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m-Bromocinnamaldehyde, scientifically known as 3-bromocinnamaldehyde, is a chemical compound with distinctive aromatic properties. It is recognized for its sweet, pleasurable aroma and is often utilized in research and development labs, particularly in the fields of organic and medicinal chemistry. As an essential precursor in the synthesis of various compounds, m-Bromocinnamaldehyde plays a significant role in chemical research. Its molecular formula is C9H7BrO, and its bromine component makes it a valuable tool for halogenation reactions in organic synthesis. It is typically stored in a cool, ventilated area, away from ignition sources, heat, and light.

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  • 15185-59-8 Structure
  • Basic information

    1. Product Name: m-Bromocinnamaldehyde
    2. Synonyms: m-Bromocinnamaldehyde;3-(3-BroMophenyl)acrylaldehyde
    3. CAS NO:15185-59-8
    4. Molecular Formula: C9H7BrO
    5. Molecular Weight: 211.05528
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 15185-59-8.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 309.7°C at 760 mmHg
    3. Flash Point: 114°C
    4. Appearance: /
    5. Density: 1.466g/cm3
    6. Vapor Pressure: 0.000628mmHg at 25°C
    7. Refractive Index: 1.611
    8. Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
    9. Solubility: N/A
    10. CAS DataBase Reference: m-Bromocinnamaldehyde(CAS DataBase Reference)
    11. NIST Chemistry Reference: m-Bromocinnamaldehyde(15185-59-8)
    12. EPA Substance Registry System: m-Bromocinnamaldehyde(15185-59-8)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 15185-59-8(Hazardous Substances Data)

15185-59-8 Usage

Uses

Used in Organic Chemistry Research:
m-Bromocinnamaldehyde is used as a precursor in the synthesis of various organic compounds, contributing to the development of new chemical entities and materials. Its bromine atom facilitates halogenation reactions, making it a versatile building block in organic synthesis.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, m-Bromocinnamaldehyde is employed as a starting material for the synthesis of pharmaceutical compounds. Its unique structure and reactivity enable the creation of potential drug candidates, with the aim of developing new therapeutic agents.
Used in Chemical Synthesis:
m-Bromocinnamaldehyde is used as a reagent in various chemical synthesis processes, allowing for the formation of complex molecules and structures. Its presence in these reactions can lead to the production of novel compounds with potential applications in various industries.
Used in Material Science:
m-Bromocinnamaldehyde is utilized in the development of new materials, such as polymers and composites, due to its ability to participate in various chemical reactions. Its incorporation into these materials can result in improved properties, such as enhanced stability or increased functionality.

Check Digit Verification of cas no

The CAS Registry Mumber 15185-59-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,5,1,8 and 5 respectively; the second part has 2 digits, 5 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 15185-59:
(7*1)+(6*5)+(5*1)+(4*8)+(3*5)+(2*5)+(1*9)=108
108 % 10 = 8
So 15185-59-8 is a valid CAS Registry Number.
InChI:InChI=1/C9H7BrO/c10-9-5-1-3-8(7-9)4-2-6-11/h1-7H/b4-2+

15185-59-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 3-(3-Bromophenyl)acrylaldehyde

1.2 Other means of identification

Product number -
Other names m-Bromzimtaldehyd

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:15185-59-8 SDS

15185-59-8Relevant articles and documents

Method for preparing olefine aldehyde by catalyzing terminal alkyne or terminal conjugated eneyne and diphosphine ligand used in method

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Paragraph 0146-0148, (2021/05/29)

The invention discloses a method for preparing olefine aldehyde by catalyzing terminal alkyne or terminal conjugated eneyne and a diphosphine ligand used in the method. According to the invention, indole-substituted phosphoramidite diphosphine ligand which is stable in air and insensitive to light is synthesized by utilizing a continuous one-pot method, and the indole-substituted phosphoramidite diphosphine ligand and a rhodium catalyst are used for jointly catalyzing to successfully achieve a hydroformylation reaction of aromatic terminal alkyne and terminal conjugated eneyne under the condition of synthesis gas for the first time, so that an olefine aldehyde structure compound can be rapidly and massively prepared, and particularly, a polyolefine aldehyde structure compound which is more difficult to synthesize in the prior art can be easily prepared and synthesized, and a novel method is provided for synthesis and modification of drug molecules, intermediates and chemical products.

Discovery and SAR of Natural-Product-Inspired RXR Agonists with Heterodimer Selectivity to PPARδ-RXR

Nakashima, Ken-Ichi,Yamaguchi, Eiji,Noritake, Chihaya,Mitsugi, Yukari,Goto, Mayuki,Hirai, Takao,Abe, Naohito,Sakai, Eiji,Oyama, Masayoshi,Itoh, Akichika,Inoue, Makoto

, p. 1526 - 1534 (2020/05/19)

A known natural product, magnaldehyde B, was identified as an agonist of retinoid X receptor (RXR) α. Magnaldehyde B was isolated from Magnolia obovata (Magnoliaceae) and synthesized along with more potent analogs for screening of their RXRα agonistic activities. Structural optimization of magnaldehyde B resulted in the development of a candidate molecule that displayed a 440-fold increase in potency. Receptor-ligand docking simulations indicated that this molecule has the highest affinity with the ligand binding domain of RXRα among the analogs synthesized in this study. Furthermore, the selective activation of the peroxisome proliferator-activated receptor (PPAR) δ-RXR heterodimer with a stronger efficacy compared to those of PPARα-RXR and PPARγ-RXR was achieved in luciferase reporter assays using the PPAR response element driven reporter (PPRE-Luc). The PPARδactivity of the molecule was significantly inhibited by the antagonists of both RXR and PPARδ, whereas the activity of GW501516 was not affected by the RXR antagonist. Furthermore, the molecule exhibited a particularly weak PPARδagonistic activity in reporter gene assays using the Gal4 hybrid system. The obtained data therefore suggest that the weak PPARδagonistic activity of the optimized molecule is synergistically enhanced by its own RXR agonistic activity, indicating the potent agonistic activity of the PPARδ-RXR heterodimer.

Highly Enantioselective Synthesis of Functionalized Glutarimide Using Oxidative N-Heterocyclic Carbene Catalysis: A Formal Synthesis of (?)-Paroxetine

Porey, Arka,Santra, Surojit,Guin, Joyram

, p. 5313 - 5327 (2019/04/16)

A simple yet highly effective approach toward enantioselective synthesis of trans-3,4-disubstituted glutarimides from readily available starting materials is developed using oxidative N-heterocyclic carbene catalysis. The catalytic reaction involves a formal [3 + 3] annulation between enals and substituted malonamides enabling the production of glutarimide derivatives in a single chemical operation via concomitant formation of C-C and C-N bonds. The reaction offers easy access to a broad range of functionalized glutarimides with excellent enantioselectivity and good yield. Synthetic application of the method is demonstrated via formal synthesis of (?)-paroxetine and other bioactive molecules.

Design, synthesis, molecular modelling, and in vitro evaluation of tricyclic coumarins against Trypanosoma cruzi

Coelho, Gleicekelly Silva,Andrade, Josimara Souza,Xavier, Viviane Flores,Sales Junior, Policarpo Ademar,Rodrigues de Araujo, Barbara Caroline,Fonseca, Kátia da Silva,Caetano, Melissa Soares,Murta, Silvane Maria Fonseca,Vieira, Paula Melo,Carneiro, Claudia Martins,Taylor, Jason Guy

, p. 337 - 350 (2018/12/05)

Chagas disease is caused by infection with the parasite protozoan Trypanosoma cruzi and affects about 8 million people in 21 countries in Latin America. The main form of treatment of this disease is still based on the use of two drugs, benznidazole and nifurtimox, which both present low cure rates in the chronic phase and often have serious side-effects. Herein, we describe the synthesis of tricyclic coumarins that were obtained via NHC organocatalysis and evaluation of their trypanocidal activity. Molecular docking studies against trypanosomal enzyme triosephosphate isomerase (TIM) were carried out, as well as a theoretical study of the physicochemical parameters. The tricyclic coumarins were tested in vitro against the intracellular forms of Trypanosoma cruzi. Among the 18 compounds tested, 10 were more active than the reference drug benznidazole. The trypanocidal activity of the lead compound was rationalized by molecular docking study which suggested the strong interaction with the enzyme TIM by T.?cruzi and therefore indicating a possible mode of action. Furthermore, the selectivity index of eight tricyclic coumarins with high anti-T.?cruzi activity was above 50 and thus showing that these lead compounds are viable candidates for further in vivo assays.

Secondary amine-catalyzed [3 + 3] benzannulation to access polysubstituted benzenes through iminium activation

Jiang, Lin,Li, Hang,Zhou, Jiang-Feng,Yuan, Ming-Wei,Li, Hong-Li,Chuan, Yong-Ming,Yuan, Ming-Long

supporting information, p. 336 - 343 (2018/02/09)

An organocatalytic [3 + 3] benzannulation to access polysubstituted benzenes from readily available α,β-unsaturated aldehydes and 1,3-bis(phenylsulfonyl)propene or 4-sulfonylcrotonates is described. The key reaction step is considered to be the iminium ac

Dehydrogenative Synthesis of Linear α,β-Unsaturated Aldehydes with Oxygen at Room Temperature Enabled by tBuONO

Wang, Mei-Mei,Ning, Xiao-Shan,Qu, Jian-Ping,Kang, Yan-Biao

, p. 4000 - 4003 (2017/06/19)

Synthesis of linear α,β-unsaturated aldehydes via a room-temperature oxidative dehydrogenation has been realized by the cocatalysis of an organic nitrite and palladium with molecular oxygen as the sole clean oxidant. Linear α,β-unsaturated aldehydes could be efficiently prepared under aerobic catalytic conditions directly from the corresponding saturated linear aldehydes. Besides linear products, the aromatic analogy could also be smoothly achieved by the same standard method. The organic nitrite redox cocatalyst and alcohol solvent play a key role for realizing this method.

Highly Enantioselective Synthesis of Alkylpyridine Derivatives through a Michael/Michael/Aldol Cascade Reaction

Meazza, Marta,Potter, Michael,Pitak, Mateusz B.,Coles, Simon J.,Mazzanti, Andrea,Rios, Ramon

supporting information, p. 719 - 725 (2017/02/05)

A method for the synthesis of pyridine derivatives based on a triple cascade reaction catalyzed by chiral secondary amines was developed. The resulting cyclohexenes (three C–C bonds were formed) were obtained in good yields with good diastereoselectivities and excellent enantioselectivities.

Isomerization of 3-unsubstituted 4,5-dihydroisoxazoles over alumina. A new synthesis of β-hydroxy nitriles

Mochalov,Fedotov,Trofimova,Gazzaeva,Zefirov

, p. 397 - 403 (2016/06/13)

3-Unsubstituted 4,5-dihydroisoxazoles obtained by nitrosation of arylcyclopropanes are capable of undergoing efficient isomerization into 3-aryl-3-hydroxypropanenitriles during chromatography on alumina.

ANALGESIC 5, 9 - METHANOCYCLOOCTA (b) PYRIDIN - 2 (1H) - ONE DERIVATIVES, THEIR PREPARATION METHOD AND USE

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Page/Page column 15, (2009/04/23)

Compounds represented by the Formula I or salts, hydrates thereof, wherein R1, R8, R11 and R12 are H or C1-4 hydrocarbonyl respectively; R2, R3, R6 and R7 are H, halogen or C1-4 hydrocarbonyl respectively; R4 is C1-6 hydrocarbonyl or Ar; or =CR4R3 is cyclopentylidene, cyclohexylidene, 1-methylpiperidyl-4-idene or indenyl-1-idene; R5 is H, 1-4 same or different F, Cl, Br, CF3, R9, OR9, NR9R10, NO2, CN, COOR9, O2CR9, CONR9R10, NR9C(O)R10, heterocyclic, aryl or groups represented by the Formula II respectively; R9 and R10 are H or C1-6 hydrocarbonyl; Ar is aromatic ring; m is 0, 1 or 2; n is 0, 1, 2, 3 or 4, for treating mammal pain, functional painful syndrome, organic painful syndrome or tissue painful syndrome, and their preparation method.

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