38594-42-2

Usage

Uses

Used in Pharmaceutical Industry:
2,3-Dichlorobenzyl alcohol is used as a synthetic intermediate for the preparation of complex organic molecules, particularly in the pharmaceutical industry. Its antiseptic nature makes it a valuable component in the development of new drugs and medicinal compounds.
Specifically, it is used in the preparation of:
1. Methyl [2,3-dichlorobenzyl 4,7,8-tri-O-acetyl-9-azido-3,5,9-trideoxy-5-(2-nitrophenylsulfonamido)-D-glycero-α-D-galacto-2-nonulopyranosid]onate
2. Methyl [2,3-dichlorobenzyl 5-acetamido-4,7,8-tri-O-acetyl-3,5,9-trideoxy-9-(4-phenylbenzamido)-D-glycero-α-D-galacto-2-nonulopyranosid]onate
These complex molecules have potential applications in the development of new drugs and therapies, highlighting the importance of 2,3-dichlorobenzyl alcohol as a key component in the pharmaceutical industry.

Upstream product

• 6334-18-5 2,3-dichlorobenzylaldehyde 
• 50-45-3 2,3-dichlorbenzoic acid 
• 32768-54-0 2,3-dichlorotoluene 
• 57915-78-3 1-(bromomethyl)-2,3-dichlorobenzene 
• 608-27-5 2,3-dichloroaniline 
• 2905-54-6 2,3-Dichlorobenzoic acid methyl ester 

Downstream Products

• 3290-01-5 2,3-dichlorobenzyl chloride 
• 3218-45-9 2,3-dichlorophenylacetonitrile 
• 6334-18-5 2,3-dichlorobenzylaldehyde 
• 39959-98-3 ethyl 2-cyano-3-(2,3-dichlorophenyl)propanoate 
• 1420468-62-7 3-(2,3-dichlorobenzyl)-5-(pyridin-4-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-7-ol 
• 57915-78-3 1-(bromomethyl)-2,3-dichlorobenzene 
• 239132-51-5 5-(2,3-dichlorophenyl)-cyclohexane-1,3-dione 
• 10236-60-9 (2,3-dichlorophenyl)acetic acid 
• 321430-36-8 2-(2,3-Dichloro-benzyloxy)-isoindole-1,3-dione 
• 227754-33-8 O-(2,3-dichlorobenzyl)hydroxylamine 
• 1209012-71-4 methyl (2,3-dichlorobenzyl 5-acetamido-4,7,8-tri-O-acetyl-9-azido-3,5,9-trideoxy-D-glycero-α-D-galacto-2-nonulopyranosid)-onate 
• 442628-43-5 2,3-dichlorobenzyl methanesulphonate 

Relevant academic research and scientific papers

Synthetic process of 2,3-dichlorobenzaldehyde

The invention discloses a synthetic process of 2,3-dichlorobenzaldehyde. The synthetic process comprises the steps that 2,3-dichlorotoluene is used as a raw material, bromine is used as an auxiliary material, azodiisobutyronitrile is used as a catalyst, the bromine utilization rate is improved through hydrogen peroxide, the generated 2,3-dichlorobenzyl bromide is hydrolyzed into 2,3-dichlorobenzaldehyde in 30 wt% of sodium carbonate water solution, the 2,3-dichlorobenzaldehyde is generated by using hydrogen bromide to catalyze hydrogen peroxide oxidization, the total yield is 70% or above, and the product purity is 99.25% or above. The raw material conversion rate and selectivity of the process are high. In addition, the by-product production rate is reduced, the bromine utilization rate is improved, the bromine usage amount is decreased, and the synthetic process is greener and environmentally friendly compared with a traditional metal-catalyzed oxidation technology.

O-alkylhydroxylamines as rationally-designed mechanism-based inhibitors of indoleamine 2,3-dioxygenase-1

Indoleamine 2,3-dioxygenase-1 (IDO1) is a promising therapeutic target for the treatment of cancer, chronic viral infections, and other diseases characterized by pathological immune suppression. Recently important advances have been made in understanding IDO1's catalytic mechanism. Although much remains to be discovered, there is strong evidence that the mechanism proceeds through a heme-iron bound alkylperoxy transition or intermediate state. Accordingly, we explored stable structural mimics of the alkylperoxy species and provide evidence that such structures do mimic the alkylperoxy transition or intermediate state. We discovered that O-benzylhydroxylamine, a commercially available compound, is a potent sub-micromolar inhibitor of IDO1. Structure-activity studies of over forty derivatives of O-benzylhydroxylamine led to further improvement in inhibitor potency, particularly with the addition of halogen atoms to the meta position of the aromatic ring. The most potent derivatives and the lead, O-benzylhydroxylamine, have high ligand efficiency values, which are considered an important criterion for successful drug development. Notably, two of the most potent compounds demonstrated nanomolar-level cell-based potency and limited toxicity. The combination of the simplicity of the structures of these compounds and their excellent cellular activity makes them quite attractive for biological exploration of IDO1 function and antitumor therapeutic applications.

Selective Pinacol-Coupling Reaction using a Continuous Flow System

The first continuous flow pinacol coupling reaction of carbonyl compounds was successfully achieved within only 2 min during a single pass through a cartridge filled with zinc(0). The optimized method allowed the efficient production of gram-scale value-added compounds with high productivity. The developed methodology is efficient for aromatic or α,β-unsaturated aldehydes but gives moderate results for more stable acetophenone derivatives. Moreover, the flow method displayed better results in terms of yield and selectivity in comparison to the corresponding batch methodology.

Simple and expeditious pinacol coupling of non usual α,β-unsaturated carbonyl compounds in water

Using zinc (0) in a 5% v AcOH aqueous solution allowed the efficient pinacol coupling of aliphatic or aromatic unusual, α,β-unsaturated carbonyl compounds such as citral A in good to excellent yields (56-99%). It can also be successfully applied to acetophenone.

Pyrazolopyrimidine derivatives as PI3 kinase inhibitors

PI3Kβ selective compounds having the structure

First pinacol coupling in emulsified water: Key role of surfactant and impact of alternative activation technologies

For the first time, the influence of surfactants on the radical pinacol coupling reaction is investigated. The rate and selectivity of this reductive C-C coupling are compared under three different activation technologies: thermal activation, microwave irradiation, and sonication. The use of IgepalCO520, a neutral surfactant, led to the successful conversion of aromatic or α,β-unsaturated aliphatic carbonyl compounds in moderate to excellent yield (55-90 %). An insight on the potential mechanism involved in the reaction is also proposed, based on microscopic observations and particle size measurement.

Selective Pinacol Coupling on Regeneratable Supported Acids in Sole Water

Efficient pinacol coupling was developed in sole water, using a reusable heterogeneous supported acid source and zinc as cheap available metal source. This medium can be easily regenerated up to 10-fold without loss of activity. Moreover, supported acids enhance the selectivity of the pinacol coupling reaction compared with homogeneous acids.

Metal-free, visible-light photoredox catalysis: Transformation of arylmethyl bromides to alcohols and aldehydes

A mild, simple, and controllable metal-free photocatalytic system for the transformation of arylmethyl bromides to corresponding alcohols and aldehydes in high yields with visible-light irradiation has been achieved. Eosin Y was found to be an efficient promoter for this oxidative dehalogenation reaction under photo irradiation conditions.

Electrophilicity and nucleophilicity of commonly used aldehydes

The present approach for determining the electrophilicity (E) and nucleophilicity (N) of aldehydes includes a kinetic study of KMNO4 oxidation and NaBH4 reduction of aldehydes. A transition state analysis of the KMNO4 promoted aldehyde oxidation reaction has been performed, which shows a very good correlation with experimental results. The validity of the experimental method has been tested using the experimental activation parameters of the two reactions. The utility of the present approach is further demonstrated by the theoretical versus experimental relationship, which provides easy access to E and N values for various aldehydes and offers an at-a-glance assessment of the chemical reactivity of aldehydes in various reactions. the Partner Organisations 2014.

PYRAZOLOPYRIMIDINE DERIVATIVES AS PI3 KINASE INHIBITORS

The present invention relates to compounds of formula (I) in which R1, R2, R3 and n have the meaning given in the specification and also relates to the use of these pyrazolopyrimidine derivatives for the modulation, notably the inhibition of the activity or function of the phosphoinositide 3'OΗ kinase family (hereinafter PI3 kinases), wherein the compounds of formula (I) are described as selective inhibitors of PI3K[beta] activity.