157437-25-7

Basic information

• Product Name: 4-Hydroxymethyl-2,2-diflu...
• Synonyms: 4-Hydroxymethyl-2,2-diflu...;4-HydroxyMethyl-2,2-difluoro-1,3-benzodioxole;(2,2-difluorobenzo[d][1,3]dioxol-4-yl)Methanol;(2,2-difluoro-2H-1,3-benzodioxol-4-yl)methanol;(2,2-Difluoro-1,3-benzodioxol-4-yl)methanol;(2,2-Difluorobenzo[d][1,3]dioxol-4-yl)
• CAS NO: 157437-25-7
• Molecular Formula: C₈H₆F₂O₃
• Molecular Weight: 188.13
• Mol File: 157437-25-7.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 234.0±40.0 °C(Predicted)
• Appearance: /
• Density: 1.51±0.1 g/cm3(Predicted)
• PKA: 14.24±0.10(Predicted)
• CAS DataBase Reference: 4-Hydroxymethyl-2,2-diflu...(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Hydroxymethyl-2,2-diflu...(157437-25-7)
• EPA Substance Registry System: 4-Hydroxymethyl-2,2-diflu...(157437-25-7)

Safety Data

• RIDADR: UN2811
• Hazardous Substances Data: 157437-25-7(Hazardous Substances Data)

Usage

General Description

4-Hydroxymethyl-2,2-difluoro-1,3-benzodioxole (HDFBD) is a chemical compound used primarily as a building block in the synthesis of pharmaceutical drugs and agrochemicals. It is a bifunctional molecule containing a hydroxyl group and a difluoromethylene group, making it valuable for creating molecules with specific biological activities. HDFBD is commonly used in the development of potential drug candidates and crop protection products due to its versatile reactivity and potential to modify the bioavailability and toxicity of active compounds. It is also utilized in the study of chemical reactions and structure-activity relationships in medicinal chemistry and agrochemical research.

Upstream product

• 1583-59-1 2,2-difluoro-1,3-benzodioxole 
• 119895-68-0 2,2-difluoro-1,3-benzodioxol-4-yl-carbaldehyde 
• 50-00-0 formaldehyd 

Downstream Products

• 531508-56-2 (2,2-difluoro-1,3-benzodioxol-4-yl)methyl benzenesulfonate 
• 157437-24-6 (2,2-difluoro-1,3-benzodioxol-4-yl)acetonitrile 

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.