(2R)-(-)-Glycidyl tosylate Chemical Properties

Melting point:

46-49 °C(lit.)

Boiling point:

340.07°C (rough estimate)

alpha 

-18 º (c=2.5,CHCl3)

Density 

1.3749 (rough estimate)

refractive index 

1.5400 (estimate)

Flash point:

>230 °F

storage temp. 

2-8°C

solubility 

dioxane: 50 mg/mL, clear

form 

powder

color 

yellow to orange

optical activity

-19.9° (C=1 g/100ml CHCL3)

Water Solubility 

decomposes

BRN 

3592142

InChI

InChI=1/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-/s3

InChIKey

NOQXXYIGRPAZJC-DJEYLCQNNA-N

SMILES

C1(=CC=C(C)C=C1)S(=O)(=O)OC[C@@H]1OC1 |&1:12,r|

CAS DataBase Reference

113826-06-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,N,T

Risk Statements 

45-41-43-51/53-68

Safety Statements 

61-45-36/37/39-26-53

RIDADR 

UN 3077 9/PG 3

WGK Germany 

3

RTECS 

RR0510000

F 

3-10-21

Hazard Note 

Irritant

HazardClass 

9

HS Code 

29109000

MSDS

• Language:English Provider:Oxiran-2-ylmethyl 4-methylbenzenesulfonate
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

(2R)-(-)-Glycidyl tosylate Usage And Synthesis

Chemical Properties

white crystalline powder

Uses

(2R)-(-)-Glycidyl Tosylate is a protected glycidol used as an intermediate in the preparation of neurochemicals.

Uses

(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.

Uses

Protected Glycidol, (2R)-(-)-Glycidyl tosylate is used as an intermediate in the preparation of neurochemicals.

Synthesis

GENERAL STEPS: Under dry conditions, p-toluenesulfonyl chloride (PTSC, 25.0 g) and (R)-oxirane-2-methanol (6.0 mL) were dissolved in anhydrous dichloromethane (DCM, 250 mL). Subsequently, triethylamine (TEA, 36.0 mL) was added slowly and dropwise at 0°C to the reaction mixture. After the reaction was stirred continuously at 0°C for 3 h, the reaction solution was concentrated by rotary evaporator. The crude product was purified by fast column chromatography (eluent: ethyl acetate/petroleum ether) to afford (R)-p-toluenesulfonic acid glycidyl ester (17.6 g) as a white solid. Yield: 85.0%; Melting point: 44-46°C; [α]D25 = +18.3 (c 1.7, acetonitrile). IR (KBr, cm-1): 1598, 1363, 1177, 969, 666, 556. 1H NMR (400 MHz, DMSO-d6) δ: 7.83 (d, J = 8.1 Hz, 2H), 7.52- 7.46 (m, 2H), 4.43 (d, J = 11.6 Hz, 1H), 3.85 (dddd, J = 7.0, 5.7, 3.7, 1.9 Hz, 1H), 3.26-3.17 (m, 1H), 2.78 (t, J = 4.6 Hz, 1H), 2.66-2.58 (m, 1H), 2.42 (s, 3H). esi -MS m/z: 251.2 [M + Na]+.

References

[1] Journal of Organic Chemistry, 2015, vol. 80, # 17, p. 8668 - 8676
[2] Chemical Communications, 2014, vol. 50, # 51, p. 6718 - 6721
[3] Organic Letters, 2012, vol. 14, # 11, p. 2834 - 2837
[4] Angewandte Chemie - International Edition, 2014, vol. 53, # 15, p. 3859 - 3862
[5] Angew.Chem.Int.Ed., 2014, vol. 53, p. 3859 - 3862,4

(2R)-(-)-Glycidyl tosylate(113826-06-5)Related Product Information

• Glycidyl acrylate
• Sodium p-toluenesulfonate
• p-Toluenesulfonic acid
• 4-CHLOROBENZOYLACETONITRILE
• Sorafenib tosylate
• Glycidol
• (S)-Oxiranemethanol
• 2-METHOXYETHYL P-TOLUENESULFONATE
• PROPYL P-TOLUENESULFONATE
• (2S)-(+)-Glycidyl tosylate
• (S)-(-)-Propylene oxide
• Methyl toluenesulfonate
• 2-METHOXYMETHYL METHANSULFONATE
• Ethyl p-toluenesulfonate
• Iminostilbene
• (R)-(-)-2-HYDROXYPROPYL P-TOLUENESULFONATE
• METHYL P-TOLUENESULFINATE
• 2-METHOXYETHYL BENZENESULFONATE