(R)-(-)-Glycidyl nosylate Chemical Properties

Melting point:

59-63 °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 

Chloroform (Slightly), DMSO (Slightly)

form 

Crystalline Needles or Powder

color 

Slightly yellow

optical activity

-22.001°(C=1.00 g/100ml, CHCL3)

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-/m1/s1

InChIKey

AIHIHVZYAAMDPM-MRVPVSSYSA-N

SMILES

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

CAS DataBase Reference

115314-17-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

37/39-26-36

RIDADR 

UN 1325 4.1/PG II

RTECS 

DB7192000

HazardClass 

4.1

PackingGroup 

II

HS Code 

29209090

MSDS

• Language:English Provider:(2R)-(-)-Glycidyl 3-nitrobenzenesulfonate
• Language:English Provider:ACROS

(R)-(-)-Glycidyl nosylate Usage And Synthesis

Chemical Properties

white to light yellow crystal powde

Uses

(R)-(-)-Glycidyl Nosylate (cas# 115314-17-5) is a compound useful in organic synthesis.

Synthesis

Preparation of Compound 3: To an anhydrous dichloromethane (10 mL) and triethylamine (1.5 mL, 10 mmol) solution of (S)-oxiran-2-ylmethanol (220 mg, 3.0 mmol) that had been cooled to 0 °C (ice bath), 3-nitrobenzenesulfonyl chloride (730 mg, 3.3 mmol) was added in batches. The resulting brown solution was stirred at 0 °C for 1 h, followed by slow warming to room temperature. The progress of the reaction was monitored by TLC every 15 min until (S)-oxiran-2-ylmethanol was completely consumed. Upon completion of the reaction, the reaction was quenched by the addition of crushed ice (1-2 g). The reaction mixture was transferred to a dispensing funnel and partitioned with dichloromethane (20 mL) and water (10 mL). The organic layer was washed sequentially with saturated aqueous NaHCO3 (10 mL x 3) and brine (10 mL x 3), followed by drying with anhydrous Na2SO4. After filtration and concentration, the residue was purified by fast column chromatography to afford (S)-(+)-m-nitrobenzenesulfonic acid glycidyl ester (Compound 3) as a brown solid (710 mg, 92%).1H NMR (400 MHz, CDCl3) δ 8.77 (s, 1H), 8.54 (d, J=8.1 Hz, 1H), 8.28 (d, J=7.9 Hz , 1H), 4.50 (d, J=11.5Hz, 1H), 4.04 (dd, J1=4.9Hz, J2=1.5Hz, 1H), 3.23 (d, J=1.8Hz, 1H), 2.85 (dd, J1=4.0Hz, J2=2.0Hz, 1H), 2.64 (dd, J1=2.4Hz, J2=2.0Hz, 1H) 1H); 13C NMR (100 MHz, CDCl3) δ 148.19, 137.92, 133.32, 130.81, 128.39, 123.16, 71.69, 48.64, 44.42.

References

[1] Patent: US2009/182011, 2009, A1. Location in patent: Page/Page column 13
[2] ACS Medicinal Chemistry Letters, 2011, vol. 2, # 9, p. 656 - 661
[3] Tetrahedron, 2009, vol. 65, # 31, p. 5984 - 5989
[4] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 8, p. 2948 - 2950
[5] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 17, p. 4792 - 4802

(R)-(-)-Glycidyl nosylate(115314-17-5)Related Product Information

• Glycidyl acrylate
• Sodium 3-nitrobenzenesulphonate
• Methanol
• ETHYLENE OXIDE
• Monostearin
• Glycidyl tertcarbonate
• 3-NITROBENZENESULFONIC ACID
• 4-Nitrophenyl chloroformate
• (R)-Glycidyl butyrate
• 2,4,6-TRINITROBENZENESULFONIC ACID
• 3-Nitrobenzenesulfonyl chloride
• Nitrobenzene
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• (S)-GLYCIDYL NOSYLATE,(S)-(+)-GLYCIDYL NOSYLATE
• Benzenesulfonic acid
• (R)-(+)-Glycidol