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712892

Sigma-Aldrich

(S)-(−)-2-(Dibenzylamino)propionaldehyde

97%

Synonym(s):

(S)-2-(Dibenzylamino)propanal, N,N-Dibenzyl-L-alaninal

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About This Item

Empirical Formula (Hill Notation):
C17H19NO
CAS Number:
111060-63-0
Molecular Weight:
253.34
Beilstein:
4293933
MDL number:
MFCD11053600
UNSPSC Code:
12352114
PubChem Substance ID:
329763158
NACRES:
NA.22

Assay

96.5-103.5% (NT)
97%

form

crystals

optical activity

[α]/D -36.0±2.0°, c = 1 in ethanol

functional group

aldehyde
amine
phenyl

storage temp.

2-8°C

SMILES string

C[C@@H](C=O)N(Cc1ccccc1)Cc2ccccc2

InChI

1S/C17H19NO/c1-15(14-19)18(12-16-8-4-2-5-9-16)13-17-10-6-3-7-11-17/h2-11,14-15H,12-13H2,1H3/t15-/m0/s1

InChI key

GFYXFRCVQSKSDO-HNNXBMFYSA-N

Application

(S)-(-)-2-(Dibenzylamino)propionaldehyde can be employed as a building block for the preparation of:
  • Linezolid dipeptide derivatives and 3-oxazolidin-2-one analogs.
  • (2R,3S)-3-Dibenzylamine-1-nitrobutan-2-ol by reacting with bromonitromethane via nitro-aldol reaction using SmI2 as a catalyst.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H317

Hazard Classifications

Acute Tox. 4 Oral - Skin Sens. 1

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
BGBB8588
1436351V
1436351

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Efficient nitro-aldol reaction using SmI2: A new route to nitro alcohols under very mild conditions
Concellon J, et al.
The Journal of Organic Chemistry, 71(20), 7919-7922 (2006)
Design, synthesis and evaluation of the antibacterial activity of new Linezolid dipeptide-type analogues
Garcia-Olaiz GD, et al.
Bioorganic Chemistry, 95, 103483-103483 (2020)
Antibacterial activity of new oxazolidin-2-one analogues in methicillin-resistant Staphylococcus aureus strains
Cordova-Guerrero, et al.
International Journal of Molecular Sciences, 15(4), 5277-5291 (2014)

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