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N-(tert-Butoxycarbonyl)-L-phenylalanine

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N-(tert-Butoxycarbonyl)-L-phenylalanine Basic information
Product Name:N-(tert-Butoxycarbonyl)-L-phenylalanine
Synonyms:n-[(1,1-dimethylethoxy)carbonyl]-l-phenylalanin;L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-;N-(tert-Butoxycarbonyl)-L-phenylalanine ,98.5%;Boc-L-phenylalanine ,98%;(2S)-2-(tert-Butoxycarbonylamino)-3-phenylpropionic acid;(S)-2-(tert-Butoxycarbonylamino)-3-phenylpropanoic acid;N-(tert-Butyloxycarbonyl)-L-phenylalanine;N-(tert-butoxycarbonyl)-L-phenylalaninal
CAS:13734-34-4
MF:C14H19NO4
MW:265.3
EINECS:237-305-5
Product Categories:Phenylalanine [Phe, F];Boc-Amino Acids and Derivative;Amino Acids;AMINOACIDS DERIVATIVES;Protected Amino Acids;Amino Acids (N-Protected);Biochemistry;Boc-Amino Acids;Boc-Amino acid series;Amino Acids & Derivatives;Aromatics;Inhibitors;1
Mol File:13734-34-4.mol
N-(tert-Butoxycarbonyl)-L-phenylalanine Structure
N-(tert-Butoxycarbonyl)-L-phenylalanine Chemical Properties
Melting point 85-87 °C(lit.)
Boiling point 408.52°C (rough estimate)
density 1.1356 (rough estimate)
refractive index 24.5 ° (C=1, EtOH)
storage temp. Keep in dark place,Sealed in dry,Room Temperature
solubility Soluble in methanol, dichloromethane, dimethylformamide and N-methyl-2-pyrrolidone.
form Fine Crystalline Powder
pka3.88±0.10(Predicted)
color White
Optical Rotation[α]20/D +25±1°, c = 1% in ethanol
BRN 2219729
Major Applicationpeptide synthesis
InChIInChI=1S/C14H19NO4/c1-14(2,3)19-13(18)15-11(12(16)17)9-10-7-5-4-6-8-10/h4-8,11H,9H2,1-3H3,(H,15,18)(H,16,17)/t11-/m0/s1
InChIKeyZYJPUMXJBDHSIF-NSHDSACASA-N
SMILESC(O)(=O)[C@H](CC1=CC=CC=C1)NC(OC(C)(C)C)=O
CAS DataBase Reference13734-34-4(CAS DataBase Reference)
EPA Substance Registry SystemL-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]- (13734-34-4)
Safety Information
Hazard Codes Xn,Xi
Risk Statements 36-22-36/37/38-20/21/22
Safety Statements 39-26-36-24/25
WGK Germany 3
TSCA TSCA listed
HS Code 29242990
Storage Class11 - Combustible Solids
MSDS Information
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N-(tert-Butoxycarbonyl)-L-phenylalanine Usage And Synthesis
Chemical PropertiesN-(tert-Butoxycarbonyl)-L-phenylalanine is white fine crystalline powder
UsesN-(tert-Butoxycarbonyl)-L-phenylalanine is used in enantioselective hydrolysis of amino acid esters. Acts as an inhibitor of gastric acid secretion.
UsesN-Boc-L-phenylalanine is a derivative of Phenylalanine used in enantioselective hydrolysis of amino acid esters.
PreparationSodium hydroxide (4.4 g, 0.11 mol) was placed in a flask, and dissolved in water (110 mL). Phenylalanine (16.5 g, 0.1 mol) was added, the suspension was stirred until a solution was obtained, and then tert-butanol (75 mL) was added. Boc2O (22.3 g, 0.12 mol) was then added with stirring over a period of 1 h, keeping the mixture near 0 ℃. A white precipitate was produced, and at the end of the addition the pH had dropped to 7.5–8.5. The mixture was then carefully acidified by the slow, continuous addition of saturated citric acid to give the product N-tert-butoxycarbonyl-L-phenylalanine (21.5 g, 81%); mp 85℃; [a]21D = t25:5 (c = 1, ethanol).
reaction suitabilityreaction type: Boc solid-phase peptide synthesis
reaction type: C-H Activation
reagent type: ligand
reaction type: Peptide Synthesis
Tag:N-(tert-Butoxycarbonyl)-L-phenylalanine(13734-34-4) Related Product Information
L-Alanine BOC-Glycine Boc-D-Glutamine BOC-MET-ONP BOC-GLU(OME)-OH Boc-L-Pyroglutamic acid methyl ester Boc-L-glutamic acid γ-allyl ester BOC-TYR(ET)-OH BOC-PHE-OSU BOC-4-NITRO-L-PHENYLALANINE BOC-L-4-Chlorophe Boc-N-methyl-L-phenylalanine N-tert-Butoxycarbonyl-L-phenylalanine amide BOC-D-Phenylalanine N-(TERT-BUTOXYCARBONYL)-L-PHENYLALANINE ACID HYDRAZIDE BOC-4-IODO-L-PHENYLALANINE BOC-DL-PHE-OH Boc-4-Amino-L-phenylalanine