Oxetan-3-ol

Base Information

• Chemical Name: Oxetan-3-ol
• CAS No.: 7748-36-9
• Molecular Formula: C3H6O2
• Molecular Weight: 74.0794
• Hs Code.: 29329990
• European Community (EC) Number: 663-648-9
• DSSTox Substance ID: DTXSID30433064
• Nikkaji Number: J1.335.544D
• Wikidata: Q72498395
• ChEMBL ID: CHEMBL4755200
• Mol file: 7748-36-9.mol

Synonyms:Oxetan-3-ol;7748-36-9;3-HYDROXYOXETANE;3-OXETANOL;Oxetane-3-ol;MFCD09056790;1,3-Epoxy-2-propanol;CHEMBL4755200;3-hydroxy-oxetane;3-Hydroxy oxetane;3-Hydroxyoxetane, 95%;DTXSID30433064;QMLWSAXEQSBAAQ-UHFFFAOYSA-N;BCP22368;BBL102002;BDBM50551691;STL555801;AKOS005146130;CS-W007362;GS-4374;PB25111;SY002910;A9806;AM20020046;FT-0602200;O0409;EN300-69923;J-512992;F0001-2584;Z1123686553

Chemical Property of Oxetan-3-ol

Chemical Property:

• Vapor Pressure: 1.255mmHg at 25°C
• Refractive Index: 1.438
• Boiling Point: 153.124 °C at 760 mmHg
• PKA: 13.68±0.20(Predicted)
• Flash Point: 77.266 °C
• PSA: 29.46000
• Density: 1.255 g/cm³
• LogP: -0.62250
• Storage Temp.: Room temperature.
• XLogP3: -0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 74.036779430
• Heavy Atom Count: 5
• Complexity: 31.9

Purity/Quality:

98%min ^*data from raw suppliers

3-Oxetanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-37/38-41
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1C(CO1)O
• General Description: Oxetan-3-ol, also known as 3-hydroxyoxetane or 3-oxetanol, serves as a key intermediate in the hydroxyl-directed reductive cleavage process to produce diastereomerically pure 1,2-diols. This methodology leverages selective ring-opening reactions of oxetanes, facilitated by reagents such as LTBA and BEt3, to achieve stereoselective synthesis of diols with secondary and tertiary centers, offering advantages over conventional approaches in terms of selectivity and functional group manipulation.

Technology Process of Oxetan-3-ol

There total 9 articles about Oxetan-3-ol 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: 96.2%

→ oxetan-3-ol (7748-36-9)

Guidance literature:

Reference yield: 95.84%

3-(benzyloxy)oxetane (95257-22-0) → oxetan-3-ol (7748-36-9)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 40 ℃; for 24h; under 7600.51 Torr; Autoclave;

Reference yield: 95.0%

3-(1-Ethoxyethoxy)oxetane (85328-36-5) → oxetan-3-ol (7748-36-9)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; at 15 - 18 ℃; for 0.75h;

upstream raw materials:

3-(1-Ethoxyethoxy)oxetane

3-tetrahydropyranyloxyoxetane

3-chloro-2-hydroxy-1-propyl acetate

ethyl vinyl ether

Refernces

Hydroxyl-directed reductive cleavage of 3-oxetanols as an entry to diastereomerically pure 1,2-diols

10.1021/jo952235c

The research describes a method for the hydroxyl-directed reductive cleavage of 3-oxetanols to synthesize diastereomerically pure 1,2-diols, which is of significant interest in organic synthesis due to the challenge of reversing the polarity of a carbonyl compound from an a1 to a d1 synthon. The researchers utilized a photocycloaddition of silyl enol ethers to aromatic aldehydes, resulting in the formation of oxetanes, which were then subjected to a selective SN2-type ring opening. The key reagents in this process included lithium tris(tert-butoxy)aluminum hydride (LTBA), triethylborane (BEt3), and tetrahydropyran (THP), as well as potassium carbonate (K2CO3) and lithium aluminum hydride (LiAlH4). The study concluded that the methodology offers a more stereoselective approach to 1,2-diols bearing a secondary and a tertiary center compared to conventional methods, with the overall yield of diastereomerically pure diol ranging between 36 and 59% for the three-step procedure. The researchers are further investigating the scope of these hydroxyl-directed ring-opening reactions.