2-Propenoic acid, 3-phenyl-, phenylmethyl ester

Base Information

• Chemical Name: 2-Propenoic acid, 3-phenyl-, phenylmethyl ester
• CAS No.: 103-41-3
• Deprecated CAS: 8014-16-2
• Molecular Formula: C16H14O2
• Molecular Weight: 238.286
• Hs Code.: 2916.12 Oral rat LD50: 5530 mg/kg
• DSSTox Substance ID: DTXSID3041663
• Wikidata: Q104376075
• ChEMBL ID: CHEMBL2361576
• Mol file: 103-41-3.mol

Synonyms:Benzylcinnamate;benzyl 3-phenylprop-2-enoate;Benzyl alcohol, cinnamate;DTXSID3041663;MFCD00004789;Cinnamic acid-benzyl ester;benzyl-3-phenyl-propenoate;CHEMBL2361576;3-Phenyl-acrylic acid benzyl ester;AKOS025243955;SY015224;FT-0622838;Cinnamic acid-benzyl ester 1000 microg/mL in Acetonitrile

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

Chemical Property:

• Appearance/Colour: clear colorless to yellowish crystalline
• Vapor Pressure: 1.05E-05mmHg at 25°C
• Melting Point: 34-37 °C(lit.)
• Refractive Index: 1.4025-1.4045
• Boiling Point: 371.2 °C at 760 mmHg
• Flash Point: 225.7 °C
• PSA: 26.30000
• Density: 1.128 g/cm³
• LogP: 3.44320
• Storage Temp.: 2-8°C
• Solubility.: alcohol: soluble(lit.)
• Water Solubility.: PRACTICALLY INSOLUBLE
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 238.099379685
• Heavy Atom Count: 18
• Complexity: 271

Purity/Quality:

99%min ^*data from raw suppliers

Benzyl cinnamate ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)C=CC2=CC=CC=C2
• Uses: In artificial flavors, in perfumes, mainly as a fixative. Benzyl cinnamate has been employed as internal standard during the determination of compounds commonly added to personal care products such as UV filters and antimicrobial agents in environmental samples.

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

There total 144 articles about 2-Propenoic acid, 3-phenyl-, phenylmethyl ester 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: 99.0%

Benzyl acetate (140-11-4) + benzaldehyde (100-52-7) → (E)-cinnamic acid benzyl ester (103-41-3,8014-16-2)

Guidance literature:

With titanium tetrachloride; triethylamine; In dichloromethane; at 0 - 25 ℃; stereoselective reaction; Inert atmosphere;

DOI:10.1016/j.tetlet.2014.04.098

Reference yield: 97.0%

Methyl cinnamate (103-26-4,1754-62-7) + benzyl alcohol (100-51-6,185532-71-2) → (E)-cinnamic acid benzyl ester (103-41-3,8014-16-2)

Guidance literature:

With N,N'-biscyclohexyl-imidazol-2-ylidene; 4 A molecular sieve; In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.1021/jo0267551

Reference yield: 97.0%

(E)-3-phenylacrylic acid (140-10-3) + benzyl bromide (100-39-0) → (E)-cinnamic acid benzyl ester (103-41-3,8014-16-2)

Guidance literature:

With caesium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 0.75h;

DOI:10.1080/00397910008086893

upstream raw materials:

Benzyl acetate

benzaldehyde

sodium trans-cinnamate

benzyl chloride

Downstream raw materials:

(2S,3R)-2,3-dihydroxy-3-phenyl-propionic acid

(2R,3S)-2,3-dihydroxy-3-phenyl-propionic acid

methyl (2S,3R)-3-phenyl-2,3-dihydroxypropanoate

methyl (2R,3S)-2,3-dihydroxy-3-phenylpropanoate

Refernces

• 1、 Shintou, Taichi,Mukaiyama, Teruaki. "Efficient Method for the Preparation of Primary, Inverted Secondary and Tertiary Alkyl Carboxylates from Alcohols and Carboxylic Acids by a New Type of Oxidation-Reduction Condensation Using Simple 1,4-Benzoquinone". . p. 1100 - 1101. Retrieved 2003.
• 2、 Mou, Fen,Sun, Yadong,Jin, Weiwei,Zhang, Yonghong,Wang, Bin,Liu, Zhiqing,Guo, Lei,Huang, Jianbin,Liu, Chenjiang. "Reusable ionic liquid-catalyzed oxidative esterification of carboxylic acids with benzylic hydrocarbons via benzylic Csp3-H bond activation under metal-free conditions". . p. 23041 - 23045. Retrieved 2017.
• 3、 Sun, Rong,Liu, Bing,Li, Bo-Geng,Jie, Suyun. "Palladium(II)@Zirconium-Based Mixed-Linker Metal–Organic Frameworks as Highly Efficient and Recyclable Catalysts for Suzuki and Heck Cross-Coupling Reactions". . p. 3261 - 3271. Retrieved 2016.
• 4、 Wang, Dong,Zhu, Yujun. "An Effective Pt-Cu/SiO2 Catalyst for the Selective Hydrogenation of Cinnamaldehyde". . . Retrieved 2018.
• 5、 Ji, Xiwang,Niu, Xiaoyu,Li, Bo,Han, Qing,Yuan, Fulong,Zaera, Francisco,Zhu, Yujun,Fu, Honggang. "Selective hydrogenation of cinnamaldehyde to cinnamal alcohol over platinum/graphene catalysts". . p. 3246 - 3253. Retrieved 2014.
• 6、 Daub, Mary Elisabeth,Jung, Hoimin,Lee, Byung Joo,Won, Joonghee,Baik, Mu-Hyun,Yoon, Tehshik P.. "Enantioselective [2+2] Cycloadditions of Cinnamate Esters: Generalizing Lewis Acid Catalysis of Triplet Energy Transfer". . p. 9543 - 9547. Retrieved 2019.
• 7、 List, Benjamin,Doehring, Arno,Hechavarria Fonseca, Maria T.,Wobser, Kathrin,Van Thienen, Hendrik,Torres, Ramon Rios,Galilea, Pedro Llamas. "Practical synthesis of (E)-α,β-unsaturated esters from aldehydes". . p. 1558 - 1560. Retrieved 2005.
• 8、 Kang, Ye-Won,Jang, Hye-Young. "NHC-catalyzed one-pot oxidation and oxidative esterification of allylic alcohols using TEMPO: The effect of alcohol additives". . p. 44486 - 44490. Retrieved 2014.
• 9、 Bah, Moustapha,Cherigo, Lilia,Cardoso Taketa, Alexandre T.,Fragoso-Serrano, Mabel,Hammond, Gerald B.,Pereda-Miranda, Rogelio. "Intrapilosins I-VII, pentasaccharides from the seeds of Ipomoea intrapilosa". . p. 1153 - 1157. Retrieved 2007.
• 10、 Maruyama, Tatsuo,Kotani, Takahiro,Yamamura, Hiroshi,Kamiya, Noriho,Goto, Masahiro. "Poly(ethylene glycol)-lipase complexes catalytically active in fluorous solvents". . p. 524 - 527. Retrieved 2004.