3,5-BIS(METHYLSULFONYL)ANILINE Chemical Properties

Melting point:

0°C

Boiling point:

0°C

Density 

1.478±0.06 g/cm3(Predicted)

Flash point:

0°C

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

pka

12.72±0.10(Predicted)

color 

White to Off-White

InChI

InChI=1S/C6H5Cl2NO/c7-5-1-4(3-10)2-6(8)9-5/h1-2,10H,3H2

InChIKey

YDGJTFCKLFLWFM-UHFFFAOYSA-N

SMILES

C1(Cl)=NC(Cl)=CC(CO)=C1

CAS DataBase Reference

101990-69-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22-36/37/38

Safety Statements 

26-36/37/39

HazardClass 

IRRITANT

HS Code 

29333990

3,5-BIS(METHYLSULFONYL)ANILINE Usage And Synthesis

Chemical Properties

White powder

Uses

2,6-Dichloro-4-pyridinemethanol is a reagent in the preparation of functionalized compounds such as bipyridines and terpyridines via Stille-type cross coupling. Also used in the preparation of fluorescent chemosensors.

Definition

ChEBI: (2,6-Dichloro-4-pyridyl)methanol is a chloropyridine.

Synthesis

The general procedure for the synthesis of 2,6-dichloropyridine-4-methanol from 2,6-dichloroisonicotinic acid was as follows: Preparation of Intermediate 3.1: To a stirred solution of 2,6-dichloroisonicotinic acid (10.0 g, 52.1 mmol) in THF (300 mL) at 0 °C was slowly added sulfadimethane-borane (1:1) complex (16.0 g, 210.5 mmol) to the THF solution. The reaction mixture was stirred at room temperature overnight. Subsequently, MeOH (22 mL) was carefully added to the stirred mixture under cooling in an ice bath. The reaction mixture was diluted with ethyl acetate (300 mL) and washed sequentially with 1N aqueous sodium hydroxide solution (100 mL) and saturated aqueous sodium chloride solution. The organic layer was concentrated and the residue was purified by silica gel column chromatography (eluent ratio: hexane/ethyl acetate = 7:1 to 3:1) to afford the target product 2,6-dichloropyridine-4-methanol (8.3 g, 46.6 mmol). The product was characterized by 1H NMR (300 MHz, CDCl3, 300 K): δ = 7.25 (2H); 4.72 (2H); 2.24 (1H).

References

[1] Journal of the American Chemical Society, 2005, vol. 127, # 29, p. 10124 - 10125
[2] Chemical Communications, 1998, # 15, p. 1567 - 1568
[3] Organic Letters, 2010, vol. 12, # 5, p. 940 - 943
[4] Journal fuer Praktische Chemie (Leipzig), 1938, vol. <2> 151, p. 65,79
[5] Tetrahedron, 2007, vol. 63, # 2, p. 291 - 298

3,5-BIS(METHYLSULFONYL)ANILINE(101990-69-6)Related Product Information

• METHYL 2,6-DICHLOROISONICOTINATE
• 3,5-BIS(METHYLSULFONYL)ANILINE
• 2,6-Dichloropyridine
• 2,3,5,6-Tetrachloropyridine-4-carboxylic acid
• (2,6-DICHLORO-4-PYRIDYL)METHYL THIOPHENE-2-CARBOXYLATE
• 3,5-DICHLOROBENZYL 2,6-DICHLOROISONICOTINATE
• 4-(CYANOMETHYL)PHENYL 2,6-DICHLOROISONICOTINATE
• (2,6-DICHLORO-4-PYRIDYL)METHYL 4-(TERT-BUTYL)BENZOATE
• ETHYL 2-([([(2,6-DICHLOROISONICOTINOYL)OXY]IMINO)(2,6-DICHLOROPHENYL)METHYL]AMINO)ACETATE
• N-[(2,6-DICHLOROISONICOTINOYL)OXY]-2-FURAMIDE
• O2-[(2,6-DICHLORO-4-PYRIDYL)CARBONYL]-5-NITROTHIOPHENE-2-CARBOHYDROXIMAMIDE
• (2,6-DICHLORO-4-PYRIDYL)METHYL 2,6-DICHLOROISONICOTINATE
• 2-[(4-CHLOROBENZYL)THIO]-4-(([(2,6-DICHLOROISONICOTINOYL)OXY]IMINO)METHYL)PYRIMIDINE
• 2-(2,6-DICHLORO-4-PYRIDYL)-5-FLUORO-4H-3,1-BENZOXAZIN-4-ONE
• (2,6-DICHLORO-4-PYRIDYL)METHYL N,N-DIMETHYLCARBAMATE
• O4-[(2,6-DICHLORO-4-PYRIDYL)CARBONYL]-3-(2,6-DICHLOROPHENYL)-5-METHYLISOXAZOLE-4-CARBOHYDROXIMAMIDE
• 2-CHLORO-4-FLUOROPHENYL 2,6-DICHLOROISONICOTINATE
• 2-ACETYLPHENYL 2,6-DICHLOROISONICOTINATE