2-Propenoic acid, 3-phenyl-

Base Information

• Chemical Name: 2-Propenoic acid, 3-phenyl-
• CAS No.: 621-82-9
• Molecular Formula: C9H8O2
• Molecular Weight: 148.161
• Hs Code.: DERIVATION
• DSSTox Substance ID: DTXSID40110056
• Wikidata: Q57826855
• NCI Thesaurus Code: C60810,C53400,C132777,C152203,C90877
• Mol file: 621-82-9.mol

Synonyms:2 Propenoic acid, 3 phenyl;2-Propenoic acid, 3-phenyl-;3-phenyl- 2-Propenoic acid;Innohep;tinzaparin;tinzaparin sodium

Chemical Property of 2-Propenoic acid, 3-phenyl-

Chemical Property:

• Appearance/Colour: monoclinic crystal
• Vapor Pressure: 0.005mmHg at 25°C
• Melting Point: 133 °C(lit.)
• Refractive Index: 1.616
• Boiling Point: 265 °C at 760 mmHg
• PKA: pK (25°) 4.46
• Flash Point: 189.5 °C
• PSA: 37.30000
• Density: 1.184 g/cm³
• LogP: 1.78440
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: 0.4 g/L (20℃)
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 148.052429494
• Heavy Atom Count: 11
• Complexity: 155

Purity/Quality:

99% ^*data from raw suppliers

Cinnamic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C=CC(=O)O
• Recent EU Clinical Trials: The impact of Thromboprophylaxis on Progression Free Survival of Patients with Advanced Pancreatic Cancer. The Pancreatic Cancer & Tinzaparin Prospective (imPaCT-PRO) study
• Uses: Cinnamic acid is an important intermediate in the preparation of its esters, which are used as fragrances, for pharmaceuticals, and for the enzymatic production of l-phenylalanine, the starting material for peptide sweeteners. Sodium cinnamate is a known corrosion inhibitor. Cinnamic acid is also used as a brightener in cyanide-free zinc electroplating baths, a corrosion inhibitor during removal of scale from zinc and in aerosol cans, a low-toxicity heat stabilizer for poly(vinyl chloride) , a cross-linking agent for dimethyl terephthalate – ethylene glycol copolymer and polyurethanes, a fireproofing agent for polycaprolactam, in laundry-resistant polyurethane adhesives for polyester fibers, and for improvement of the storage stability of drying-oil-modified alkyd resin coatings. fragrance & flavoring agent, antidiabetic cinnamic acid has sunscreen capabilities. Some manufacturers use it to replace PABA because of its lower allergic and phototoxic reaction incidence. Cinnamic acid is found in cinnamon leaves and cocoa leaves, and is an essential oil of certain mushrooms. It may cause allergic skin rashes. Cinnamic Acid is a flavoring agent that consists of crystalline scales, white in color, with an odor resembling honey and flowers. it is slightly soluble in water, soluble in alcohol, chloroform, acetic acid, acetone, benzene, and most oils, and alkali salts soluble in water. it is obtained by chemical synthesis. it is also termed 3-phenylpro- penoic acid.
• Production method: Commercial synthesis of cinnamic acid almost always results in the trans isomer. The Perkin reaction is the oldest known method of producing cinnamic acid commercially. In this reaction benzaldehyde [100-52-7] is condensed with acetic anhydride in the presence of sodium acetate as catalyst. Benzal chloride reacts with alkali acetate in an alkaline medium to give a high yield of cinnamic acid. Cinnamic acid can be obtained by this reaction in the presence of amines such as pyridine in more than 80 % yield. It can also be prepared through: mixing the benzoylacetone, sodium carbonate and bleach, generating sodium cinnamic acid, followed by processing with sulfate.
• Description: Cinnamic acid is a white crystalline organic acid, which is slightly soluble in water. It is obtained from oil of cinnamon, or from balsams such as storax. It is also found in shea butter and is the best indication of its environmental history and post-extraction conditions. It can also be made synthetically. Cinnamic acid is used in flavors, synthetic indigo, and certain pharmaceuticals, though its primary use is in the manufacturing of the methyl, ethyl, and benzyl esters for the perfume industry. Cinnamic acid has a honey- like odor; it and its more volatile ethyl ester (ethyl cinnamate) are flavor components in the essential oil of cinnamon, in which related cinnamaldehyde is the major constituent. Cinnamic acid is also part of the biosynthetic shikimate and phenyl propanoid pathways. Its biosynthesis is performed by action of the enzyme phenylalanine ammonia - lyase (PAL) on phenylalanine. Cinnamic acid is freely soluble in benzene, diethyl ether, acetone, and it is insoluble in hexane. Cinnamic acid is also a kind of self-inhibitor produced by fungal spore to prevent germination.

Technology Process of 2-Propenoic acid, 3-phenyl-

There total 444 articles about 2-Propenoic acid, 3-phenyl- 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: 40.0%

3-Phenylpropenol (104-54-1) → benzaldehyde (100-52-7) + Cinnamic acid (621-82-9) + acetophenone (98-86-2) + 1-phenyl-propan-1-one (93-55-0) + benzoic acid (65-85-0,8013-63-6)

Guidance literature:

With tert.-butylhydroperoxide; manganese(II) acetate; trifluoroacetic acid; In acetonitrile; at 80 ℃; for 21h; under 15001.5 Torr; chemoselective reaction; Mechanism;

DOI:10.1039/c4cy00255e

Reference yield:

cinnamaldehyde-(O-[1]naphthylcarbamoyl oxime ) + furan-2,3,5(4H)-trione pyridine (1:1) → 1,3-dinaphthalen-1-ylurea (607-56-7) + 1-amino-naphthalene (134-32-7) + Cinnamic acid (621-82-9)

Guidance literature:

α-naphthylcarbamic acid-derivative of β-cinnamaldoxime;

Reference yield:

4-nitro-phenyl cinnamate (18736-43-1) → 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + Cinnamic acid (621-82-9)

Guidance literature:

With hydroxide; In 1,4-dioxane; water; at 50 ℃; Rate constant;

DOI:10.1021/ja00232a031

upstream raw materials:

piperidine

malonic acid

benzaldehyde

pyridine

Downstream raw materials:

(carbonic acid ethyl ester)-cinnamic acid-anhydride

1,3,4,6-tetraphenylhexane-1,6-dione

2-hydroxyethyl 3-(phenyl)-2-propenoate

3-methylphenyl cinnamate

Refernces

• 1、 Suzuki, Noriyuki,Haraga, Kenji,Shimamura, Tatsuki,Masuyama, Yoshiro. "Synthesis and Structures of Ti-Pd Heterobimetallic Complexes". . p. 5480 - 5487. Retrieved 2015.
• 2、 Gunasekaran,Bhuvanesh,Karvembu. "Synthesis, characterization and catalytic oxidation property of copper(I) complexes containing monodentate acylthiourea ligands and triphenylphosphine". . p. 39 - 45. Retrieved 2017.
• 3、 Hwang, Young Kyu,Hong, Do-Young,Chang, Jong-San,Jhung, Sung Hwa,Seo, You-Kyong,Kim, Jinheung,Vimont, Alexandre,Daturi, Marco,Serre, Christian,Ferey, Gerard. "Amine grafting on coordinatively unsaturated metal centers of MOFs: Consequences for catalysis and metal encapsulation". . p. 4144 - 4148. Retrieved 2008.
• 4、 Durndell, Lee J.,Cucuzzella, Costanza,Parlett, Christopher M.A.,Isaacs, Mark A.,Wilson, Karen,Lee, Adam F.. "Platinum catalysed aerobic selective oxidation of cinnamaldehyde to cinnamic acid". . . Retrieved 2018.
• 5、 Durndell, Lee J.,Isaacs, Mark A.,Li, Chao'En,Parlett, Christopher M. A.,Wilson, Karen,Lee, Adam F.. "Cascade Aerobic Selective Oxidation over Contiguous Dual-Catalyst Beds in Continuous Flow". . p. 5345 - 5352. Retrieved 2019.
• 6、 Gubica, Tomasz,Pelka, Agnieszka,Palka, Katarzyna,Temeriusz, Andrzej,Kanska, Marianna. "The influence of cyclomaltooligosaccharides (cyclodextrins) on the enzymatic decomposition of L-phenylalanine catalyzed by phenylalanine ammonia-lyase". . p. 1855 - 1859. Retrieved 2011.
• 7、 Wang, Zhen,Hu, Liang,Chekshin, Nikita,Zhuang, Zhe,Qian, Shaoqun,Qiao, Jennifer X.,Yu, Jin-Quan. "Ligand-controlled divergent dehydrogenative reactions of carboxylic acids via C–H activation". . p. 1281 - 1285. Retrieved 2021/12/10.
• 8、 Sang, Dayong,Yue, Huaxin,Fu, Yang,Tian, Juan. "Cleavage of Carboxylic Esters by Aluminum and Iodine". . p. 4254 - 4261. Retrieved 2021/03/09.