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464015

Sigma-Aldrich

(S)-(+)-2-Benzyl-1-(p-tolylsulfonyl)aziridine

98%

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Synonym(s):
(S)-2-Benzyl-1-tosylaziridine
Empirical Formula (Hill Notation):
C16H17NO2S
CAS Number:
62596-64-9
Molecular Weight:
287.38
MDL number:
MFCD00799479
UNSPSC Code:
12352005
PubChem Substance ID:
24870129
NACRES:
NA.22

Assay

98%

optical activity

[α]20/D +8.8°, c = 1.3 in toluene

mp

92-94 °C (lit.)

SMILES string

Cc1ccc(cc1)S(=O)(=O)N2C[C@@H]2Cc3ccccc3

InChI

1S/C16H17NO2S/c1-13-7-9-16(10-8-13)20(18,19)17-12-15(17)11-14-5-3-2-4-6-14/h2-10,15H,11-12H2,1H3/t15-,17?/m0/s1

InChI key

ISURUORMAKCTFF-MYJWUSKBSA-N

Application

(S)-(+)-2-Benzyl-1-(p-tolylsulfonyl)aziridine can be used:
  • To prepare tert-butyl(S)-6-((4-methylphenyl)sulfonamido)-3-oxo-7-phenylheptanoate, an intermediate for the synthesis of substituted octahydroindoles.
  • In the preparation of ortho-bromo phenethylamine products, which are further used to synthesize chiral 2-substituted indolines.
  • In the synthesis of β-aryltelluro amines as potent carbonic anhydrase inhibitors.

(S)-(+)-2-Benzyl-1-(p-tolylsulfonyl)aziridine may be used in the preparation of (R)-ethyl (5-benzyl-2-oxo-1-tosyl)pyrrolidine-3-carboxylate by reacting with diethyl potassiomalonate.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Hazard Classifications

Acute Tox. 4 Oral

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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First evaluation of organotellurium derivatives as carbonic anhydrase I, II, IV, VII and IX inhibitors
Angeli A, et al.
Bioorganic Chemistry, 76(17), 268-272 (2018)
Stereochemical studies. 44. Exploitation of the new synthetic scheme for chiral additives usable in asymmetric syntheses. Novel syntheses of optically active. GAMMA.-amino acids and pyrrolidines from L-a-amino acids.
Tseng CC, et al.
Chemical & Pharmaceutical Bulletin, 25(1), 29-40 (1977)
Asymmetric Synthesis of Octahydroindoles via a Domino Robinson Annulation/5-Endo Intramolecular Aza-Michael Reaction
Parra C, et al.
The Journal of Organic Chemistry, 81(21), 10172-10179 (2016)
Ring opening of aziridines with ortho-bromophenyl metal reagents: synthesis of 2-substituted indolines
Michaelis DJ and Dineen TA
Tetrahedron Letters, 50(17), 1920-1923 (2009)

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