24856-58-4

Basic information

• Product Name: 4-BROMOBENZALDEHYDE DIMETHYL ACETAL
• Synonyms: P-BROMO BENZALDEHYDE DIMETHYLACETAL;4-BROMOBENZALDEHYDE DIMETHYL ACETAL;(4-Bromophenyl)dimethoxymethane;1-(Dimethoxymethyl)-4-bromobenzene;1-Bromo-4-(dimethoxymethyl)benzene;4-BroMobenzaldehyde diMethyl acetal 98%
• CAS NO: 24856-58-4
• Molecular Formula: C₉H₁₁BrO₂
• Molecular Weight: 231.09
• Product Categories: Adehydes, Acetals & Ketones;Bromine Compounds;Acetals/Ketals/Ortho Esters;Organic Building Blocks;Oxygen Compounds
• Mol File: 24856-58-4.mol

Chemical Properties

• Boiling Point: 254 °C(lit.)
• Flash Point: >230 °F
• Appearance: /Liquid
• Density: 1.383 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0612mmHg at 25°C
• Refractive Index: n20/D 1.532(lit.)
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility: Insoluble in water.
• CAS DataBase Reference: 4-BROMOBENZALDEHYDE DIMETHYL ACETAL(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BROMOBENZALDEHYDE DIMETHYL ACETAL(24856-58-4)
• EPA Substance Registry System: 4-BROMOBENZALDEHYDE DIMETHYL ACETAL(24856-58-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 24856-58-4(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
4-Bromobenzaldehyde dimethyl acetal is used as an intermediate in the production of other chemicals, specifically for synthesizing 1-Bromo-4-bromomethyl-benzene at ambient temperature. This application takes advantage of its reactivity and ability to form new chemical bonds.
Used in the Synthesis of Specialty Compounds:
In the field of organic chemistry, 4-Bromobenzaldehyde dimethyl acetal is used as a reagent in the synthesis of complex organic compounds, such as [2-(4-dimethoxymethylphenyl)-vinyl]-trimethyl-silane and di(4-formylphenyl)diphenylsilane. These compounds have potential applications in various industries, including materials science and pharmaceuticals, due to their unique structures and properties.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, given its role in the synthesis of various organic compounds, 4-Bromobenzaldehyde dimethyl acetal may also find use in the pharmaceutical industry as a building block for the development of new drugs or drug candidates.
Used in Materials Science:
Similarly, the unique properties of compounds synthesized using 4-Bromobenzaldehyde dimethyl acetal may be exploited in materials science for the development of novel materials with specific characteristics, such as improved mechanical, electrical, or thermal properties.

InChI:InChI=1/C9H11BrO2/c1-11-9(12-2)7-3-5-8(10)6-4-7/h3-6,9H,1-2H3

Upstream product

• 1122-91-4 4-bromo-benzaldehyde 
• 149-73-5 trimethyl orthoformate 
• 67-56-1 methanol 
• 106-38-7 para-bromotoluene 
• 188050-05-7 (4-Bromo-phenyl)-methanesulfinic acid methyl ester 

Downstream Products

• 619-42-1 4-methoxycarbonylphenyl bromide 
• 104865-88-5 trimethyl 4-bromobenzoate 
• 114533-82-3 1-Bromo-4-(1,3,3-trimethoxy-propyl)-benzene 
• 129413-28-1 (1S,2R,5R,6R,7S,8R,12S,13S,17R)-15-(4-Bromo-phenyl)-7-hydroxy-2,5,6,8,12,17-hexamethyl-4,14,16-trioxa-bicyclo[11.3.1]heptadecane-3,9-dione 
• 119887-69-3 (1S,2R,5R,6R,7R,8R,9R,12S,13S,17R)-15-(4-Bromo-phenyl)-7,9-dihydroxy-2,5,6,8,12,17-hexamethyl-10-methylene-4,14,16-trioxa-bicyclo[11.3.1]heptadecan-3-one 
• 103561-09-7 methyl 3‐(4‐formylphenoxy)benzoate 
• 156766-84-6 (2R,3S,4R,5S,6S,8S,9R,10R,11R,12R,13R)-3,5-<(p-bromobenzylidene)dioxy>-8,8-(epoxymethano)-9,11-dihydroxy-2,4,6,10,12,13-hexamethyltetradecanolide 
• 1122-91-4 4-bromo-benzaldehyde 
• 589-15-1 1-bromomethyl-4-bromobenzene 
• 589-17-3 p-bromobenzyl chloride 
• 111734-82-8 C₃₁H₄₁⁽²⁾H₄BrO₈ 
• 142581-73-5 4-(2-hydroxy-2-propyl)benzaldehyde dimethyl acetal 
• 134360-17-1 4-(N,N-dimethylthiocarbamoyl)benzaldehyde dimethyl acetal 
• 134619-70-8 4-bromo-4-(4-bromo-phenyl)-but-1-ene 

Relevant articles and documents

Preparation of a Yb(III)-Incorporated porous polymer by post-Coordination: Enhancement of gas adsorption and catalytic activity

We synthesized a Yb(III)-incorporated microporous polymer (Yb-ADA) and studied its gas adsorption property and catalytic activity. The adamantane-based porous polymer (ADA) was obtained from an ethynyl-functionalized adamantane derivative and 2,5-dibromoterephthalic acid through Sonogashira-Hagihara cross-coupling. ADA had two carboxyl groups which were used for Yb(III) coordination under basic conditions. The Brunauer-Emmett-Teller (BET) surface area of ADA was 970 m2 g-1. As Yb(III) ions were incorporated into ADA, the surface area of the polymer (Yb-ADA) was reduced to 885 m2 g-1. However, Yb-ADA exhibited a significantly enhanced CO2 adsorption capacity despite the reduction of surface area. The CO2 uptakes of ADA and Yb-ADA were 1.56 and 2.36 mmol g-1 at 298 K, respectively. The H2 uptake of ADA also increased after coordination with Yb(III) from 1.15 to 1.40 wt % at 77 K. Yb-ADA showed high catalytic activity in the acetalization of 4-bromobenzaldehyde and furfural with trimethyl orthoformate and could be reused after recovery without severe loss of activity.

Practical acetalization and transacetalization of carbonyl compounds catalyzed by recyclable PVP-I

A novel PVP-I catalyzed acetalizations/transacetalizations of carbonyl compounds has been developed processing with a mild and easy handling fashion. Different types of Acyclic and cyclic acetals were prepared from carbonyl compounds or their acetals successfully. Further applications of newly developed catalytic combination were testified. This protocol featured with simplicity of operation, mild reaction condition, short reaction time, recyclable of catalyst and broad substrates scope with excellent yields.

Preparation method of acetal or ketal compound

The invention discloses a preparation method of an acetal or ketal compound. The preparation method comprises the following steps: oscillating aldehyde or ketone, alcohol and a catalyst at 60 DEG C, and carrying out post-treatment after the reaction is finished to obtain the acetal compound, wherein the catalyst comprises alpha-chymotrypsin, the aldehyde or ketone has a structure represented by acompound A, R1 and R2 are respectively and independently selected from aryl, H and alkyl, the alcohol has a structure represented by a compound B, and R3 is selected from saturated alkane. The preparation method provided by the invention is catalyzed by alpha-chymotrypsin, is mild in reaction condition, simple in operation process, low in cost and environment-friendly, and has popularization and application values.

α-Chymotrypsin-Induced Acetalization of Aldehydes and Ketones with Alcohols

This is the first report of a simple and general method for acetalization of aldehydes via an α-chymotrypsin-induced reaction under mild conditions. A broad range of aromatic and heteroaromatic aldehydes have been acetalized under neutral conditions in good yields using a catalytic amount of chymotrypsin.

Photochemical synthesis of acetals utilizing Schreiner's thiourea as the catalyst

Acetalization of aldehydes is an area of great importance in Organic Chemistry for both synthetic and biological puproses. Herein, we report a mild, inexpensive and green photochemical protocol, where Schreiner's thiourea (N,N′-bis[3,5-bis(trifluoromethyl)-phenyl]-thiourea) is utilized as the catalyst and cheap household lamps as the light source. A variety of aromatic and aliphatic aldehydes were converted into acetals in good to high yields (23 examples, 36-96% yield) and an example of the synthesis of a cyclic acetal is provided. The reaction mechanism was also studied.

Synthesis, structural determination and catalytic study of a new 2-D chloro-substituted zinc phosphate, (C8N2H20)[ZnCl(PO3(OH))]2

A novel chloro-substituted zinc-phosphate, (C8N2H20)[ZnCl(PO3(OH))], has been synthesized by a slow evaporation method in the presence of 1,3-cyclohexanebis- (methylamine), which acts as a template. The structure consists of vertex linked ZnO3Cl and PO3(OH) tetrahedral, assembled into corrugated porous layers [ZnCl(PO3(OH))2]∞ with (4.82) topology. The optical properties were also investigated using Diffuse Reflecting Spectroscopy (DRS), showing that the title compound has semiconducting properties. In addition, the catalytic activity of (C8N2H20)[ZnCl(PO3(OH))]2 has been tested in the acetalisation reaction of aldehydes. The title compound displayed a high catalytic activity with practically total conversion in many examples using MeOD as solvent and as the sole source of acetalisation. More importantly, the reaction crudes are very clean and only the preferred products are found in the NMR spectra.

Photo-organocatalytic synthesis of acetals from aldehydes

A mild and green photo-organocatalytic protocol for the highly efficient acetalization of aldehydes has been developed. Utilizing thioxanthenone as the photocatalyst and inexpensive household lamps as the light source, a variety of aromatic and aliphatic aldehydes have been converted into acyclic and cyclic acetals in high yields. The reaction mechanism was extensively studied.

Nickel-Catalyzed Chemoselective Acetalization of Aldehydes With Alcohols under Neutral Conditions

A molecularly defined NiII-complex catalyzing the chemoselective acetalization of aldehydes with alcohols under neutral conditions is reported. The reaction is general, efficient and showed a wide substrate scope (including aliphatic aldehydes) as well as excellent functional group tolerance. Reusability of the present nickel catalyst is also demonstrated.

Chemoselective Nucleophilic Functionalizations of Aromatic Aldehydes and Acetals via Pyridinium Salt Intermediates

The development of a novel chemoselective functionalization can diversify the strategy for synthesizing the target molecules. The perfect chemoselectivity between aromatic and aliphatic aldehydes is difficult to achieve by the previous methods. The aromatic aldehyde-selective nucleophilic addition in the presence of aliphatic aldehydes was newly accomplished. Namely, the aromatic aldehyde-selective nucleophilic addition using arenes and allyl silanes proceeded in the presence of trialkylsilyl triflate and 2,2′-bipyridyl, while the aliphatic aldehydes completely remained unchanged. The reactive pyridinium-type salt intermediate derived from an aromatic aldehyde chemoselectively underwent the nucleophilic substitution. Moreover, the aromatic acetals as the protected aldehydes could be directly transformed into similar pyridinium salt intermediates, which reacted with various nucleophiles coexisting with the aliphatic aldehydes.

Formation of Acetals and Ketals from Carbonyl Compounds: A New and Highly Efficient Method Inspired by Cationic Palladium

The development of a new, highly efficient, and simple method for masking carbonyl groups as acetals and ketals is described. This methodology relies on the nature of the palladium catalyst to direct the acetalization/ketalization reaction. This new protocol is mild and proceed with a very low catalyst loading at ambient temperatures. The method has been extended to a wide variety of different carbonyl compounds with various steric encumbrances to form the corresponding acetals and ketals in excellent yields.