ChemicalBook Product Catalog Chemical Reagents Organic reagents Epoxide (R)-(+)-Glycidol

(R)-(+)-Glycidol

Product Name(R)-(+)-Glycidol
CAS57044-25-4
MFC3H6O2
MW74.08
EINECS404-660-4
MOL File57044-25-4.mol

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.)
Flash point	178 °F
storage temp.	-20°C
Water Solubility	Completely miscible in water
solubility	Chloroform (Slightly), DMSO (Slightly)
pka	14.62±0.10(Predicted)
color	Colorless to Light yellow
optical activity	[α]23/D +15°, neat
BRN	79782
Stability	Moisture Sensitive
InChI	1S/C3H6O2/c4-1-3-2-5-3/h3-4H,1-2H2/t3-/m1/s1
InChIKey	CTKINSOISVBQLD-GSVOUGTGSA-N
SMILES	OC[C@@H]1CO1
CAS DataBase Reference	57044-25-4(CAS DataBase Reference)
NIST Chemistry Reference	Oxiranemethanol, (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
F	10-21
HazardClass	6.1
PackingGroup	Ⅲ
HS Code	29109000
Storage Class	5.2 - Organic peroxides and self-reacting hazardous materials
Hazard Classifications	Acute Tox. 2 Inhalation Acute Tox. 4 Dermal Acute Tox. 4 Oral Carc. 1B Eye Dam. 1 Muta. 2 Repr. 1B Self-react. C Skin Corr. 1B STOT SE 3

MSDS

Provider	Language
SigmaAldrich	English

Usage And Synthesis

Synthesis

Under stirring, NaOH (36.19 g, 0.905 mol) was slowly added to a solution of chlorodiol (100.0 g, 0.905 mol) and ethanol (200 mL) at 0-5°C. The reaction mixture was then stirred at 0-5°C for 2 hours. After the reaction was complete, the reaction mixture was filtered to remove the insoluble solid precipitate. The filtrate was concentrated under vacuum at 40°C to obtain the target product (R)-(+)-Glycidol (note that (R)-(+)-Glycidol has a low boiling point and requires low-temperature treatment during vacuum concentration in post-processing).

Synthesis of 57044-25-4

Figure: Synthetic route of (R)-(+)-Glycidol

Chemical Properties

Colorless 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.

Definition

ChEBI: (R)-glycidol is a glycidol. It is functionally related to a (R)-1,2-epoxypropane. It is an enantiomer of a (S)-glycidol.

General Description

Enantioselective 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

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

Preparation Products And Raw materials

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