260352-79-2

Basic information

• Product Name: N-BUTYL 2,2-DIFLUOROCYCLOPROPANECARBOXYLATE
• Synonyms: N-BUTYL 2,2-DIFLUOROCYCLOPROPANECARBOXYLATE;1-BUTYL 2,2-DIFLUOROCYCLOPROPANECARBOXYLATE;Butyl 2,2-difluorocyclopropanecarboxylate;tert-butyl 2,2-difluorocyclopropanecarboxylate;2,2-Difluorocyclopropanecarboxylic acid butyl ester
• CAS NO: 260352-79-2
• Molecular Formula: C₈H₁₂F₂O₂
• Molecular Weight: 178.18
• Mol File: 260352-79-2.mol

Chemical Properties

• Boiling Point: 175.2 °C at 760 mmHg
• Flash Point: 58.6 °C
• Appearance: /
• Density: 1.13 g/cm³
• Storage Temp.: 2-8°C
• CAS DataBase Reference: N-BUTYL 2,2-DIFLUOROCYCLOPROPANECARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: N-BUTYL 2,2-DIFLUOROCYCLOPROPANECARBOXYLATE(260352-79-2)
• EPA Substance Registry System: N-BUTYL 2,2-DIFLUOROCYCLOPROPANECARBOXYLATE(260352-79-2)

Safety Data

• Hazardous Substances Data: 260352-79-2(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
N-BUTYL 2,2-DIFLUOROCYCLOPROPANECARBOXYLATE is used as a reagent in organic synthesis for its ability to facilitate various chemical reactions, contributing to the formation of complex organic molecules.
Used in Pharmaceutical Production:
In the pharmaceutical industry, N-BUTYL 2,2-DIFLUOROCYCLOPROPANECARBOXYLATE serves as an intermediate in the production of various drugs. Its role is crucial in the synthesis of active pharmaceutical ingredients, enhancing the development of new medications.
Used in Agrochemical Production:
N-BUTYL 2,2-DIFLUOROCYCLOPROPANECARBOXYLATE is also utilized as an intermediate in the creation of agrochemicals, playing a part in the synthesis of compounds that contribute to crop protection and enhancement of agricultural yields.
Used in the Synthesis of Fluorinated Compounds:
As a potential building block for fluorinated compounds, N-BUTYL 2,2-DIFLUOROCYCLOPROPANECARBOXYLATE is instrumental in the development of new chemical products that incorporate fluorine atoms, which can significantly alter the chemical properties and reactivity of the resulting compounds.

Upstream product

• 111-66-0 oct-1-ene 
• 141-32-2 acrylic acid n-butyl ester 
• 757203-27-3 triethylsilyl fluorosulfonyldifluoroacetate 
• 120801-75-4 trimethylsilyl-2,2-difluoro-2-(fluorosulphonyl)acetate 
• 680-15-9 2,2-difluoro-2-(fluorosulfonyl)acetate 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 87189-16-0 potassium 2-bromo-2,2-difluoroacetate 
• 667-27-6 Ethyl bromodifluoroacetate 

Downstream Products

• 1186609-06-2 3-(2,2-difluorocyclopropyl)-3-oxopropanenitrile 
• 107873-03-0 2,2-difluorocyclopropane-1-carboxylic acid 

Relevant articles and documents

Difluorocarbene transfer from a cobalt complex to an electron-deficient alkene

We report the synthesis of the trifluoromethyl cobalt(iii)tetraphenylporphyrinato complex [Co(TPP)CF3], which loses fluoride upon one-electron reduction and transfers a difluorocarbene moiety to n-butyl acrylate to produce the corresponding gem-difluorocyclopropane. Catalytic CF2 transfer from Me3SiCF3 to n-butyl acrylate becomes possible when directly using the divalent cobalt(ii) porphyrin catalysts in the presence of NaI.

PREPARATION OF A PYRIMIDINYL-3,8-DIAZABICYCLO[3.2.1]OCTANYLMETHANONE DERIVATIVE AND SALT THEREOF

Methods for preparing ((S)-2,2-difluorocyclopropyl)-((1R,5S)-3-(2-((1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)-3,8-diazabicyclo[3.2.1]-octan-8-yl)methanone and intermediates used in the processes of preparation thereof.

Large-Scale Cyclopropanation of Butyl Acrylate with Difluorocarbene and Classical Resolution of a Key Fluorinated Building Block

To address challenges in the preparation of a key building block containing a difluorocyclopropane moiety, we have developed a new protocol for difluorocarbene generation that relies on a Krapcho-type dealkylation of ethyl bromodifluoroacetate (EBDFA), an inexpensive and readily available fluorinated feedstock. Application of DoE and kinetic modeling was used to understand key reaction parameters and identify an optimal process. We report two variants of this procedure that offer different processing advantages and that have both been scaled successfully multiple times to deliver hundreds of kilograms of the resulting difluorocyclopropane. To access a single enantiomer of the target compound, we have also developed a classical resolution strategy and recycling protocol for the undesired enantiomer to replace previous chromatographic methods for separation.

Transition Metal-free gem-difluorocyclopropanation of Alkenes with CF3SiMe3?NaI System: a Recipe for Electron-deficient Substrates

Reaction of various electron-deficient alkenes, as well as functionalized styrene derivatives with CF3SiMe3?NaI system is studied. Relative reactivity of the substrates is established. It is shown that many α,β-unsaturated esters can

PYRIMIDINE AND TRIAZINE DERIVATIVES AND THEIR USE AS AXL INHIBITORS

Compounds of the general formula(I): (I) processes for the preparation of these compounds, compositions containing these compounds, and the uses of these compounds.

Methyl 2,2-difluoro-2-(fluorosulfonyl)acetate, a difluorocarbene reagent with reactivity comparable to that of trimethylsilyl 2,2-difluoro-2- (fluorosulfonyl)acetate (TFDA)

Under specific high concentration, high temperature conditions, methyl 2,2-difluoro-2-(fluorosulfonyl)acetate (MDFA) has been found to act as a very efficient source of difluorocarbene, exhibiting carbene reactivity characteristics comparable to those exhibited by trimethylsilyl 2,2-difluoro-2-(fluorosulfonyl)acetate (TFDA). For example, in reaction with highly unreactive n-butyl acrylate and using only 2 equiv of MDFA, a yield of 76% of difluorocyclopropane product was obtained after 2 days.

Competitive kinetic processes in the thermal rearrangement of 1,1-difluoro-2-(dideuteriomethylene)-cyclopropane

The synthesis of 1,1-difluoro-2-(dideuteriomethylene)-cyclopropane is reported along with the kinetics of its competing, reversible, first order rearrangements: (a) the degenerate rearrangement to 1,1-difluoro-3,3-dideuterio- 2-methylene-cyclopropane, and

Trimethylsilyl fluorosulfonyldifluoroacetate (TFDA): A new, highly efficient difluorocarbene reagent

TFDA is readily prepared from the reaction of fluorosulfonyldifluoroacetic acid with trimethylsilyl chloride, and it is a very effective and efficient source of difluorocarbene for use in addition reactions to alkenes of a broad scope of reactivities. Acid-sensitive substrates may require an additional purification step involving treatment of the distilled TFDA with sufficient Et3N to remove the acid impurity. Other trialkylsilyl fluorosulfonyldifluoroacetates can also be prepared, and they have been found to have reactivities similar to TFDA. The triethyl derivative, TEFDA is more convenient to prepare in a pure state and has similar reactivity to TFDA. Thus, it may prove to be a superior reagent.

A novel and highly efficient synthesis of gem-difluorocyclopropanes

(Formula presented) A new and highly versatile source of difluorocarbene is reported. Trimethylsilyl fluorosulfonyldifluoroacetate (TFDA) undergoes decomposition in the presence of catalytic fluoride to form difluorocarbene under conditions that allow its addition to relatively electron deficient alkenes in high yield. For example, unprecedented CF2: addition to n-butyl acrylate proceeded in 73percent yield.