tert-Butanesulfinamide Chemical Properties

Melting point:

97-101 °C(lit.)

Boiling point:

220.0±23.0 °C(Predicted)

Density 

1.124

storage temp. 

2-8°C

solubility 

Soluble in methanol.

pka

10.11±0.50(Predicted)

form 

Powder or Crystals

color 

White to tan

InChI

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

InChIKey

CESUXLKAADQNTB-UHFFFAOYSA-N

SMILES

CC(C)(S(N)=O)C

CAS DataBase Reference

146374-27-8(CAS DataBase Reference)

Safety Information

WGK Germany 

3

HS Code 

29309090

MSDS

• Language:English Provider:SigmaAldrich

tert-Butanesulfinamide Usage And Synthesis

Description

(S)-tert-Butanesulfinamide (also known as 2-Methyl-2-propanesulfinamide) is used for the synthesis of 4-sulfonyliminopiperidine and its reaction with benzyl Grignard to form an important pharmaceutical building block, 4-benzyl-4-aminopiperidne.It can be also used to prepare spiro tosylaziridines via methylene insertion into the derived sulfonylimine1,2-(R)-(+)-2-Methyl-2-propanesulfinamide may be used to prepare N-(1-cyclohexylmethylidene)-2-methylpropane-2-sulfinamide via copper mediated condensation with cyclohexane carboxaldehyde. It may also be used to prepare (20E)-N-[t-butyl-(R)-sulfinyl]-3β-(t-butyldimethylsilyloxy)-pregn-5-en-20-imine, an intermediate for the development of androgen receptor antagonists. (S)-(-)-2-Methyl-2-propanesulfinamide may be used to develop benzofuran-based farnesyltransferase inhibitors as anti-cancer agents.

Chemical Properties

white to light yellow crystal powde

Uses

(±)-2-Methyl-2-propanesulfinamide is used in the synthesis of 4-sulfonyliminopiperidine and its reaction with benzyl Grignard to form an important pharmaceutical building block, 4-benzyl-4-aminopiperidne. It is also used to prepare spiro tosylaziridines via methylene insertion into the derived sulfonylimine.

Uses

Ellman′s Sulfinamides

Synthesis

1. A solution of 2-methylpropanethiol (14.1 cm3, 125 mmol) in DCM (50 mL) was cooled at -40°C. The solution was then purified and the solution was allowed to cool for 30 minutes. At an interval of 30 min, a suspension (50 mL) of m-chlorobenzoic acid (63.2 g, 256 mmol, 2.05 eq.) was added. Under vigorous stirring (exothermic reaction), a solution of DCM (500 mL) pre-cooled to -78 °C was added in batches. The resulting white suspension was stirred at -30°C overnight, then cooled to -78°C and filtered. The filtrate was concentrated under reduced pressure and dried under high vacuum to give crude tert-butyl sulfinic acid (13.5 g, 88%). 2. Thionyl chloride (40.3 mL, 552.5 mmol, 5 eq.) was added to the above sulfinic acid at -40 °C under nitrogen protection. The yellow solution was slowly warmed to room temperature and stirred for 2 hours. Concentration under high vacuum gave tert-butyl sulfinyl chloride (12.9 g, 83%) as a brown oil. 3. 3. DCM solution of tert-butylsulfinyl chloride (582 mL) was slowly added to ammonia (38% aqueous, 582 mL, 220 mmol, 2.4 eq.) and stirred for 1 hour at room temperature. The aqueous layer was washed with saturated NaCl solution and extracted with DCM (4 x 600 cm3). The organic phases were combined, dried over MgSO? and concentrated under reduced pressure to give tert-butylsulfinamide (9.2 g, 83%) as a white solid which could be recrystallized from hexane. Product characterization: Rf = 0.23 (EtOAc); melting point 103-104 °C [(S)-enantiomer 106 °C (TCI)]; IR (νmax/cm?1) 3231, 2799, 2959, 2928, 2869, 1677, 1570, 1475, 1461, 1364, 1309, 1193, 1132, 1030, 893; 1H NMR (300 MHz, CDCl?) δ 1.19 [9H, s, C(CH?)? , 3.96 (2H, br s, NH?); 13C NMR (75 MHz, CDCl?) δ 22.1, 55.2; MS (CI+) m/z 139 (M?+1, 800%), 122 (M?+1, 100%).

References

[1] Journal of Organic Chemistry, 1999, vol. 64, # 15, p. 5472 - 5478
[2] Tetrahedron Letters, 2009, vol. 50, # 26, p. 3482 - 3484
[3] Journal of the American Chemical Society, 2005, vol. 127, # 7, p. 2104 - 2113
[4] Journal of Organic Chemistry, 2009, vol. 74, # 7, p. 2646 - 2650
[5] Journal of Organic Chemistry, 2009, vol. 74, # 7, p. 2891 - 2892

tert-Butanesulfinamide(146374-27-8)Related Product Information

• Kresoxim-methyl
• 4-tert-Butylcatechol
• tert-Butyl acetate
• Di-tert-butyl peroxide
• tert-Butyl hydroperoxide
• METSULFURON METHYL
• tert-Butyldimethylsilyl chloride
• tert-Butyl peroxyacetate
• Pirimiphos-methyl
• Methyl acetate
• Methyl 4-tert-butylbenzoate
• 4-tert-Butylphenol
• tert-Butyl methyl ether
• Methyl salicylate
• tert-Butyllithium
• tert-Butanol
• Tribenuron methyl
• Thiophanate-methyl