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Merck
CN

213853

α-Acetamidocinnamic acid

98%

Synonym(s):

N-Acetyldehydrophenylalanine

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About This Item

Linear Formula:
C6H5CH=C(NHCOCH3)COOH
CAS Number:
5469-45-4
Molecular Weight:
205.21
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24852809
EC Number:
226-795-6
Beilstein/REAXYS Number:
1912549
MDL number:
MFCD00008680

Key Documents

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Product Name

α-Acetamidocinnamic acid, 98%

InChI key

XODAOBAZOQSFDS-YFHOEESVSA-N

InChI

1S/C11H11NO3/c1-8(13)12-10(11(14)15)7-9-5-3-2-4-6-9/h2-7H,1H3,(H,12,13)(H,14,15)/b10-7-

SMILES string

CC(=O)N\C(=C/c1ccccc1)C(O)=O

assay

98%

mp

188-190 °C (lit.)

solubility

methanol: soluble 100 mg/mL, clear, yellow-green
95% ethanol: soluble 5%, clear, yellow

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General description

Asymmeteric hydrogenation of α-acetamidocinnamic acid with chiral rhodium (I) complexes on charcoal has been reported. α-Acetamidocinnamic acid undergoes asymmetric hydrogenation in ionic liquid catalyzed by rhodium complex to yield (S)-phenylalanine.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000021717
0000001890
BGBC2878V
014231/1V
BCBB1904V

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Asymmetric hydrogenation of a-acetamidocinnamic acid with chiral rhodium complexes of DIOP and BPPM on charcoal.
Masami I, et al.
Chemical & Pharmaceutical Bulletin, 31(10), 3371-3376 (1983)
Choong Eui Song
Chemical communications (Cambridge, England), 9(9), 1033-1043 (2004-04-30)
Recent developments in the enantioselective chemo- and bio-catalysis in ionic liquids are reviewed. In many cases, the use of ionic liquids provides many advantages over reactions in conventional organic solvents in terms of activity, enantioselectivity, stability and the reusability of

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