2-Acetamido-3-phenylacrylic acid

Base Information

• Chemical Name: 2-Acetamido-3-phenylacrylic acid
• CAS No.: 5469-45-4
• Molecular Formula: C₁₁H₁₁NO₃
• Molecular Weight: 205.213
• Hs Code.: 2924299090
• European Community (EC) Number: 226-795-6
• NSC Number: 25333
• Nikkaji Number: J1.052.192K
• Mol file: 5469-45-4.mol

Synonyms:2-acetamido-3-phenylacrylic acid;64590-80-3;5469-45-4;alpha-Acetamidocinnamic acid;2-(ACETYLAMINO)-3-PHENYL-2-PROPENOIC ACID;(E)-2-Acetamido-3-phenylacrylic acid;2-Propenoic acid, 2-(acetylamino)-3-phenyl-, (2E)-;1-Acetamidocinnamic acid;(2E)-2-acetamido-3-phenylprop-2-enoic acid;MFCD00188416;2-Acetylamino-3-phenylprop-2-enoic acid;EINECS 226-795-6;2-(acetylamino)-3-phenylacrylic acid;e-acetylaminocinnamic acid;Cinnamic acid, a-acetamido-;(2E)-2-(acetylamino)-3-phenylprop-2-enoic acid;alpha -acetamidocinnamic acid;alpha-Acetylaminocinnamic Acid;NSC25333;AB6004;AC9153;NSC 25333;NSC-25333;STK667577;(E)-2-Acetamido-3-phenylacrylicacid;AKOS000120829;PS-5302;CS-0094408;CS-0369375;(E)-2-acetamido-3-phenyl-prop-2-enoic acid;A-0205;AE-641/01171036;SR-01000508836;SR-01000508836-1

Chemical Property of 2-Acetamido-3-phenylacrylic acid

Chemical Property:

• Appearance/Colour: Orange-yellow solid.
• Vapor Pressure: 4.39E-09mmHg at 25°C
• Melting Point: 188-190 °C(lit.)
• Refractive Index: 1.605
• Boiling Point: 455.4 °C at 760 mmHg
• PKA: 3.52±0.10(Predicted)
• Flash Point: 229.2 °C
• PSA: 66.40000
• Density: 1.252 g/cm³
• LogP: 1.63910
• Storage Temp.: 2-8°C
• Solubility.: methanol: soluble100mg/mL, clear, yellow-green
• XLogP3: 0
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 205.07389321
• Heavy Atom Count: 15
• Complexity: 278

Purity/Quality:

99% ^*data from raw suppliers

α-Acetamidocinnamic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)NC(=CC1=CC=CC=C1)C(=O)O
• Isomeric SMILES: CC(=O)N/C(=C/C1=CC=CC=C1)/C(=O)O
• Uses: A protein kinase C inhibitor test substance for asymmetric hydrogenations

Technology Process of 2-Acetamido-3-phenylacrylic acid

There total 47 articles about 2-Acetamido-3-phenylacrylic acid 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: 95.0%

Ac-N-carboxy α-dehydrophenylalanine anhydride (80465-38-9) → N-acetamido cinnamic acid (55065-02-6,64590-80-3,5469-45-4)

Guidance literature:

With water; triethylamine; In tetrahydrofuran; for 0.666667h; Ambient temperature;

DOI:10.1248/cpb.32.3934

Reference yield: 93.0%

(Z)-4-benzylidene-2-methyl-5(4H)-oxazolone (38879-46-8) → N-acetamido cinnamic acid (55065-02-6,64590-80-3,5469-45-4)

Guidance literature:

With sodium hydroxide; In methanol; at 20 ℃; for 0.5h;

DOI:10.1080/00397910701265895

Reference yield: 75.0%

acetamide (60-35-5) + 2-oxo-3-(phenyl)propionic acid (156-06-9) → N-acetamido cinnamic acid (55065-02-6,64590-80-3,5469-45-4)

Guidance literature:

In acetonitrile; at 140 ℃; for 4h;

upstream raw materials:

pyridine

N-hydroxy-phenylalanine

acetic anhydride

acetamide

Downstream raw materials:

Phenylalanine

2-oxo-3-(phenyl)propionic acid

(R,S)-N-acetyl phenylalanine

2-acetylamino-3-cyclohexylpropanoic acid

Refernces

• 1、 Nguyen, Dat P.,Sladek, Rudolph N.,Do, Loi H.. "Scope and limitations of reductive amination catalyzed by half-sandwich iridium complexes under mild reaction conditions". supporting information. . Retrieved 2020/07/15.
• 2、 Hou, Shicheng,Xu, Henan,Hu, Jianshu,Hou, Jian,Wang, Yan,Jin, Zhe,Wan, David C. C.,Hu, Chun. "Synthesis, β-catenin translocation capability and ALP activation activity of 7h-thiazolo[3,2-b]-1,2,4-triazin-7-one derivatives". . p. 67 - 73. Retrieved 2018/02/14.