7169-07-5

Basic information

• Product Name: 2,3,4-TRIMETHOXY-BENZOYL CHLORIDE
• Synonyms: 2,3,4-TRIMETHOXY-BENZOYL CHLORIDE
• CAS NO: 7169-07-5
• Molecular Formula: C₁₀H₁₁ClO₄
• Molecular Weight: 230.64
• Mol File: 7169-07-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,3,4-TRIMETHOXY-BENZOYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4-TRIMETHOXY-BENZOYL CHLORIDE(7169-07-5)
• EPA Substance Registry System: 2,3,4-TRIMETHOXY-BENZOYL CHLORIDE(7169-07-5)

Safety Data

• Hazardous Substances Data: 7169-07-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,3,4-Trimethoxy-benzoyl chloride is used as an intermediate for the synthesis of various pharmaceutical compounds. Its reactivity as an acylating agent allows for the formation of esters and amides, which are essential in the development of new drugs and medicinal agents.
Used in Agrochemical Industry:
In the agrochemical sector, 2,3,4-Trimethoxy-benzoyl chloride is utilized as a key component in the production of pesticides and other agricultural chemicals. Its role in creating esters and amides contributes to the effectiveness and functionality of these products.
Used in Organic Synthesis:
2,3,4-Trimethoxy-benzoyl chloride is employed as a reagent in organic synthesis, where it aids in the formation of complex organic molecules. Its ability to participate in acylation reactions makes it a valuable tool in creating a wide array of organic compounds.
Used in Aromatic Compound Production:
As a precursor in the production of aromatic compounds, 2,3,4-Trimethoxy-benzoyl chloride is integral to the creation of fragrances, dyes, and other specialty chemicals that rely on aromatic structures for their properties. Its versatility in chemical reactions ensures its broad applicability in this field.

Upstream product

• 573-11-5 2,3,4-Trimethoxy-benzoic acid 

Downstream Products

• 92288-79-4 (2,3,4-trimethoxy-phenyl)-glyoxylonitrile 
• 88440-82-8 N,N-diethyl-2,3,4-trimethoxybenzamide 
• 99425-55-5 4,4-dimethyl-2-(2-isopropyl-3,4-dimethoxyphenyl)-2-oxazoline 
• 370559-34-5 1-(2,3,4-trimethoxybenzoyl)-3-phenyl-3-(2-hydroxyethyl)pyrrolidine 
• 1236971-83-7 C₆₄H₈₄N₂O₂₀S₂ 
• 1421252-20-1 2-bis-(3,4,5-trimethoxybenzoyl)amino-3-chloro-1,4-naphthoquinone 
• 1609138-38-6 C₂₈H₃₆N₄O₇S₂ 
• 99425-57-7 2-<2-(4-methoxyphenyl)-3,4-dimethoxyphenyl>-4,4-dimethyl-2-oxazoline 
• 99425-56-6 2-(2-phenyl-3,4-dimethoxyphenyl)-4,4-dimethyl-2-oxazoline 
• 85010-19-1 4,4-dimethyl-2-(2,3,4-trimethoxyphenyl)-4,5-oxazoline 

Relevant articles and documents

Design, synthesis and apoptosis inducing activity of nonsteroidal flavone-methanesulfonate derivatives on MCF-7 cell line as potential sulfatase inhibitor

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Synthesis of 3-aryl-1-phosphinoimidazo[1,5-a]pyridine ligands for use in Suzuki-Miyaura cross-coupling reactions

3-Aryl-1-phosphinoimidazo[1,5-a]pyridine ligands were synthesized from 2-aminomethylpyridine as the initial substrateviatwo complementary routes. The first synthetic pathway underwent the coupling of 2-aminomethylpyridine with substituted benzoyl chlorides, followed by cyclization, iodination and palladium-catalyzed cross-coupling phosphination reactions sequence to give our phosphorus ligands. In the second route, 2-aminomethylpyridine was cyclized with aryl aldehydes, followed by the iodination and palladium-catalyzed cross-coupling phosphination reactions to yield our phosphorus ligands. The 3-aryl-1-phosphinoimidazo[1,5-a]pyridine ligands were evaluated in palladium-catalyzed sterically-hindered biaryl and heterobiaryl Suzuki-Miyaura cross-coupling reactions.

6,7-Dimethoxy-2-phenethyl-1,2,3,4-tetrahydroisoquinoline amides and corresponding ester isosteres as multidrug resistance reversers

Aiming to deepen the structure–activity relationships of the two P-glycoprotein (P-gp) modulators elacridar and tariquidar, a new series of amide and ester derivatives carrying a 6,7-dimethoxy-2-phenethyl-1,2,3,4-tetrahydroisoquinoline scaffold linked to different methoxy-substituted aryl moieties were synthesised. The obtained compounds were evaluated for their P-gp interaction profile and selectivity towards the two other ABC transporters, multidrug-resistance-associated protein-1 and breast cancer resistance protein, showing to be very active and selective versus P-gp. Two amide derivatives, displaying the best P-gp activity, were tested in co-administration with the antineoplastic drug doxorubicin in different cancer cell lines, showing a significant sensitising activity towards doxorubicin. The investigation on the chemical stability of the derivatives towards spontaneous or enzymatic hydrolysis, showed that amides are stable in both models while some ester compounds were hydrolysed in human plasma. This study allowed us to identify two chemosensitizers that behave as non-transported substrates and are characterised by different selectivity profiles.

Design, synthesis, biological evaluation, NMR and DFT studies of structurally simplified trimethoxy benzamides as selective P-glycoprotein inhibitors: the role of molecular flatness

In a recent investigation carried out on a panel of trimethoxybenzanilides, we showed that the formation of an intramolecular hydrogen bond is a key element for tuning P-gp inhibitory activity. In this study, we designed new structurally simplified trimet

Beyond directed ortho metalation: Ru-catalyzed CAr-O activation/cross-coupling reaction by amide chelation

Disclosed is a new, catalytic, and general methodology for the chemical synthesis of biaryl, heterobiaryl, and polyaryl molecules by the cross-coupling of o-methoxybenzamides with aryl boroneopentylates. The reaction is based on the activation of the unreactive C-OMe bond by the proximate amide directing group using catalytic RuH2(CO)(PPh3)3 conditions. A one-step, base-free coupling process is thereby established that has the potential to supersede the useful two-step directed ortho metalation/cross- coupling reaction involving cryogenic temperature and strong base conditions. High regioselectivity, orthogonality with the Suzuki-Miyaura reaction, operational simplicity, minimum waste, and convenient scale-up make these reactions suitable for industrial applications.

Discovery and early clinical development of 2-{6-[2-(3,5-dichloro-4- pyridyl)acetyl]-2,3-dimethoxyphenoxy}- N -propylacetamide (LEO 29102), a soft-drug inhibitor of phosphodiesterase 4 for topical treatment of atopic dermatitis

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Trimethoxybenzanilide-based P-glycoprotein modulators: An interesting case of lipophilicity tuning by intramolecular hydrogen bonding

One of the principal reasons for the chemotherapy failure is the overexpression of drug efflux pumps, ABCB1 (also known as MDR1 or P-gp) and ABCC1 (also known as MRP1), whose inhibition remains a priority to circumvent drug resistance. We have recently sh

N,N+hu 1 +l SUBSTITUTED PIPERAZINES HAVING COMBINED ANTIAGGREGANT, ANTICOAGULANT AND VASODILATORY ACTIVITY, AND METHOD FOR PRODUCING SAME

The invention relates to derivatives of N,N′-substituted piperazines of the general formula (I): where R1 and R2 denote linear or branched (C1-C4)alkyl, linear or branched (C1-C4)alkoxy, CH

Synthesis and biological evaluation of phenyl substituted polyoxygenated xanthone derivatives as anti-hepatoma agents

A series of novel derivatives of phenyl substituted tetramethoxy xanthone were synthesized and evaluated for their in vitro cytotoxicity against human hepatocellular carcinoma (HCC) and non-tumor hepatic cells. Among these derivatives, compound 6 was more potent than positive control 5-fluorouracil (5-Fu) on QGY-7703 and SMMC-7721 cells with IC50 values of 6.27 μM, 7.50 μM and 15.56 μM, 14.55 μM, respectively. Furthermore, compounds 6, 14, 16, and 29 exhibited much better selectivity toward the normal hepatic cell line QSG-7701 than 5-Fu. Additionally, compound 6 significantly induced cell apoptosis in QGY-7703 cells. Our findings suggested that these phenylxanthone derivatives may hold promise as chemotherapeutic agents for the treatment of human HCC.

Process development of the PDE4 inhibitor K-34

A short and practical synthesis of the PDE4 inhibitor K-34 (1) was developed. This synthesis was achieved in four steps and with a 58% overall yield. The unique spiro acetal was created with exceptionally high yield by utilizing the neighbor carboxylic acid assistance. This synthesis also features efficient ketone construction with 4-pyridinylmethyl anion 9 and ester 18, in which overreaction should be prohibited by quick in situ enolate formation. The overall synthesis was carried out under mild conditions and used a simple procedure suitable for large-scale production.