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4-(3-METHYLPHENYL)BENZALDEHYDE, also known as 4-Formyl-3''-methyl-1,1''-biphenyl, is an organic compound with the molecular formula C14H12O. It is a derivative of benzaldehyde, featuring a methyl group attached to the third position of the phenyl ring and a formyl group (aldehyde) at the fourth position of the other phenyl ring. 4-(3-METHYLPHENYL)BENZALDEHYDE is known for its potential applications in various industries due to its unique chemical structure and reactivity.

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  • 400744-83-4 Structure
  • Basic information

    1. Product Name: 4-(3-METHYLPHENYL)BENZALDEHYDE
    2. Synonyms: [1,1'-BIPHENYL]-4-CARBOXALDEHYDE, 3'-METHYL-;AKOS BAR-0057;3'-METHYL[1,1'-BIPHENYL]-4-CARBALDEHYDE;3'-METHYL [1,1'-BIPHENYL]-4-CARBOXALDEHYDE;3'-METHYLBIPHENYL-4-CARBALDEHYDE;3'-METHYL-BIPHENYL-4-CARBOXALDEHYDE;4-(3-METHYLPHENYL)BENZALDEHYDE;4-(3-Tolyl)benzaldehyde
    3. CAS NO:400744-83-4
    4. Molecular Formula: C14H12O
    5. Molecular Weight: 196.24
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 400744-83-4.mol
  • Chemical Properties

    1. Melting Point: 45-49℃
    2. Boiling Point: 332.9 °C at 760 mmHg
    3. Flash Point: >110°(230°F)
    4. Appearance: /
    5. Density: 1.074 g/cm3
    6. Refractive Index: N/A
    7. Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
    8. Solubility: N/A
    9. Sensitive: Air Sensitive
    10. CAS DataBase Reference: 4-(3-METHYLPHENYL)BENZALDEHYDE(CAS DataBase Reference)
    11. NIST Chemistry Reference: 4-(3-METHYLPHENYL)BENZALDEHYDE(400744-83-4)
    12. EPA Substance Registry System: 4-(3-METHYLPHENYL)BENZALDEHYDE(400744-83-4)
  • Safety Data

    1. Hazard Codes: Xi
    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: 400744-83-4(Hazardous Substances Data)

400744-83-4 Usage

Uses

Used in Chemical Synthesis:
4-(3-METHYLPHENYL)BENZALDEHYDE is used as a reagent for the preparation of cyclodextrin-supported palladium complexes. These complexes are efficient catalysts for Suzuki-Miyaura cross-coupling reactions, which are widely employed in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and advanced materials.
In the field of organic chemistry, 4-(3-METHYLPHENYL)BENZALDEHYDE can be utilized as a building block for the synthesis of more complex molecules, such as dyes, pigments, and other specialty chemicals. Its reactivity as an aldehyde allows for various chemical transformations, making it a versatile compound in the synthesis of a wide range of products.
Additionally, due to its aromatic structure, 4-(3-METHYLPHENYL)BENZALDEHYDE may also find applications in the development of new materials with specific properties, such as optoelectronic devices, sensors, and advanced polymers.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, 4-(3-METHYLPHENYL)BENZALDEHYDE, given its structural similarity to various biologically active compounds, could potentially be used in the pharmaceutical industry as a starting material for the synthesis of new drugs or drug candidates. Its ability to form palladium complexes, which are known for their catalytic properties, may also be exploited in the development of novel drug synthesis methods.

Check Digit Verification of cas no

The CAS Registry Mumber 400744-83-4 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 4,0,0,7,4 and 4 respectively; the second part has 2 digits, 8 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 400744-83:
(8*4)+(7*0)+(6*0)+(5*7)+(4*4)+(3*4)+(2*8)+(1*3)=114
114 % 10 = 4
So 400744-83-4 is a valid CAS Registry Number.

400744-83-4SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-(3-METHYLPHENYL)BENZALDEHYDE

1.2 Other means of identification

Product number -
Other names 3'-methyl-biphenyl-4-carbaldehyde

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:400744-83-4 SDS

400744-83-4Downstream Products

400744-83-4Relevant articles and documents

Design, synthesis and biological evaluation of novel oseltamivir derivatives as potent neuraminidase inhibitors

Wang, Zhen,Cheng, Li Ping,Zhang, Xing Hua,Pang, Wan,Li, Liang,Zhao, Jin Long

, p. 5429 - 5435 (2017)

Neuraminidase (NA) is one of the particular potential targets for novel antiviral therapy. In this work, a series of neuraminidase inhibitors with the cyclohexene scaffold were studied based upon the combination of 3D-QSAR, molecular docking, and molecular dynamics techniques. The results indicate that the built 3D-QSAR models yield reliable statistical information: the correlation coefficient (r2) and cross-validation coefficient (q2) of CoMFA (comparative molecular field analysis) are 0.992 and 0.819; the r2 and q2 of CoMSIA (comparative molecular similarity analysis) are 0.992 and 0.863, respectively. Molecular docking and MD simulations were conducted to confirm the detailed binding mode of enzyme-inhibitor system. The new NA inhibitors had been designed, synthesized, and their inhibitory activities against group-1 neuraminidase were determined. One agent displayed excellent neuraminidase inhibition, with IC50 value of 39.6 μM against NA, while IC50 value for oseltamivir is 61.1 μM. This compound may be further investigated for the treatment of infection by the new type influenza virus.

Nickel- and Palladium-Catalyzed Cross-Coupling of Stibines with Organic Halides: Site-Selective Sequential Reactions with Polyhalogenated Arenes

Ghaderi, Arash,Kambe, Nobuaki,Le, Liyuan,Lu, Hao,Qiu, Renhua,Tang, Ting,Tong, Zhou,Wong, Wai-Yeung,Xu, Zhi,Yin, Shuang-Feng,Zeng, Dishu,Zhang, Dejiang,Zhang, Zhao

, p. 854 - 867 (2022/01/19)

Herein, we disclose a general and efficient method for the synthesis of Sb-aryl and Sb-alkyl stibines by the nickel-catalyzed cross-coupling of halostibines with organic halides. The synthesized Sb-aryl stibines couple with aryl halides to give biaryls efficiently via palladium catalysis. Sequential reactions of stibines with polyhalogenated arenes bearing active C–I/C–Br sites and inactive C–Cl sites successfully proceeded, resulting in the formation of a variety of complex molecules with good site selectivity. Drugs such as diflunisal and fenbufen, as well as a fenofibrate derivative, were synthesized on gram scales in good yields, together with the high recovery of chlorostibine. Furthermore, catalytic mechanisms are proposed based on the results of control experiments.

Gold Catalysts Can Generate Nitrone Intermediates from a Nitrosoarene/Alkene Mixture, Enabling Two Distinct Catalytic Reactions: A Nitroso-Activated Cycloheptatriene/Benzylidene Rearrangement

Cheng, Mu-Jeng,Kardile, Rahul Dadabhau,Kuo, Tung-Chun,Liu, Rai-Shung,More, Sayaji Arjun

supporting information, p. 5506 - 5511 (2021/07/31)

Gold-catalyzed reactions of cycloheptatrienes with nitrosoarenes yield nitrone derivatives efficiently. This reaction sequence enables us to develop gold-catalyzed aerobic oxidations of cycloheptatrienes to afford benzaldehyde derivatives using CuCl and nitrosoarenes as co-catalysts (10-30 mol %). Our density functional theory calculations support a novel nitroso-activated rearrangement, tropylium → benzylidene. With the same nitrosoarenes, we developed their gold-catalyzed [2 + 2 + 1]-annulations between nitrosobenzene and two enol ethers to yield 5-alkoxyisoxazolidines using 1,4-cyclohexadienes as hydrogen donors.

Nickel- and Palladium-Catalyzed Cross-Coupling Reactions of Organostibines with Organoboronic Acids

Zhang, Dejiang,Le, Liyuan,Qiu, Renhua,Wong, Wai-Yeung,Kambe, Nobuaki

supporting information, p. 3104 - 3114 (2020/12/11)

A strategy for the formation of antimony-carbon bond was developed by nickel-catalyzed cross-coupling of halostibines. This method has been applied to the synthesis of various triaryl- and diarylalkylstibines from the corresponding cyclic and acyclic halostibines. This protocol showed a wide substrate scope (72 examples) and was compatible to a wide range of functional groups such as aldehyde, ketone, alkene, alkyne, haloarenes (F, Cl, Br, I), and heteroarenes. A successful synthesis of arylated stibine 3 a in a scale of 34.77 g demonstrates high synthetic potential of this transformation. The formed stibines (R3Sb) were then used for the palladium-catalyzed carbon–carbon bond forming reaction with aryl boronic acids [R?B(OH)2], giving biaryls with high selectivity, even the structures of two organomoieties (R and R′) are very similar. Plausible catalytic pathways were proposed based on control experiments.

The Discovery of Novel ACA Derivatives as Specific TRPM2 Inhibitors that Reduce Ischemic Injury Both in Vitro and in Vivo

Zhang, Han,Yu, Peilin,Lin, Hongwei,Jin, Zefang,Zhao, Siqi,Zhang, Yi,Xu, Qingxia,Jin, Hongwei,Liu, Zhenming,Yang, Wei,Zhang, Liangren

, p. 3976 - 3996 (2021/05/04)

The transient receptor potential melastatin 2 (TRPM2) channel is associated with ischemia/reperfusion injury, inflammation, cancer, and neurodegenerative diseases. However, the limit of specific inhibitors impedes the development of TRPM2-targeted therapeutic agents. To discover more potent and selective TRPM2 inhibitors, 59 N-(p-amylcinnamoyl) anthranilic acid (ACA) derivatives were synthesized and evaluated using calcium imaging and electrophysiology approaches. Systematic structure-activity relationship studies resulted in some potent compounds inhibiting the TRPM2 channel with sub-micromolar half-maximal inhibitory concentration values. Among them, the preferred compound A23 exhibited TRPM2 selectivity over TRPM8 and TRPV1 channels as well as phospholipase A2 and showed neuroprotective activity in vitro. Following pharmacokinetic studies, A23 was further evaluated in a transient middle cerebral artery occlusion model in vivo, which significantly reduced cerebral infarction. These data indicate that A23 might serve as a useful tool for TRPM2-related research as well as a lead compound for the development of therapeutic agents for ischemic injury.

N,N′-bridged binuclear NHC palladium complexes: A combined experimental catalytic and computational study for the Suzuki reaction

Chen, Ming-Tsz,Hsieh, Bing-Yan,Liu, Yi-Hung,Wu, Kuo-Hui,Lussari, Natália,Braga, Ataualpa A.C.

, (2020/07/06)

This work examines how N-donor bridged spacer ligands affect N-heterocyclic carbene (NHC) palladium complexes catalytic activities for Suzuki coupling reaction. Different degrees of structural flexibility binuclear NHC palladium complexes were synthesized. The more flexible nitrogen-based alkyl chain ligand shows similar performance with cycloamine counterparts in the Suzuki coupling reaction. Suzuki coupling examples were used in air and ambient temperature to reach moderate to completion yields in short time. Density functional theory calculations showed that the chelate effect, associated with a single Pd complex mechanism, plays a fundamental role in the pre-catalysis stage, supporting a reasonable of the kinetic activity observed experimentally.

(N-Heterocyclic carbene) ion-pair palladium complexes: Suzuki–Miyaura cross-coupling studies in neat water under mild conditions

Chen, Ming-Tsz,Lin, Yu-Hsuan,Jian, Kun-Han

, (2020/08/05)

The synthesis and characterization of a series of (N-heterocyclic carbene)PdCl3?(NMe3H)+ ion-pair complexes are presented. Applying the quaternary ammonium salt as the function with NHC–Pd(II) complexes yields the new ion-pair complexes. The NHC–Pd(II) ion-pair complexes work well by undergoing the Suzuki–Miyaura reaction with aryl chloride substrates in water under mild conditions in air at room temperature. Twenty products resulting from Suzuki–Miyaura coupling reactions carried out in the presence of the new NHC–Pd(II) ion-pair complex under mild optimal conditions were examined to determine the optimum yields.

An active catalytic system for Suzuki-Miyaura cross-coupling reactions using low levels of palladium loading

Yan, Meng-Qi,Yuan, Jia,Lan, Fang,Zeng, Si-Hao,Gao, Meng-Yue,Liu, Sheng-Hua,Chen, Jian,Yu, Guang-Ao

supporting information, p. 3924 - 3929 (2017/07/10)

An easily available Pd(OAc)2/(2-(anthracen-9-yl)-1H-inden-3-yl) dicyclohexylphosphine/toluene/iPrOH/water catalytic system was developed, which shows high catalytic activity in the Suzuki-Miyaura cross-coupling reactions of a diverse array of aryl and heteroaryl chlorides with Pd loadings down to 0.01 mol%.

Cyclodextrin-supported palladium complex: A highly active and recoverable catalyst for Suzuki–Miyaura cross-coupling reaction in aqueous medium

Guo, Yafei,Li, Jiuling,Shi, Xiwei,Liu, Yang,Xie, Kai,Liu, Yuqi,Jiang, Yubo,Yang, Bo,Yang, Rui

, (2017/03/24)

A water-soluble, cyclodextrin-supported palladium complex (DACH-Pd-β-CD) catalytic system was designed and synthesized, which can efficiently catalyze Suzuki–Miyaura cross-coupling reactions between aryl halides and arylboronic acid in water under mild conditions. The catalyst was successfully characterized using the methods of transmission electron microscopy, energy-dispersive X-ray spectrometry, X-ray diffraction, thermogravimetric analysis, and Fourier transform infrared and NMR spectroscopies. Furthermore, the catalyst can be easily separated from the reaction mixture and still maintain high catalytic activity after ten cycles. No leaching of palladium into the reaction solution occurred. The advantages of green solvent (water), short reaction times (2–6?h), low catalyst loading (0.001?mol%), excellent yields (up to 99%) and reusability of the catalyst mean it will have potential applications in green chemical synthesis.

SYNTHESES OF METAL HETEROCYCLIC CARBENE ENOLATES AS COUPLING REACTIONS CATALYSTS

-

Page/Page column 18; 19; 20; 32, (2017/07/01)

The invention relates to the synthesis methods of N-heterocyclic carbene NHCE metal complexes and their catalytic activities in carbon-carbon coupling reactions.

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