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273910

Sigma-Aldrich

N,N-Dimethyl-L-phenylalanine

99%

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Synonym(s):
(2S)-2-(Dimethylamino)-3-phenylpropanoic acid, N,N-Dimethylphenylalanine
Linear Formula:
C6H5CH2CH[N(CH3)2]CO2H
CAS Number:
Molecular Weight:
193.24
Beilstein/REAXYS Number:
2966581
MDL number:
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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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1 of 4

This Item
147966857459P5482
vibrant-m

273910

N,N-Dimethyl-L-phenylalanine

-
vibrant-m

147966

DL-Phenylalanine

-
vibrant-m

857459

N-Acetyl-L-phenylalanine

-
vibrant-m

P5482

L-Phenylalanine

Premium Grade
form

powder

form

powder, crystals or granules

form

powder

form

powder

Quality Level

100

Quality Level

200

Quality Level

100

Quality Level

300

optical activity

[α]20/D +77°, c = 1.3 in H2O

optical activity

-

optical activity

[α]22/D +40.0°, c = 1 in methanol

optical activity

-

mp

225-227 °C (lit.)

mp

266-267 °C (dec.) (lit.)

mp

171-173 °C (lit.)

mp

270-275 °C (dec.) (lit.)

reaction suitability

reaction type: solution phase peptide synthesis

reaction suitability

reaction type: solution phase peptide synthesis

reaction suitability

reaction type: C-H Activation, reaction type: solution phase peptide synthesis, reagent type: ligand
reaction type: Peptide Synthesis

reaction suitability

-

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Synthesis of 5-(3-indolyl) oxazole natural products. Structure revision of Almazole D.
Miyake F, et al.
Tetrahedron, 66(26), 4888-4893 (2010)
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)
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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