1-(Mesitylene-2-sulfonyl)-3-nitro-1,2,4-triazole Chemical Properties

Melting point:

134-139 °C(lit.)

Boiling point:

533.4±60.0 °C(Predicted)

Density 

1.4470 (rough estimate)

refractive index 

1.6270 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,Store in freezer, under -20°C

solubility 

Soluble in Chloroform.

pka

-5.80±0.50(Predicted)

form 

Crystalline Powder

color 

Yellow

BRN 

4328921

InChI

InChI=1S/C11H12N4O4S/c1-7-4-8(2)10(9(3)5-7)20(18,19)14-6-12-11(13-14)15(16)17/h4-6H,1-3H3

InChIKey

SFYDWLYPIXHPML-UHFFFAOYSA-N

SMILES

N1(S(C2=C(C)C=C(C)C=C2C)(=O)=O)C=NC([N+]([O-])=O)=N1

CAS DataBase Reference

74257-00-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26

WGK Germany 

3

HS Code 

29350090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

1-(Mesitylene-2-sulfonyl)-3-nitro-1,2,4-triazole Usage And Synthesis

Chemical Properties

Light Yellow Solid

Uses

Condensing reagent for oligonucleotide synthesis.

Uses

This reagent was originally used as a coupling reagent in phosphotriester oligonucleotide synthesis

Uses

An efficient coupling reagent in oligonucleotide synthesis by the phosphotriesters approach

Synthesis

An oven-dried 1.0-liter round-bottomed flask equipped with a magnetic stirring bar was assembled with a Claisen adapter. To the reaction flask was added 3-nitro-1,2,4-triazole (19.5 g, 0.171 mol), anhydrous dioxane (200 mL), and triethylamine (17.3 g, 0.171 mol, 1.0 eq.), and the solution was cooled to 0°C. A 200 mL pressure-equalizing dosing funnel was assembled through the Claisen adapter, and a dioxane solution (150 mL) of homotrimethylbenzenesulfonyl chloride ( 37.4 g, 0.171 mol) of dioxane solution (150 mL) to the funnel. Slowly add the homotrimethylbenzenesulfonyl chloride solution dropwise to the reaction mixture. After the dropwise addition was completed, the reaction mixture was continued to be stirred for 0.5 hours, followed by warming to room temperature and continued stirring for 1 hour. After completion of the reaction, the precipitated triethylamine hydrochloride was removed by filtration and the filtrate was concentrated under reduced pressure to give a yellow solid. The solid was dissolved in dichloromethane (150 mL) and the organic layer was washed with water (150 mL). The organic layer was dried with anhydrous sodium sulfate, filtered and the solvent evaporated under reduced pressure to give a yellow solid. Recrystallization by boiling toluene (20-30 mL) followed by washing with ice-cold toluene and drying overnight at 1.9 mmHg gave 1-(2-trimethylbenzenesulfonyl)-3-nitro-1,2,4-triazole 24-25 g (46%-48% yield) as a pale yellow solid with a melting point of 131°C-133°C (literature values 130°C-132°C). Thin Layer Chromatography (TLC) Rf = 0.23 (unfolding agent: dichloromethane solution of 20% hexane, UV detection).1H NMR (300 MHz, CDCl3) δ: 8.84 (s, 1H), 7.07 (s, 2H), 2.69 (s, 6H), 2.34 (s, 3H).13C NMR (75 MHz, CDCl3) δ. 162.9, 147.5, 145.2, 142.5, 133.0, 127.9, 23.2, 21.3. IR (solid) νmax: 3126, 2983, 2947, 1597 cm-1. Calculated elemental values (C11H12N4O4S): C, 44.59; H, 4.08; N, 18.91. Measured values: C , 44.69; H, 3.88; N, 18.72. The purity of the product was determined to be 96% by reversed-phase high-performance liquid chromatography (RP-HPLC), with a retention time of tR = 8.41 min (detection wavelength 254 nm).

References

[1] Organic Preparations and Procedures International, 2014, vol. 46, # 3, p. 267 - 271
[2] Tetrahedron Letters, 1986, vol. 27, # 45, p. 5529 - 5532

1-(Mesitylene-2-sulfonyl)-3-nitro-1,2,4-triazole(74257-00-4)Related Product Information

• Triphenylphosphine
• 1,2,4-Triazole
• 3-SULFOLENE
• 1-Phenyl-2-nitropropene
• 2,4-Dimethylbenzenethiol
• p-Toluenesulfonamide
• (S)-4-Methylbezenesulfinamide
• 1-(p-Toluenesulfonyl)-3-nitro-1,2,4-triazole
• 2,6-DIMETHYLTHIOPHENOL
• 2,4,6-TRIMETHYLTHIOPHENOL
• 1-MESITYLENESULFONYL-1,2,4-TRIAZOLE
• 3-Nitro-1,2,4-triazole
• 1-(Mesitylene-2-sulfonyl)-3-nitro-1,2,4-triazole
• NITROGEN DIOXIDE
• Phenylacetone
• 2-Methylbenzene-1-sulfonamide
• (R)-(-)-4-Methylbezenesulfinamide
• Nitromethane