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693626

Sigma-Aldrich

S-N-(3,5-Di-tert-butylphenyl)-3-methyl-2-(N-formyl-N-methylamino)butanamide

96%

Synonym(s):

Sigamide

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About This Item

Empirical Formula (Hill Notation):
C21H34N2O2
CAS Number:
928789-96-2
Molecular Weight:
346.51
MDL number:
MFCD10565635
UNSPSC Code:
12352002
PubChem Substance ID:
329761605
NACRES:
NA.22

Assay

96%

form

solid

optical activity

[α]22/D -170°, c = 1 in chloroform

mp

180-186 °C

functional group

amide

storage temp.

2-8°C

SMILES string

CC(C)[C@H](N(C)C=O)C(=O)Nc1cc(cc(c1)C(C)(C)C)C(C)(C)C

InChI

1S/C21H34N2O2/c1-14(2)18(23(9)13-24)19(25)22-17-11-15(20(3,4)5)10-16(12-17)21(6,7)8/h10-14,18H,1-9H3,(H,22,25)/t18-/m0/s1

InChI key

OVKNTNIBDGTNQY-SFHVURJKSA-N

Application

Used in the synthesis of chiral 1,2-diarylsubstituted aziridines.[1][2]

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H319

Precautionary Statements

P305 + P351 + P338

Hazard Classifications

Eye Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
15318TH

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Andrei V Malkov et al.
The Journal of organic chemistry, 72(4), 1315-1325 (2007-02-10)
Asymmetric reduction of ketimines 1 with trichlorosilane can be catalyzed by N-methylvaline-derived Lewis-basic formamides 3a-d with high enantioselectivity (< or =95% ee) and low catalyst loading (1-5 mol %) at room temperature in toluene. Appending a fluorous tag, as in
Andrei V Malkov et al.
Organic letters, 6(13), 2253-2256 (2004-06-18)
[reaction: see text] Asymmetric reduction of ketimines 1 with trichlorosilane can be catalyzed by a new N-methyl L-valine derived Lewis basic organocatalyst, such as 4d, with high enantioselectivity. The structure-reactivity investigation suggests hydrogen bonding and arene-arene interactions between the catalyst
Enantioselective synthesis of 1,2-diarylaziridines by the organocatalytic reductive amination of alpha-chloroketones.
Andrei V Malkov et al.
Angewandte Chemie (International ed. in English), 46(20), 3722-3724 (2007-04-07)

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