(R)-(+)-2-Methyl-2-propanesulfinamide Chemical Properties

Melting point:

103-107 °C(lit.)

alpha 

4 º (c=1, CHCl3 + amylenes)

Boiling point:

220.0±23.0 °C(Predicted)

Density 

0.903 g/mL at 25 °C

refractive index 

4 ° (C=1, CHCl3)

Flash point:

-17℃

storage temp. 

2-8°C

solubility 

Soluble in chloroform, methanol, tetrahydrofuran, dichloromethane, dimethyl sulfoxide and most organic solvents.

pka

10.11±0.50(Predicted)

form 

Powder

color 

White, light pink, light yellow to brown

optical activity

[α]22/D +1.0°, c = 0.5% in chloroform

Stability:

store cold

InChIKey

CESUXLKAADQNTB-SSDOTTSWSA-N

CAS DataBase Reference

196929-78-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn,F

Risk Statements 

11-19-36/37-40-36/37/38

Safety Statements 

22-24/25-36/37-26-16-36/37/39

RIDADR 

UN 2056 3 / PGII

WGK Germany 

3

Hazard Note 

Irritant/Keep Cold

TSCA 

No

HS Code 

29309090

MSDS

• Language:English Provider:SigmaAldrich

(R)-(+)-2-Methyl-2-propanesulfinamide Usage And Synthesis

Chemical Properties

(R)-(+)-2-Methyl-2-propanesulfinamide is white to light yellow crystal powde

Uses

suzuki reaction, useful reagent for synthesizing chiral amines.

Uses

Chiral ligand used in pharmaceutical compositions

Uses

(R)-(+)-2-Methyl-2-propanesulfinamide is a chiral ligand, which is used in pharmaceutical compositions. Further, it is used in the preparation of beta-chloro sulfinamides in the synthesis of chiral azridines. It is involved in the preparation of organocatalyst for enantioselective reduction of imines. It serves as a reagent for synthesizing chiral amines. In addition to this, it is converted into P,N-sulfinyl imine ligands through condensation with aldehydes and ketones which undergoes iridium-catalyzed asymmetric hydrogenation of olefins.

Preparation

Acetic acid (70 g), R-tert-butylsulfinylhydrazine (42 g), zinc powder (60.5 g) and dichloromethane (150 mL) were added to the reaction flask. The temperature was slowly heated to 35-42 °C . After 16 hours, the filtrate was poured into 70 mL water. Dichloromethane (75 g×5) was added for extraction. Collected the organic phase, added 48% NaOH to adjust ρΗ (7-8). Then added NaCl, the layers were separated and the organic phase was washed with 15 g saturated aqueous solution of sodium chloride. The solution was dried over magnesium sulfate. After filterED, filtrate was concentrated under reduced pressure at 25-30 °C until no slipping. N-heptane was replaced, 28 g mixed solvent of N-heptane and toluene (N-heptane: toluene = 6:1) were added to perform beating at low temperature, filtered to obtain (R)-(+)-2-Methyl-2-propanesulfinamide. Yield=83%

References

[1] Qian X, et al. A stereoselective synthesis of (S)-2-(((3-fluoro-4-methylphenoxy)carbonyl)(1-(4-((5-methyl-2-phenyloxazol-4-yl)methoxy)phenyl)ethyl)amino)acetic acid, a highly potent PPAR α/γ dual agonist. Tetrahedron, 2015; 71: 9408-9414.

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