56479-63-1

Basic information

• Product Name: 3-bromo-4-dimethylamino-benzaldehyde
• Synonyms: 3-bromo-4-dimethylamino-benzaldehyde;3-bromo-4-(dimethylamino)benzaldehyde(SALTDATA: FREE);Benzaldehyde, 3-bromo-4-(dimethylamino)-
• CAS NO: 56479-63-1
• Molecular Formula: C₉H₁₀BrNO
• Molecular Weight: 228.1
• Mol File: 56479-63-1.mol
• Article Data: 28

Chemical Properties

• Boiling Point: 311.6°Cat760mmHg
• Flash Point: 142.2°C
• Appearance: /
• Density: 1.468
• Vapor Pressure: 0.000559mmHg at 25°C
• Refractive Index: 1.626
• CAS DataBase Reference: 3-bromo-4-dimethylamino-benzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 3-bromo-4-dimethylamino-benzaldehyde(56479-63-1)
• EPA Substance Registry System: 3-bromo-4-dimethylamino-benzaldehyde(56479-63-1)

Safety Data

• Hazardous Substances Data: 56479-63-1(Hazardous Substances Data)

Usage

Description

3-bromo-4-dimethylamino-benzaldehyde is an organic compound with the molecular formula C8H9BrNO. It is a derivative of benzaldehyde, featuring a bromine atom at the 3-position and an N,N-dimethylamino group at the 4-position. 3-bromo-4-dimethylamino-benzaldehyde is known for its unique chemical properties and potential applications in various industries.

Uses

Used in Pharmaceutical Industry:
3-bromo-4-dimethylamino-benzaldehyde is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows it to be a key component in the development of new drugs, particularly those targeting specific receptors or enzymes in the body.
Used in Chemical Synthesis:
In the field of organic chemistry, 3-bromo-4-dimethylamino-benzaldehyde serves as a valuable building block for the creation of more complex molecules. Its bromine and dimethylamino substituents can be further modified or used as starting points for the synthesis of a wide range of organic compounds, including dyes, pigments, and other specialty chemicals.
Used in Material Science:
3-bromo-4-dimethylamino-benzaldehyde's unique structure and properties make it a candidate for use in the development of new materials with specific characteristics. For example, it could be used in the design of novel polymers, coatings, or other materials with tailored properties for various applications, such as electronics, sensors, or energy storage devices.
Used in Research and Development:
3-bromo-4-dimethylamino-benzaldehyde is also utilized in academic and industrial research settings as a model compound for studying various chemical reactions and processes. Its reactivity and structural features make it an interesting subject for exploring new synthetic methods, understanding reaction mechanisms, and developing innovative applications in various fields.

InChI:InChI=1/C9H10BrNO/c1-11(2)9-4-3-7(6-12)5-8(9)10/h3-6H,1-2H3

Upstream product

• 100-10-7 4-dimethylamino-benzaldehyde 
• 7726-95-6 bromine 
• 64-19-7 acetic acid 
• 67-56-1 methanol 

Downstream Products

• 84562-58-3 N'-[1-(3-Bromo-4-dimethylamino-phenyl)-meth-(E)-ylidene]-2,6-dichloro-benzene-1,4-diamine 
• 118630-31-2 1-<3-Bromo-4-(dimethylamino)benzyl>piperazine 
• 118630-45-8 C₁₆H₂₂BrN₅S 
• 532440-28-1 4-dimethylamino-3-(3-dimethylamino-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)benzaldehyde 
• 1402432-05-6 (E)-2-[3-bromo-4-(dimethylamino)benzylidene]-5,6-dimethoxyindan-1-one 
• 1584546-66-6 (E)-3-(3-bromo-4-dimethylamino-benzylidene)-6-bromochroman-4-one 

Relevant articles and documents

Supramolecular organization of bis(3-halo-4-dimethylaminobenzylidene) hydrazines

Bis(3-bromo-4-dimethylaminobenzylidene)hydrazine and bis(3-chloro-4- dimethylaminobenzylidene)hydrazine have been synthesized, and their monoclinic crystal structures solved in space group P21/c. For the bromo derivative at 150 K, a = 10.4505(2

Ni-NiO heterojunctions: a versatile nanocatalyst for regioselective halogenation and oxidative esterification of aromatics

Herein, we report a facile method for the synthesis of Ni-NiO heterojunction nanoparticles, which we utilized for the nuclear halogenation reaction of phenol and substituted phenols usingN-bromosuccinimide (NBS). A remarkablepara-selectivity was achieved for the halogenated products under semi-aqueous conditions. Interestingly, blocking of thepara-position of phenol offeredortho-selective halogenation. In addition, the Ni-NiO nanoparticles catalyzed the oxidative esterification of carbonyl compounds with alcohol, diol or dithiol in the presence of a catalytic amount of NBS. It was observed that the aromatic carbonyls substituted with an electron-donating group favoured nuclear halogenation, whereas an electron-withdrawing group substitution in carbonyl compounds facilitated the oxidation reaction. In addition, the catalyst was magnetically separated and recycled 10 times. The tuned electronic structure at the Ni-NiO heterojunction controlled selectivity and activity as no suchpara-selectivity was observed with commercially available NiO or Ni nanoparticles.

Stepwise mechanism for the bromination of arenes by a hypervalent iodine reagent

A mild, metal-free bromination method of arenes has been developed using the combination of bis(trifluoroacetoxy)iodobencene and trimethylsilyl bromide. In situ-formed dibromo(phenyl)-λ3-iodane (PhIBr2) is proposed as the reactive intermediate. This methodology using PIFA/TMSBr has been applied with success to a great number of substrates (25 examples). The treatment of mono-substituted activated arenes led to para-brominated products (2u-z) in excellent 83-96% yields. Density functional theory calculations indicate a stepwise mechanism involving a double bromine addition followed by a type II dyotropic reaction with concomitant re-aromatization of the six-membered ring.

Environmentally benign indole-catalyzed position-selective halogenation of thioarenes and other aromatics

Halogenated aromatic compounds are the cores of many pharmaceutical, agricultural and chemical products but they are commonly prepared using electrophilic halogenation reactions in non-green chlorinated solvents under harsh conditions. A separate problem happens in the aromatic halogenation of thioarenes because they readily undergo oxidative side-reactions. Herein we report an environmentally benign electrophilic bromination of aromatics using an indole-catalytic protocol, which is suitable for a wide range of substrates including thioarenes.