334-56-5

Basic information

• Product Name: 1-FLUORODECANE
• Synonyms: 1-FLUORODECANE;N-DECYL FLUORIDE;1-fluoro-decan;Decyl fluoride;decylfluoride;1-Fluorodecane98%;Decyl fluoride 98%
• CAS NO: 334-56-5
• Molecular Formula: C₁₀H₂₁F
• Molecular Weight: 160.27
• EINECS: 206-380-6
• Product Categories: Alkyl;Building Blocks;Chemical Synthesis;Halogenated Hydrocarbons;Organic Building Blocks
• Mol File: 334-56-5.mol

Chemical Properties

• Melting Point: -35°C
• Boiling Point: 185-187 °C(lit.)
• Flash Point: 175 °F
• Appearance: /
• Density: 0.809 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.927mmHg at 25°C
• Refractive Index: n20/D 1.409(lit.)
• CAS DataBase Reference: 1-FLUORODECANE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-FLUORODECANE(334-56-5)
• EPA Substance Registry System: 1-FLUORODECANE(334-56-5)

Safety Data

• Hazard Codes: T+,N,F
• Statements: 28-50/53
• Safety Statements: 28-36/37-45-60-61
• RIDADR: UN 2810 6.1/PG 1
• WGK Germany: 3
• RTECS: HD8575000
• Hazardous Substances Data: 334-56-5(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Canadian Journal of Chemistry, 43, p. 3173, 1965 DOI: 10.1139/v65-442

InChI:InChI=1/C10H21F/c1-2-3-4-5-6-7-8-9-10-11/h2-10H2,1H3

Upstream product

• 2050-77-3 Iododecane 
• 20157-33-9 n-decylmagnesium chloride 
• 112-30-1 1-Decanol 
• 90238-20-3 N,N-diethyl-α,α-difluorobenzylamine 
• 110-53-2 1-Bromopentane 
• 5509-08-0 decyl p-toluenesulfonate 
• 112-29-8 1-bromo dodecane 
• 1002-69-3 decyl chloride 
• 4665-35-4 2-decyl-1,1-diphenyl-isourea; hydrofluoride 
• 41233-29-8 methanesulfonic acid decyl ester 

Downstream Products

• 25727-94-0 4-decylmorpholine 
• 30189-87-8 N-decyl-N-methylaniline 
• 4537-13-7 2-phenyldecane 
• 104-72-3 decylbenzene 
• 4537-11-5 (1-butylhexyl)benzene 
• 1198605-32-1 [HPMes₃][B(C₆F₅)4] 
• 4621-36-7 (1-ethyloctyl)benzene 
• 4537-12-6 1-propylheptylbenzene 
• 64154-08-1 2-iododecane 
• 2050-77-3 Iododecane 
• 768-93-4 1-iodoadamantane 
• 124-18-5 decane 
• 111-65-9 octane 
• 111-84-2 nonane 

Relevant articles and documents

DARSTELLUNG VON PRIMAEREN ALKYLFLUORIDEN UNTER EINSATZ DER PHASEN TRANSFER KATALYSE

The influence of the following factors on the solid-liquid PTC fluorination reaction of primary alkyl halides was studied: the catalyst quantity applied, the water content of solid alkali fluoride salt, and the type of catalyst.Kinetic curves at different temperatures were found for the reaction.The maximum yield is a function of the interaction of two parallel running reactions, namely the direct fluorination reaction and the catalyst decomposition.

Efficient protocol for the SO2F2-mediated deoxyfluorination of aliphatic alcohols

Alkyl fluorides are prevalent in both the pharmaceutical and agrochemical industries. As such, there has been significant interest over the past 40 years in the development of new synthetic methods to access these important fluorinated motifs. Herein we report the sulfuryl fluoride-mediated deoxyfluorination of alcohols using room temperature reaction conditions in only an hour. A wide range of primary aliphatic alcohols were efficiently converted to the corresponding fluoride in 46-70% isolated yields. Secondary alcohols were also effectively deoxyfluorinated in 50–92% yields. Chiral secondary alcohols were cleanly converted to the corresponding alkyl fluoride with only a minor deterioration of the enantioenrichment. A steroid derivative also underwent deoxyfluorination in 50% yield and 5.9:1 dr, with the major product resulting from net inversion of the stereocenter.

Stereospecific Electrophilic Fluorination of Alkylcarbastannatrane Reagents

We report the use of isolable primary and secondary alkylcarbastannatrane nucleophiles in site-specific fluorination reactions. These reactions occur without the need for transition metal catalysis or in situ activation of the nucleophile. In the absence of the carbastannatrane backbone, alkyltin nucleophiles exhibit no activity towards fluorination. When enantioenriched alkylcarbastannatranes are employed, fluorination occurs predominately via a stereoinvertive mechanism to generate highly enantioenriched alkyl fluoride compounds. These conditions can also be extended to stereospecific chlorination, bromination, and iodination reactions.

Synthesis, Characterization, and Reactivity of Thermally Stable Anhydrous Quaternary Ammonium Fluorides

The synthesis and properties of a new class of anhydrous quaternary ammonium fluorides, based on the rigid skeleton azabicyclo[2.2.2]octane, is described. Compounds 2a-d were easily prepared by passing the corresponding ammonium iodides over fluoride-based resin followed by drying their hydrated form at 100 or 140 °C under reduced pressure. The stability (experimental and theoretical study), solubility, reactivity, and characterization by solution and solid-state MAS NMR are discussed.

Selective mono-acylation of 1,2- and 1,3-diols using (α,α- difluoroalkyl)amines

In the reaction of N,N-diethyl-α,α-difluorobenzylamine (DFBA) with 1,2- or 1,3-diols, selective mono-benzoylation occurs to afford mono-esters of the diols in good yield. The reaction is completed under mild conditions in a short reaction time. Further, prim-, sec-, and tert-diols and catechol can be converted to the corresponding mono-benzoates. DFBA is used for the protection of the hydroxy group in sugars. The selective mono-nicotinylation, formylation and pivaloylation of diols are also performed by using the corresponding difluoroalkylamines.

Preparation of Mono-/Difluorinated Hydrocarbon Compounds

Mono- or difluorinated hydrocarbon compounds are prepared from an alcohol or a carbonylated compound by reacting one of these with a fluorinating reagent, optionally in the presence of a base, the fluorinating agent comprising a pyridinium reactant having the following formula (F), wherein R0 is an alkyl or cycloalkyl radical:

DEHYDROXYLATED FLUORINATING AGENT

There is provided a novel, useful dehydroxyfluorination agent containing sulfuryl fluoride (SO2F2) and an organic base that is free from a free hydroxyl group in the molecule. According to the present dehydroxyfluorination agent, it is not necessary to use perfluoroalkanesulfonyl fluoride, which is not preferable in large-scale use, and it is possible to advantageously produce optically-active fluoro derivatives, which are important intermediates of medicines, agricultural chemicals and optical materials, for example, 4-fluoroproline derivatives, 2'-deoxy-2'-fluorouridine derivatives, optically-active α-fluorocarboxylate derivatives, and monofluoromethyl derivatives, even in large scale.

PROCESS FOR PRODUCTION OF FLUORO DERIVATIVE

A fluoro derivative can be produced by reacting a hydroxy derivative with sulfuryl fluoride (SO2F2) in the presence of an organic base or in the presence of an organic base and a salt or complex composed of an organic base and hydrogen fluoride. This process enables to advantageously produce an optically active fluoro derivative (e.g., a 4-fluoroproline derivative, a 2'-deoxy-2'-fluorouridine derivative and an optically active α-fluorocarboxylate ester derivative) which is an important intermediate for the production of a pharmaceutical or agricultural agent or an optical material, even in large quantity without using a perfluoroalkanesulfonyl fluoride which is undesirable for industrial applications.

Fluorination of carbinols with 2,2-difluoro-1,3-dimethylimidazolidine in ionic liquid

The utility of ionic liquids for fluorination using 2,2-difluoro-1,3-dimethylimidazolidine (DFI) is described. Further, the fluorination of chiral epoxyalcohols gave the chiral monofluoromethylated epoxides.

Process for the production of fluorinated organic compounds and fluorinating agents

A process for the production of a fluorinated organic compound, characterized by fluorinating an organic compound having a hydrogen atoms using IF5; and a novel fluorination process for fluorinating an organic compound having a hydrogen atoms by using a fluorinating agent containing IF5 and at least one member selected from the group consisting of acids, bases, salts and additives.