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Merck
CN

278750

(1R,2S,5R)-(−)-Menthyl (S)-p-toluenesulfinate

98%

Synonym(s):

(−)-(1R)-Menthyl (S)-p-toluenesulfinate, (S)-(−)-Menthyl p-toluenesulfinate

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About This Item

Empirical Formula (Hill Notation):
C17H26O2S
CAS Number:
1517-82-4
Molecular Weight:
294.45
NACRES:
NA.22
PubChem Substance ID:
24856828
UNSPSC Code:
12352000
Beilstein/REAXYS Number:
3207468
Assay:
98%
Form:
solid

Key Documents

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InChI

1S/C17H26O2S/c1-12(2)16-10-7-14(4)11-17(16)19-20(18)15-8-5-13(3)6-9-15/h5-6,8-9,12,14,16-17H,7,10-11H2,1-4H3/t14-,16+,17-,20+/m1/s1

SMILES string

C[C@@H]1CC[C@@H](C(C)C)[C@@H](C1)OS(=O)c2ccc(C)cc2

InChI key

NQICGNSARVCSGJ-ASKNOMKYSA-N

assay

98%

form

solid

optical activity

[α]20/D −195°, c = 2 in acetone

mp

102-104 °C (lit.)

functional group

sulfinic acid

storage temp.

−20°C

General description

(1R,2S,5R)-(-)-Menthyl (S)-p-toluenesulfinate is mainly used for the introduction of p-toluenesulfinyl group in asymmetric synthesis.

Application

(1R,2S,5R)-(-)-Menthyl (S)-p-toluenesulfinate can react with:
  • metal ketimines to form enantiopure sulfinimines
  • p-(methylthio)benzaldehyde to form (S)-(-)-N-(4-methylthiobenzylidene)-p-toluenesulfinimine

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
BCBW9869
BCBW6721
BCBB6259V
BCBB8117V
BCBB6259

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Asymmetric synthesis and properties of sulfinimines (thiooxime S-oxides).
Davis FA, et al.
The Journal of Organic Chemistry, 62(8), 2555-2563 (1997)
Asymmetric synthesis of the antibiotic (+)-thiamphenicol using cis-N-(p-toluenesulfinyl) aziridine 2-carboxylic acids
Davis FA and Zhou P.
Tetrahedron Letters, 35(41), 7525-7528 (1994)

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