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

(R)-(+)-2-Methyl-2-propanesulfinamide Basic information

Product Name:	(R)-(+)-2-Methyl-2-propanesulfinamide
Synonyms:	R- tert butyl sulfenaMide;(R)-(+)-TERT-BUTANESULFINAMIDE;(R)-TERT-BUTANESULFINAMIDE;(R)-(+)-T-BUTANESULFINAMIDE;(R)-(+)-T-BUTYLMETHYLSULFINAMIDE;(R)-(+)-T-BUTYLSULFINAMIDE;(R)-(+)-TERT-BUTYLSULFINAMIDE;(R)-(+)-TERT-BUTYL SULPHINAMIDE
CAS:	196929-78-9
MF:	C4H11NOS
MW:	121.2
EINECS:	676-338-3
Product Categories:	organosulfur compound;chiral;blocks;BuildingBlocks;Heterocyclic Compounds;CHIRAL COMPOUNDS;Sulfonamides;Asymmetric Synthesis;Sulfur Compounds (for Synthesis);Synthetic Organic Chemistry;CHIRAL CHEMICALS;Sulfur Compounds;Chiral Compound;Amines;Chiral Reagents;Intermediates;Sulfur & Selenium Compounds;Asymmetric Synthesis;Chiral Auxiliaries;Sulfur-Based
Mol File:	196929-78-9.mol

(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)
Fp	-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 Information

Provider	Language
SigmaAldrich	English

(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	(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.
Uses	Chiral ligand used in pharmaceutical compositions
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.

(R)-(+)-2-Methyl-2-propanesulfinamide Preparation Products And Raw materials

Raw materials

Hydrochloric acid-->Ethyl acetate-->Methanol-->Diethyl ether-->Sulfuric acid-->Tetrahydrofuran-->Dichloromethane-->Thionyl chloride-->PETROLEUM ETHER-->Potassium carbonate-->Sodium sulfate-->Triethylamine-->Ammonia-->Hydrogen peroxide-->Palladium-->Ammonium chloride-->Magnesium-->Sulfur dioxide-->Lithium-->2-Chloro-2-methylpropane-->L-1-Phenylethylamine-->Vanadyl acetylacetonate-->(R)-(+)-1-Phenylethylamine-->Ferric nitrate-->3,5-Di-tert-butylsalicylaldehyde-->(S)-TERT-LEUCINOL-->Di-tert-butyl disulfide

Methylparaben Methyl 4-tert-Butylcatechol 4-tert-Butylphenol Bensulfuron methyl tert-Butyl methyl ether Parathion-methyl tert-Butyldimethylsilyl chloride tert-Butyl hydroperoxide Methyl 4-tert-butylbenzoate 2-tert-Butylphenol tert-Butylbenzene Kresoxim-methyl Thiophanate-methyl Methyl acrylate Methyl acetate Methyl bromide METSULFURON METHYL

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

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