7228-38-8

Usage

Uses

Used in Chemical Synthesis:
5-Chloro-1,3-benzodioxole is used as a chemical intermediate for the synthesis of various organic compounds, including safrole derivatives. Its unique structure allows for versatile chemical reactions and transformations, making it a valuable building block in the development of new molecules with potential applications in various industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 5-chloro-1,3-benzodioxole can be used as a key component in the synthesis of drug candidates with potential therapeutic properties. Its ability to be converted into various derivatives makes it a promising starting material for the development of new drugs with improved efficacy and safety profiles.
Used in Agrochemical Industry:
5-Chloro-1,3-benzodioxole can also be utilized in the agrochemical industry as a precursor for the synthesis of pesticides and other agrochemicals. Its chemical properties enable the creation of novel compounds with enhanced pest control capabilities and reduced environmental impact.
Used in Flavor and Fragrance Industry:
In the flavor and fragrance industry, 5-chloro-1,3-benzodioxole can be employed as a building block for the development of new aroma chemicals and flavor compounds. Its unique structure and reactivity can contribute to the creation of innovative and complex scents and tastes for various applications, such as perfumes, cosmetics, and food products.

InChI:InChI=1/C14H18N4O4/c1-20-10-5-8(6-11(21-2)12(10)22-3)4-9-7-18(19)14(16)17-13(9)15/h5-7,19H,4H2,1-3H3,(H3,15,16,17)

Upstream product

• 274-09-9 Methylenedioxybenzene 
• 94839-07-3 3,4-(methylenedioxy)-benzeneboronic acid 

Downstream Products

• 18113-10-5 4-chloro-2-ethoxyphenol 
• 68756-52-5 2-benzo[1,3]dioxol-5-yl-2-benzoyloxy-propane 
• 52287-50-0 benzo[d][1,3]dioxol-5-yltrimethylsilane 
• 274-09-9 Methylenedioxybenzene 
• 379229-83-1 5-chloro-1,3-benzodioxole-4-carboxylic acid 
• 24382-05-6 3,4-methylenedioxybiphenyl 
• 89346-90-7 4'-methoxy-3,4-(methylenedioxy-)biphenyl 
• 94-59-7 1-allyl-3,4-methylenedioxybenzene 
• 379228-45-2 5-chlorobenzo[d][1,3]dioxolcyclopenten-4-amine 
• 379229-84-2 tert-butyl (5-chloro-1,3-benzodioxol-4-yl)carbamate 
• 954367-93-2 3,4-methylenedioxy-2',3',5',6'-tetramethyl-biphenyl 
• 4421-09-4 piperonylonitrile 
• 2620-44-2 5-nitro-1,3-benzodioxole 
• 14268-66-7 benzo[1,3]dioxolo-5-ylamine 

Relevant academic research and scientific papers

Visible-light photocatalytic activation of N-chlorosuccinimide by organic dyes for the chlorination of arenes and heteroarenes

A variety of arenes and heteroarenes are chlorinated in moderate to excellent yields using N-chlorosuccinimide (NCS) under visible-light activated conditions. A screening of known organic dye photocatalysts resulted in the identification of methylene green as the most efficient catalyst to use with NCS. According to mechanistic studies described within, the reaction is speculated to proceed via a single electron oxidation of NCS utilizing methylene green under visible-light photoredox pathway. The photo-oxidation of NCS amplifies the electrophilicity of the chlorine atom of the NCS, thus leading to enhanced reactivity as a chlorinating reagent with aromatic substrates.

Amplification of Trichloroisocyanuric Acid (TCCA) Reactivity for Chlorination of Arenes and Heteroarenes via Catalytic Organic Dye Activation

Heteroarenes and arenes that contain electron-withdrawing groups are chlorinated in good to excellent yields (scalable to gram scale) using trichloroisocyanuric acid (TCCA) and catalytic Brilliant Green (BG). Visible-light activation of BG serves to amplify the electrophilic nature of TCCA, providing a mild alternative approach to acid-promoted chlorination of deactivated (hetero)aromatic substrates. The utility of the TCCA/BG system is demonstrated through comparison to other chlorinating reagents and by the chlorination of pharmaceuticals including caffeine, lidocaine, and phenazone.

Synthesis of important intermediate of berberine

The invention discloses synthesis of an important intermediate of berberine. A synthesis method comprises the following steps: reacting 1,3-benzodioxole with chlorine in an organic solvent to produce5-chloro-1,3-benzodioxole; reacting 5-chloro-1,3-benzodioxole with a magnesium rod in an ether solvent to produce a Grignard reagent; reacting 2,3-dimethoxybenzoic acid with aziridine in an organic solvent under the action of a dehydrating agent to produce 1-aziridine-2,3-dimethoxyphenylethanone; and under the action of the Grignard reagent, subjecting 1-aziridine-2,3-dimethoxyphenylethanone to ring opening so as to obtain the important intermediate of berberine, i.e., N-(2-(benzo[d][1,3]dioxin-5-yl)ethyl)-2,3-dimethoxybenzamide. The synthesis method is mild in reaction conditions and simple to operate.

A highly efficient heterogeneous copper-catalyzed chlorodeboronation of arylboronic acids leading to chlorinated arenes

A highly efficient heterogeneous copper-catalyzed chlorodeboronation of arylboronic acids with inexpensive N-chlorosuccinimide (NCS) was achieved in MeCN in the presence of 10 mol% of l-proline-functionalized MCM-41-immobilized copper(i) complex [MCM-41-l-proline-CuCl] under mild conditions, yielding a variety of aryl chlorides in excellent yields. This method proved to be tolerant of a broad range of functional groups and particularly useful for the conversion of electron-deficient arylboronic acids to aryl chlorides, a transformation that is inefficient without copper catalysis. This heterogeneous copper catalyst can be recovered by a simple filtration of the reaction solution and recycled for at least 10 times without any decreases in activity.

Practical and metal-free electrophilic aromatic halogenation by interhalogen compounds generated in situ from N-halosuccinimide and catalytic TMSCL

Halomonochloride compounds (ClCl, BrCl, ICl) generated in situ from N-halosuccinimide and catalytic chlorotrimethylsilane (TMSCl, 0.1 equiv) can efficiently halogenate aromatic compounds to give halogenated products in good to excellent yields and selectivities. The reaction can be carried out at room temperature or at lower temperatures, requires only one hour, is practical to apply to a wide range of substrates, and provides a simple access to a variety of haloarene compounds. Georg Thieme Verlag Stuttgart New York.

METHOD FOR PRODUCING 4-HALOCATECHOL COMPOUND

Disclosed is a method for producing a 4-halocatechol compound, which is characterized in that a catechol compound is reacted with 1,3-dihalo-5,5-dimethylhydantoin. Also disclosed are a high-purity 4-chloromethylenedioxybenzene which is characterized in that the methylenedioxybenzene content is not more than 0.5% by mass and the 4,5-dichloromethylenedioxybenzene content is not more than 0.5% by mass, and a method for producing such a high-purity 4-chloromethylenedioxybenzene.

Efficient halogenation of aromatic systems using N-halosuccinimides in ionic liquids

A simple, rapid and highly regioselective green protocol has been developed for the halogenation of aromatic systems with N-halosuccinimides using room temperature ionic liquids (ILs) as novel and recyclable reaction media to produce the corresponding halogenated aromatic compounds in high to quantitative yields. N-Halosuccinimides show enhanced reactivity in ionic liquids thereby reducing the reaction times dramatically and improving the yields substantially.

QUINAZOLINE DERIVATIVES FOR USE IN THE TREATMENT OF CANCER

The invention concerns quinazoline derivatives of Formula (I) wherein each of Z, m, R1, n, R3,Z2 and R14 have any of the meanings defined hereinbefore in the description; processes for their preparation, pharmaceutical compositions containing them and their use in the manufacture of a medicament for use as an anti-invasive or anti-proliferative agent in the containment and/or treatment of solid tumour disease.

SUBSTITUTED 3-CYANOQUINOLINES AS MEK INHIBITORS

The invention concerns quinoline derivatives of Formula (I) wherein each of Z1, m, R1, n, R3, Z2 and R14 have any of the meanings defined hereinbefore in the description; processes for their preparation, pharmaceutical compositions containing them and their use in the manufacture of a medicament for use as an anti-invasive or anti-proliferative agent in the containment and/or treatment of solid tumour disease.

A novel and efficient ceric ammonium nitrate catalyzed oxidative nuclear chlorination of activated aromatic compounds by acetyl chloride

A mild and efficient oxidative chlorination of activated aromatic compounds have been achieved in excellent yields using acetyl chloride in the presence of a catalytic amount of ceric ammonium nitrate at room temperature. However, chlorination failed to occur with deactivated aromatic rings.