336105-23-8

Basic information

• Product Name: (R)-(-)-N-[(1E)-(4-chlorophenyl)methylene]-2-methyl-2-propanesulfinamide
• Synonyms: (R)-(-)-N-[(1E)-(4-chlorophenyl)methylene]-2-methyl-2-propanesulfinamide
• CAS NO: 336105-23-8
• Molecular Weight: 243.757
• Mol File: 336105-23-8.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (R)-(-)-N-[(1E)-(4-chlorophenyl)methylene]-2-methyl-2-propanesulfinamide(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(-)-N-[(1E)-(4-chlorophenyl)methylene]-2-methyl-2-propanesulfinamide(336105-23-8)
• EPA Substance Registry System: (R)-(-)-N-[(1E)-(4-chlorophenyl)methylene]-2-methyl-2-propanesulfinamide(336105-23-8)

Safety Data

• Hazardous Substances Data: 336105-23-8(Hazardous Substances Data)

Upstream product

• 104-88-1 4-chlorobenzaldehyde 
• 196929-78-9 (R)-2-methylpropane-2-sulfinamide 

Downstream Products

• 163837-57-8 (R)-(4-chlorophenyl)(phenyl)methylamine 
• 163837-32-9 (S)-4-chloro-α-phenyl-benzenemethanamine 
• 439695-64-4 (R(S))-N-((R)-1-(4-chlorophenyl)-1-phenylmethyl)-2-methylpropane-2-sulfinamide 
• 439695-63-3 (R_S,S)-(1-(4-chlorophenyl)-1-phenylmethyl)-2-methylpropanesulfinamide 
• 865355-01-7 2-Methyl-propane-2-sulfinic acid [(1S,2R)-1-(4-chloro-phenyl)-2-hydroxy-3-methyl-butyl]-amide 
• 955941-86-3 (R_S,S)-N-[(1-phenylsulfonyl-1H-indol-2-yl)(p-chlorophenyl)methyl]-tert-butanesulfinylamide 
• 955942-02-6 (R_S,S)-N-[(1-phenylsulfonyl-1H-3-methyl-indol-2-yl)(p-chlorophenyl)methyl]-tert-butanesulfinylamide 
• 955942-03-7 (R_S,S)-N-[(1-phenylsulfonyl-1H-4-nitro-indol-2-yl)(p-chlorophenyl)methyl]-tert-butanesulfinylamide 
• 938463-90-2 C₂₁H₁₉F₂NS 
• 1298087-68-9 C₂₈H₃₉ClN₂O₅SSi 
• 1443323-64-5 (R_S,2R,3R)-N-(tert-butanesulfinyl)-2-(4-chlorophenyl)-3-vinylaziridine 
• 1029701-08-3 pinacol (R)-1-N-sulfinyl-4-chlorophenyl-1-boronate 
• 451503-28-9 (α¹S)-4-chloro-α-phenyl-benzenemethanamine hydrochloride 
• 451503-28-9 (α¹R)-4-chloro-α-phenyl-benzenemethanamine hydrochloride 

Relevant articles and documents

Indium mediated allylation of WteRR-butanesulftnyl imines with 1,3-dibromopropene: Stereoselective synthesis of aziridines

- The reaction of TV-fer?-butanesulfinyl imines 1 with 1,3-dibromopropene (2), in the presence of indium metal, in saturated aqueous solution of sodium bromide, produced bromohomoallylamine derivatives 3 with total facial diastereoselectivity for the imine addition, and moderate yields. These compounds were easily transformed into the corresponding vinyl aziridines 5 upon deprotonation with KHMDS in THF, the intramolecular cyclization taking place in a stereospecific manner in moderate to high yields.

Effective tuning of the arene and alkanesulfinamides for highly enantioselective synthesis of (S)-4-chlorophenylphenylmethylamine, a key intermediate for antihistamic (S)-cetirizine

High diastereoselectivity (>94%) has been achieved in the phenylMgBr addition process to chlorophenyl aldimine derived from the new and sterically hindered triisopropylbenzene sulfinamide (TIPBSA) in the synthesis of a key intermediate of (S)-Cetirizine. Surprisingly, under the same reaction conditions, toluenesulfinamide derived chlorophenyl aldimine provided only 10% ee.

Asymmetric synthesis of cetirizine dihydrochloride

Practical route technology for the preparation of (S)-cetirizine·2HCl via diastereoselective organometallic addition to N-tert-butanesulfinyl aldimines is disclosed.