16414-34-9

Basic information

• Product Name: 5-BROMOPROTOCATECHUALDEHYDE
• Synonyms: 3-BROMO-4,5-DIHYDROXYBENZALDEHYDE;5-BROMOPROTOCATECHUALDEHYDE;5-BROMO-3,4-DIHYDROXYBENZALDEHYDE;AKOS BBS-00004672;AKOS B029187;3,4-Dihydroxy-5-bromobenzaldehyde;Bromoprotocatechualdehyde;NSC 139675
• CAS NO: 16414-34-9
• Molecular Formula: C₇H₅BrO₃
• Molecular Weight: 217.02
• EINECS: 240-463-8
• Product Categories: Aromatic Aldehydes & Derivatives (substituted)
• Mol File: 16414-34-9.mol

Chemical Properties

• Melting Point: 230 °C
• Boiling Point: 297.4 °C at 760mmHg
• Flash Point: 133.7 °C
• Appearance: Light yellow powder
• Density: 1.7054 (rough estimate)
• Vapor Pressure: 0.000762mmHg at 25°C
• Refractive Index: 1.4630 (estimate)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 6.09±0.23(Predicted)
• CAS DataBase Reference: 5-BROMOPROTOCATECHUALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BROMOPROTOCATECHUALDEHYDE(16414-34-9)
• EPA Substance Registry System: 5-BROMOPROTOCATECHUALDEHYDE(16414-34-9)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36-43
• Safety Statements: 26-36/37
• HazardClass: IRRITANT
• Hazardous Substances Data: 16414-34-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
5-Bromoprotocatechualdehyde is used as a starting material in organic synthesis for the preparation of various compounds. Its unique structure and the presence of a bromine atom make it a versatile building block for the creation of a wide range of chemical entities.
Used in Pharmaceutical Development:
In the pharmaceutical industry, 5-Bromoprotocatechualdehyde is utilized as a key intermediate in the synthesis of biologically active molecules and certain pharmaceuticals. Its potential role in the development of new drugs highlights its importance in advancing medicinal chemistry.
Used as a Reagent in Organic Chemistry Reactions:
5-Bromoprotocatechualdehyde also serves as a reagent in various organic chemistry reactions, facilitating the synthesis of complex organic molecules and contributing to the advancement of synthetic methodologies.
Used in Medicinal Chemistry Research:
5-BROMOPROTOCATECHUALDEHYDE's unique structure and properties make it a valuable asset in medicinal chemistry research, where it can be employed to explore novel therapeutic agents and enhance our understanding of molecular interactions and mechanisms of action.

InChI:InChI=1/C7H5BrO3/c8-5-1-4(3-9)2-6(10)7(5)11/h1-3,10-11H

Upstream product

• 139-85-5 3,4-dihydroxybenzaldehyde 
• 121-33-5 vanillin 
• 23354-30-5 3-bromo-4-methoxy-5-hydroxybenzaldehyde 
• 621-59-0 isovanillin 
• 2973-76-4 5-bromo-4-hydroxy-3-methoxybenzaldehyde 

Downstream Products

• 19522-96-4 7-bromo-benzo[1,3]dioxole-5-carbaldehyde 
• 119734-73-5 (6R,7R)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-1-carboxy-1-methyl-ethoxyimino]-acetylamino}-3-[(3-bromo-4,5-dihydroxy-benzoylamino)-methyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 
• 52897-61-7 3-bromo-4,5-dihydroxybenzyl alcohol 
• 124662-50-6 3,4-Bis(benzyloxy)-5-brombenzaldehyd 
• 156605-28-6 3-bromo-4,5-bis(methoxymethoxy)benzaldehyde 
• 6948-30-7 5-bromoveratralaldehyde 
• 511257-05-9 3-allyloxy-5-bromo-4-methoxy-benzaldehyde 
• 511257-06-0 (3-allyloxy-5-bromo-4-methoxy-phenyl)-acetonitrile 
• 511257-07-1 [2-(3-bromo-5-hydroxy-4-methoxy-phenyl)-ethyl]-carbamic acid tert-butyl ester 
• 511257-13-9 2-[(E)-Benzyloxyimino]-3-(3-bromo-5-hydroxy-4-methoxy-phenyl)-propionic acid ethyl ester 
• 511257-11-7 3-(3-allyloxy-5-bromo-4-methoxy-phenyl)-2-(tert-butyl-dimethyl-silanyloxy)-acrylic acid ethyl ester 
• 511257-12-8 3-(3-Allyloxy-5-bromo-4-methoxy-phenyl)-2-[(E)-benzyloxyimino]-propionic acid ethyl ester 
• 511257-08-2 {2-[3-bromo-5-(2-bromo-4-formyl-phenoxy)-4-methoxy-phenyl]-ethyl}-carbamic acid tert-butyl ester 
• 511257-09-3 {2-[3-bromo-5-(2-bromo-4-cyanomethyl-phenoxy)-4-methoxy-phenyl]-ethyl}-carbamic acid tert-butyl ester 

Relevant articles and documents

Radical formation and coupling of hydroxycinnamic acids containing 1,2-dihydroxy substituents

Hydroxycinnamic acids involved in the deposition and cross-linking of plant cell-wall polymers do not usually contain 1,2-dihydroxy substituents, despite the presence of both 3,4-dihydroxycinnamic acid and 4,5-dihydroxy-3-methoxycinnamic acid as intermediates in the biogenesis of lignin. Since the O-methyl transferases, enzymes catalysing methylation, are targets for the genetic manipulation of lignin biosynthesis, the potential incorporation of these 1,2-dihydroxated substrates becomes increasingly significant. Using EPR spectroscopy, it was observed that 1,2-dihydroxy substituents did not have an inhibitory effect on radical formation. Increasing the extent of hydroxylation and methoxylation, resulted in an increased ease of substrate oxidation. Despite formation of the parent radicals, coupling did not proceed, under conditions that generally result in phenylpropanoid polymerisation. It is postulated that intermolecular radical-coupling reactions are inhibited due to rapid conversion to the o-quinone. In contrast, when methoxylated at C3, as in 4,5-dihydroxy-3-methoxycinnamic acid, radical coupling proceeds with the major product resulting from 8-O-3 radical coupling and formation of a substituted 2,3-dihydro-1,4-dioxin ring.

Psammaplin A derivative as well as preparation method and application thereof

The invention provides a Psammaplin A derivative as well as a preparation method and application thereof, and belongs to the field of medicinal chemistry, wherein the Psammaplin A derivative has a structural formula represented by a formula (I), wherein in the formula, R1, R2, R3, R4, R5 and R6 are respectively selected from any one of H, OH, OCH3, Br, 3,5-di-fluoro-benzyloxy, 2-fluoro-benzyloxy, 3-fluoro-benzyloxy, 4-cyano-benzyloxy and 4-trifluoromethyl-benzyloxy; R1 and R4 are the same or different, R2 and R5 are the same or different, and R3 and R6 are the same or different. According to the invention, a new structure and thought are provided for the design of a novel HDAC inhibitor, and the developed Psammaplin A derivative has a good anti-tumor cytotoxicity effect, and also provides an important theoretical reference for the development of HDAC-based anti-tumor drugs.

Bromophenol-pyrazoline compound as well as synthesis method and application thereof (by machine translation)

The invention relates to a compound, in particular to a bromophenol-pyrazoline compound as well as a synthesis method and application thereof. The bromophenol-pyrazoline compound has the following structural general formula: The bromophenol-pyrazoline compound provided by the invention has high-efficiency main protease MPro Activity can be inhibited, and the replication of coronavirus can be disturbed in cells, so that the compound has the efficacy of treating coronavirus pneumonia, and has wide application prospects in preparation of medicines for treating coronavirus pneumonia. (by machine translation)

Anchimerically Assisted Selective Cleavage of Acid-Labile Aryl Alkyl Ethers by Aluminum Triiodide and N, N-Dimethylformamide Dimethyl Acetal

Aluminum triiodide is harnessed by N,N-dimethylformamide dimethyl acetal (DMF-DMA) for the selective cleavage of ethers via neighboring group participation. Various acid-labile functional groups, including carboxylate, allyl, tert-butyldimethylsilyl (TBS), and tert-butoxycarbonyl (Boc), suffer the conditions intact. The method offers an efficient approach to cleaving catechol monoalkyl ethers and to uncovering phenols from acetal-type protecting groups such as methoxymethyl (MOM), methoxyethoxymethyl (MEM), and tetrahydropyranyl (THP) chemoselectively.

Selective ether bond breaking method of aryl alkyl ether

The invention discloses a selective aryl alkyl ether cracking method, which comprises that aryl alkyl ether, aluminum iodide and an additive are subjected to a selective ether bond cleavage reaction in an organic solvent at a temperature of -20 DEG C to a reflux temperature to generate phenol and derivatives thereof. The method is mild in condition and simple and convenient to operate, is suitablefor cracking aryl alkyl ether containing o-hydroxyl and o-carbonyl and acetal ether, and can also be used for removing tertiary carbon hydroxyl protecting groups with higher steric hindrance, such astriphenylmethyl, tertiary butyl and the like.

PYRIMIDONE DERIVATIVES AS SELECTIVE CYTOTOXIC AGENTS AGAINST HIV INFECTED CELLS

The present disclosure is directed to pyrimidone derivatives of Formula I and their use for selectively killing HIV infected GAG-POL expressing cells without concomitant cytotoxicity to HIV nave cells, and for the treatment or prophylaxis of infection by HIV, or for the treatment, prophylaxis or delay in the onset or progression of AIDS or AIDS Related Complex (ARC).

Compound for treating or preventing hepatopathy (by machine translation)

The invention discloses a compound, an optical isomer or a pharmaceutically acceptable salt, an optical isomer or a pharmaceutically acceptable salt thereof for treating or preventing hepatopathy, and the compound, optical isomer or pharmaceutically acceptable salt thereof can be applied to the preparation of a medicine for treating or preventing liver diseases. (by machine translation)

SUBSTITUTED AMINOTHIAZOLES AS INHIBITORS OF NUCLEASES

The invention provides compounds represented by the structural formula (1): wherein R1, R2, R3, R4, R5, R6 are as defined in the claims. The compounds are inhibitors of nucleases, and are useful in particular in a method of treatment and/or prevention of proliferative diseases, neurodegenerative diseases, and other genomic instability associated diseases.

Cleavage of Catechol Monoalkyl Ethers by Aluminum Triiodide-Dimethyl Sulfoxide

Using eugenol and vanillin as model substrates, a practical method is developed for the cleavage o -hydroxyphenyl alkyl ethers. Aluminum oxide iodide (O=AlI), generated in situ from aluminum triiodide and dimethyl sulfoxide, is the reactive ether cleaving species. The method is applicable to catechol monoalkyl ethers as well as normal phenyl alkyl ethers for the removal of methyl, ethyl, isopropyl, and benzyl groups. A variety of functional groups such as alkenyl, allyl, amide, cyano, formyl, keto, nitro, and halogen are well tolerated under the optimum conditions. Partial hydrodebromination was observed during the demethylation of 4-bromoguaiacol, and was resolved using excess DMSO as an acid scavenger. This convenient and efficient procedure would be a practical tool for the preparation of catechols.

Toward a treatment of diabesity: In vitro and in vivo evaluation of uncharged bromophenol derivatives as a new series of PTP1B inhibitors

Protein tyrosine phosphatase 1B (PTP1B) has been considered as a validated biological target for type 2 diabetes treatment, but past endeavors to develop inhibitors of PTP1B into drugs have been unsuccessful. Two challenging aspects are selective inhibition and cell permeability. A structure-based strategy was employed to develop uncharged bromophenols as a new series of PTP1B inhibitors. The most potent compound 22 (LXQ46) inhibited PTP1B with an IC50 value of 0.190 μM, and showed remarkable selectivity over other protein tyrosine phosphatases (PTPs, 20–200 folds). In the SPR study, increasing concentrations of compound 22 led to concentration-dependent increases in binding responses, indicating that compound 22 could bind to the surface of PTP1B via noncovalent means. By treating insulin-resistant C2C12 myotubes with compound 22, enhanced insulin and leptin signaling pathways were observed. Long-term oral administration of compound 22 reduced the blood glucose level of diabetic BKS db mice. The glucose tolerance tests (OGTT) and insulin tolerance tests (ITT) in BKS db mice showed that oral administration of compound 22 could increase insulin sensitivity. In addition, long-term oral administration of compound 22 could protect mice from obesity, which was not the result of toxicity. Our pharmacokinetics results from the rat-based assays showed that orally administered compound 22 was absorbed rapidly from the gastrointestinal tract, extensively distributed to the tissues, and rapidly eliminated from the body. All these results indicate that compound 22 could serve as a qualified agent to treat type II diabetes.