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3,4,5-Trimethoxy-2-nitrobenzoic acid, a derivative of benzoic acid with the chemical formula C10H11NO6, is characterized by the presence of three methoxy groups and one nitro group on its benzene ring. This organic compound is widely utilized in organic synthesis and medicinal chemistry as a key building block for the development of pharmaceutical compounds. Its biological activities, such as anti-inflammatory and anti-cancer properties, have garnered significant interest, making it a promising candidate for the treatment of various diseases. Furthermore, 3,4,5-Trimethoxy-2-nitrobenzoic acid has been investigated for its potential antioxidant capabilities and as an intermediate in the synthesis of other organic compounds.

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  • 66907-52-6 Structure
  • Basic information

    1. Product Name: 3,4,5-TRIMETHOXY-2-NITROBENZOIC ACID
    2. Synonyms: 3,4,5-TRIMETHOXY-2-NITROBENZOIC ACID;2-NITRO-3,4,5-TRIMETHOXYBENZOIC ACID
    3. CAS NO:66907-52-6
    4. Molecular Formula: C10H11NO7
    5. Molecular Weight: 257.2
    6. EINECS: 266-518-6
    7. Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts
    8. Mol File: 66907-52-6.mol
  • Chemical Properties

    1. Melting Point: 166 °C
    2. Boiling Point: 440 °C at 760 mmHg
    3. Flash Point: 219.9 °C
    4. Appearance: /
    5. Density: 1.384 g/cm3
    6. Vapor Pressure: 1.62E-08mmHg at 25°C
    7. Refractive Index: N/A
    8. Storage Temp.: Sealed in dry,Room Temperature
    9. Solubility: N/A
    10. PKA: 2.22±0.25(Predicted)
    11. CAS DataBase Reference: 3,4,5-TRIMETHOXY-2-NITROBENZOIC ACID(CAS DataBase Reference)
    12. NIST Chemistry Reference: 3,4,5-TRIMETHOXY-2-NITROBENZOIC ACID(66907-52-6)
    13. EPA Substance Registry System: 3,4,5-TRIMETHOXY-2-NITROBENZOIC ACID(66907-52-6)
  • 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: 66907-52-6(Hazardous Substances Data)

66907-52-6 Usage

Uses

Used in Pharmaceutical Industry:
3,4,5-Trimethoxy-2-nitrobenzoic acid is used as a building block for the synthesis of various pharmaceutical compounds due to its unique chemical structure and functional groups. Its presence in the molecular structure of these compounds can potentially enhance their therapeutic effects and pharmacological properties.
Used in Organic Synthesis:
3,4,5-Trimethoxy-2-nitrobenzoic acid is used as an intermediate in the synthesis of other organic compounds, contributing to the formation of complex molecular structures with diverse applications in various industries.
Used in Medicinal Chemistry:
3,4,5-Trimethoxy-2-nitrobenzoic acid is used as a key component in the development of new drugs, leveraging its biological activities such as anti-inflammatory and anti-cancer properties. Its incorporation into drug molecules can potentially improve their efficacy in treating various diseases.
Used in Antioxidant Research:
3,4,5-Trimethoxy-2-nitrobenzoic acid is studied for its potential as an antioxidant, which can help protect cells from oxidative damage and contribute to the prevention of various diseases associated with oxidative stress.
Used in Disease Treatment:
3,4,5-Trimethoxy-2-nitrobenzoic acid is explored for its potential use in the treatment of various diseases, including inflammatory and cancerous conditions, due to its biological activities and therapeutic properties.

Check Digit Verification of cas no

The CAS Registry Mumber 66907-52-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,6,9,0 and 7 respectively; the second part has 2 digits, 5 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 66907-52:
(7*6)+(6*6)+(5*9)+(4*0)+(3*7)+(2*5)+(1*2)=156
156 % 10 = 6
So 66907-52-6 is a valid CAS Registry Number.
InChI:InChI=1/C10H11NO7/c1-16-6-4-5(10(12)13)7(11(14)15)9(18-3)8(6)17-2/h4H,1-3H3,(H,12,13)/p-1

66907-52-6SDS

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 3,4,5-TRIMETHOXY-2-NITROBENZOIC ACID

1.2 Other means of identification

Product number -
Other names Nitrogallussaeure-trimethylaether

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:66907-52-6 SDS

66907-52-6Relevant articles and documents

Synthesis and antitumor activity of novel 6,7,8-trimethoxy N-aryl-substituted-4-aminoquinazoline derivatives

Liu, Fang,Huai, Ziyou,Xia, Guotai,Song, Liuping,Li, Sha,Xu, Yulan,Hong, Kangjun,Yao, Mingyue,Liu, Gang,Huang, Yinjiu

, p. 2561 - 2565 (2018/06/20)

A series of 6,7,8-trimethoxy N-aryl-substituted-4-aminoquinazoline derivatives were synthesized as epidermal growth factor receptor (EGFR) inhibitors, and their antitumor activities were assessed in the gastric cancer cell line SGC7901 using MTT assay. All compounds of Tg1–14 were found to inhibit SGC7901 cell proliferation, and compound Tg11 (IC50 = 0.434 μM) was found to be slightly more effective against SGC7901 cells than epirubicin (IC50 = 5.16 μM). This suggests that compound Tg11 can be used as a new substitution structure to develop more efficacious antitumor agents. Western blot analysis showed that treatment with Tg11 (40 μM for 30 min) resulted in near complete inhibition of EGF-induced ERK1/2 phosphorylation, indicating that its anti-proliferative effect is largely associated with inhibition of ERK1/2 activation. These data imply that Tg11 is a potential anticancer agent capable of inhibiting cell proliferation.

Synthesis, biological evaluation and molecular docking studies of 2-amino-3,4,5-trimethoxyaroylindole derivatives as novel anticancer agents

Patel, Vijay K.,Rajak, Harish

supporting information, p. 2115 - 2118 (2016/04/20)

A series of novel 2-amino-3,4,5 trimethoxyaroylindole derivatives was synthesized and evaluated against selected human cancer cell lines of breast (MCF-7) and colon (HT-29). Introduction of an amino group at the C-2 position on ring A of 3,4,5-trimethoxyaroylindole derivatives resulted in novel compounds, i.e., 2-amino-3,4,5-trimethoxyaroylindole derivatives exhibiting excellent cytotoxic activity against human cancer cell lines. Substitution with methoxy group at R6 in 2-amino-3,4,5-trimethoxyaroylindole 5d exhibited excellent cytotoxic activity against MCF-7 (0.013 μM) and colon HT-29 (0.143 μM) indicating slightly higher potency than Combretastatin A-4. Molecular modeling studies of 2-amino-3,4,5-trimethoxyaroylindole derivatives have similar structural alignment as colchicine in protein (PDB code: 1SA0) and exhibited hydrogen bond interaction between para position of 3,4,5-trimethoxyphenyl ring with CYS 241 and N-H molecule of indole ring with Val 315 of receptor molecule.

Concise syntheses of N-aryl-5,6,7-trimethoxyindoles as antimitotic and vascular disrupting agents: Application of the copper-mediated Ullmann-type arylation

Lee, Hsueh-Yun,Chang, Jang-Yang,Chang, Ling-Yin,Lai, Wen-Yang,Lai, Mei-Jung,Shih, Kuang-Hsing,Kuo, Ching-Chuan,Chang, Chi-Yen,Liou, Jing-Ping

supporting information; experimental part, p. 3154 - 3157 (2011/05/12)

In an attempt to mimic the 3,4,5-trimethoxyphenyl-Z-stilbene moiety of combretastatin A-4, a series of N-aryl-5,6,7-trimethoxyindoles were synthesized via copper-catalyzed Ullmann-type N-arylation through the corresponding 5,6,7-trimethoxyindole and aryl halides. These synthesized compounds demonstrated potent antiproliferative activity providing a novel skeleton for potent tubulin polymerization inhibitors.

Cr/Ni-catalyzed vinylation of aldehydes: A mechanistic study on the catalytic roles of nickel and chromium

Harnying, Wacharee,Kaiser, Andre,Klein, Axel,Berkessel, Albrecht

experimental part, p. 4765 - 4773 (2011/06/19)

The roles of nickel and chromium catalysts in the coupling reaction of vinyl halides and aldehydes, the so-called Nozaki-Hiyama-Kishi (NHK) reaction, have been studied by UV/Vis spectroscopy, electrochemical, and spectroelectrochemical methods. Electrochemical studies revealed that nickel plays the central role in activating the vinyl halide by reductive cleavage, to form a rapidly decomposing vinyl-Ni species. The latter can, however, be stabilized in the presence of the Cr complex. The redox behavior of the Ni complexes in the presence of vinyl halide demonstrated that the vinyl halide activation results from interaction with a one-electron reduced nickel species [formally NiI], not necessarily with a Ni0 species. It was furthermore shown by UV/Vis spectroscopy and spectroelectrochemical methods that low-valent nickel [Ni0] results from the interaction of the NiII catalyst with CrCl2. It takes two to tango! The initial stages of the Cr/Ni-catalyzed vinylation of aldehydes (the Nozaki-Hiyama-Kishi reaction) were analyzed by electrochemical methods. The role of low-valent nickel in the C-halogen(Hal) cleavage of the vinyl halide was established, as well as the generation of the former from NiII and CrII. Copyright

Microwave assisted synthesis of novel 6,7,8-trimethoxy N-substituted-4- aminoquinazoline compounds

Liu, Gang,Sun, Lin,Liu, Chunping,Ji, Chunnuan,Wen, Quanwu,Ma, Songmei

, p. 759 - 764 (2008/09/21)

(Chemical Equation Presented) A fast, efficient and convenient reaction of 6,7,8-trimethoxy-4-chloroquinazoline and aryl (or benzyl) amines was achieved under microwave irradiation in isopropyl alcohol, providing a simple method for synthesis of novel 6,7,8-trimethoxy N-substituted-4-aminoquinazoline compounds in good yield in short time. The title compounds were evaluated for their in vitro anti-proliferative activities against PC3 cell by MTT method.

Synthesis and bioactivities of 6,7,8-trimethoxy-N-aryl-4-aminoquinazoline derivatives

Liu, Gang,Hu, De-Yu,Jin, Lin-Hong,Song, Bao-An,Yang, Song,Liu, Ping-Shen,Bhadury, Pinaki S.,Ma, Yao,Luo, Hui,Zhou, Xian

, p. 6608 - 6617 (2008/03/27)

A series of 4-aminoquinazoline derivatives is prepared by the nucleophilic substitution reaction of 6,7,8-trimethoxy-4-chloroquinazoline and aryl amine. The structures of the compounds are confirmed by elemental analysis, IR, and 1H NMR spectral data. The compounds are also evaluated for their ability to inhibit tumor cells PC3, A431, Bcap-37, and BGC823 by MTT assays. Among them, 6b and 6e are found as potent inhibitors, with IC50 values ranging from 5.8 to 9.8 μM, in vitro assay.

Synthesis and biological activity of novel N-substituted 4-amino-6,7,8-trimethoxyquinazoline compounds

Liu, Gang,Liu, Chunping,Sun, Lin,Qu, Rongjun,Chen, Hou,Ji, Chunnuan

, p. 1290 - 1300 (2008/12/21)

A series of N-substituted 4-amino-6,7,8-trimethoxyquinazoline derivatives has been synthesized from 4-chloro-6,7,8-trimethoxyquinazoline and aryl (or benzyl) amines using 2-propanol as a solvent. The starting material 4-chloro-6,7,8-trimethoxyquinazoline has been synthesized from natural gallic acid by a novel route. Their structures have been verified by elemental analysis and IR, 1H, and 13C NMR spectroscopy. The title compounds have been evaluated for their in vitro antiproliferative activities against some cancer cells by the MTT method. Unfortunately, most of the compounds tested have exhibited a weaker anticancer activity than the reference standard drug PD153035.

Pyrrolobenzodiazepines

-

, (2008/06/13)

Compounds of the formulae Ia and Ib: wherein: A is CH2, or a single bond; R2 is selected from: R, OH, OR, CO2H, CO2R, COH, COR, SO2R, CN; R6, R7 and R9 are independently selected from H, R, OH, OR, halo, amino, NHR, nitro, Me3Sn; and R8 is selected from H, R, OH, OR, halo, amino, NHR, nitro, Me3Sn, where R is as defined above, or the compound is a dimer with each monomer being the same or different and being of formula Ia or Ib, where the R8 groups of the monomers form together a bridge having the formula —X—R′—X— linking the monomers, where R′ is an alkylene chain containing from 3 to 12 carbon atoms, which chain may be interrupted by one or more hetero-atoms and/or aromatic rings and may contain one or more carbon-carbon double or triple bonds, and each X is independently selected from O, S, or N; except that in a compound of formula Ia when A is a single bond, then R2 is not CH═CH(CONH2) or CH═CH(CONMe2). Other related compounds are also disclosed.

Cyclic diamine compound with condensed-ring groups

-

, (2008/06/13)

A cyclic diamine compound of formula (1): wherein R1 and R2 are individually a hydrogen atom or a methoxy group, provided R1 is a methoxy group when R2 is a hydrogen atom, or a hydrogen atom when R2 is a methoxy group; A is an oxygen atom, a sulfur atom, CH═CH, CH═N or NR3, in which R3 is a hydrogen atom, or a lower alkyl, hydroxy lower alkyl, lower alkoxy lower alkyl, aryl or aryl lower alkyl group; B is a nitrogen atom, CH or CR4, in which R4 is a hydrogen atom, or a lower alkyl, hydroxy lower alkyl, lower alkoxy lower alkyl, aryl or aryl lower alkyl group; m is 1 or 2; and n is a number of 1 to 5, an acid-addition salt thereof, or a hydrate thereof. The compound has inhibitory effects on cell adhesion and is useful for treatment of allergy, asthma, rheumatism, arteriosclerosis, and inflammation.

Pyrrolobenzodiazepines

-

Page 69, 122, (2010/11/29)

Compounds of the formulae Ia and Ib: wherein:A is CH2, or a single bond;R2 is selected from: R, OH, OR, CO2H, CO2R, COH, COR, SO2R, CN;R6, R7 and R9 are independently selected from H, R, OH, OR, halo, amino, NHR, nitro, Me3Sn;and R8 is selected from H, R, OH, OR, halo, amino, NHR, nitro, Me3Sn, where R is as defined above, or the compound is a dimer with each monomer being the same or different and being of formula Ia or Ib, where the R8 groups of the monomers form together a bridge having the formula -X-R'-X- linking the monomers, where R' is an alkylene chain containing from 3 to 12 carbon atoms, which chain may be interrupted by one or more hetero-atoms and/or aromatic rings and may contain one or more carbon-carbon double or triple bonds, and each X is independently selected from O, S, or N; except that in a compound of formula Ia when A is a single bond, then R2 is not CH=CH(CONH2) or CH=CH(CONMe2). Other related compounds are also disclosed.

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