35822-58-3

Usage

Uses

Used in Organic Synthesis:
2-BROMOBENZALDEHYDE DIETHYL ACETAL is used as a reagent for the protection of aldehyde groups in organic synthesis. Its selective and mild nature allows for the efficient shielding of aldehyde groups during chemical reactions, preventing unwanted side reactions and facilitating the synthesis of complex organic molecules.
Used in Research Settings:
In laboratories and research environments, 2-BROMOBENZALDEHYDE DIETHYL ACETAL is utilized for its reactivity and versatility in organic synthesis. It aids researchers in exploring new chemical pathways and developing innovative synthetic methods, contributing to the advancement of chemical science.
Used in Pharmaceutical Industry:
2-BROMOBENZALDEHYDE DIETHYL ACETAL is employed in the pharmaceutical industry as a key intermediate in the synthesis of various pharmaceutical compounds. Its ability to protect aldehyde groups simplifies the synthesis process and enhances the yield of desired products, leading to the development of new and effective drugs.
Used in Chemical Reactions and Transformations:
2-BROMOBENZALDEHYDE DIETHYL ACETAL is used as a reagent in various chemical reactions and transformations, including the synthesis of complex organic molecules, the formation of new chemical bonds, and the modification of existing structures. Its selective protection of aldehyde groups allows for greater control over reaction outcomes and the production of high-quality products.

InChI:InChI=1/C11H15BrO2/c1-3-13-11(14-4-2)9-7-5-6-8-10(9)12/h5-8,11H,3-4H2,1-2H3

Upstream product

• 998-30-1 Triethoxysilane 
• 6630-33-7 ortho-bromobenzaldehyde 
• 64-17-5 ethanol 
• 107-21-1 ethylene glycol 
• 122-51-0 orthoformic acid triethyl ester 

Downstream Products

• 871919-39-0 1-(2-diethoxymethyl-phenyl)-2,3,4,5-tetramethyl-cyclopent-2-enol 
• 6630-33-7 ortho-bromobenzaldehyde 
• 951024-23-0 (S)-2-(p-tolylsulfinyl)benzaldehyde diethyl acetal 
• 17887-55-7 2-trimethylsilylbenzaldehyde 
• 22112-81-8 tetrasodium tetrakis(2'-sulfonatophenyl)porphyrin 
• 28192-56-5 2-Butyltellanyl-benzoic acid ethyl ester 
• 28192-57-6 C₁₃H₁₈Cl₂O₂Te 
• 28192-55-4 bis(ortho-formylphenyl)ditelluride 
• 103890-70-6 2-(diethoxymethyl)benzaldehyde 
• 879397-93-0 tris(2-diethyl acetal formylphenyl)stibine 
• 142598-69-4 2-(naphthalene-1-yl)benzaldehyde 

Relevant academic research and scientific papers

Multistep Photoisomerization of Dimesitylboron-Functionalized Stilbene Analogues

Dimesitylboron-functionalized stilbene derivatives have been found to undergo an unusual regioselective photoisomerization upon irradiation at 365 nm. Using NMR to follow the photoreaction, the structures of key reaction intermediates and the final produc

Copper-Catalyzed One-Pot Cascade Cyclization for the Synthesis of Isoindolo[2,1-a]quinoxalines

A copper-catalyzed one-pot cascade cyclization of 2-(1-(acetyloxy)propargyl)benzaldehydes with o-phenylenediamines for an access to substituted isoindolo[2,1-a]quinoxalines has been developed. The reaction features readily available starting materials, simple operational procedure, and broad substrate scopes. Under optimal conditions, various isoindolo[2,1-a]quinoxalines were afforded in 41–88% yields. (Figure presented.).

Construction of complex bisether-bridged medium-sized cyclic compounds from o-(1-(acyloxy)propargyl)benzaldehydes under base and acid catalysis

We report herein our serendipitous discovery of the rapid and straightforward accesses to unprecedented diverse complex molecular structures from readily available starting materials. Catalyzed by 1,8-diazabicyclo[5.4.0]undec-7-ene under mild conditions, o-(1-(acyloxy)propargyl)benzaldehydes 1 underwent efficient and selective dimerization reactions to produce novel complex bisether-bridged tricyclic products 3 and 4. The reactions proceeded most probably through dimerizations between 3-methylene-3H-isochromene intermediate and its zwitterionic resonance structures which were generated from a concerted 6-πelectrocyclic ring closure reaction from the initially formed (2-formylphenyl)allene intermediates derived directly from o-(1-(acyloxy)propargyl)benzaldehydes. Treatment of the resulting product simply with NaOEt in ethanol and aqueous HCl, respectively, enabled further development of complex molecular diversities.

Asymmetric Synthesis of Multifunctionalized 2,3-Benzodiazepines by a One-Pot N-heterocyclic Carbene/Chiral Palladium Sequential Catalysis

We report the first example of the construction of chiral 2,3-benzodiazepine compounds which are of biologic and pharmaceutical relevance by asymmetric catalysis. Catalyzed by a thiazolium-derived carbene and a palladium-chiral bidentate phosphine complex

Direct anodic (thio)acetalization of aldehydes with alcohols (thiols) under neutral conditions, and computational insight into the electrochemical formation of the acetals

A versatile protocol for the production of acetals/thioacetals by means of direct electrochemical oxidation is developed here under neutral conditions, providing (thio)acetals with good functional group tolerance and a wide scope for both aldehydes and (thio)alcohols. DFT calculations reveal that direct electron transfer from the anode plays a key role in carbonyl activation during this acid free acetalization process.

Heterocoumarins Are Selective Carbonic Anhydrase IX and XII Inhibitors with Cytotoxic Effects against Cancer Cells Lines

We have synthesized a new series of coumarin-based compounds demonstrating high selectivity and potent effects with low nanomolar affinity against the tumor associated carbonic anhydrase (CA, EC 4.2.1.1) isoforms hCA IX and XII. A number of these compounds were evaluated ex vivo against human prostate (PC3) and breast (MDA-MB-231) cancer cell lines. Compounds 4b and 15 revealed effective cytotoxic effects after 48 h of incubation in both normoxic and hypoxic conditions with PC3 cancer cell line. However, compound 3 showed selective cytotoxic effects against MDA-MB-231 in hypoxic condition. These results may be of particular importance for the choice of future drug candidates targeting hypoxic tumors and metastases, considering the fact that a selective carbonic anhydrase CA IX inhibitor (SLC-0111) is presently in phase II clinical trials.

Antimony(v) catalyzed acetalisation of aldehydes: An efficient, solvent-free, and recyclable process

A highly selective, solvent-free process for the acetalisation of aldehydes was achieved by the use of a readily accessible antimony(v) catalyst which we previously prepared in our lab as a tetraarylstibonium triflate salt ([1][OTf]). High yields of the acetals were achieved in the presence of stoichimetric amounts of either triethoxymethane or triethoxysilane. It was found that triethoxymethane reactions required longer time to reach completion when compared to triethoxysilane reactions which were completed upon mixing of the reagents. The products can be easily separated from the catalyst by distillation which enabled further use of [1][OTf] in additional calytic reactions (up to 6 cycles). Moreover, [1]+ also catalyzed the deprotection of the acetals into their corresponding aldehydes using only water as a solvent.

Hypervalent iodine(III)-mediated benzannulation of enamines with alkynes: An efficient synthesis of substituted aminonaphthoic acid derivatives

An intermolecular two C-C bond formation procedure for the synthesis of carbocycles mediated by hypervalent iodine(III) reagents was developed. This metal free protocol provided a new approach for the synthesis of useful substituted 1-amino-2-naphthoic ac

SUBSTITUTED BENZYLAMINES AND THEIR USE FOR THE TREATMENT OF DEPRESSION

The present invention relates to certain novel benzylamine derivatives of formula (I) wherein R and R, which may be the same or different, are each selected from C6-12aryl, C2-14heteroaryl, C6-12arylC1-6alkyl, C2-14heteroarylC1-6alkyl (where the alkyl, aryl or heteroaryl moiety may be optionally substituted by one or more substituents selected from C1-6alkoxy, C1-6alkyl, C3-6cycloalkyl, C4-6cycloalkenyl, C6-12aryl, C2-14heteroaryl, halogen, amino, hydroxy, haloC1-6alkyl, nitro, C1-6alkylthio, sulphonamide, C1-6alkylsulphonyl, hydroxy-C1-6alkyl, C1-6alkoxycarbonyl, carboxyl, carboxyC1-6alkyl, carboxamide and C1-6alkylcarboxamide), hydrogen, C1-6alkyl, C3-6cycloalkyl, C4-6cycloalkenyl, C2-6alkenyl, C2-6alkynyl and C1-6alkoxyC1-6alkyl (where the alkyl, cycloalkyl, cycloalkenyl, alkenyl, alkynyl, or alkoxyalkyl moieties may be optionally substituted by one or more substituents selected from amino, halogen, hydroxy, C1-6alkylcarboxamide, carboxamide, carboxy, C1-6alkoxycarbonyl, C1-6alkylcarboxy and carboxyC1-6alkyl) or one of R and R are as hereinbefore defined and one is hydroxy; R and R, which may be the same or different, are each selected from C6-12aryl, C2-14heteroaryl, C6-12arylC1-6alkyl, C2-14heteroarylC1-6alkyl (where the alkyl, aryl or heteroaryl moiety may be optionally substituted by one or more substituents selected from C1-6alkoxy, C1-6alkyl, C3-6cycloalkyl, C4-6cycloalkenyl, C6-12aryl, C2-14heteroaryl, halogen, amino, hydroxy, haloC1-6alkyl, nitro, C1-6alkylthio, sulphonamide, C1-6alkylsulphonyl, hydroxyC1-6alkyl, C1-6alkoxycarbonyl, carboxyl, carboxyC1-6alkyl, C1-6alkylcarboxamide and carboxamide), hydrogen, C1-6alkyl, C3-6cycloalkyl, C3-6cycloalkylC1-6alkyl, C4-6cycloalkenyl, C2-6alkenyl, C2-6alkynyl, C1-6alkoxy-C1-6alkyl, haloC1-6alkyl, haloC2-6alkenyl, haloC2-6alkynyl, cyano, carboxyl, C1-6alkylcarboxy and carboxyC1-6alkyl (where the alkyl, cycloalkyl, cycloalkenyl, alkenyl, alkynyl, or alkoxyalkyl moieties may be optionally substituted by one or more substituents selected from amino, hydroxy, C1-6alkylcarboxamide, carboxamide, carboxy, C1-6alkoxycarbonyl, C1-6alkylcarboxy and carboxyC1-6alkyl); or one of R or R together with one of R or R and the N atom to which it is attached form a 5- or 6-membered heterocyclic ring. R represents one or more ring substituents selected from halogen, hydrogen C1-6alkyl and C1-6alkoxy; and R represents a single ring substituent of formula (A) wherein the dotted line represents an optional bond; Y is oxygen or -NR (where R is hydrogen or C1-6alkyl) and R represents one or more substituents selected from hydrogen, halogen, haloC1-6alkyl, C1-6alkyl and C1-6alkoxy; or a pharmaceutically acceptable salt or solvate thereof. The invention also relates to processes for their preparation, to pharmaceutical formulations containing them and to their use in medical therapy, particularly in the treatment of depression.

Benzylamine derivatives which are useful in treating psychiatric disorders

The present invention relates to certain novel benzylamine derivatives, to processes for their preparation, to pharmaceutical formulations containing them and to their use in medical therapy, particularly in the treatment of depression.