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(S)-(−)-Glycidol

97%, optical purity ee: 98% (GLC)

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Synonym(s):
(S)-(−)-2,3-Epoxy-1-propanol, (S)-(−)-Oxirane-2-methanol
Empirical Formula (Hill Notation):
C3H6O2
CAS Number:
Molecular Weight:
74.08
Beilstein/REAXYS Number:
79783
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

97%

optical activity

[α]20/D −15°, neat

optical purity

ee: 98% (GLC)

refractive index

n20/D 1.433 (lit.)

bp

66-67 °C/19 mmHg (lit.)

density

1.116 g/mL at 20 °C (lit.)

storage temp.

−20°C

SMILES string

OC[C@H]1CO1

InChI

1S/C3H6O2/c4-1-3-2-5-3/h3-4H,1-2H2/t3-/m0/s1

InChI key

CTKINSOISVBQLD-VKHMYHEASA-N

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General description

Glycidol or 2,3-epoxy-1-propanol is a highly reactive epoxy derivative, which is generally used as a monomer in the preparation of many polymers like polyesters, polycarbonates, polyurethanes, and polyamides. It is also used in the preparation of detergents, rubbers, perfumes, fabric dyes, varnishes, cosmetics, and paints.

Application

Employed in the synthesis of chiral (E)-allylic alcohol side-chains for introduction into prostacyclin and prostaglandin frameworks by cross-metathesis.

pictograms

Skull and crossbonesHealth hazard

signalword

Danger

Hazard Classifications

Acute Tox. 2 Inhalation - Acute Tox. 4 Dermal - Acute Tox. 4 Oral - Carc. 1B - Eye Irrit. 2 - Muta. 2 - Repr. 1B - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

flash_point_f

161.6 °F

flash_point_c

72 °C

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter


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One-pot synthesis of glycidol from glycerol and dimethyl carbonate over KF/sepiolite catalyst
Algoufi YT, et al.
Applied Catalysis A: General, 487, 181-188 (2014)
A simplified early stage assessment of process intensification: glycidol as a value-added product from epichlorohydrin industry wastes
Cespi D, et al.
Green Chemistry, 18(16), 4559-4570 (2016)
Neil A Sheddan et al.
Organic letters, 8(14), 3101-3104 (2006-06-30)
[reaction: see text] A cross metathesis (CM) approach has been successfully applied to introduce fully functionalized omega-side chain appendages of various prostacyclin and prostaglandin analogues, resulting in high (E)-selectivities for the C13-C14 double bond and leading to the total syntheses
Nicolas M B Brancucci et al.
Cell, 171(7), 1532-1544 (2017-11-14)
Transmission represents a population bottleneck in the Plasmodium life cycle and a key intervention target of ongoing efforts to eradicate malaria. Sexual differentiation is essential for this process, as only sexual parasites, called gametocytes, are infective to the mosquito vector. Gametocyte production
Troy D Haines et al.
Journal of the American Oil Chemists' Society, 88(1), 1-14 (2011-02-26)
Analysis of MCPD esters and glycidyl esters in vegetable oils using the indirect method proposed by the DGF gave inconsistent results when salting out conditions were varied. Subsequent investigation showed that the method was destroying and reforming MCPD during the

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