Skip to Content
Merck
All Photos(1)

Key Documents

540110

Sigma-Aldrich

(2R)-(−)-Glycidyl tosylate

98%

Synonym(s):

(R)-(−)-Glycidyl p-toluenesulfonate, (R)-(−)-Glycidyl tosylate, (R)-(−)-Oxirane-2-methanol p-toluenesulfonate salt

Sign Into View Organizational & Contract Pricing


About This Item

Empirical Formula (Hill Notation):
C10H12O4S
CAS Number:
Molecular Weight:
228.26
Beilstein:
3592142
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22

Assay

98%

mp

46-49 °C (lit.)

functional group

ether
tosylate

storage temp.

2-8°C

SMILES string

Cc1ccc(cc1)S(=O)(=O)OC[C@H]2CO2

InChI

1S/C10H12O4S/c1-8-2-4-10(5-3-8)15(11,12)14-7-9-6-13-9/h2-5,9H,6-7H2,1H3/t9-/m1/s1

InChI key

NOQXXYIGRPAZJC-SECBINFHSA-N

Looking for similar products? Visit Product Comparison Guide

Application

(2R)-(-)-Glycidyl tosylate may be used to prepare:
  • 1-O-hexadecyl-sn-glycerol 3-O-p-toluenesulfonate by reacting with 1-hexadecanol in the presence of boron trifluoride etherate.
  • 4-Oxiranylmethoxy-(1H)-indole by reacting with 4-hydroxyindole in the presence of sodium hydride.
  • [18F]Epifluorohydin, an intermediate for preparing of [18F]fluoromisonidazole.
It can also be used as a starting material in the synthesis of 1,2-diacyl-sn-3-glycerophosphocholines.

Legal Information

Manufactured under license by Sterling Pharma Solutions Limited, using Jacobsen HKR technology.

Signal Word

Danger

Hazard Statements

Hazard Classifications

Aquatic Chronic 2 - Carc. 1B - Eye Dam. 1 - Muta. 2 - Skin Sens. 1

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

>230.0 °F

Flash Point(C)

> 110 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Facile diacylation of glycidyl tosylate. Chiral synthesis of symmetric-chain glycerophospholipids.
Ali S and Bittman R
The Journal of Organic Chemistry, 53(23), 5547-5549 (1988)
A Radiosynthesis of fluorine-18.
Grierson JR, et al.
Journal of Nuclear Medicine, 30, 343-350 (1989)
Isosteric phosphonate analogs of ET-16-OMe. Synthesis and biological evaluation of the enantiomers of 2'-(Trimethylammonio) ethyl 4-(hexadecyloxy)-3-methoxybutanephosphonate and 2'-(trimethylammonio) ethyl 4-(hexadecylthio)-3-methoxybutanephosphonate.
Bittman R, et al.
Journal of Medicinal Chemistry, 37(3), 425-430 (1994)
Novel aryloxy-8-azabicyclo [3.2. 1] oct-3-enes with 5-HT transporter and 5-HT 1A affinity.
Gilbert AM, et al.
Bioorganic & Medicinal Chemistry Letters, 14(21), 5281-5284 (2004)
Henry, N. et al.
Tetrahedron Letters, 45, 1465-1465 (2004)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service