3395-81-1

Basic information

• Product Name: 4-CHLOROBENZALDEHYDE DIMETHYL ACETAL 9&
• Synonyms: 4-CHLOROBENZALDEHYDE DIMETHYL ACETAL 9&;4-Chlorobenzaldehyde dimethyl acetal 98%
• CAS NO: 3395-81-1
• Molecular Formula: C₉H₁₁ClO₂
• Molecular Weight: 186.637
• Product Categories: Acetals/Ketals/Ortho Esters;Organic Building Blocks;Oxygen Compounds
• Mol File: 3395-81-1.mol

Chemical Properties

• Boiling Point: 114-115 °C19 mm Hg(lit.)
• Flash Point: 215 °F
• Appearance: /
• Density: 1.128 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.282mmHg at 25°C
• Refractive Index: n20/D 1.508(lit.)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4-CHLOROBENZALDEHYDE DIMETHYL ACETAL 9&(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLOROBENZALDEHYDE DIMETHYL ACETAL 9&(3395-81-1)
• EPA Substance Registry System: 4-CHLOROBENZALDEHYDE DIMETHYL ACETAL 9&(3395-81-1)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 3395-81-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Chlorobenzaldehyde dimethyl acetal is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique structure and reactivity allow for the development of new drugs with potential therapeutic applications.
Used in Flavor and Fragrance Industry:
4-CHLOROBENZALDEHYDE DIMETHYL ACETAL 9& is also used as a building block in the creation of unique fragrances and flavors. Its distinct chemical properties contribute to the development of novel scents and tastes for various consumer products.
Used in Chemical Research:
4-Chlorobenzaldehyde dimethyl acetal serves as a valuable research tool in organic chemistry. It is used to study reaction mechanisms, explore new synthetic routes, and develop innovative chemical processes.
Used in Agrochemical Industry:
In the agrochemical sector, 4-Chlorobenzaldehyde dimethyl acetal is utilized as a precursor for the development of new pesticides and other agrochemical products. Its unique structure allows for the creation of compounds with improved efficacy and selectivity.

InChI:InChI=1/C9H11ClO2/c1-11-9(12-2)7-3-5-8(10)6-4-7/h3-6,9H,1-2H3

Upstream product

• 110-89-4 piperidine 
• 67-56-1 methanol 
• 104-88-1 4-chlorobenzaldehyde 
• 149-73-5 trimethyl orthoformate 
• 86340-78-5 2,2-difluoro-1-phenyl-1-trimethylsiloxyethene 
• 1073-67-2 4-vinylbenzyl chloride 
• 64-17-5 ethanol 
• 106-43-4 para-chlorotoluene 
• 1878-66-6 4-chlorophenylacetic Acid 
• 89712-45-8 N,N-dimethylformamide dimethyl sulfate adduct 
• 16361-37-8 4,4'-((4-chlorophenyl)methylene)dimorpholine 
• 10359-09-8 2-(4-chlorophenyl)-1,3-dithiane 
• 3510-48-3 4-chlorobenzaldehyde azine 
• 104-83-6 1-Chloro-4-(chloromethyl)benzene 

Downstream Products

• 56377-71-0 (α,4-Dichlorbenzyl)methylether 
• 63523-32-0 N-[(4-chloro-phenyl)-methoxy-methyl]-4-methoxy-thiobenzamide 
• 77961-17-2 5-[2-(4-Chloro-phenyl)-2-methoxy-ethyl]-2-methoxy-2,4-dimethyl-2,3-dihydro-benzo[b]oxepine 
• 126855-52-5 (2E,4E)-5-(4-Chloro-phenyl)-3-methylsulfanyl-1-phenyl-penta-2,4-dien-1-one 
• 126855-53-6 2-(4-chlorophenyl)-2,3-dihydro-6-phenyl-4H-pyran-4-one 
• 126855-54-7 (2E,4E)-1,5-Bis-(4-chloro-phenyl)-3-methylsulfanyl-penta-2,4-dien-1-one 
• 126855-55-8 2,6-Bis-(4-chloro-phenyl)-2,3-dihydro-pyran-4-one 
• 253148-37-7 meso-1,2-bis-(4'-chlorophenyl)-1,2-dimethoxyethane 
• 26434-37-7 d,l-1,2-bis-(4'-chlorophenyl)-1,2-dimethoxyethane 
• 104-88-1 4-chlorobenzaldehyde 
• 104-83-6 1-Chloro-4-(chloromethyl)benzene 
• 622-95-7 4-chlorobenzyl bromide 
• 33225-02-4 2-(4-chlorophenyl)-2-methoxyacetonitrile 
• 879492-11-2 1-methoxy-3,3-dimethyl-1-phenylbutan-2-ol 

Relevant articles and documents

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.

Thiol-initiated photocatalytic oxidative cleavage of the C=C bond in olefins and its extension to direct production of acetals from olefins

The oxidative cleavage of olefins to produce aldehydes/ketones is an important reaction in organic syntheses. In this manuscript, a mild and operationally simple protocol for the aerobic oxidation of olefins to produce carbonyl compounds was realized over ZnIn2S4under visible light, using air as the oxidant and a thiol as the initiator. It was proposed that the photogenerated holes over ZnIn2S4attack the thiol to produce thiyl radicals, which initiate the oxidative cleavage of the C=C bond in olefins to produce aldehydes/ketones. By further coupling with the condensation between the as-obtained aldehydes/ketones and alcohols, this strategy can also be applied to the production of different acetals directly from the olefins. This study demonstrates a new pathway to realize the oxidative cleavage of olefins to produce aldehydes/ketones, and also provides a new protocol for the production of acetals directly from the olefins.

Systematic Study of Regioselective Reductive Ring-Opening Reactions of 4,6- O-Halobenzylidene Acetals of Glucopyranosides

Reductive openings of cyclic acetals are widely used in modern synthetic organic chemistry for the regioselective introduction of protecting groups. A systematic study was performed on the applicability and efficacy of various hydride donor and protic or Lewis acid reagent combinations in the reductive ring opening of glucosidic 4,6-halobenzylidene acetals bearing an ortho-, meta-, and para-chloro- or -bromo substituent on the benzene ring. Most of the reagent combinations tested cleaved the 4,6-O-halobenzylidene acetal rings at O4 or O6 efficiently and with the expected regioselectivity. The LiAlH4-AlCl3 and the BH3·THF-TMSOTf combinations produced the 4-O-halobenzyl ether/6-OH products with complete regioselectivity and high yields. The use of Me3N·BH3-AlCl3 reagent system in toluene was also effective in cleaving the acetal ring at O6 but was accompanied by Al-chelation-assisted debenzylation side reactions. The NaCNBH3-HCl and the Et3SiH-BF3·Et2O combinations were highly effective in yielding the 6-halobenzyl ether/4-OH derivatives. Et3SiH, in combination with TfOH, produced the 6-O-ether/4-OH products in rapid reactions but also triggered silylation and reductive halobenzylation as secondary transformations. Reductive opening of the 1,3-dioxane ring of pyranosidic 4,6-O-halobenzylidene acetals by the proper reagent combination was found to be an efficient method for the regioselective introduction of versatile halobenzyl protecting groups onto the pyranose ring.

Amino acid derivative, feed composition and application thereof

The invention provides an amino acid derivative, a feed composition and application thereof, and belongs to the technical field of animal feed additives. The amino acid derivative is a compound with astructure shown as a formula (I), and a stereoisomer, a tautomer, a solvate, a metabolite, a feed acceptable salt or a prodrug thereof. In formula (I) shown in the specification, Z is a C1-C3 alkylene group. X is an indole ring group with a structure shown as a formula (II). The formula (II) is shown in the specification, wherein Y is phenyl with the structure shown in the formula (III) shown inthe specification. The amino acid derivative is used as an animal feed additive, and can promote the growth of animals and improve the feed conversion.

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.

Remote ‘Imidazole’ Based Ruthenium(II) p-Cymene Precatalyst for Selective Oxidative Cleavage of C?C Multiple Bonds

The dual role of remote ‘imidazole’ attached with the precatalyst [(p-cymene)RuII(L)Y]+ (L=2-(4-substituted-phenyl)-1H-imidazo[4,5-f][1,10] phenanthroline, Y=chloride/solvent) was explored for the selective oxidative cleavage of C?C multiple bonds to acetals/aldehydes. The presence of ‘imidazole’ in the precatalysts was found to be useful for the activation of oxidant and release of p-cymene from the precatalysts, which in turn was not effective without the ‘imidazole’ moiety. The mechanistic aspects of the precatalyst were evaluated from spectroscopic, kinetic, and few other controlled experiments. The loss of p-cymene is the key step for the reaction and found to be faster in solvated precatalyst, [(p-cymene)RuII(L)(MeOH)]++ and thus showed 3–4-fold more effective as compared to [(p-cymene)RuII(L)Cl]+.

Industrial production method of atazanavir intermediate tert-butyl 2-[4-(2-pyridyl)benzyl]-carbazate

The invention relates to the technical field of biological industry, in particular to an industrial production method of atazanavir intermediate tert-butyl 2-[4-(2-pyridyl)benzyl]-carbazate. The industrial production method includes: subjecting p-chlorobenzaldehyde as a raw material to aldolization, carrying out Grignard coupling reaction, carrying out reductive amination to generate phenylhydrazone, and carrying out hydrogenation to obtain the target product tert-butyl 2-[4-(2-pyridyl)benzyl]-carbazate. Compared with the prior art, the industrial production method has the advantages of high efficiency, good stability, low cost, good operational convenience and the like, and is suitable for continuous production of high-quality products, with product purity reaching 99% and above and unknow impurity content less than 0.3%.

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.

Synthesis of (E)-α,β-unsaturated carboxylic esters derivatives from cyanoacetic acid via promiscuous enzyme-promoted cascade esterification/Knoevenagel reaction

A new enzymatic protocol based on lipase-catalyzed cascade toward (E)-α,β-unsaturated carboxylic esters is presented. The proposed methodology consists of elementary organic processes starting from acetals and cyanoacetic acid leading to the formation of desired products in a cascade sequence. The combination of enzyme promiscuous abilities gives a new opportunity to synthesize complex molecules in the one-pot procedure. Results of studies on the influence of an enzyme type, solvent, and temperature on the cascade reaction course are reported. The presented methodology provides meaningful qualities such as significantly simplified process, excellent E-selectivity of obtained products and recycling of a biocatalyst.