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
• Article Data: 48

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

Description

4-Bromobenzaldehyde dimethyl acetal is an acetal derivative of 4-bromobenzaldehyde, characterized by its ability to produce other chemicals and its specific enthalpy of vaporization at boiling point (527.15K), which is 46.499 kJ/mol. It can be synthesized by reacting 4-bromobenzaldehyde with methanol in the presence of triethylamine and titanium chloride.

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.

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.

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.