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3-Benzyloxy-4-methoxybenzaldehyde is an organic compound that serves as an important intermediate in the synthesis of various complex organic molecules, particularly in the pharmaceutical industry. It is characterized by its unique structure, which includes a benzyloxy group at the 3-position and a methoxy group at the 4-position of a benzaldehyde moiety. This structural feature endows it with specific chemical properties that make it a valuable building block in organic synthesis.

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  • 6346-05-0 Structure
  • Basic information

    1. Product Name: 3-Benzyloxy-4-methoxybenzaldehyde
    2. Synonyms: AKOS BBS-00003177;O-BENZYLISOVANILLIN;Benzaldehyde, 4-methoxy-3-(phenylmethoxy)-;3-Benzyloxy-p-anisaldehyde;4-Methoxy-3-(benzyloxy)benzaldehyde;3-Benzyloxy-4-methoxybenzaldehyde,98%;3-Benzyloxy-4-methox;Isovanillin benzyl ether
    3. CAS NO:6346-05-0
    4. Molecular Formula: C15H14O3
    5. Molecular Weight: 242.27
    6. EINECS: 228-752-7
    7. Product Categories: Aromatic Aldehydes & Derivatives (substituted);Aromatics;Aldehydes;C10 to C21;Carbonyl Compounds
    8. Mol File: 6346-05-0.mol
  • Chemical Properties

    1. Melting Point: 61-64 °C(lit.)
    2. Boiling Point: 120 °C / 5mmHg
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: 1.1515 (rough estimate)
    6. Refractive Index: 1.5570 (estimate)
    7. Storage Temp.: Store below +30°C.
    8. Solubility: Dichloromethane, Ethyl Acetate, Methanol
    9. Sensitive: Air Sensitive
    10. BRN: 794627
    11. CAS DataBase Reference: 3-Benzyloxy-4-methoxybenzaldehyde(CAS DataBase Reference)
    12. NIST Chemistry Reference: 3-Benzyloxy-4-methoxybenzaldehyde(6346-05-0)
    13. EPA Substance Registry System: 3-Benzyloxy-4-methoxybenzaldehyde(6346-05-0)
  • Safety Data

    1. Hazard Codes: Xi
    2. Statements: N/A
    3. Safety Statements: 24/25
    4. WGK Germany: 3
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 6346-05-0(Hazardous Substances Data)

6346-05-0 Usage

Uses

Used in Pharmaceutical Synthesis:
3-Benzyloxy-4-methoxybenzaldehyde is used as a key intermediate in the synthesis of complex organic molecules, particularly in the development of pharmaceutical compounds. Its unique structural features allow it to be a versatile building block in the creation of various drug candidates.
Used in the Synthesis of (+)-9-Benzyloxy-α-Dihydrotetrabenazine:
3-Benzyloxy-4-methoxybenzaldehyde is used as a starting material in the synthesis of (+)-9-benzyloxy-α-dihydrotetrabenazine, a compound with potential therapeutic applications. Its role in this synthesis highlights its importance in the development of new pharmaceutical agents.
Used in the Total Synthesis of (-)-Galipeine:
3-Benzyloxy-4-methoxybenzaldehyde also plays a crucial role in the total synthesis of (-)-galipeine, a complex organic molecule with potential applications in the pharmaceutical industry. Its involvement in this synthesis further underscores its utility as a key intermediate in the preparation of bioactive compounds.

Check Digit Verification of cas no

The CAS Registry Mumber 6346-05-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 6,3,4 and 6 respectively; the second part has 2 digits, 0 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 6346-05:
(6*6)+(5*3)+(4*4)+(3*6)+(2*0)+(1*5)=90
90 % 10 = 0
So 6346-05-0 is a valid CAS Registry Number.
InChI:InChI=1/C15H14O3/c1-17-14-8-7-13(10-16)9-15(14)18-11-12-5-3-2-4-6-12/h2-10H,11H2,1H3

6346-05-0 Well-known Company Product Price

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  • (Code)Product description
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  • Alfa Aesar

  • (L06830)  3-Benzyloxy-4-methoxybenzaldehyde, 98%   

  • 6346-05-0

  • 10g

  • 393.0CNY

  • Detail
  • Alfa Aesar

  • (L06830)  3-Benzyloxy-4-methoxybenzaldehyde, 98%   

  • 6346-05-0

  • 50g

  • 1313.0CNY

  • Detail

6346-05-0SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 3-Benzyloxy-4-methoxybenzaldehyde

1.2 Other means of identification

Product number -
Other names 4-methoxy-3-phenylmethoxybenzaldehyde

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:6346-05-0 SDS

6346-05-0Relevant articles and documents

Isoquinoline Derivatives, Methods of Synthesis and Uses Thereof

-

, (2022/01/04)

Described herein are compounds, pharmaceutical compositions and methods of using these compounds and pharmaceutical compositions for treating and/or preventing conditions such as amyotrophic lateral sclerosis. These compounds and pharmaceutical compositions are also useful as antivirals and antimicrobial agents.

Design, Synthesis and Structure-Activity Relationship Studies of Glycosylated Derivatives of Marine Natural Product Lamellarin D

Zheng, Liuliu,Gao, Tingting,Ge, Zhiwei,Ma, Zhongjun,Xu, Jinzhong,Ding, Wanjing,Shen, Li

, (2021/02/16)

Lamellarin D, a marine natural product, acts as a potent inhibitor of DNA topoisomerase I (Topo I). To modify its physicochemical property and biological activity, a series of mono- and di-glycosylated derivatives were designed and synthesized through 22–26 multi-steps. Their inhibition of human Topo I was evaluated, and most of the glycosylated derivatives exhibited high potency in inhibiting Topo I activity as well as lamellarin D. All the 15 target compounds were evaluated for their cytotoxic activities against five human cancer cell lines. The typical lamellarin derivative ZL?3 exhibited the best activity with IC50 values of 3 nM, 10 nM, and 15 nM against human lung cancer A549 cells, human colon cancer HCT116 cells and human hepatocellular carcinoma HepG2 cells. Compound ZL?1 exhibited anti-cancer activity with IC50 of 14 nM and 24 nM against human colon cancer HCT116 cells and human hepatocellular carcinoma HepG2 cells, respectively. Cell cycle analysis in MDA-MB-231 suggested ZL?3 inhibited cell growth through arresting cells at the G2/M phase of the cell cycle. Further tests showed a significant improvement in aqueous solubility of ZL?1 and ZL?7. This study suggested that glycosylation could be utilized as a useful strategy to optimize lamellarin D derivatives as Topo I inhibitors and anticancer agents.

Identification of Pyruvate Carboxylase as the Cellular Target of Natural Bibenzyls with Potent Anticancer Activity against Hepatocellular Carcinoma via Metabolic Reprogramming

Chen, Yuwen,Huang, Yulan,Jiao, Wei,Li, Fu,Li, Suiyan,Li, Wenhua,Lin, Yuan,Liu, Wanli,Ma, Yuling,Sheng, Yuwen,Suksamrarn, Apichart,Wang, Fei,Wang, Jing,Wei, Xiao,Wisanwattana, Wisanee,Wu, Wenbi,Zeng, Zhongqiu,Zhang, Guolin,Zhang, Jichao,Zhu, Qiyu

, (2022/01/03)

Cancer cell proliferation in some organs often depends on conversion of pyruvate to oxaloacetate via pyruvate carboxylase (PC) for replenishing the tricarboxylic acid cycle to support biomass production. In this study, PC was identified as the cellular target of erianin using the photoaffinity labeling-click chemistry-based probe strategy. Erianin potently inhibited the enzymatic activity of PC, which mediated the anticancer effect of erianin in human hepatocellular carcinoma (HCC). Erianin modulated cancer-related gene expression and induced changes in metabolic intermediates. Moreover, erianin promotes mitochondrial oxidative stress and inhibits glycolysis, leading to insufficient energy required for cell proliferation. Analysis of 14 natural analogs of erianin showed that some compounds exhibited potent inhibitory effects on PC. These results suggest that PC is a cellular target of erianin and reveal the unrecognized function of PC in HCC tumorigenesis; erianin along with its analogs warrants further development as a novel therapeutic strategy for the treatment of HCC.

An Expeditious Modular Hybrid Strategy for the Diversity-Oriented Synthesis of Lamellarins/Azalamellarins with Anticancer Cytotoxicity

Klumthong, Kanawut,Chalermsub, Papornchanok,Sopha, Pattarawut,Ruchirawat, Somsak,Ploypradith, Poonsakdi

, p. 14883 - 14902 (2021/09/13)

A modular hybrid strategy has been developed for the diversity-oriented synthesis of lamellarins/azalamellarins. The common pentacyclic pyrrolodihydroisoquinoline lactone/lactam core was formed via the Michael addition/ring closure (Mi-RC) and the copper(I) thiophene-2-carboxylate (CuTC)-catalyzed C-O/C-N Ullmann coupling. Subsequent direct functionalization at C1, DDQ-mediated C5C6 oxidation, and global deprotection of all benzyl-type O- and N-protecting groups furnished the desired lamellarins/azalamellarins. The late-stage functionalization at C1 provided a handle to accommodate a wider scope of functional groups as they need to tolerate only the DDQ oxidation and global deprotection. Moreover, with the C1-H pyrrole as the late-stage common intermediate, it was also possible to divergently exploit not only its nucleophilic nature to react with some electrophilic species but also some transition-metal-catalyzed cross-coupling reactions (via the intermediacy of the C1-iodopyrrole) to incorporate diversity at this position. Overall, this strategy simplifies the preparation of lamellarins/azalamellarins; including the Mi-RC, these C1-structurally diverse analogues could be prepared efficiently in 6-7 steps from the easily accessed 1-acetoxymethyldihydroisoquinoline and β-nitrocinnamate. Some selected azalamellarins were evaluated for their inhibitory effect against HeLa cervical cancer cells. An acute induction of intrinsic apoptosis was detected and may lead to growth suppression of or cytotoxicity against cancer cells.

Synthesis and analysis of dihydrotetrabenazine derivatives as novel vesicular monoamine transporter 2 inhibitors

Du, Guangying,Tian, Jingwei,Wang, Hongbo,Wang, Wenyan,Yang, Yifei,Ye, Liang,Yu, Dawei,Zhang, Rui,Zhu, Xiaoyin,Zou, Fangxia

, (2021/07/31)

Vesicular monoamine transporter 2 (VMAT2) is essential for synaptic transmission of all biogenic amines in the brain including serotonin, norepinephrine, histamine, and dopamine (DA). Given its crucial role in the neurophysiology and pharmacology of the central nervous system, VMAT2 is recognized as an important therapeutic target for various neurological disorders such as tardive dyskinesia (TD). Here, a novel series of dihydrotetrabenazine derivative analogs were designed and synthesized to evaluate their effects on [3H]dihydrotetrabenazine (DTBZ) binding and [3H]DA uptake at VMAT2. Of these analogs, compound 13e showed a high binding affinity for VMAT2 (IC50 = 5.13 ± 0.16 nM) with excellent inhibition of [3H]DA uptake (IC50 = 6.04 ± 0.03 nM) in striatal synaptosomes. In human liver microsomes, 13e was more stable (T1/2 = 161.2 min) than other reported VMAT2 inhibitors such as DTBZ (T1/2 = 119.5 min). In addition, 13e effectively inhibited the spontaneous locomotor activity (percent inhibition at 3 μmol/kg = 64.7%) in Sprague-Dawley rats. Taken together, our results indicate that 13e might be a promising lead compound for the development of novel treatments of TD.

Chromium-Salen Complex/Nitroxyl Radical Cooperative Catalysis: A Combination for Aerobic Intramolecular Dearomative Coupling of Phenols

Nagasawa, Shota,Fujiki, Shogo,Sasano, Yusuke,Iwabuchi, Yoshiharu

, p. 6952 - 6968 (2021/05/29)

We describe an aerobic intramolecular dearomative coupling reaction of tethered phenols using a catalytic system consisting of a chromium-salen (Cr-salen) complex combined with a nitroxyl radical. This novel catalytic system enables formation of various spirocyclic dienone products including those unable to be accessed by previously reported methods efficiently under mild reaction conditions.

Synthesis and characterisation of novel tricyclic and tetracyclic furoindoles: Biological evaluation as SAHA enhancer against neuroblastoma and breast cancer cells

Arndt, Greg M.,Bingul, Murat,Black, David Stc.,Cheung, Belamy B.,Kumar, Naresh,Marshall, Glenn M.

, (2021/09/28)

The dihydropyranoindole structures were previously identified as promising scaffolds for improving the anti-cancer activity of histone deacetylase inhibitors. This work describes the synthesis of related furoindoles and their ability to synergize with suberoylanilide hydroxamic acid (SAHA) against neuroblastoma and breast cancer cells. The nucleophilic substitution of hydroxyin-dole methyl esters with α-haloketones yielded the corresponding arylether ketones, which were subsequently cyclized to tricyclic and tetracyclic furoindoles. The furoindoles showed promising individual cytotoxic efficiency against breast cancer cells, as well as decent SAHA enhancement against cancer cells in select cases. Interestingly, the best IC50 value was obtained with the non-cyclized intermediate.

Total Synthesis of Lamellarins G, J, L, and Z Using One-Pot Halogen Dance/Negishi Coupling

Mori, Atsunori,Morii, Kazuki,Morikawa, Daiki,Okano, Kentaro,Yasuda, Yuto

, p. 13388 - 13401 (2021/10/12)

A bottom-up synthesis of lamellarins G, J, L, and Z was achieved via one-pot halogen dance/Negishi coupling of a lithiated dibromopyrrole derivative. The easily accessible dibromopyrrole bearing an ester moiety underwent halogen dance smoothly at -78 °C within 10 min. The resultant α-pyrrolyllithium was transmetalated to the corresponding organozinc species, which was then coupled with an aryl iodide in the presence of catalytic palladium to provide the fully substituted pyrrole. Subsequent halogen-lithium exchange was performed to incorporate a boronate group exclusively at the β position proximal to the ester moiety. This synthetic intermediate allowed stepwise diarylation for the total synthesis of lamellarins G, J, L, and Z.

Vanadium-Catalyzed Oxidative Intramolecular Coupling of Tethered Phenols: Formation of Phenol-Dienone Products

Gilmartin, Philip H.,Kozlowski, Marisa C.

supporting information, p. 2914 - 2919 (2020/04/10)

A mild and efficient method for the vanadium-catalyzed intramolecular coupling of tethered free phenols is described. The corresponding phenol-dienone products are prepared directly in good yields with low catalyst loadings. Electronically diverse tethered phenol precursors are well tolerated, and the catalytic method was effectively applied as the key step in syntheses of three natural products and a synthetically useful morphinan alkaloid precursor.

ANTI-INFLAMMATORY COMPOUND, AND PREPARATION AND USE THEREOF

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Paragraph 0175-0179, (2020/12/13)

The present invention provides an anti-inflammatory compound, which is a compound having a structure (I) as shown below: The compound is a target that is important for autoimmune activation, and that has strong inhibitory effect on PDE4 and penetrates the skin easily, and is a new type anti-inflammatory compound that is easily degraded.

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