Methyl 2-(hydroxy(4-nitrophenyl)methyl)acrylate

Base Information

• Chemical Name: Methyl 2-(hydroxy(4-nitrophenyl)methyl)acrylate
• CAS No.: 114106-93-3
• Molecular Formula: C₁₁H₁₁NO₅
• Molecular Weight: 237.212
• ChEMBL ID: CHEMBL352041
• DSSTox Substance ID: DTXSID40463771
• Nikkaji Number: J839.265J
• Mol file: 114106-93-3.mol

Synonyms:114106-93-3;methyl 2-(hydroxy(4-nitrophenyl)methyl)acrylate;2-[Hydroxy-(4-nitro-phenyl)-methyl]-acrylic acid methyl ester;Methyl 2-[hydroxy-(4-nitrophenyl)methyl]prop-2-enoate;CHEMBL352041;SCHEMBL11938478;DTXSID40463771;AKOS000208951

Chemical Property of Methyl 2-(hydroxy(4-nitrophenyl)methyl)acrylate

Chemical Property:

• Melting Point: 72-73.5 °C
• Boiling Point: 406.0±45.0 °C(Predicted)
• PKA: 12.10±0.20(Predicted)
• Density: 1.316±0.06 g/cm3(Predicted)
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 237.06372245
• Heavy Atom Count: 17
• Complexity: 314

Purity/Quality:

98% ^*data from raw suppliers

2-[HYDROXY-(4-NITRO-PHENYL)-METHYL]-ACRYLIC ACID METHYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC(=O)C(=C)C(C1=CC=C(C=C1)[N+](=O)[O-])O

Technology Process of Methyl 2-(hydroxy(4-nitrophenyl)methyl)acrylate

There total 17 articles about Methyl 2-(hydroxy(4-nitrophenyl)methyl)acrylate 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%

4-nitrobenzaldehdye (555-16-8) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → methyl 2-[hydroxy(4-nitrophenyl)methyl]prop-2-enoate (114106-93-3)

Guidance literature:

With dmap; at 76 ℃; for 5h;

DOI:10.1081/SCC-120018699

Reference yield: 99.0%

methyl 2-(((tertbutoxycarbonyl)oxy)(4-nitrophenyl)methyl)acrylate (688012-87-5) → methyl 2-[hydroxy(4-nitrophenyl)methyl]prop-2-enoate (114106-93-3)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; water; In N,N-dimethyl-formamide; at 20 ℃; for 0.5h;

DOI:10.1021/jo201096e

Reference yield: 91.0%

methanol (67-56-1) + 4-nitrobenzaldehdye (555-16-8) → methyl 2-[hydroxy(4-nitrophenyl)methyl]prop-2-enoate (114106-93-3)

Guidance literature:

Multistep reaction.;

DOI:10.1055/s-2007-966013

upstream raw materials:

4-nitrobenzaldehdye

acrylic acid methyl ester

toluene-4-sulfonamide

α-deuterio-4-nitro-benzaldehyde

Downstream raw materials:

(±)-methyl 2-((tert-butyldimethylsilyloxy)(4-nitrophenyl)methyl)acrylate

methyl 3-benzoylaminocarbonyloxy-2-methylene-3-(4-nitrophenyl)propanoate

methyl 2-(((tertbutoxycarbonyl)oxy)(4-nitrophenyl)methyl)acrylate

methyl (E)-2-formyl-3-(4-nitrophenyl)propenoate

Refernces

• 1、 Kohn, Luciana K.,Pavam,Veronese,Coelho,De Carvalho,Almeida, Wanda P.. "Antiproliferative effect of?Baylis-Hillman adducts and?a?new phthalide derivative on?human tumor cell lines". . p. 738 - 744. Retrieved 2006.
• 2、 Carpanez, Arthur G.,Coelho, Fernando,Amarante, Giovanni W.. "On the tandem Morita-Baylis-Hillman/transesterification processes. Mechanistic insights for the role of protic solvents". . p. 83 - 91. Retrieved 2018.
• 3、 Lin, Yu-Sheng,Liu, Chih-Wei,Tsai, Thomas Y. R.. "1-Methylimidazole 3-N-oxide as a new promoter for the Morita-Baylis-Hillman reaction". . p. 1859 - 1861. Retrieved 2005.
• 4、 Zhao, Sanhu,Chen, Zhaobin. "The N,N,N′,N′-tetramethylethylenediamine mediated Baylis-Hillman reaction". . p. 121 - 127. Retrieved 2005.
• 5、 Aggarwal, Varinder K.,Mereu, Andrea. "Superior amine catalysts for the Baylis-Hillman reaction: The use of DBU and its implications". . p. 2311 - 2312. Retrieved 1999.
• 6、 Sheng, Shou-Ri,Huang, Fang-Fang,Lin, Shu-Ying,Liu, Xiao-Ling,Huang, Xian. "Solid-phase synthesis of 3-hydroxy-2-methylenealkanoates and their derivatives using polymer-supported 2-(phenylseleno)propanoate". . p. 1373 - 1377. Retrieved 2007.
• 7、 Octavio, Rodrigo,De Souza,Vasconcellos, Mario Luiz A. A.. "The use of DMAP as catalyst in the baylis-hillman reaction between methyl acrylate and aromatic aldehydes". . p. 1383 - 1389. Retrieved 2003.
• 8、 Pereira, Susana Isabel,Adrio, Javier,Silva, Artur M. S.,Carretero, Juan Carlos. "Ferrocenylphosphines as new catalysts for Baylis-Hillman reactions". . p. 10175 - 10177. Retrieved 2005.
• 9、 Santos, Marilia S.,Fernandes, Daniara C.,Rodrigues, Manoel T.,Regiani, Thais,Andricopulo, Adriano D.,Ruiz, Ana Lúcia T. G.,Vendramini-Costa, Débora B.,De Carvalho, Jo?o E.,Eberlin, Marcos N.,Coelho, Fernando. "Diastereoselective Synthesis of Biologically Active Cyclopenta[b]indoles". . p. 6626 - 6639. Retrieved 2016.
• 10、 Khan, Faiz Ahmed,Upadhyay, Sarasij K.. "A stereoselective C7nC5x free-radical cascade route to optically pure and potentially useful tetracyclic amines". . p. 6111 - 6114. Retrieved 2008.