2,3-Dimethoxycinnamic acid

Base Information

• Chemical Name: 2,3-Dimethoxycinnamic acid
• CAS No.: 7345-82-6
• Molecular Formula: C11H12 O4
• Molecular Weight: 208.214
• European Community (EC) Number: 231-249-5,679-802-3
• NSC Number: 235795
• Nikkaji Number: J278.864K,J505.005G
• Wikidata: Q63398874
• Mol file: 7345-82-6.mol

Synonyms:2,3-Dimethoxycinnamic acid;7345-82-6;7461-60-1;trans-2,3-Dimethoxycinnamic acid;(E)-3-(2,3-Dimethoxyphenyl)acrylic acid;3-(2,3-dimethoxyphenyl)acrylic acid;(2E)-3-(2,3-dimethoxyphenyl)acrylic acid;(E)-3-(2,3-dimethoxyphenyl)prop-2-enoic acid;(2E)-3-(2,3-dimethoxyphenyl)prop-2-enoic acid;2-Propenoic acid, 3-(2,3-dimethoxyphenyl)-;2-Propenoic acid, 3-(2,3-dimethoxyphenyl)-, (2E)-;(E)-3-(2,3-dimethoxy-phenyl)-acrylic acid;(~{E})-3-(2,3-dimethoxyphenyl)prop-2-enoic acid;2',3'-Dimethoxycinnamic acid;2,3-Dimethoxycinnamicacid;MFCD00004376;EINECS 231-249-5;SCHEMBL457033;SCHEMBL1056670;3-(2,3-dimethoxyphenyl)acrylicacid;AC8832;NSC235795;AKOS000263419;MS-8959;NSC 235795;NSC 403612;NSC-235795;trans-2,3-Dimethoxycinnamic acid, 97%;AC-10326;D2326;EN300-16895;EN300-832861;trans-3-(2,3-Dimethoxyphenyl)-2-propenoic Acid;A838178;SR-01000597141;SR-01000597141-1;W-104415;Q63398874;Z2942851155;6-(2-Hydroxy-ethyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylicacid;8N2;InChI=1/C11H12O4/c1-14-9-5-3-4-8(11(9)15-2)6-7-10(12)13/h3-7H,1-2H3,(H,12,13)/b7-6

Chemical Property of 2,3-Dimethoxycinnamic acid

Chemical Property:

• Vapor Pressure: 1.51E-05mmHg at 25°C
• Melting Point: 180-184 ºC
• Boiling Point: 351.6oC at 760 mmHg
• PKA: 4.40±0.10(Predicted)
• Flash Point: 136.7oC
• PSA: 55.76000
• Density: 1.203±0.06 g/cm3(Predicted)
• LogP: 1.80160
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 208.07355886
• Heavy Atom Count: 15
• Complexity: 237

Purity/Quality:

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

(E)-3-(2,3-Dimethoxyphenyl)acrylicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=CC(=C1OC)C=CC(=O)O
• Isomeric SMILES: COC1=CC=CC(=C1OC)/C=C/C(=O)O
• Uses: 2,3-Dimethoxycinnamic acid is used in the synthesis of (2E,2?E,2??E)-N,N?,N??-(nitrilotri-2,1-ethanediyl)tris[3-(2,3-dimethoxyphenyl)-2-propenamide]. trans-2,3-Dimethoxycinnamic acid was used in the synthesis of (2E,2′E,2′′E)-N,N′,N′′-(nitrilotri-2,1-ethanediyl)tris[3-(2,3-dimethoxyphenyl)-2-propenamide].

Technology Process of 2,3-Dimethoxycinnamic acid

There total 4 articles about 2,3-Dimethoxycinnamic 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: 98.0%

malonic acid (141-82-2) + 2,3-dimethyoxybenzaldehyde (86-51-1) → trans-2,3-dimethoxycinnamic acid (7345-82-6)

Guidance literature:

piperidine; In pyridine; Heating;

DOI:10.1021/jo00186a010

Reference yield: 51.0%

(E)-4-(2,3-dimethoxyphenyl)-but-3-en-2-one (5424-52-2) → trans-2,3-dimethoxycinnamic acid (7345-82-6)

Guidance literature:

With copper(l) iodide; hydroxylamine hydrochloride; oxygen; In dimethyl sulfoxide; at 100 ℃; for 12h;

DOI:10.1039/c5ob01569c

Reference yield: 40.0%

malonic acid (141-82-2) + 2,3-dimethyoxybenzaldehyde (86-51-1) → trans-2,3-dimethoxycinnamic acid (7345-82-6) + 3-Amino-3-(2,3-dimethoxy-phenyl)-propionic acid (34840-98-7,752198-18-8)

Guidance literature:

With ammonium acetate; In butan-1-ol; Heating;

DOI:10.1007/s11176-005-0377-9

upstream raw materials:

malonic acid

2,3-dimethyoxybenzaldehyde

(E)-4-(2,3-dimethoxyphenyl)-but-3-en-2-one

Downstream raw materials:

methyl 3-(2,3-dimethoxyphenyl)propenoate

(E)-N-(6-Amino-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-3-(2,3-dimethoxy-phenyl)-acrylamide

(E)-2,3-dimethoxycinnamic acid 2-formylphenyl ester

benzene-1,2-diol

Refernces

• 1、 Sathyanarayana, Pochampalli,Ravi, Owk,Muktapuram, Prathap Reddy,Bathula, Surendar Reddy. "Copper catalyzed oxygen assisted C(CNOH)-C(alkyl) bond cleavage: A facile conversion of aryl/aralkyl/vinyl ketones to aromatic acids". supporting information. p. 9681 - 9685. Retrieved 2015/09/28.
• 2、 Day, Jonathan P.,Lindsay, Barbara,Riddell, Tracy,Jiang, Zhong,Allcock, Robert W.,Abraham, Achamma,Sookup, Sebastian,Christian, Frank,Bogum, Jana,Martin, Elisabeth K.,Rae, Robert L.,Anthony, Diana,Rosair, Georgina M.,Houslay, Daniel M.,Huston, Elaine,Baillie, George S.,Klussmann, Enno,Houslay, Miles D.,Adams, David R.. "Elucidation of a structural basis for the inhibitor-driven, p62 (SQSTM1)-dependent intracellular redistribution of cAMP phosphodiesterase-4A4 (PDE4A4)". supporting information; experimental part. p. 3331 - 3347. Retrieved 2011/07/09.