19522-96-4

Basic information

• Product Name: 7-Bromobenzo[1,3]dioxole-5-carbaldehyde
• Synonyms: 7-Bromo-2H-1,3-benzodioxole-5-carbaldehyde;7-Bromobenzo[1,3]dioxole-5-carbaldehyde;7-Bromobenzo[1,3]dio;7-bromo-1,3-benzodioxole-5-carbaldehyde;7-bromo-1,3-benzodioxole-5-carboxaldehyde;1,3-Benzodioxole-5-carboxaldehyde,7-bromo-;7-Bromobenzo[1,3]Dioxole-5-Carbaldehyde(WX622056)
• CAS NO: 19522-96-4
• Molecular Formula: C₈H₅BrO₃
• Molecular Weight: 229.03
• Mol File: 19522-96-4.mol

Chemical Properties

• Boiling Point: 316.7 °C at 760 mmHg
• Flash Point: 145.3 °C
• Appearance: /
• Density: 1.782 g/cm³
• Vapor Pressure: 0.000403mmHg at 25°C
• Refractive Index: 1.65
• CAS DataBase Reference: 7-Bromobenzo[1,3]dioxole-5-carbaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Bromobenzo[1,3]dioxole-5-carbaldehyde(19522-96-4)
• EPA Substance Registry System: 7-Bromobenzo[1,3]dioxole-5-carbaldehyde(19522-96-4)

Safety Data

• Hazardous Substances Data: 19522-96-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
7-Bromobenzo[1,3]dioxole-5-carbaldehyde is used as an intermediate in the synthesis of pharmaceuticals for its ability to participate in various chemical reactions and organic syntheses.
Used in Organic Compounds Synthesis:
7-Bromobenzo[1,3]dioxole-5-carbaldehyde is used as an intermediate in the synthesis of organic compounds due to its aromatic and aldehyde properties, which allow it to be involved in a range of chemical reactions and syntheses.
It is important to handle 7-Bromobenzo[1,3]dioxole-5-carbaldehyde with caution as it can be harmful if ingested, inhaled, or comes in contact with the skin.

InChI:InChI=1/C8H5BrO3/c9-6-1-5(3-10)2-7-8(6)12-4-11-7/h1-3H,4H2

Upstream product

• 16414-34-9 3-bromo-4,5-dihydroxybenzaldehyde 
• 74-95-3 1,1-dibromomethane 
• 120-57-0 piperonal 
• 75-11-6 diiodomethane 
• 74-97-5 chlorobromomethane 
• 59682-83-6 N-(2H-benzo[3,4-d]-1,3-dioxolen-5-ylmethyl)acetamide 
• 139-85-5 3,4-dihydroxybenzaldehyde 

Downstream Products

• 4877-93-4 2,2'-Dimethoxybiphenyl 
• 459423-07-5 7-(2-methoxyphenyl)benzo[d][1,3]dioxole-5-carbaldehyde 
• 2132-80-1 4,4'-Dimethoxybiphenyl 
• 66799-93-7 7-bromobenzo[d][1,3]-dioxole-5-carboxylic acid 
• 81805-94-9 3-bromo-N-cyclohexyl-4,5-methylenedioxybenzylideneimine 
• 120-57-0 piperonal 
• 81805-98-3 3-Hydroxy-4,5-(methylenedioxy)benzaldehyde 
• 5780-07-4 3-methoxy-4,5-methylenedioxybenzaldehyde 
• 13120-66-6 2-(1,5-dimethyl-4-hexenyl)-3-hydroxy-5-methyl-1,4-benzoquinone 
• 312327-45-0 5-[2-(benzyloxycarbonylamino)-1-(tert-butyldimethyl-silyloxy)ethyl]-1,3-dioxolan-7-ylaminomethylene-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 312327-46-1 O-benzyl N-2-(tert-butyldimethylsilyloxy)-2-[1,3-dioxolo[4,5-h]-6(9H)-quinolinon-6-yl]ethyl carbamate 

Relevant articles and documents

Design and microwave synthesis of new (5z) 5-arylidene-2-thioxo-1,3-thiazolinidin-4-one and (5z) 2-amino-5-arylidene-1,3-thiazol-4(5h)-one as new inhibitors of protein kinase dyrk1a

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Selective and efficient oxidation of benzylic alcohols to benzaldehydes and methyl benzoates by dibromo-5,5-dimethylhydantoin

A selective and efficient method of oxidizing benzyl alcohols to benzaldehydes and methyl benzoates by using 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) as oxidant is developed. One-step conversion of benzyl alcohols to methyl benzoates in methanol at room temperature for 12 hours is achieved without any catalysts. Moreover, para-substituted benzyl alcohols are obtained in 86-98% yield. When dichloromethane is used as solvent, further oxidation of benzaldehydes to esters is well controlled, selectively affording benzaldehydes in 89-99% yield within 30 minutes.

Direct oxidation of N-benzylamides to aldehydes or ketones by N-bromosuccinimide

A simple and efficient approach for the one-pot transformation of N-benzylamides to aldehydes or ketones under mild conditions was reported. All the 20 substrates gave moderate to excellent oxidative yields under the optimized conditions. Our study may provide a new approach for the one-pot synthesis of aldehydes or ketones from the corresponding amides. Copyright Taylor & Francis Group, LLC.

Synthesis of deuterium-labelled standards of (±)-DOM and (±)-MMDA

This study describes the synthesis of deuterium-labelled (±)-4-methyl-2,5-dimethoxyamphetamine (DOM) and (+)-l-(7-methoxy-l,3- benzodioxol-5-yl)propan-2-amine (MMDA). The isotopically labelled compounds are potentially used as internal standards in gas chromatography-mass spectrometry (GC-MS) assays. Copyright

MACROCYCLIC COMPOUNDS USEFUL AS PHARMACEUTICALS

The present invention provides compounds having formula (I), and additionally provides methods for the synthesis thereof and methods for the use thereof in the treatment of various disorders including inflammatory or autoimmune disorders, and disorders involving malignancy or increased angiogenesis, wherein R1 -R11, t, X, Y, Z, and n are as defined herein.

Heterocyclic derivatives for the treatment of cancer and other proliferative diseases

The invention relates to certain heterocyclic compounds useful for the treatment of cancer and other diseases, having the Formula (I): wherein: (a) m is an integer 0 or 1; (b) R12 is an alkyl, a substituted alkyl, a cycloalkyl, a substituted cycloalkyl, a heterocyclic, a substituted heterocyclic, a heteroaryl, a substituted heteroaryl, an aryl or a substituted aryl residue; (c) Ar3 is an aryl, a substituted aryl, a heteroaryl or a substituted heteroaryl residue; (d) Ar4 is an aryl, a substituted aryl, a heteroaryl or a substituted heteroaryl residue; (e) R5 is hydrogen, hydroxy, alkyl or substituted alkyl; (f) - - - - - represents a bond present or absent; and (g) W, X, Y and Z are independently or together C(O)—, C(S), S, O, or NH; or a pharmaceutically acceptable salt thereof.

Solid state nuclear bromination with N-bromosuccinimide. Part 2. Experimental and theoretical studies of reactions with some substituted benzaldehydes

N-Bromosuccinimide reacts with aromatic aldehydes in the solid state to yield exclusively nuclear brominated products while a similar reaction in the solution phase produces a number of products under varied conditions. The reactivity and regioselectivity have been studied in terms of the energies of HOMO, HOMO-LUMO difference, reaction free energy, reaction conditions and crystal packing. Single crystal X-ray structural analysis of 3,4-dihydroxybenzaldehyde has been carried out. Crystal packing energies of some of the reactive and unreactive benzaldehydes indicate the importance of molecular bromine diffusion in the solid state.

Synthesis of 8-methoxy-1-methyl-1H-benzo[de][1-6]naphthyridin-9-ol (isoaaptamine) and analogues

8-Methoxy-1-methyl-1H-benzo[de][1,6]naphthyridin-9-ol, isoaaptamine, a PKC inhibitor isolated from sponge was synthesized. The synthesis parallels a synthesis of 8,9-dimethoxybenzo[de][1,6]-naphthyridine, aaptamine, but uses a nitromethyl substituent as a precursor of the key 5-(2-aminoethyl)-1H-quinolin-4-one intermediate. The quinolone intermediates were prepared by thermolysis (220-240 °C) of anilinomethylene derivatives of Meldrum's acid. The quinolone intermediates were N-methylated prior to cyclization to the benzo[de][1,6]naphthyridine derivatives. Aaptamine and several analogues of aaptamine and isoaaptamine were prepared including 9-demethylaaptamine, 1-methyl-8-demethylaaptamine, 1-methylaaptamine, and the 8,9-methylenedioxy analogues of aaptamine and 1-methylaaptamine.

Aromatic Hydroxylation. Hydroxybenzaldehydes from Bromobenzaldehydes via Reaction of in Situ Generated, Lithiated α-Morpholinobenzyl Alkoxides with Nitrobenzene

A general method for the one-step conversion of bromobenzaldehydes to the corresponding hydroxybenzaldehydes has been developed.The method involves in situ protection of the aldehyde function of the bromobenzaldehyde as its lithium morpholinoalkoxide, followed by lithium-bromine exchange, reaction with nitrobenzene at -75 deg C, and a subsequent acidic workup.The method has been applied to the synthesis of 4,5-dimethoxy-3-hydroxy- (1a), 3,5-dimethoxy-2-hydroxy- (2a), 3,5-bis(benzyloxy)-2-hydroxy- (2b), 3,4-dimethoxy-2-hydroxy- (14), 3-hydroxy-4,5-(methylenedioxy)- (16), and 4,5-dimethoxy-2-hydroxybenzaldehydes (18) from the bromobenzaldehydes 4, 12a, 12b, 13, 15, and 17, respectively.