(R)-(+)-Glycidol

(R)-(+)-Glycidol Basic information
Product Name:(R)-(+)-Glycidol
Synonyms:(R)-(+)-1-Hydroxy-2,3-epoxypropane (R)-(+)-2-(Hydroxymethyl)oxirane;(R)-(+)-Glycidol 97%, optical purity ee: 98% (GLC);2-Oxiranemethanol, (2R)-;(R)-(+)-1-Hydroxy-2,3-epoxypropane;(R)-(+)-Glycidol≥ 99% (GC);(R)-(+)-Oxirane-2-methanol (R)-(+)-1-Hydroxy-2,3-epoxypropane (R)-(+)-2-(Hydroxymethyl)oxirane;(r)-oxiranemethano;(R)-(+)-2,3-EPOXY-1-PROPANOL
CAS:57044-25-4
MF:C3H6O2
MW:74.08
EINECS:404-660-4
Product Categories:Chiral Compound;CHIRAL COMPOUNDS;chiral;API intermediates
Mol File:57044-25-4.mol
(R)-(+)-Glycidol Structure
(R)-(+)-Glycidol Chemical Properties
Boiling point 56-57 °C11 mm Hg(lit.)
density 1.116 g/mL at 20 °C(lit.)
refractive index n20/D 1.43(lit.)
Fp 178 °F
storage temp. -20°C
Water Solubility Completely miscible in water
solubility Chloroform (Slightly), DMSO (Slightly)
pka14.62±0.10(Predicted)
form neat
color Colorless to Light yellow
optical activity[α]23/D +15°, neat
BRN 79782
Stability:Moisture Sensitive
InChIKeyCTKINSOISVBQLD-GSVOUGTGSA-N
CAS DataBase Reference57044-25-4(CAS DataBase Reference)
NIST Chemistry ReferenceOxiranemethanol, (R)-(57044-25-4)
Safety Information
Hazard Codes T,E
Risk Statements 45-60-2-21/22-23-34-68-41-37/38
Safety Statements 53-45-36/37/39-26
RIDADR UN 2922 8/PG 2
WGK Germany 3
RTECS RR0508000
10-21
HazardClass 6.1
PackingGroup 
HS Code 29109000
MSDS Information
ProviderLanguage
SigmaAldrich English
(R)-(+)-Glycidol Usage And Synthesis
Chemical PropertiesColorless to light yellow liqui
Uses(R)-(+)-Glycidol may be used in the following synthesis:
  • heteroarylpropane-2,3-diols, useful for combinatorial oligomer synthesis
  • enantiomerically pure (2S,3S)- and (2S,3R)-threoninol and -hydroxyphenylalaninol
  • 2-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 derivatives
  • 1-(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
Uses(R)-(+)-Glycidol can be used to construct chiral building blocks of epoxyvinyl iodide intermediates in the synthesis of furanocembrane, a marine natural product.
DefinitionChEBI: (R)-glycidol is a glycidol. It is functionally related to a (R)-1,2-epoxypropane. It is an enantiomer of a (S)-glycidol.
General DescriptionEnantioselective esterification of (R)-(+)-glycidol with n-butyric acid in organic media using hybrid gel-entrapped lipase on Celite has been reported.
Purification Methods[S(-)-isomer, § also available on polymer support, has b 49-50o/7mm, 66-67o/19mm, [ ] D -1 5o(neat)], [R(+)-isomer has b 56 -5 6 . 5o/11mm, d 4 1.117, n D 1.429, [ ] D +15o (neat)]. Purify glycidol by fractional distillation.
(R)-(+)-Glycidol Preparation Products And Raw materials
Preparation Products(S)-(+)-Methyl glycidyl ether-->(S)-(+)-Glycidyl butyrate-->1,2-Propanediol, 3-(dodecyloxy)-, (2R)--->(S)-2-((2-FLUOROPHENOXY)METHYL)OXIRANE
4-[(S,S)-2,3-EPOXYHEXYLOXY]PHENYL 4-(DECYLOXY)BENZOATE (S)-Glycidol 3-Nitrobenzenesulfonate Cinobufotalin (2S)-(+)-2-METHYLGLYCIDYL 4-NITROBENZOATE Cinobufagin Methyl 3-(4-methoxyphenyl)oxirane-2-carboxylate ETHYL (2S)-2,3-EPOXYPROPANOATE (2R,3R)-(+)-3-(4-NITROPHENYL)GLYCIDOL) ETHYL (2S,3S)-2,3-EPOXY-3-METHYLPROPANOATE Ethylene glycol diglycidyl ether 1,2,3-PROPANETRIOL GLYCIDYL ETHER (R)-(+)-Glycidol (2R,3R)-3-PHENYLGLYCIDOL (2S)-(+)-GLYCIDYL 4-NITROBENZOATE Phenol, polymer with formaldehyde, glycidyl ether, polymers with (methylphenoxy)methyloxirane and triethylenetetramine (S)-(+)-Benzyl glycidyl ether (2R)-(+)-3 3-DIMETHYLGLYCIDYL CHLOROPHOSPHONAZO III

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