(S)-(+)-Glycidyl nosylate Chemical Properties

Melting point:

61-65 °C

alpha 

21.5 º (c=2, CHCl3)

Boiling point:

432.2±20.0 °C(Predicted)

Density 

1.5881 (rough estimate)

refractive index 

1.5270 (estimate)

storage temp. 

Inert atmosphere,2-8°C

solubility 

Soluble in chloroform, methylene chloride and tetrahydrofuran. Insoluble in hexane.

form 

Needles or Powder

color 

Off-white to yellow-brown

Sensitive 

Moisture Sensitive

InChI

InChI=1S/C9H9NO6S/c11-10(12)7-2-1-3-9(4-7)17(13,14)16-6-8-5-15-8/h1-4,8H,5-6H2/t8-/m0/s1

InChIKey

AIHIHVZYAAMDPM-QMMMGPOBSA-N

SMILES

C1(S(OC[C@@H]2CO2)(=O)=O)=CC=CC([N+]([O-])=O)=C1

CAS DataBase Reference

115314-14-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-5

Safety Statements 

37/39-26-36

RIDADR 

UN 1325 4.1/PG II

RTECS 

DB7192010

HazardClass 

4.1

PackingGroup 

II

HS Code 

29209090

MSDS

• Language:English Provider:(S)-(+)-Oxirane-2-methanol 3-nitrobenzenesulfonate
• Language:English Provider:ACROS

(S)-(+)-Glycidyl nosylate Usage And Synthesis

Uses

(S)-(+)-Glycidyl Nosylate is a compound useful in organic synthesis.

Chemical Properties

white to light yellow crystal powde

Uses

(S)-(+)-Glycidyl Nosylate (cas# 115314-14-2) is a compound useful in organic synthesis.

Synthesis

General procedure for the synthesis of (S)-(+)-m-nitrobenzenesulfonic acid glycidyl ester from 3-nitrobenzenesulfonyl chloride and (R)-oxirane-2-methanol: at -20 °C, m-nitrobenzenesulfonyl chloride (12.6 g, 57 mmol) was slowly added to a solution containing (R)-(+)-glycidol (5.5 g, 74 mmol) and triethylamine (TEA, 10.3 mL. 74 mmol) in a cold solution. The reaction mixture was stirred continuously at -20 °C for 96 hours. Upon completion of the reaction, the reaction solution was filtered and the filtrate was washed sequentially with 10% (w/w) aqueous tartaric acid, saturated saline and deionized water. The washed organic phase was concentrated to afford the target product (S)-(+)-m-nitrobenzenesulfonic acid glycidyl ester in 97% yield. The structure of the product was confirmed by 1H NMR (CDCl3): δ 2.62 (dd, 1H), 2.84 (dd, 1H), 3.22 (m, 1H), 4.07 (dd, 1H), 4.49 (dd, 1H), 7.80 (t, 1H), 8.25 (m, 1H), 8.52 (m, 1H), 8.78 (m, 1H).

References

[1] Angewandte Chemie - International Edition, 2013, vol. 52, # 20, p. 5305 - 5308
[2] Angew. Chem., 2013, vol. 125, # 20, p. 5413 - 5416,4
[3] European Journal of Organic Chemistry, 2014, vol. 2014, # 19, p. 4053 - 4069
[4] Patent: US2004/229900, 2004, A1. Location in patent: Page 14
[5] Organic and Biomolecular Chemistry, 2006, vol. 4, # 16, p. 3067 - 3076

(S)-(+)-Glycidyl nosylate(115314-14-2)Related Product Information

• (R)-Glycidyl butyrate
• 1-Chloro-3-nitrobenzene
• ETHYLENE OXIDE
• Glycidyl tertcarbonate
• Sodium 3-nitrobenzenesulphonate
• Methanol
• 3-Nitrobenzaldehyde
• 4-Nitrophenyl chloroformate
• Glycidyl acrylate
• 3-Nitrobenzenesulfonyl chloride
• 3-NITROBENZENESULFONIC ACID
• 2,4,6-TRINITROBENZENESULFONIC ACID
• Benzenesulfonic acid
• (R)-(-)-GLYCIDYL NOSYLATE,(R)-GLYCIDYL NOSYLATE
• 1,3-Dinitrobenzene
• (R)-(+)-Glycidol
• Glycidol
• Glycerol