5-Bromo-1,3-benzodioxole-4-carboxaldehyde

Base Information

• Chemical Name: 5-Bromo-1,3-benzodioxole-4-carboxaldehyde
• CAS No.: 72744-54-8
• Molecular Formula: C8H5 Br O3
• Molecular Weight: 229.03
• Hs Code.: 2932999099
• DSSTox Substance ID: DTXSID30452639
• Nikkaji Number: J1.225.372I
• Wikidata: Q82273396
• Mol file: 72744-54-8.mol

Synonyms:5-Bromo-1,3-benzodioxole-4-carboxaldehyde;72744-54-8;5-bromo-1,3-benzodioxole-4-carbaldehyde;5-bromobenzo[d][1,3]dioxole-4-carbaldehyde;1,3-Benzodioxole-4-carboxaldehyde,5-bromo-;SCHEMBL863397;1,3-BENZODIOXOLE-4-CARBOXALDEHYDE, 5-BROMO-;RVCGOVWXRXITJA-UHFFFAOYSA-;DTXSID30452639;RVCGOVWXRXITJA-UHFFFAOYSA-N;5-Bromo-4-formyl-1,3-benzodioxole;MFCD02069012;AKOS015889257;5-bromo-1,3-dioxaindane-4-carbaldehyde;CS-16526;5-Bromo-1,3-benzodioxol-4-carboxaldehyde;5-bromobenzo[d][1,3]dioxol-4-carbaldehyde;CS-0099708;FT-0747056;D76021;EN300-205413;5-BROMO-1,3-BENZODIOXOLE-4-CARBOXALDEHY;5-Bromo-1,3-benzodioxole-4-carboxaldehyde, 96%;AE-641/30608013;5-BROMO-2H-1,3-BENZODIOXOLE-4-CARBALDEHYDE;Z1269219805;InChI=1/C8H5BrO3/c9-6-1-2-7-8(5(6)3-10)12-4-11-7/h1-3H,4H2

Chemical Property of 5-Bromo-1,3-benzodioxole-4-carboxaldehyde

Chemical Property:

• Vapor Pressure: 0.001mmHg at 25°C
• Melting Point: 162-166 °C(lit.)
• Refractive Index: 1.65
• Boiling Point: 309.28°C at 760 mmHg
• Flash Point: 140.848°C
• PSA: 35.53000
• Density: 1.783g/cm³
• LogP: 1.99030
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 227.94221
• Heavy Atom Count: 12
• Complexity: 185

Purity/Quality:

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

5-Bromo-1,3-benzodioxole-4-carboxaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 5-Bromo-1,3-benzodioxole-4-carboxaldehyde

There total 7 articles about 5-Bromo-1,3-benzodioxole-4-carboxaldehyde 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: 95.0%

1,2-(methylenedioxy)-4-bromobenzene (2635-13-4) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 5-bromo-benzo[1,3]dioxole-4-carbaldehyde (72744-54-8)

Guidance literature:

1,2-(methylenedioxy)-4-bromobenzene; With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -78 ℃; for 1h; Inert atmosphere;

N,N-dimethyl-formamide; In tetrahydrofuran; hexane; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1002/anie.201302327

Reference yield: 74.2%

6-bromo-2,3-dihydroxybenzaldehyde (83983-71-5) + 1,1-dibromomethane (74-95-3) → 5-bromo-benzo[1,3]dioxole-4-carbaldehyde (72744-54-8)

Guidance literature:

With potassium carbonate; copper(II) oxide; In N,N-dimethyl-formamide; at 110 ℃; for 4h;

Reference yield:

6-bromo-2-hydroxy-3-methoxybenzaldehyde (20035-41-0) → 5-bromo-benzo[1,3]dioxole-4-carbaldehyde (72744-54-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 77 percent / BBr₃ / CH₂Cl₂ / 1.) 20 deg C, 2 h, 2.) room temp., 12 h

2: 62 percent / K₂CO₃, CuO / dimethylformamide / 4 h / 110 °C

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

upstream raw materials:

6-bromo-2,3-dihydroxybenzaldehyde

1,1-dibromomethane

1,2-(methylenedioxy)-4-bromobenzene

N,N-dimethyl-formamide

Downstream raw materials:

5-bromobenzo[d][1,3]dioxole-4-carboxylic acid

norsanguinarine

6,7-dipropyl-N-p-tolyl-8H-indeno[5,4-d][1,3]dioxol-8-amine