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273910

Sigma-Aldrich

N,N-Dimethyl-L-phenylalanine

99%

Synonym(s):

(2S)-2-(Dimethylamino)-3-phenylpropanoic acid, N,N-Dimethylphenylalanine

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About This Item

Linear Formula:
C6H5CH2CH[N(CH3)2]CO2H
CAS Number:
17469-89-5
Molecular Weight:
193.24
Beilstein:
2966581
MDL number:
MFCD00082539
UNSPSC Code:
12352200
eCl@ss:
32160406
PubChem Substance ID:
24856552
NACRES:
NA.22

Quality Level

100

Assay

99%

form

powder

optical activity

[α]20/D +77°, c = 1.3 in H2O

reaction suitability

reaction type: solution phase peptide synthesis

mp

225-227 °C (lit.)

application(s)

peptide synthesis

SMILES string

CN(C)[C@@H](Cc1ccccc1)C(O)=O

InChI

1S/C11H15NO2/c1-12(2)10(11(13)14)8-9-6-4-3-5-7-9/h3-7,10H,8H2,1-2H3,(H,13,14)/t10-/m0/s1

InChI key

HOGIQTACRLIOHC-JTQLQIEISA-N

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Application

N,N-Dimethyl-L-phenylalanine is commonly used to prepare Cu(II)-L-amino acid complex, which is a chiral mobile phase additive for the resolution of enantiomers. It can also be used in the total synthesis of (−)-paliurine E and almazole D.

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Non-ionic surfactant modified ligand exchange chromatography using copper (II) complex of N, N-dimethyl-l-phenylalanine as the chiral additive for enantioselective amino acids separation.
Dimitrova P and Bart H J
Analytica Chimica Acta, 663(1), 109-116 (2010)
Total Synthesis of the Cyclopeptide Alkaloid Paliurine E. Insights into Macrocyclization by Ene? Enamide RCM.
Toumi M, et al.
The Journal of Organic Chemistry, 73(4), 1270-1281 (2008)
Synthesis of 5-(3-indolyl) oxazole natural products. Structure revision of Almazole D.
Miyake F, et al.
Tetrahedron, 66(26), 4888-4893 (2010)
Different approaches of impregnation for resolution of enantiomers of atenolol, propranolol and salbutamol using Cu (II)-l-amino acid complexes for ligand exchange on commercial thin layer chromatographic plates.
Bhushan R and Tanwar S
Journal of Chromatography A, 1217(8), 1395-1398 (2010)

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