tert-Butanesulfinamide
Description- Product Name
- tert-Butanesulfinamide
- CAS No.
- 146374-27-8
- Chemical Name
- tert-Butanesulfinamide
- Synonyms
- 2-METHYL-2-PROPANESULFINAMIDE;(S)-tert-Butanesulfinamide;2-METHYL-PROPANE-2-SULFINIC ACID AMIDE;T-BUTYLSULFINAMIDE;Methyl-2-propanesulfinaMide;S-(-)-2-Methyl-2-propanesulfinamide;tert-ButanesuL;(S)-(C4H11NOS-);ert-Butylsulfinamide;TERT-BUTYLSULPHINAMIDE
- CBNumber
- CB7209954
- Molecular Formula
- C4H11NOS
- Formula Weight
- 121.2
- MOL File
- 146374-27-8.mol
tert-Butanesulfinamide Property
- 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
- WGK Germany
- 3
- HS Code
- 29309090
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P271Use only outdoors or in a well-ventilated area.
P280Wear protective gloves/protective clothing/eye protection/face protection.
N-Bromosuccinimide Price
- Product number
- 560871
- Product name
- 2-Methyl-2-propanesulfinamide
- Purity
- 97%, racemic
- Packaging
- 5g
- Price
- $121.6
- Updated
- 2025/07/31
- Product number
- 560871
- Product name
- 2-Methyl-2-propanesulfinamide
- Purity
- 97%, racemic
- Packaging
- 1g
- Price
- $25
- Updated
- 2023/06/20
- Product number
- B2926
- Product name
- tert-Butylsulfinamide
- Purity
- >97.0%(GC)
- Packaging
- 1g
- Price
- $18
- Updated
- 2025/07/31
- Product number
- B2926
- Product name
- tert-Butylsulfinamide
- Purity
- >97.0%(GC)
- Packaging
- 5g
- Price
- $54
- Updated
- 2025/07/31
- Product number
- 560871
- Product name
- 2-Methyl-2-propanesulfinamide
- Purity
- 97%, racemic
- Packaging
- 25g
- Price
- $473
- Updated
- 2025/07/31
tert-Butanesulfinamide Chemical Properties,Usage,Production
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
Synthesis
31562-43-3
146374-27-8
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
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View Lastest Price from tert-Butanesulfinamide manufacturers
- Product
- tert-Butanesulfinamide 146374-27-8
- Price
- US $10.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 10 mt
- Release date
- 2025-03-11
- Product
- tert-Butanesulfinamide 146374-27-8
- Price
- US $0.00-0.00/kg
- Min. Order
- 1kg
- Purity
- 98%
- Supply Ability
- 1Ton
- Release date
- 2022-09-29
- Product
- tert-Butanesulfinamide 146374-27-8
- Price
- US $0.00-0.00/KG
- Min. Order
- 5mg
- Purity
- 99% HPLC
- Supply Ability
- 2000tons
- Release date
- 2019-12-30