4-Bromocinnamic acid

Base Information

• Chemical Name: 4-Bromocinnamic acid
• CAS No.: 1200-07-3
• Molecular Formula: C9H7BrO2
• Molecular Weight: 227.057
• Hs Code.: 29163990
• European Community (EC) Number: 214-850-7
• NSC Number: 218449
• Nikkaji Number: J535.787J,J217.043D
• Wikidata: Q106956355
• ChEMBL ID: CHEMBL98045
• Mol file: 1200-07-3.mol

Synonyms:4-Bromocinnamic acid;1200-07-3;3-(4-bromophenyl)acrylic acid;p-Bromocinnamic acid;17916-60-8;trans-4-Bromocinnamic acid;(E)-3-(4-bromophenyl)acrylic acid;(2E)-3-(4-bromophenyl)prop-2-enoic acid;2-Propenoic acid, 3-(4-bromophenyl)-, (2E)-;C9H7BrO2;(E)-3-(4-bromophenyl)prop-2-enoic acid;4-Bromocinnamic acid, predominantly trans;4-bromo cinnamic acid;MFCD00004394;3-(4-BROMOPHENYL)-2-PROPENOIC ACID;3-(4-bromophenyl)prop-2-enoic acid;p-Bromzimtsaure;(E)-3-(4-Bromo-phenyl)-acrylic acid;(E)-4-bromocinnamic acid;CHEMBL98045;SCHEMBL119183;3-(4-bromophenyl)prop-2-enal;CPDDDTNAMBSPRN-ZZXKWVIFSA-;(E)-3-(4-bromophenyl)acrylicacid;E-3-(4-bromophenyl)propenoic acid;AB6442;BBL037328;NSC218449;STK301576;AKOS000263376;AKOS025149076;2-Propenoic acid,3-(4-bromophenyl)-;CS-W013013;NSC-218449;PS-5778;trans-4-Bromocinnamic acid,predominantly;NCGC00342454-01;4-Bromocinnamic acid predominately trans-;AC-10323;B1690;EN300-17554;EN300-248205;4-Bromocinnamic acid, predominantly trans, 98%;AB01102359-03;A804410;SR-01000597221;SR-01000597221-1;W-108489;F0850-6838;Z2237493681;InChI=1/C9H7BrO2/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6H,(H,11,12)/b6-3+;DQZ

Chemical Property of 4-Bromocinnamic acid

Chemical Property:

• Appearance/Colour: colorless or white crystalline solid
• Vapor Pressure: 2.43E-05mmHg at 25°C
• Melting Point: 260-265 °C
• Boiling Point: 344.9 °C at 760 mmHg
• PKA: 4.35±0.10(Predicted)
• Flash Point: 162.4 °C
• PSA: 37.30000
• Density: 1.607 g/cm³
• LogP: 2.54690
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO
• Water Solubility.: Soluble in alcohol, ethyl acetate, DMSO. Insoluble in water.
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 225.96294
• Heavy Atom Count: 12
• Complexity: 181

Purity/Quality:

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

4-Bromocinnamic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,Xi
• Statements: 36/37/38-22
• Safety Statements: 36/37/39-26-22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C=CC(=O)O)Br
• Isomeric SMILES: C1=CC(=CC=C1/C=C/C(=O)O)Br
• Uses: 4-Bromocinnamic acid has been used in the preparation of: (E)-β-bromo-4-bromostyrene, 2-amino-7-(piperidin-4-yl)isoquinoline, brominated dansyl derivative (4-bromophenyl)-4-(5-(dimethylamino)naphthalene-1-sulfonamido)butanoic acid.

Technology Process of 4-Bromocinnamic acid

There total 51 articles about 4-Bromocinnamic 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) + 4-bromo-benzaldehyde (1122-91-4) → trans-4-bromocinnamic acid (1200-07-3,5676-63-1,17916-60-8)

Guidance literature:

With piperidine; pyridine; at 90 ℃; for 1h;

DOI:10.3998/ark.5550190.p009.905 DOI:10.24820/ark.5550190.p009.905

Reference yield: 95.0%

1,4-bromoiodobenzene (589-87-7) + acrylic acid (79-10-7) → trans-4-bromocinnamic acid (1200-07-3,5676-63-1,17916-60-8)

Guidance literature:

With triethylamine; In water; at 100 ℃; for 12h;

DOI:10.1016/j.cclet.2019.09.006

Reference yield: 93.0%

4-bromo-benzaldehyde (1122-91-4) → trans-4-bromocinnamic acid (1200-07-3,5676-63-1,17916-60-8)

Guidance literature:

With piperidine; pyridine; malonic acid; for 2h; Reflux;

DOI:10.1021/acs.jmedchem.5b00515

upstream raw materials:

p-aminocinnamic acid

acetic anhydride

4-bromo-benzaldehyde

malonic acid

Downstream raw materials:

(E)-N,N-diethyl-3-(4-bromophenyl)acrylamide

4-Brom-o-nitrozimtsaeure

(2E)-3-(4-bromo-3-nitrophenyl)acrylic acid

(E)-1-bromo-4-(2-bromovinyl)benzene

Refernces

• 1、 Xiao, Jian,Zhang, Haonan,Ejike, Anyaegbu Chima,Wang, Lu,Tao, Minli,Zhang, Wenqin. "Phenanthroline functionalized polyacrylonitrile fiber with Pd(0) nanoparticles as a highly active catalyst for the Heck reaction". . . Retrieved 2021.
• 2、 Devine, William,Woodring, Jennifer L.,Swaminathan, Uma,Amata, Emanuele,Patel, Gautam,Erath, Jessey,Roncal, Norma E.,Lee, Patricia J.,Leed, Susan E.,Rodriguez, Ana,Mensa-Wilmot, Kojo,Sciotti, Richard J.,Pollastri, Michael P.. "Protozoan Parasite Growth Inhibitors Discovered by Cross-Screening Yield Potent Scaffolds for Lead Discovery". . p. 5522 - 5537. Retrieved 2015.
• 3、 Mikroyannidis, John A.,Spiliopoulos, Ioakim K.,Kasimis, Theodoros S.,Kulkarni, Abhishek P.,Jenekhe, Samson A.. "Synthesis, photophysics, and electroluminescence of conjugated poly(p-phenylenevinylene) derivatives with 1,3,4-oxadiazoles in the backbone". . p. 9295 - 9302. Retrieved 2003.
• 4、 Balla, Venkata Sasidhar,Bathula, Srikanth,Fang, Francis G.,Girish, Dixit,Gotoda, Masaharu,Gusovsky, Fabian,Kalla, Vijay,Khile, Anil Shahaji,Melillo, Bruno,Mitasev, Branko,Rayaprolu, Pavan Kumar,Schreiber, Stuart L.,Sugandham, Srinivasa Rao,Talabhakthula, Ravi Kumar,Terli, Chiranjeevi,Vaddi, Anand,Vikram, Venugopalarao,Yang, Jiong. "Crystallization-Based Synthetic Route to Antimalarial Agent BRD5018: Diazocene Ring Formation via a Staudinger-aza-Wittig Reaction on an Azetidine-Ribose Template". . . Retrieved 2021/10/01.
• 5、 Das, Aniruddha,Anbu, Nagaraj,Gogoi, Chiranjib,Dhakshinamoorthy, Amarajothi,Biswas, Shyam. "Amino Group Functionalized Hf-Based Metal-Organic Framework for Knoevenagel-Doebner Condensation". . p. 3396 - 3403. Retrieved 2021/08/20.