2810 6.1 / PGIII |
| Water hazard class (WGK, DE) | 3 |
| Hazard codes (EU) | T |
| Risk statements (R) | 45-60-21/22-23-37/38-41-68 |
| Safety statements (S) | 53-26-36/37/39-45 |
Hazard information is provided for guidance. Always consult the product Safety Data Sheet (SDS), available on request, before handling.
Documentation
Every batch ships with a Certificate of Analysis covering assay, identity and purity; the grade is confirmed against your enquiry. Safety Data Sheets and technical data sheets are available on request.
Supply & logistics
Samples for technical evaluation; bulk MOQ by grade and packaging. In-stock material ships in 7–10 working days, worldwide, with full export documentation.
What is (S)-(−)-Glycidol used for?
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(S)-(−)-Glycidol is primarily used in asymmetric synthesis, especially for preparing chiral (E)-allylic alcohol side-chains for prostacyclin and prostaglandin frameworks, and as a general chiral building block in organic synthesis.
What is the CAS number and chemical formula for (S)-(−)-Glycidol?
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The CAS number is 60456-23-7 and the chemical formula is C3H6O2.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies (S)-(−)-Glycidol with a minimum assay of 97% and an optical purity of ee: 98%. We do not represent this product as USP, BP, EP or other pharmacopoeial grades unless explicitly stated.
How should (S)-(−)-Glycidol be handled safely?
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(S)-(−)-Glycidol is a hazardous substance (GHS05, GHS06, GHS08, Danger). It is harmful if swallowed or in contact with skin, causes skin irritation, serious eye damage, and is suspected of causing genetic defects, cancer, and damaging fertility or the unborn child. It is also toxic if inhaled and may cause respiratory irritation. Appropriate personal protective equipment, including eyeshields, face shields, gloves, and respiratory protection, must be used. Handle in a well-ventilated area and avoid exposure.
Is (S)-(−)-Glycidol a controlled substance?
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The provided data does not indicate that (S)-(−)-Glycidol is a controlled substance. However, users should verify local regulations.
How is (S)-(−)-Glycidol packaged and shipped?
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(S)-(−)-Glycidol is stored at -20°C and shipped according to its hazard classification (UN 2810 6.1 / PGIII). Specific packaging details can be provided upon request.
How can I request a sample or quote for (S)-(−)-Glycidol?
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To request a sample or a quote for (S)-(−)-Glycidol, please contact our sales team through the website or by phone, providing your specific requirements.
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