(S)-(-)-2-Methyl-2-propanesulfinamide Chemical Properties

Melting point:

97-101 °C(lit.)

alpha 

-4.5 º (c=1, CHCl3)

Boiling point:

220.0±23.0 °C(Predicted)

Density 

1.124

storage temp. 

2-8°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

pka

10.11±0.50(Predicted)

form 

Crystalline Powder

color 

White

optical activity

[α]20/D 4.5°, c = 1 in chloroform

Stability:

store cold

InChI

InChI=1/C4H11NOS/c1-4(2,3)7(5)6/h5H2,1-3H3/t7-/s3

InChIKey

CESUXLKAADQNTB-SSDOTTSWSA-N

SMILES

CC(C)([S@@](N)=O)C |&1:3,r|

CAS DataBase Reference

343338-28-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn,F

Risk Statements 

11-19-36/37-40

Safety Statements 

16-26-36/37-24/25

WGK Germany 

3

Hazard Note 

Irritant/Keep Cold

TSCA 

No

HS Code 

29309090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

(S)-(-)-2-Methyl-2-propanesulfinamide Usage And Synthesis

Description

Acid labile protecting groups are important in organic synthesis. The tert‐butyl group is commonly used for protection of a large variety of functional groups, e.g., acids, alcohols, phenols, and sulfonamides. Among them, s-tert-butyl sulfonamide is a chiral ligand used in pharmaceutical compositions. P, n-sulfoxide imine ligands were synthesized by condensation of s-tert-butylsulfonamide with aldehydes and ketones, and they can be used for asymmetric hydrogenation of olefins under iridium catalysis.

Physical properties

white to light yellow crystal powder

Uses

(S)-(-)-2-Methyl-2-propanesulfinamide may be used to develop benzofuran-based farnesyltransferase inhibitors as anti-cancer agents. It may also be used to prepare (20E)-N-[t-butyl-(S)-sulfinyl]-3β-(t-butyldimethylsilyloxy)-pregn-5-en-20-imine, an intermediate for the preparation of androgen receptor antagonists.

Uses

(S)-(-)-2-Methyl-2-propanesulfinamide is used in Suzuki reaction. It is also employed as a reagent for synthesizing chiral amines. It acts as a chiral auxiliary used in an asymmetric synthesis of trifluoroethylamines by conversion of trifluoroacetaldehyde to a chiral imine. It is also involved in the transformation of P,N-sulfinyl imine ligands through condensation with aldehydes and ketones, which can undergo iridium-catalyzed asymmetric hydrogenation of olefins. Further, it serves as a reagent for the preparation of chemicals and pharmaceutical intermediates.

Synthesis

The general procedure for the synthesis of S-tert-butylsulfinamide from (S)-tert-butylsulfinic acid thio-tert-butyl ester was as follows: in the third step, 120 mL of diethoxymethane was added to the reaction flask and the reaction temperature was controlled between -60 °C and -70 °C. Liquid ammonia (23.8 g, 1.40 mol) was slowly added dropwise to 2.6 mL of 2.3 M n-hexyl lithium (0.96 mol) solution, at which point a white solid gradually appeared in the solution. The reaction was maintained at this condition for 0.5 hr. Subsequently, a mixture of (S)-tert-butylsulfinyl tert-butyl thioester (169.8 g, 0.87 mol, 96.5% ee) and ethyl chloride (80.4 g, 1.25 mol) was added dropwise to the above mentioned diethoxymethane solution (which is the solution of the product obtained from the second step of the reaction) and cooled to 0 °C. After the dropwise addition was completed, the reaction was continued under stirring for 1 hour to ensure that the reaction was complete. Upon completion of the reaction, the reaction solution was concentrated to dryness under reduced pressure, 1400 mL of methyl tert-butyl ether was added, and the solvent was removed by filtration through diatomaceous earth and subsequent evaporation. The residue was slurried with 135 mL of n-heptane between -10 °C and 0 °C to afford fine needle-like crystals of S-tert-butylsulfinamide 79.1 g in 75% yield, 99.7% HPLC purity, and an enantiomeric excess value (ee) of 99.4%.

References

[1] Patent: CN106478471, 2017, A. Location in patent: Paragraph 0018; 0019

(S)-(-)-2-Methyl-2-propanesulfinamide(343338-28-3)Related Product Information

• N-BENZYLQUININIUM CHLORIDE
• TERT-BUTYLSULFONAMIDE
• (R)-(+)-2-METHYL-2-PROPANESULFINAMIDE,(R)-2-METHYL-2-PROPANESULFINAMIDE
• Trimethoprim
• tert-Butanol
• Silver sulfate
• Boric acid
• (R)-(+)-4-Isopropyl-2-oxazolidinone
• (R)-(-)-4-Phenyl-2-oxazolidinone
• (4S)-(-)-4-Isopropyl-2-oxazolidinone
• (R)-4-Benzyl-2-oxazolidinone
• (S)-4-Benzyl-2-oxazolidinone
• (S)-(+)-4-Phenyl-2-oxazolidinone
• Di-tert-butylphosphine
• Tri-tert-butylphosphine
• Thionyl chloride
• Triisopropyl borate
• N-ISOPROPYL-2-NITROBENZENESULPHONAMIDE