2-Methylpropane-2-sulfinamide

Base Information

• Chemical Name: 2-Methylpropane-2-sulfinamide
• CAS No.: 343338-28-3
• Molecular Formula: C3H11CNOS
• Molecular Weight: 121.203
• Hs Code.: 29309090
• European Community (EC) Number: 926-811-8,619-964-4
• UNII: 42F4K704G0,I85YC2ZA8O,7FEC1T720F
• DSSTox Substance ID: DTXSID20391967,DTXSID90463241
• Nikkaji Number: J796.219C
• Wikipedia: Tert-Butanesulfinamide
• Wikidata: Q7705231
• Mol file: 343338-28-3.mol

Synonyms:tert-butanesulfinamide

Chemical Property of 2-Methylpropane-2-sulfinamide

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0.322mmHg at 25°C
• Melting Point: 97-101 °C(lit.)
• Refractive Index: 1.493
• Boiling Point: 220 °C at 760 mmHg
• PKA: 10.11±0.50(Predicted)
• Flash Point: 86.8 °C
• PSA: 62.30000
• Density: 1.124 g/cm³
• LogP: 1.97330
• Storage Temp.: Keep Cold
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 0
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 121.05613515
• Heavy Atom Count: 7
• Complexity: 84.2

Purity/Quality:

99% ^*data from raw suppliers

(S)-tert-Butylsulfinamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn,F
• Statements: 11-19-36/37-40
• Safety Statements: 16-26-36/37-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)S(=O)N
• 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 powde
• Uses: It is also employed as a reagent for synthesizing chiral amines. (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.

Technology Process of 2-Methylpropane-2-sulfinamide

There total 9 articles about 2-Methylpropane-2-sulfinamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

2-Methyl-propane-2-sulfinic acid (1R,2S)-1-(2,4,6-trimethyl-benzenesulfonylamino)-indan-2-yl ester (861821-86-5) → (S)-2-methylpropane-2-sulfinamide (343338-28-3)

Guidance literature:

With lithium amide; ammonia; In tetrahydrofuran; at -78 ℃;

DOI:10.1016/j.tet.2005.03.122

Reference yield: 90.0%

2-Methyl-propane-2-sulfinic acid (1R,2S)-1-phenyl-2-(toluene-4-sulfonylamino)-propyl ester (594836-47-2) → N-((1R,2S)-1-hydroxy-1-phenylpropan-2-yl)-4-methylbenzene sulfonamide (108591-33-9) + (S)-2-methylpropane-2-sulfinamide (343338-28-3)

Guidance literature:

With ammonia; lithium; ferric nitrate; In tetrahydrofuran; at -78 - -45 ℃;

DOI:10.1016/j.tet.2005.03.122

Reference yield: 84.0%

(SS)-((1R,2S)-N-methylephedrine) tert-butanesulfinate → (S)-2-methylpropane-2-sulfinamide (343338-28-3)

Guidance literature:

With Iron(III) nitrate nonahydrate; lithium amide; ammonia; In tetrahydrofuran; at -78 - -45 ℃; for 1.33333h; optical yield given as %ee;

DOI:10.1016/j.tetlet.2009.03.020

upstream raw materials:

2-Methyl-propane-2-sulfinic acid (1R,2S)-1-(2,4,6-trimethyl-benzenesulfonylamino)-indan-2-yl ester

di-tert-butyl disulfide

2-Methyl-propane-2-sulfinic acid (1R,2S)-1-(2,4,6-trimethyl-benzenesulfonylamino)-indan-2-yl ester

2-Methyl-propane-2-sulfinic acid (1R,2S)-1-phenyl-2-(toluene-4-sulfonylamino)-propyl ester

Downstream raw materials:

(S)-2-methyl-propane-2-sulfinic acid 1-(4-nitrophenyl)-meth-(E)-ylideneamide

2-Methyl-propane-2-sulfinic acid [(R)-3-methyl-cyclohex-(Z)-ylidene]-amide

(E)-(S)-2-methyl-propane-2-sulfinic acid [(E)-3-phenyl-prop-2-enylidene]-amide

(S)-2-methyl-propane-2-sulfinic acid 1-(4-trifluoromethyl-phenyl)-meth-(E)-ylideneamide

Refernces

• 1、 -. "Method of synthesizing enantiomerically pure tert-butanesulfinamide". Paragraph 0060. . Retrieved 2018/09/11.
• 2、 -. "Method for preparing pure enantio-methylpropane-2-sulfinamide". Paragraph 0015; 0041; 0058; 0060. . Retrieved 2018/10/19.