3',4',5'-Trimethoxycinnamoyl chloride

Base Information

• Chemical Name: 3',4',5'-Trimethoxycinnamoyl chloride
• CAS No.: 10263-19-1
• Molecular Formula: C12H13 Cl O4
• Molecular Weight: 256.686
• European Community (EC) Number: 233-601-3
• Nikkaji Number: J1.634.279C,J227.142G
• Mol file: 10263-19-1.mol

Synonyms:3',4',5'-Trimethoxycinnamoyl chloride;10263-19-1;89652-61-9;(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl chloride;(2E)-3-(3,4,5-TRIMETHOXYPHENYL)PROP-2-ENOYL CHLORIDE;EINECS 233-601-3;2-Propenoyl chloride, 3-(3,4,5-trimethoxyphenyl)-;C12H13ClO4;2-Propenoyl chloride, 3-(3,4,5-trimethoxyphenyl)-, (2E)-;3,4,5-trimethoxycinnamoyl chloride;F2190-0092;SCHEMBL8637983;SCHEMBL8637989;C12-H13-Cl-O4;MFCD00128239;AKOS022262496;3-(3,4,5-trimethoxyphenyl)acryloyl chloride;EN300-239592;(e)-3-(3,4,5-trimethoxyphenyl)acryloyl chloride;3-(3,4,5-Trimethoxyphenyl)acrylic acid chloride

Chemical Property of 3',4',5'-Trimethoxycinnamoyl chloride

Chemical Property:

• Vapor Pressure: 7.6E-06mmHg at 25°C
• Boiling Point: 375.8°C at 760 mmHg
• Flash Point: 153.8°C
• Density: 1.216g/cm³
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 256.0502366
• Heavy Atom Count: 17
• Complexity: 266

Purity/Quality:

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=CC(=C1OC)OC)C=CC(=O)Cl
• Isomeric SMILES: COC1=CC(=CC(=C1OC)OC)/C=C/C(=O)Cl

Technology Process of 3',4',5'-Trimethoxycinnamoyl chloride

There total 7 articles about 3',4',5'-Trimethoxycinnamoyl chloride 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: 100.0%

(E)-3,4,5-trimethoxy-cinnamic acid (20329-98-0,20329-99-1,90-50-6) → (E)-3-(3,4,5-trimethoxyphenyl)acryloyl chloride (10263-19-1,89652-61-9)

Guidance literature:

With thionyl chloride;

DOI:10.1039/b503163j

Reference yield: 97.0%

3,4,5-trimethoxycinnamic acid (90-50-6) → 3',4',5'-trimethoxycinnamoyl chloride (10263-19-1)

Guidance literature:

With oxalyl dichloride; at 20 ℃; for 1h;

DOI:10.1139/cjc-79-11-1546

Reference yield:

3,4,5-trimethoxy-benzaldehyde (86-81-7) → (E)-3-(3,4,5-trimethoxyphenyl)acryloyl chloride (10263-19-1,89652-61-9)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine; piperidine

2: thionyl chloride; N,N-dimethylformamide / 1,2-dichloro-ethane / 6 h / Heating

With piperidine; pyridine; thionyl chloride; N,N-dimethyl-formamide; In 1,2-dichloro-ethane; 1: Knoevenagel reaction;

DOI:10.1016/S0223-5234(02)01414-9

upstream raw materials:

(E)-3,4,5-trimethoxy-cinnamic acid

3,4,5-trimethoxy-benzaldehyde

3,4,5-trimethoxycinnamic acid

Downstream raw materials:

3,4,5-trimethoxy-trans-cinnamic acid-(4-pyrrolidino-butyl ester)

3,4,5-trimethoxy-trans-cinnamic acid-(4-pyrrolidino-butylamide)

3,4,5-trimethoxy-trans-cinnamic acid-(4-piperidino-butyl ester)

3,4,5-trimethoxy-trans-cinnamic acid-(4-piperidino-butylamide)

Refernces

• 1、 Subramani, Muthuraman,Rajendran, Saravana Kumar. "Mild, Metal-Free and Protection-Free Transamidation of N-Acyl-2-piperidones to Amino Acids, Amino Alcohols and Aliphatic Amines and Esterification of N-Acyl-2-piperidones". . p. 3677 - 3686. Retrieved 2019.
• 2、 Chen, Liu Zeng,Shu, Hai Yang,Wu, Jing,Yu, Yun Long,Ma, Duo,Huang, Xin,Liu, Ming Ming,Liu, Xin Hua,Shi, Jing Bo. "Discovery and development of novel pyrimidine and pyrazolo/thieno-fused pyrimidine derivatives as potent and orally active inducible nitric oxide synthase dimerization inhibitor with efficacy for arthritis". . . Retrieved 2021.
• 3、 Podlipnik, Crtomir,Velter, Ingrid,Ferla, Barbara La,Marcou, Gilles,Belvisi, Laura,Nicotra, Francesco,Bernardi, Anna. "First round of a focused library of cholera toxin inhibitors". . p. 1651 - 1660. Retrieved 2007.
• 4、 Angapelly, Srinivas,Ramya, P.V. Sri,Angeli, Andrea,Del Prete, Sonia,Capasso, Clemente,Arifuddin, Mohammed,Supuran, Claudiu T.. "Development of sulfonamides incorporating phenylacrylamido functionalities as carbonic anhydrase isoforms I, II, IX and XII inhibitors". . p. 5726 - 5732. Retrieved 2017.
• 5、 Mazitschek, Ralph,Huwe, Axel,Giannis, Athanassios. "Synthesis and biological evaluation of novel fumagillin and ovalicin analogues". . p. 2150 - 2154. Retrieved 2005.
• 6、 Santos, Carla C. F.,Paradela, Luciana S.,Novaes, Luiz F. T.,Dias, Sandra M. G.,Pastre, Julio C.. "Design and synthesis of cenocladamide analogues and their evaluation against breast cancer cell lines". . p. 755 - 766. Retrieved 2017.
• 7、 Liu, Sheng,Li, Yubin,Wei, Wanxing,Wang, Kuiwu,Wang, Lisheng,Wang, Jianyi. "Design, synthesis, molecular docking studies and anti-HBV activity of phenylpropanoid derivatives". . p. 1 - 9. Retrieved 2016.
• 8、 Shi, Jing Bo,Chen, Liu Zeng,Wang, Bao Shi,Huang, Xin,Jiao, Ming Ming,Liu, Ming Ming,Tang, Wen Jian,Liu, Xin Hua. "Novel Pyrazolo[4,3- d]pyrimidine as Potent and Orally Active Inducible Nitric Oxide Synthase (iNOS) Dimerization Inhibitor with Efficacy in Rheumatoid Arthritis Mouse Model". . p. 4013 - 4031. Retrieved 2019.
• 9、 Paul, Nawal K.,Jha, Mamta,Bhullar, Khushwant S.,Rupasinghe, H.P. Vasantha,Balzarini, Jan,Jha, Amitabh. "All trans 1-(3-arylacryloyl)-3,5-bis (pyridin-4-ylmethylene)piperidin-4-ones as curcumin-inspired antineoplastics". . p. 461 - 470. Retrieved 2014.
• 10、 Teodori, Elisabetta,Contino, Marialessandra,Riganti, Chiara,Bartolucci, Gianluca,Braconi, Laura,Manetti, Dina,Romanelli, Maria Novella,Trezza, Alfonso,Athanasios, Asimidis,Spiga, Ottavia,Perrone, Maria Grazia,Giampietro, Roberta,Gazzano, Elena,Salerno, Milena,Colabufo, Nicola Antonio,Dei, Silvia. "Design, synthesis and biological evaluation of stereo- and regioisomers of amino aryl esters as multidrug resistance (MDR) reversers". . . Retrieved 2019.