144584-66-7

Basic information

• Product Name: 4-Bromo-2,2-difluoro-1,3-benzodioxole
• Synonyms: 4-BROMO-2,2-DIFLUORO-1,3-BENZODIOXOLE;4-BROMO-2,2-DIFLUORO-BENZO(1,3)-DIOXOLE;5-BROMO-2,2-DIFLUORO-BENZO[1,3]DIOXOLE;1-Bromo-2,3-[(difluoromethylene)dioxy]benzene~2,3-[(Difluoromethylene)dioxy]bromobenzene;4-Bromo-2,2-difluoro-1,3-benzodioxole, 97+%;1-bromo-2,3-[(difluoromethylene)dioxy]benzene;2,3-[(difluoromethylene)dioxy]bromobenzene;4-Bromo-2,2-difluoro-1,3-benzodioxole 98%
• CAS NO: 144584-66-7
• Molecular Formula: C₇H₃BrF₂O₂
• Molecular Weight: 237
• Product Categories: Aromatic Halides (substituted)
• Mol File: 144584-66-7.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 190.3 °C at 760 mmHg
• Flash Point: 90℃
• Appearance: /
• Density: 1.721 g/mL at 25 °C
• Vapor Pressure: 0.754mmHg at 25°C
• Refractive Index: 1.4968
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: 4-Bromo-2,2-difluoro-1,3-benzodioxole(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Bromo-2,2-difluoro-1,3-benzodioxole(144584-66-7)
• EPA Substance Registry System: 4-Bromo-2,2-difluoro-1,3-benzodioxole(144584-66-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 1
• HazardClass: IRRITANT
• Hazardous Substances Data: 144584-66-7(Hazardous Substances Data)

Usage

Uses

4-Bromo-2,2-difluoro-1,3-benzodioxole is used as a pharmaceutical intermediate.

InChI:InChI=1/C7H3BrF2O2/c8-4-2-1-3-5-6(4)12-7(9,10)11-5/h1-3H

Upstream product

• 1583-59-1 2,2-difluoro-1,3-benzodioxole 

Downstream Products

• 125941-12-0 4-(2,2-difluoro-1,3-benzodioxolyl)lithium 
• 64115-88-4 1-bromo-2-(trifluoromethoxy)benzene 
• 1092476-50-0 (+/-)-N'-[3,5-bis(trifluoromethyl)phenyl]-2-(2,2-difluoro-1,3-benzodioxol-4-yl)-2-(4-methyl-1-piperazinyl)acetohydrazide 
• 1259026-52-2 4-(2,2-difluorobenzo[d][1,3]dioxol-4-yl)-2-nitroaniline 
• 126120-87-4 (2,2-difluorobenzo[d][1,3]dioxol-4-yl)boronic acid 
• 531508-58-4 3-(2,2-difluoro-1,3-benzodioxol-4-yl)propyl benzenesulfonate 

Relevant articles and documents

A homologous series of O- and N-functionalized 2,2-difluoro-1,3-benzodioxoles: An exercise in organometallic methodology

The conversion of 2,2-difluoro-1,3-benzodioxole, an exceptionally acidic arene, via a 4-lithiated intermediate into more than three dozen new derivatives was conceived as a case study. The lithiated species was trapped by C0-electrophiles (4-toluenesulfonyl azide, fluorodimethoxyborane, iodine), C1-electrophiles (carbon dioxide, N,N-dimethylformamide, formaldehyde, dimethyl sulfate), C2-electrophiles (oxalic acid diesters, oxirane), C3-electrophiles (oxetane), and higher alkyl iodides. The resulting carboxylic acid 1a may be treated with organolithium compounds to afford ketones (e.g. 10) and the aldehyde 9 can be condensed with nitromethane or acetic anhydride under basic conditions. If not oxidized with chromium trioxide to the corresponding carboxylic acids, the alcohols 2b, 2c, and 2d can be transformed into the corresponding bromides (12) or sulfonates (13). Their condensation with nitrogen-containing C0-nucleophiles (hydroxylamine, sodium azide, potassium phthalimide), C1-nucleophiles (potassium cyanide), and C2-nucleophiles (aceto-nitrile) opens a convenient access to the amines 3. Other reactions gave, despite a proven track record in other areas, only moderate yields. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

Derivatives of 2,2-dihalogenobenzo[1,3]dioxoles substituted in the 4-position, processes for their preparation and their use

New 2,2-dihalogeno-benzo[1,3]dioxoles substituted in the 4-position, of the general formula (I) STR1 in which R represents fluorine, chlorine, bromine or nitro and Hal represents chlorine or fluorine, and their use as starting substances for the synthesis of highly active compounds, for example in the field of plant protection and pharmaceuticals. The compounds of the formula (I) can be prepared by analogous processes, for example by chlorination from corresponding benzo[1,3]dioxoles substituted in the 4-position, and these substances according to the invention can be further reacted with hydrogen fluoride to give substances to which the invention likewise relates.