(R)-Glycidol

Base Information

• Chemical Name: (R)-Glycidol
• CAS No.: 57044-25-4
• Molecular Formula: C3H6O2
• Molecular Weight: 74.0794
• Hs Code.: 29109000
• European Community (EC) Number: 404-660-4,629-598-7
• DSSTox Substance ID: DTXSID40904710
• Nikkaji Number: J425.695F
• Wikidata: Q27109084
• Metabolomics Workbench ID: 53646
• Mol file: 57044-25-4.mol

Synonyms:(R)-Glycidol;57044-25-4;(R)-(+)-Glycidol;(R)-Oxiran-2-ylmethanol;[(2R)-oxiran-2-yl]methanol;(R)-Oxiranemethanol;(+)-Glycidol;Oxiranemethanol, (2R)-;(R)-3-hydroxy-1,2-epoxypropane;(2R)-oxiran-2-ylmethanol;(R)-(+)-Oxirane-2-methanol;(R)-(+)-2,3-Epoxy-1-propanol;2-Oxiranylmethanol #;R(+)-glycidol;R-2,3-epoxy-1-propanol;rac-glycidol;(+) glycidol;R(+) glycidol;EC 404-660-4;(r )-(+)-glycidol;(r)-1-oxiranyl-methanol;(2R)-2-oxiranylmethanol;2,3 Epossipropan-1-Olo;CHEBI:18664;DTXSID40904710;(R)-(+)-2-(Hydroxymethyl)oxirane;AKOS016842463;AC-7042;AM81447;CS-W013757;(R)-(+)-Glycidol, analytical standard;(R)-(+)-1-Hydroxy-2,3-epoxypropane;AS-11738;G0363;EN300-80398;A831293;Q27109084;Z1222330631;(R)-(+)-Glycidol, 97%, optical purity ee: 98% (GLC)

Chemical Property of (R)-Glycidol

Chemical Property:

• Appearance/Colour: Colorless to light yellow liquid
• Refractive Index: n20/D 1.43(lit.)
• Boiling Point: 162.4 °C at 760 mmHg
• PKA: 14.62±0.10(Predicted)
• Flash Point: 81.1 °C
• PSA: 32.76000
• Density: 1.178 g/cm³
• LogP: -0.62250
• Storage Temp.: 2-8°C
• Water Solubility.: Completely miscible in water
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 74.036779430
• Heavy Atom Count: 5
• Complexity: 35.9

Purity/Quality:

99% ^*data from raw suppliers

(R)-(+)-Glycidol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T, E
• Hazard Codes: T,E
• Statements: 45-60-2-21/22-23-34-68-41-37/38
• Safety Statements: 53-45-36/37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(O1)CO
• Isomeric SMILES: C1[C@H](O1)CO
• Uses: (R)-(+)-Glycidol may be used in the following synthesis:heteroarylpropane-2,3-diols, useful for combinatorial oligomer synthesisenantiomerically pure (2S,3S)- and (2S,3R)-threoninol and -hydroxyphenylalaninol2-amino-1,4-anhydro-pentitol and 3-amino-1,5-anhydro-4-deoxy-hexitol with the arabino configuration(S)-4-tosyloxymethyl-2-oxazolidinone, required for the synthesis of protected amino alcohol derivatives1-(S)-[3-hydroxy-2-(phosphonomethoxy)propyl]cytosine [(S)-HPMPC]chiral building block used to construct an epoxyvinyl iodide intermediate in a synthesis of a furanocembrane, a marine natural product (R)-(+)-Glycidol can be used to construct chiral building blocks of epoxyvinyl iodide intermediates in the synthesis of furanocembrane, a marine natural product.

Technology Process of (R)-Glycidol

There total 27 articles about (R)-Glycidol 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: 88.0%

(2R)-3-chloro-1,2-propanediol (57090-45-6) → (R)-oxiranemethanol (57044-25-4)

Guidance literature:

With potassium carbonate; In dichloromethane; for 18h; Ambient temperature;

DOI:10.1021/jo981332d

Reference yield: 88.0%

(2R)-3-bromo-1,2-propanediol (14437-88-8) → (R)-oxiranemethanol (57044-25-4)

Guidance literature:

With potassium carbonate; In dichloromethane; for 18h; Ambient temperature;

DOI:10.1021/jo981332d

Reference yield: 45.0%

allyl alcohol (107-18-6) → (R)-oxiranemethanol (57044-25-4) + (S)-oxiranemethanol (60456-23-7)

Guidance literature:

With tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate; tantalum pentaethoxide; In dichloromethane; at 0 ℃; for 48h; Product distribution / selectivity; Molecular sieve;

upstream raw materials:

(R)-3-tosyloxy-1,2-propanediol

Pentanoic acid oxiranylmethyl ester

phenylacetate of 2,3-epoxypropan-1-ol

vinyl acetate

Downstream raw materials:

4-{4-[(2S)-oxiran-2-ylmethoxy]-1,2,5-thiadiazol-3-yl}morpholine

(R)-3-<<4-(benzyloxy)phenyl>amino>-1,2-propanediol

(R)-3-<<4-<(3-chlorophenyl)methoxy>phenyl>amino>-1,2-propanediol

(2R,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-((S)-1-oxiranylmethoxy)-tetrahydro-pyran

Refernces

• 1、 Palomo, Jose M.,Segura, Rosa L.,Fernandez-Lorente, Gloria,Guisan, Jose M.,Fernandez-Lafuente, Roberto. "Enzymatic resolution of (±)-glycidyl butyrate in aqueous media. Strong modulation of the properties of the lipase from Rhizopus oryzae via immobilization techniques". . p. 1157 - 1161. Retrieved 2004.
• 2、 Kiljunen, Eero,Kanerva, Liisa T.. "Novel applications of chloroperoxidase: Enantioselective oxidation of racemic epoxyalcohols". . p. 3529 - 3535. Retrieved 1999.
• 3、 -. "A high selective (S)-β-hydroxy-γ-butyrolactone simple method for preparing". Paragraph 0048-0050; 0053-0056; 0065-0067; 0070-0072. . Retrieved 2019/02/04.
• 4、 Chen, Weiqi,Xiong, Fangjun,Liu, Qian,Xu, Lingjun,Wu, Yan,Chen, Fener. "Substrate stereocontrol in bromine-induced intermolecular cyclization: Asymmetric synthesis of pitavastatin calcium". . p. 4730 - 4737. Retrieved 2015/07/27.