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474789

Sigma-Aldrich

(S)-(−)-Glycidol

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

Synonym(s):

(S)-(−)-2,3-Epoxy-1-propanol, (S)-(−)-Oxirane-2-methanol

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About This Item

Empirical Formula (Hill Notation):
C3H6O2
CAS Number:
Molecular Weight:
74.08
Beilstein:
79783
MDL number:
UNSPSC Code:
12352005
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

Signal Word

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 Code

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

WGK

WGK 3

Flash Point(F)

161.6 °F

Flash Point(C)

72 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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