176504-70-4

Basic information

• Product Name: 3-Bromo-2-formyltoluene, 6-Bromo-o-tolualdehyde
• Synonyms: 2-Bromo-6-methylbenzaldehyde 96%;3-Bromo-2-formyltoluene, 6-Bromo-o-tolualdehyde;2-broMo-6-Methylbenzaldehyde;2-Bromo-6-methylbenzaldehyde96%
• CAS NO: 176504-70-4
• Molecular Formula: C₈H₇BrO
• Molecular Weight: 199.04458
• Mol File: 176504-70-4.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-Bromo-2-formyltoluene, 6-Bromo-o-tolualdehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Bromo-2-formyltoluene, 6-Bromo-o-tolualdehyde(176504-70-4)
• EPA Substance Registry System: 3-Bromo-2-formyltoluene, 6-Bromo-o-tolualdehyde(176504-70-4)

Safety Data

• Hazardous Substances Data: 176504-70-4(Hazardous Substances Data)

Usage

General Description

3-Bromo-2-formyltoluene and 6-Bromo-o-tolualdehyde are both organic compounds belonging to the class of brominated aldehydes. 3-Bromo-2-formyltoluene is also known as 3-bromo-2-methylbenzaldehyde and is commonly used as a building block in the synthesis of various pharmaceuticals and agrochemicals. It is also used as a starting material for the preparation of other organic compounds. 6-Bromo-o-tolualdehyde, also known as 6-bromo-2-methylbenzaldehyde, is another brominated aldehyde that is used as an intermediate in the synthesis of pharmaceuticals and other organic compounds. Both chemicals are important in the field of organic chemistry and have various industrial and research applications.

Upstream product

• 1055969-07-7 (2-bromo-6-methylphenyl)methanol 
• 90259-31-7 2-bromo-6-methylbenzoic acid 
• 529-20-4 2-methylphenyl aldehyde 
• 74-88-4 methyl iodide 
• 591-17-3 meta-bromotoluene 
• 100-97-0 hexamethylenetetramine 

Downstream Products

• 148517-72-0 2-bromo-6-methyl-α-methylbenzyl alcohol 
• 210631-68-8 topramezone 
• 1156004-04-4 C₁₅H₂₀BrNOSe 

Relevant articles and documents

Preparation method and application of topramezone

The invention discloses a preparation method and application of topramezone, and the preparation method comprises the following steps: taking 2-methylbenzaldehyde, a bromination reagent, a catalyst, hydroxylamine hydrochloride, an alkali, ethylene gas, a sulfonylation reagent and a preset solvent as reaction raw materials, and preparing 3-[3-bromo-methyl-6-(methylsulfonyl) phenyl]-4, 5-dihydroisoxazole through a first reaction process; taking diethyl malonate, triethyl orthoformate, nickel sulfate, monobasic saturated carboxylic acid, methylhydrazine, a hydrocarbon solvent, an ethanol solutionand hydrochloric acid as reaction raw materials, and carrying out a second reaction process to prepare 1-methyl-5-hydroxypyrazole; and taking the 3-[3-bromo-methyl-6-(methylsulfonyl) phenyl]-4, 5 dihydroisoxazole,-1-methyl-5-hydroxypyrazole, triethylamine, potassium carbonate, palladium chloride, triphenylphosphine, 1, 4-dioxane, water, a saturated NaHCO3 solution and a hydrochloric acid solutionas reaction raw materials, and carrying out a third reaction process to prepare the topramezone. The problems that a sulfur-containing intermediate can emit odor and the raw materials are difficult to obtain in the existing process are solved.

Palladium-catalyzed ortho-C(sp2)[sbnd]H bromination of benzaldehydes via a monodentate transient directing group strategy

A facile and efficient monodentate transient directing group strategy was developed to enable the palladium-catalyzed ortho-C(sp2)[sbnd]H bromination of benzaldehydes. A broad scope of benzaldehydes were transformed into the desired products by employing 2-amino-5-chlorobenzotrifluoride as a monodentate transient directing group, demonstrating good functional group tolerance. Mild reaction conditions and no requirement for a silver salt are also features of this strategy.

Chemoselective Reduction of Sterically Demanding N,N-Diisopropylamides to Aldehydes

A sequential one-pot process for chemoselectively reducing sterically demanding N,N-diisopropylamides to aldehydes has been developed. In this reaction, amides are activated with EtOTf to form imidates, which are reduced with LiAlH(OR)3 [R = t-Bu, Et] to give aldehydes by hydrolysis of the resulting hemiaminals. The non-nucleophilic base 2,6-DTBMP remarkably improves reaction efficiency. The combination of EtOTf/2,6-DTBMP and LiAlH(O-t-Bu)3 was found to be optimal for reducing alkyl, alkenyl, alkynyl, and 2-monosubstituted aryl N,N-diisopropylamides. In contrast, EtOTf and LiAlH(OEt)3 in the absence of base were found to be optimal for reducing extremely sterically demanding 2,6-disubstituted N,N-diisopropylbenzamides. The reaction tolerates various reducible functional groups, including aldehyde and ketone. 1H NMR studies confirmed the formation of imidates stable in water. The synthetic usefulness of this methodology was demonstrated with N,N-diisopropylamide-directed ortho-metalation and C-H bond activation.