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
• Article Data: 23

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

General Description

2,3,4-Trimethoxy-benzoyl chloride, also known as 4-chloro-2,3,5-trimethoxybenzoyl chloride, is a chemical compound with the molecular formula C10H11ClO4. It is a white to pale yellow solid that is commonly used as an intermediate in the synthesis of pharmaceuticals and agrochemicals. 2,3,4-TRIMETHOXY-BENZOYL CHLORIDE is a reactive acylating agent and is often used in the preparation of esters and amides. It is also used in organic synthesis and as a reagent in the production of various aromatic compounds. 2,3,4-Trimethoxy-benzoyl chloride is an important building block in chemical research and production, and it is essential for the development of various pharmaceutical and agricultural products.

Upstream product

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

Downstream Products

• 31127-54-5 2,3,4,4'-tetrahydroxybenzophenone 
• 92288-79-4 (2,3,4-trimethoxy-phenyl)-glyoxylonitrile 
• 103692-11-1 N-(2-Hydroxy-1,1-dimethyl-ethyl)-2,3,4-trimethoxy-benzamide 
• 42833-67-0 2,4,6-trimethoxy-2'-hydroxy-3',4'-dimethoxybenzophenone 
• 145353-99-7 4,6-dimethoxy-2-hydroxy-2',3',4'-trimethoxybenzophenone 
• 3660-86-4 1,3,5,6-tetramethyoxyxanthone 
• 145354-00-3 (2-hydroxy-3,4-dimethoxyphenyl) (2',3',4'-trimethoxyphenyl)methanone 
• 129103-76-0 2,3,4-Trimethoxy-benzoic acid 1-iodo-naphthalen-2-yl ester 
• 88773-07-3 Phenyl-O-<2,3-di-O-benzyl-4,6-didesoxy-4-(2,3,6-trimethoxyphenylcarbonylamino)-β-D-glucopyranosyl>-(1->4)-O-(2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosid 
• 88773-04-0 Phenyl-O-<2,3-di-O-benzyl-4,6-didesoxy-4-(2,3,4-trimethoxyphenylcarbonylamino)-α-D-glucopyranosyl>-(1->4)-O-(2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosid 
• 120697-46-3 1-(pyrrolidinocarbonylmethyl)-4-(2,3,4-trimethoxybenzoyl)piperazine 

Relevant articles and documents

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

In recent years, focusing on new potent anticancer agents with selective activity is one of the greatest challenges in cancer therapy. Breast cancer is the most common cancer and the main cause of cancer deaths in women. The sulfatase enzyme plays an important role in converting the sulfated steroids into non-sulfate steroid hormones, which increases the growth and development of many hormone-dependent cancers, such as breast cancer. In this regard, structure-based optimization was conducted to design novel flavone-sulfonates pharmacophore as a new steroid sulfatase inhibitor. In the present work, the conventional methods for the synthesis of 4-oxo-2-phenyl-4H-chromen-7-yl methanesulfonate derivatives were reported. Their cytotoxicity was evaluated with MTT assay against a breast cancer cell line (MCF-7). The apoptosis inducing activity of the most cytotoxic compound 3c with an IC50 value of 0.615 μM was evaluated in comparison to docetaxel in the presence of estradiol which is a crucial growth factor to survive the cancerous cells. The results of double staining Annexin V-FITC/PI analysis suggested that the cytotoxic activity of this compound 3c in MCF-7 cells occurs via apoptosis. Molecular docking studies were conducted to clarify the inhibition mode of the most promising compound (3c) over the sulfatase (1P49) binding site. The analysis revealed the role of hydrogen bond interaction with Gly181 and hydrophobic interactions through the 1P49 active site in the ligand-receptor complex as significant descriptors to rationalize the potential inhibition activity. [Figure not available: see fulltext.]

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.

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.