115787-50-3

Basic information

• Product Name: 5-Bromoacetyl-2-hydroxybenzaldehyde
• Synonyms: 5-Bromoacetyl-2-hydroxybenzaldehyde;5-(Bromoacetyl)salicylaldehyde;Benzaldehyde,5-(2-broMoacetyl)-2-hydroxy-
• CAS NO: 115787-50-3
• Molecular Formula: C₉H₇BrO₃
• Molecular Weight: 243.05408
• EINECS: 1308068-626-2
• Product Categories: Intermediate
• Mol File: 115787-50-3.mol

Chemical Properties

• Melting Point: 117-118 °C(Solv: dichloromethane (75-09-2))
• Boiling Point: 368.3±32.0 °C(Predicted)
• Appearance: /
• Density: 1.685±0.06 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly, Heated)
• PKA: 5.93±0.20(Predicted)
• Stability: Moisture Sensitive
• CAS DataBase Reference: 5-Bromoacetyl-2-hydroxybenzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Bromoacetyl-2-hydroxybenzaldehyde(115787-50-3)
• EPA Substance Registry System: 5-Bromoacetyl-2-hydroxybenzaldehyde(115787-50-3)

Safety Data

• Hazardous Substances Data: 115787-50-3(Hazardous Substances Data)

Usage

Chemical Properties

Brown Solid

Uses

Intermediate in the preparation of Salmeterol (S090100).

InChI:InChI=1S/C9H7BrO3/c10-4-9(13)6-1-2-8(12)7(3-6)5-11/h1-3,5,12H,4H2

Upstream product

• 22118-09-8 2-bromoacetyl chloride 
• 90-02-8 salicylaldehyde 
• 598-21-0 2-Bromoacetyl bromide 
• 5663-67-2 2-acetoxybenzaldehyde 
• 68840-08-4 5-acetyl-2-hydroxy-benzaldehyde 

Downstream Products

• 115787-54-7 5-<<(1,1-Dimethylethyl)amino>acetyl>-2-hydroxybenzaldehyde p-toluenesulfonate 
• 115787-56-9 2-Bromo-1-<3-<<(1,1-dimethylethyl)imino>methyl>-4-hydroxyphenyl>ethanone 
• 163923-19-1 2-hydroxy-5-<<<6,6-(4-phenylbutoxy)hexylbenzyl>amino>acetyl>benzaldehyde 
• 89365-50-4 salmeterol 
• 934842-69-0 4-hydroxy-1-[[[6-(4-phenylbutoxy)hexyl](phenylmethyl)amino]methyl]-1,3-benzenedimethanol 
• 18559-94-9 Salbutamol 
• 115787-53-6 5-<<(1,1-Dimethylethyl)amino>acetyl>-2-hydroxybenzaldehyde hydrochloride 
• 115787-52-5 5-(2-tert-Butylamino-acetyl)-2-hydroxy-benzaldehyde 
• 62932-94-9 2-bromo-1-[4-hydroxy-3-(hydroxymethyl)-phenyl]ethanone 
• 1056135-44-4 [2-(3-formyl-4-hydroxyphenyl)-2-oxoethyl]-[6-(4-phenylbutoxy)hexyl]carbamic acid tert-butyl ester 
• 1424337-27-8 3-(3-(2-(tert-butyldimethylsilyloxy)-2-(2,2-dimethyl-4H-benzo[d][1,3]dioxin-6-yl)ethylamino)propoxy)-N-(3,5-dichloropyridin-4-yl)-4-methoxybenzamide 
• 1424337-28-9 3-(4-(2-(tert-butyldimethylsilyloxy)-2-(2,2-dimethyl-4H-benzo[d][1,3]dioxin-6-yl)ethylamino)butoxy)-N-(3,5-dichloropyridin-4-yl)-4-methoxybenzamide 
• 1424337-29-0 3-(5-(2-(tert-butyldimethylsilyloxy)-2-(2,2-dimethyl-4H-benzo[d][1,3]dioxin-6-yl)ethylamino)pentyloxy)-N-(3,5-dichloropyridin-4-yl)-4-methoxybenzamide 
• 1424337-30-3 3-(6-(2-(tert-butyldimethylsilyloxy)-2-(2,2-dimethyl-4H-benzo[d][1,3]dioxin-6-yl)ethylamino)hexyloxy)-N-(3,5-dichloropyridin-4-yl)-4-methoxybenzamide 

Relevant articles and documents

Real-time monitoring of a photoactivated hydrogen persulfide donor for biological entities

Hydrogen persulfide (H2S2) plays an important role in sulfur-based redox signaling mechanisms. Herein, we developed a visible light activated ESIPT based H2S2 donor using a p-hydroxyphenacyl phototrigger. The unique feature of the designed H2S2 donor system is the ability to monitor the H2S2 release in real time through a non-invasive fluorescence color change approach, with the color changing from green to blue. Next, we demonstrated the detection and quantification of H2S2 using a fluorescein based "turn-on" fluorescent probe. Furthermore, in vitro studies of the designed H2S2 donor demonstrated the real-time monitored H2S2 release and cytoprotective ability in the highly oxidizing cellular environment of MDA-MB-468 cells.

A chromatography-free synthesis of racemic salbutamol hemisulfate

Our efforts to achieve an efficient synthesis of racemic salbutamol hemisulfate are described. The selected chemical route starts from commodity chemicals and allows the generation of salbutamol hemisulfate in 5 steps and 44% overall yield without any purification by column chromatography. The reaction sequence has been optimized to provide the title compound using robust procedures. Emphasis on reproducibility and experimental simplicity drove the work described herein.

Tetraphenylethylene conjugated: P -hydroxyphenacyl: Fluorescent organic nanoparticles for the release of hydrogen sulfide under visible light with real-time cellular imaging

Hydrogen sulfide (H2S) behaves like a two-edged sword, at low concentrations it has beneficial and cytoprotective effects, while at higher concentrations it exhibits toxicity. Hence there is a keen interest in developing light responsive H2S donors with a spatio-temporal controlled release. Herein, we report visible light activatable tetraphenylethylene conjugated p-hydroxyphenacyl (TPE-pHP-H2S) nanoparticles for the release of hydrogen sulfide (H2S) with a real time monitoring ability. Our newly designed photoresponsive single component organic nanoparticle based H2S donor is built by integrating the tetraphenylethylene (TPE) moiety and p-hydroxyphenacyl (pHP) group so that it can display both aggregation-induced emission (AIE) and excited state intramolecular proton transfer (ESIPT) properties. Aggregation-induced emission enhancement was exhibited by our TPE-pHP-H2S NP donor, which was then explored for the cellular imaging application. The ESIPT by the pHP moiety provided unique advantages to our TPE-pHP-H2S NP donor which include (i) the excitation wavelength extended to >410 nm (ii) a large Stokes shift (iii) a low inner filter effect and (iv) real-time monitoring of H2S release by a simple fluorescent colour change. In vitro studies showed that the TPE-pHP-H2S NP donor presents excellent properties like real-time monitoring, photoregulated H2S release and biocompatibility.

A new synthetic approach to salmeterol

In the present work a short and convenient route for the synthesis of salmeterol from salicylaldehyde has been developed.

A p-Hydroxyphenacyl-Benzothiazole-Chlorambucil Conjugate as a Real-Time-Monitoring Drug-Delivery System Assisted by Excited-State Intramolecular Proton Transfer

Among the well-known phototriggers, the p-hydroxyphenacyl (pHP) group has consistently enabled the very fast, efficient, and high-conversion release of active molecules. Despite this unique behavior, the pHP group has been ignored as a delivery agent, particularly in the area of theranostics, because of two major limitations: Its excitation wavelength is below 400 nm, and it is nonfluorescent. We have overcome these limitations by incorporating a 2-(2′-hydroxyphenyl)benzothiazole (HBT) appendage capable of rapid excited-state intramolecular proton transfer (ESIPT). The ESIPT effect also provided two unique advantages: It assisted the deprotonation of the pHP group for faster release, and it was accompanied by a distinct fluorescence color change upon photorelease. In vitro studies showed that the p-hydroxyphenacyl-benzothiazole-chlorambucil conjugate presents excellent properties, such as real-time monitoring, photoregulated drug delivery, and biocompatibility.

'AIE + ESIPT' assisted photorelease: Fluorescent organic nanoparticles for dual anticancer drug delivery with real-time monitoring ability

'Aggregation Induced Emission + Excited State Intramolecular Proton Transfer (AIE + ESIPT)'-assisted photorelease of an anticancer drug by a p-hydroxyphenacyl (pHP) phototrigger with real-time monitoring has been demonstrated.

Synthesis method of salbutamol sulfate intermediate

The invention discloses a synthesis method of a salbutamol sulfate intermediate, which comprises the following steps: by taking salicylaldehyde as a raw material, carrying out three-step reaction of Friedel-Crafts acylation, reduction, propylidene protection and N alkylation, and obtaining the target product salbutamol intermediate with the reaction yield of more than 60% in each step. The synthesis method of the salbutamol sulfate intermediate has the advantages of few reaction steps, simple post-treatment and high product purity.

Synthesis method of 5-(2-bromoacetyl)-2-hydroxybenzaldehyde

The invention discloses a synthesis method of 5-(2-bromoacetyl)-2-hydroxybenzaldehyde, and belongs to the field of medicine synthesis. According to the method, the acylation reaction is conducted withsalicylaldehyde as the raw material to obtain 2-(acetoxyl)-benzaldehyde, then the rearrangement reaction is conducted, and finally the bromination reaction is conducted to obtain 5-(2-bromoacetyl)-2-hydroxybenzaldehyde. The preparing method has the advantages of being high in product purity and high in yield.

Light triggered uncaging of hydrogen sulfide (H2S) with real-time monitoring

An ESIPT based light activated hydrogen sulfide (H2S) donor using a p-hydroxyphenacyl phototrigger has been developed. The unique feature of our H2S donor system is that it provides real-time monitoring of H2S release by a non-invasive fluorescence colour change approach.

Levalbuterol intermediate and synthetic method of levalbuterol hydrochloride

The invention provides a levalbuterol intermediate and a levalbuterol hydrochloride synthesis method, and relates to a levalbuterol intermediate and a method for preparing levalbuterol hydrochloride from the intermediate. The method comprises steps as follows: 2-halogenate-1-(2,2-dimelthyl-4-hydrogen-benzo [d][1,3] dioxane)-butanone and organic amine have a Hoffman alkylation reaction to prepare a compound in the formula 2, the structural formula of the compound is shown in the specification, and the compound in the formula 2 is subjected to a reduction reaction, optically pure organic acid resolution and deprotection by hydrochloric acid to obtain levalbuterol hydrochloride. The method does not need processes of protection or deprotection and the like of hydroxyl groups on a benzene ring, protection, deprotection and purification processes are reduced, the synthesis route is short, operation is simple, meanwhile, borane-thioether does not need to be used as a reduction agent, and safety and environmental protection are realized.