4-Cyano-L-Phenylalanine

Base Information

• Chemical Name: 4-Cyano-L-Phenylalanine
• CAS No.: 167479-78-9
• Molecular Formula: C10H10N2O2
• Molecular Weight: 190.202
• Hs Code.: 2926909090
• European Community (EC) Number: 640-517-4
• DSSTox Substance ID: DTXSID30937335
• Nikkaji Number: J1.088.885I
• Wikidata: Q27454596
• Mol file: 167479-78-9.mol

Synonyms:4-cyano-L-phenylalanine;p-cyanophenylalanine

Chemical Property of 4-Cyano-L-Phenylalanine

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 6.43E-07mmHg at 25°C
• Melting Point: -243oC
• Refractive Index: 1.595
• Boiling Point: 394.1 °C at 760 mmHg
• PKA: 2.13±0.10(Predicted)
• Flash Point: 192.1 °C
• PSA: 87.11000
• Density: 1.28 g/cm³
• LogP: 1.21298
• Storage Temp.: -15°C
• Water Solubility.: Slightly soluble in water.
• XLogP3: -1.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 190.074227566
• Heavy Atom Count: 14
• Complexity: 248

Purity/Quality:

98%,99%, ^*data from raw suppliers

4-Cyano-L-phenylalanine 99+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1CC(C(=O)O)N)C#N
• Isomeric SMILES: C1=CC(=CC=C1C[C@@H](C(=O)O)N)C#N
• Uses: 4-Cyano-L-phenylalanine used as a intermediate in organic synthesis, pharmaceutical, chemical research and biochemical application.

Technology Process of 4-Cyano-L-Phenylalanine

There total 7 articles about 4-Cyano-L-Phenylalanine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 70.7%

N-acetyl-4-cyano-D,L-phenylalanine (146664-08-6,193270-06-3) → (S)-4-Cyanophenylalanine (167479-78-9)

Guidance literature:

With lithium hydroxide; for 56h; porcine kidney acylase, pH 7.2-7.5;

DOI:10.1021/jm950112e

Reference yield: 58.0%

3-(4-cyanophenyl)acrylic acid (18664-39-6) → (S)-4-Cyanophenylalanine (167479-78-9)

Guidance literature:

With ammonium hydroxide; borane-ammonia complex; In aq. buffer; at 37 ℃; pH=9.6; Reagent/catalyst; Enzymatic reaction;

DOI:10.1002/anie.201410670

Reference yield:

4-cyanobenzyl bromide (17201-43-3) → (S)-4-Cyanophenylalanine (167479-78-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: KI; NaOEt / dioxane / Heating

1.2: aq. NaOH / Heating

2.1: acylase / H₂O / 36 °C / pH 6.5

With acylase; sodium ethanolate; potassium iodide; In 1,4-dioxane; water; 1.1: Condensation / 1.2: Hydrolysis / 2.1: Deacetylation;

DOI:10.1016/S0960-894X(99)00412-6

upstream raw materials:

N-acetyl-4-cyano-D,L-phenylalanine

para-methylbenzonitrile

4-cyanobenzyl bromide

N-acetyl-4-cyano-α-(ethoxycarbonyl)phenylalanine ethyl ester

Downstream raw materials:

(S)-2-((tert-butoxycarbonyl)amino)-3-(4-cyanophenyl)propanoic acid

(S)-2-allyloxycarbonylamino-3-(4-cyanophenyl)propionic acid

Refernces

• 1、 Weise, Nicholas J.,Parmeggiani, Fabio,Ahmed, Syed T.,Turner, Nicholas J.. "The bacterial ammonia lyase EncP: A tunable biocatalyst for the synthesis of unnatural amino acids". supporting information. p. 12977 - 12983. Retrieved 2015/10/28.
• 2、 Pearson, Daniel A.,Lister-James, John,McBride, William J.,Wilson, David M.,Martel, Lawrence J.,Civitello, Edgar R.,Dean, Richard T.. "Thrombus imaging using technetium-99m-labeled high-potency GPIIb/IIIa receptor antagonists. Chemistry and initial biological studies". . p. 1372 - 1382. Retrieved 2007/10/03.