5-Bromobenzo[1,3]dioxole-4-carboxylic acid

Base Information

• Chemical Name: 5-Bromobenzo[1,3]dioxole-4-carboxylic acid
• CAS No.: 72744-56-0
• Molecular Formula: C8H5 Br O4
• Molecular Weight: 245.0269
• Hs Code.: 2932999099
• European Community (EC) Number: 623-141-5
• DSSTox Substance ID: DTXSID50500989
• Wikidata: Q82353057
• Mol file: 72744-56-0.mol

Synonyms:72744-56-0;5-Bromobenzo[1,3]dioxole-4-carboxylic acid;5-BROMO-1,3-BENZODIOXOLE-4-CARBOXYLIC ACID;5-Bromobenzo[d][1,3]dioxole-4-carboxylic acid;5-Bromo-2H-1,3-benzodioxole-4-carboxylic acid;SCHEMBL423788;DTXSID50500989;HDNXEXSQANVCKC-UHFFFAOYSA-N;MFCD00837590;AKOS023820848;5-bromo-1,3-dioxaindane-4-carboxylic acid;CS-0195091;E89522;5 Cbromobenzo[d][1,3]dioxole-4-carboxylic acid;EN300-6478519;5-BROMO-1,3-BENZODIOXOLE-4-CARBOXYLICACID;5-Bromobenzo[1,3]dioxole-4-carboxylic acid, 97%;Z1269165961

Chemical Property of 5-Bromobenzo[1,3]dioxole-4-carboxylic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 169-173 °C
• Refractive Index: 1.648
• Boiling Point: 353.188°C at 760 mmHg
• PKA: 2.62±0.20(Predicted)
• Flash Point: 167.403°C
• PSA: 55.76000
• Density: 1.895g/cm³
• LogP: 1.87600
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 243.93712
• Heavy Atom Count: 13
• Complexity: 220

Purity/Quality:

99% ^*data from raw suppliers

5-Bromobenzo[1,3]dioxole-4-carboxylic acid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1OC2=C(O1)C(=C(C=C2)Br)C(=O)O

Technology Process of 5-Bromobenzo[1,3]dioxole-4-carboxylic acid

There total 5 articles about 5-Bromobenzo[1,3]dioxole-4-carboxylic 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%

5-bromo-benzo[1,3]dioxole-4-carbaldehyde (72744-54-8) → 5-bromobenzo[d][1,3]dioxole-4-carboxylic acid (72744-56-0)

Guidance literature:

With sodium hydroxide; silver nitrate; In water; acetonitrile; at 20 ℃; for 16h;

DOI:10.1021/jm8005433

Reference yield: 81.0%

1,2-(methylenedioxy)-4-bromobenzene (2635-13-4) + carbon dioxide (124-38-9,18923-20-1) → 5-bromobenzo[d][1,3]dioxole-4-carboxylic acid (72744-56-0)

Guidance literature:

1,2-(methylenedioxy)-4-bromobenzene; With lithium diisopropyl amide; In tetrahydrofuran; cyclohexane; at -78 ℃; for 1h;

carbon dioxide; In tetrahydrofuran; cyclohexane; at -78 - 20 ℃;

DOI:10.1016/j.bmc.2003.11.015

Reference yield:

3-ethoxysalicylaldehyde (492-88-6) → 5-bromobenzo[d][1,3]dioxole-4-carboxylic acid (72744-56-0)

Guidance literature:

Multi-step reaction with 4 steps

2: 96.5 percent / BBr₃ / CH₂Cl₂ / 20 °C

3: 74.2 percent / K₂CO₃, CuO / dimethylformamide / 4 h / 110 °C

4: 51 percent / KMnO₄ / pyridine; H₂O / 2 h / 20 °C

With potassium permanganate; boron tribromide; potassium carbonate; copper(II) oxide; In pyridine; dichloromethane; water; N,N-dimethyl-formamide;

upstream raw materials:

5-bromo-benzo[1,3]dioxole-4-carbaldehyde

1,2-(methylenedioxy)-4-bromobenzene

carbon dioxide

3-ethoxysalicylaldehyde

Downstream raw materials:

N-(5-bromo-1,3-benzodioxol-4-yl)carbamic acid 1,1-dimethylethyl ester

(+)-12-(3-chlorobenzoyloxy)-10b,11-dihydroxy-5-methyl-2,3:7,8-bis(methylenedioxy)-4b,5,6,10b,11,12-hexahydrobenzo[c]phenanthridin-6(5H)-one

(+)-12-(3-chlorobenzoyloxy)-11-hydroxy-5-methyl-2,3:7,8-bis(methylenedioxy)-10b-triethylsilyloxy-4b,5,6,10b,11,12-hexahydrobenzo[c]phenanthridin-6(5H)-one

(-)-11-hydroxy-5-methyl-2,3:7,8-bis(methylenedioxy)-4b,5,6,10b,11,12-hexahydrobenzo[c]phenanthridine

Refernces

• 1、 Ning, Xiao-Shan,Liang, Xin,Hu, Kang-Fei,Yao, Chuan-Zhi,Qu, Jian-Ping,Kang, Yan-Biao. "Pd-tBuONO Cocatalyzed Aerobic Indole Synthesis". supporting information. p. 1590 - 1594. Retrieved 2018/04/30.
• 2、 Boy, Kenneth M.,Dee, Michael,Yevich, Joseph,Torrente, John,Gao, Qi,Iben, Lawrence,Stark, Arlene,Mattson, Ronald J.. "Ligand conformation has a definitive effect on 5-HT1A and serotonin reuptake affinity". . p. 4467 - 4470. Retrieved 2007/10/03.