tert-Butylsulfinamide, (R)-(+)-
(R)-2-METHYLPROPANE-2-SULFINAMIDE · (R)-TERT-BUTANESULFINAMIDE · (R)-N-tert-Butanesulfinamide · (R)-2-METHYL-2-PROPANESULFINAMIDE · (R)-(+)-TERT-BUTYLSULFINAMIDE · Trityl glycidyl ether · (R)-(+)-TERT-BUTANESULFINAMIDE · DASO-002
Identifiers & Physical Properties
| CAS No. | 196929-78-9 |
|---|---|
| Molecular formula | C4H11NOS |
| Average molar mass | 121.2 g/mol |
| Monoisotopic mass | 121.05613497 g/mol |
| SMILES | CC(C)(C)[S@](N)=O |
| InChIKey | CESUXLKAADQNTB-SSDOTTSWSA-N |
| PubChem CID | 10964479 |
| EC No. | 676-338-3 |
| DTXSID | DTXSID40449939 |
Chemical & Physical Properties
| XLogP | 0 |
|---|---|
| Topological polar surface area | 62.3 |
| Hydrogen bond donors | 1 |
| Hydrogen bond acceptors | 3 |
| Rotatable bonds | 1 |
| Heavy atoms | 7 |
| Formal charge | 0 |
| Complexity | 84.2 |
| 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 conditions | 2-8°C |
| Solubility | Soluble in chloroform, methanol, tetrahydrofuran, dichloromethane, dimethyl sulfoxide and most organic solvents. |
| pKa (acidity coefficient) | 10.11±0.50(Predicted) |
| Physical state | Powder |
| Color | White, light pink, light yellow to brown |
| optical activity | [α]22/D +1.0°, c = 0.5% in chloroform |
| Stability | store cold |
| InChI | 1S/C4H11NOS/c1-4(2,3)7(5)6/h5H2,1-3H3/t7-/m1/s1 |
| InChIKey | CESUXLKAADQNTB-SSDOTTSWSA-N |
| SMILES | CC(C)(C)S(N)=O |
| CAS DataBase Reference | 196929-78-9(CAS DataBase Reference) |
| FDA UNII | 7FEC1T720F |
| UNSPSC Code | 12352111 |
| NACRES | NA.22 |
| GHS pictogram | GHS02,GHS07,GHS08 |
| Signal word | Danger |
| GHS hazard statements | H225-H302-H319-H335-H351 |
| GHS precautionary statements | P210-P280-P301+P312+P330-P305+P351+P338-P370+P378-P403+P235 |
| Personal protective equipment (PPE) | Eyeshields, Gloves, type N95 (US) |
| Hazard symbols | Xi,Xn,F |
| Risk statements (R) | 11-19-36/37-40-36/37/38 |
| Safety statements (S) | 22-24/25-36/37-26-16-36/37/39 |
| UN transport number | UN 2056 3 / PGII |
| Water hazard class (WGK) | 3 |
| Hazard Note | Irritant/Keep Cold |
| TSCA inventory status | No |
| Customs code | 29309090 |
| Storage class | 11 - Combustible Solids |
| REACH registrations | Active |
Safety & Regulations
| GHS classification | This chemical does not meet GHS hazard criteria for 33.3% (4 of 12) of reports.WarningH315 (66.7%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 12 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatory information | Status: Active Update: 04-12-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/30159 |
| Hazard Classes and Categories | Skin Irrit. 2 (66.7%) |
| Personal protective equipment (PPE) | Eyeshields, Gloves, type N95 (US) |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | No |
| UN transport number | UN 2056 3 / PGII |
| Customs code | 29309090 |
| Risk statements (R) | 11-19-36/37-40-36/37/38 |
| Signal word | Danger |
| GHS pictogram | GHS02,GHS07,GHS08 |
| Hazard symbols | Xi,Xn,F |
| hazard_note | Irritant/Keep Cold |
| Safety statements (S) | 22-24/25-36/37-26-16-36/37/39 |
| Storage class | 11 - Combustible Solids |
| GHS hazard statements | H225-H302-H319-H335-H351 |
| REACH registrations | Active |
| GHS precautionary statements | P210-P280-P301+P312+P330-P305+P351+P338-P370+P378-P403+P235 |
Applications & Uses
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 & Synthesis
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%