7228-38-8

Basic information

• Product Name: 5-CHLORO-1,3-BENZODIOXOLE
• Synonyms: 3,4-METHYLENEDIOXYCHLOROBENZENE;1-CHLORO-3,4-METHYLENEDIOXYBENEZENE;1-CHLORO-3,4-METHYLENEDIOXYBENZENE;5-CHLOR-1,2-(METHYLENEDIOXY)BENZENE;5-CHLORO-1,3-BENZODIOXOLE;5-Chloro-benzo-1,3-dioxole;3-BENZODIOOXOLE;5-CHLORO-1
• CAS NO: 7228-38-8
• Molecular Formula: C₇H₅ClO₂
• Molecular Weight: 156.57
• Product Categories: Chlorine Compounds;Miscellaneous Compounds;Organic Building Blocks;Oxygen Compounds;Protected Alcohols/Phenols
• Mol File: 7228-38-8.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 185-187 °C(lit.)
• Flash Point: 201 °F
• Appearance: liquid
• Density: 1.34 g/mL at 25 °C(lit.)
• Vapor Pressure: 3.28E-10mmHg at 25°C
• Refractive Index: n20/D 1.556(lit.)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 5-CHLORO-1,3-BENZODIOXOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-CHLORO-1,3-BENZODIOXOLE(7228-38-8)
• EPA Substance Registry System: 5-CHLORO-1,3-BENZODIOXOLE(7228-38-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 7228-38-8(Hazardous Substances Data)

Usage

General Description

5-Chloro-1,3-benzodioxole was converted into a safrole derivative via one-pot process involving two consecutive irradiations.

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

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

Downstream Products

• 68756-52-5 2-benzo[1,3]dioxol-5-yl-2-benzoyloxy-propane 
• 24382-05-6 3,4-methylenedioxybiphenyl 
• 89346-90-7 4'-methoxy-3,4-(methylenedioxy-)biphenyl 
• 94-59-7 1-allyl-3,4-methylenedioxybenzene 
• 4421-09-4 piperonylonitrile 
• 126266-78-2 1-(benzo[d][1,3]dioxol-5-yl)-3-phenylpropan-1-one 
• 1266672-49-4 3-(5-chloro-1,3-benzodioxol-2-yl)cyclohexanone 
• 2620-50-0 1,3-benzodioxol-5-ylmethyl amine 
• 432009-40-0 C₁₆H₁₃NO₅ 
• 1393651-46-1 1-(2-(benzo[d][1,3]dioxol-5-yl)-4-methoxyphenyl)ethanone 
• 14268-66-7 benzo[1,3]dioxolo-5-ylamine 
• 190728-30-4 benzo[d][1,3]dioxol-5-yl(4-methoxyphenyl)methanone 
• 81329-90-0 4-(2,hydroxyethyl)amino-1,2-methylenedioxybenzene 
• 1346136-93-3 5-(2',4',6'-trimethylphenyl)-1,3-benzodioxole 

Relevant articles and documents

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.

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.

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.