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4-Nitro-3-phenyl-L-alanine

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4-Nitro-3-phenyl-L-alanine Basic information

Product Name:
4-Nitro-3-phenyl-L-alanine
Synonyms:
  • H-L-Phe(4-NH2)-OH*1.5H2O
  • 4-NITRO-L-PHENYLALALANINE HYDRATE
  • 4-Nitro-L-Phenylalanine, p-Nitro-L-Phenylalanine
  • (S)-α-Amino-4-nitrobenzenepropionic acid
  • 4-Nitro-L-phenylalanine ,98%
  • 4-Nitro-3-phenyl-L-a
  • DL-4-NO2-Phe-OH 4-Nitro-L-Phenylalanine
  • 4-L-Nitrophenylalanine
CAS:
949-99-5
MF:
C9H10N2O4
MW:
210.19
EINECS:
213-446-8
Product Categories:
  • Phenylalanine analogs and other aromatic alpha amino acids
  • Amino ACIDS SERIES
  • Amino Acids
  • Phenylalanine [Phe, F]
  • chiral
Mol File:
949-99-5.mol
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4-Nitro-3-phenyl-L-alanine Chemical Properties

Melting point:
236-239°C (dec.)
Boiling point:
414.1±35.0 °C(Predicted)
Density 
1.408±0.06 g/cm3(Predicted)
storage temp. 
Keep in dark place,Inert atmosphere,Room temperature
solubility 
Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
form 
Powder
pka
2.12±0.10(Predicted)
Appearance
Off-white to light brown Solid
InChI
InChI=1S/C9H10N2O4/c10-8(9(12)13)5-6-1-3-7(4-2-6)11(14)15/h1-4,8H,5,10H2,(H,12,13)/t8-/m0/s1
InChIKey
GTVVZTAFGPQSPC-QMMMGPOBSA-N
SMILES
C(O)(=O)[C@H](CC1=CC=C([N+]([O-])=O)C=C1)N
CAS DataBase Reference
949-99-5(CAS DataBase Reference)
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Safety Information

Hazard Codes 
Xn,C,F
Risk Statements 
36/37/38-22-34-11
Safety Statements 
26-36/37/39-22-45-16
RIDADR 
2811
RTECS 
AY7400000
Hazard Note 
Harmful
HS Code 
29224999

MSDS

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4-Nitro-3-phenyl-L-alanine Usage And Synthesis

Chemical Properties

white to light yellow crystal powde

Uses

4-Nitro-L-phenylalanine is used in the studies on the rational manipulation of protein structures for the expansion of the genetic code with non natural amino acids into protein via in vitro translation.

Synthesis

63-91-2

949-99-5

General steps: 1. dissolve L-phenylalanine (16.5 g, 100 mmol) in 85% sulfuric acid (50 ml). 2. under stirring conditions, add slowly and dropwise a pre-prepared and cooled to room temperature acid mixture of concentrated nitric acid and concentrated sulfuric acid (1.4:1.1 by volume). 3. Stir the reaction mixture continuously for 5 hours at room temperature. 4. The pH of the reaction solution was adjusted to 2-3 using 40% sodium hydroxide solution, at which time a large amount of precipitate was formed. 5. Collect the precipitate by filtration and wash with deionized water until the filtrate is neutral. 6. 6. Dry the precipitate under reduced pressure to obtain 4-nitro-L-phenylalanine (20 g, yield 95.2%).

References

[1] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 8, p. 3118 - 3125
[2] Patent: US2009/247470, 2009, A1. Location in patent: Page/Page column 12
[3] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 18, p. 5352 - 5360
[4] Russian Journal of Organic Chemistry, 2016, vol. 52, # 11, p. 1681 - 1685
[5] Zh. Org. Khim., 2016, vol. 52, # 11, p. 1686 - 1690,5

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