62781-99-1

Basic information

• Product Name: cyclopentyl formate
• Synonyms: cyclopentanol, formate; Cyclopentyl formate
• CAS NO: 62781-99-1
• Molecular Formula: C₆H₁₀O₂
• Molecular Weight: 114.1424
• Mol File: 62781-99-1.mol

Chemical Properties

• Boiling Point: 140.7°C at 760 mmHg
• Flash Point: 38.8°C
• Density: 1g/cm³
• Vapor Pressure: 6.07mmHg at 25°C
• Refractive Index: 1.439
• CAS DataBase Reference: cyclopentyl formate(CAS DataBase Reference)
• NIST Chemistry Reference: cyclopentyl formate(62781-99-1)
• EPA Substance Registry System: cyclopentyl formate(62781-99-1)

Safety Data

• Hazardous Substances Data: 62781-99-1(Hazardous Substances Data)

Upstream product

• 64-18-6 formic acid 
• 96-41-3 Cyclopentanol 
• 63064-31-3 4-methylphenyl sulfonic acid (2-cyclopropylethyl) ester 
• 872-53-7 cyclopentanealdehyde 
• 20452-67-9 phenylethylketene 
• 137-43-9 Cyclopentyl bromide 
• 930-68-7 cyclohexenone 
• 614-45-9 tert-Butyl peroxybenzoate 
• 109-94-4 formic acid ethyl ester 
• 150760-95-5 formic acid cyanomethyl ester 
• 142-29-0 cyclopentene 

Downstream Products

• 21777-87-7 2-cyclopentylethynyl benzene 
• 96-41-3 Cyclopentanol 

Relevant articles and documents

Group-Transfer Reactions of a Cationic Iridium Alkoxycarbene Generated by Ether Dehydrogenation

Despite broad interest in metal carbene complexes, there remain few examples of catalytic transformations of ethers that proceed via alkoxycarbene intermediates generated by α,α-dehydrogenation. We demonstrate that both neutral and cationic alkoxycarbene derivatives are accessible via ether dehydrogenation at a PNP(iPr)4 pincer-supported iridium complex (PNP(iPr)4 = 2,6-bis((diisopropylphosphino)methyl)pyridine). Both cationic and neutral alkoxycarbene complexes undergo group transfer imination with azides, with the cationic derivative serving as a more efficient catalyst for cyclopentyl ether imination. Mechanistic studies support an iridium(I)dinitrogen complex as the resting state in the dark and a role for light-promoted N2 dissociation. Isoamyl nitrite and phenyl ethyl ketene are also found to engage with the cationic alkoxycarbene complex in formal alkoxide and O atom transfer reactions, respectively. In the former case an isolable dialkoxyalkyliridium complex is obtained, representing only the second example of a structurally characterized dialkoxyalkyl complex of a transition metal.

ACETOLYSIS AND FORMOLYSIS OF (R)- AND (S)-1-DEUTERIO-2-CYCLOPROPYLETHYL p-TOLUENESULFONATES

Acetolysis and formolysis of the enantiomers of 1-deuterio-2-cyclopropylethyl tosylate, 3-OTs and 4-OTs, led to 17-18percent retention (cyclopropyl participation) and 82-83percent inversion (nucleophilic solvent assistance) of configuration in the 2-cyclopropylethyl product.

Enabling the Use of Alkyl Thianthrenium Salts in Cross-Coupling Reactions by Copper Catalysis

Alkyl groups are one of the most widely used groups in organic synthesis. Here, a a series of thianthrenium salts have been synthesized that act as reliable alkylation reagents and readily engage in copper-catalyzed Sonogashira reactions to build C(sp3)?C(sp) bonds under mild photochemical conditions. Diverse alkyl thianthrenium salts, including methyl and disubstituted thianthrenium salts, are employed with great functional breadth, since sensitive Cl, Br, and I atoms, which are poorly tolerated in conventional approaches, are compatible. The generality of the developed alkyl reagents has also been demonstrated in copper-catalyzed Kumada reactions.

Consecutive addition esterification and hydrolysis of cyclic olefins catalyzed by multi-SO3H functionalized multi heteropolyanion-based ionic hybrids undersolvent-free conditions

An efficient protocol for the synthesis of cycloalkyl carboxylates and alcohols from cyclic olefins is described. The cyclic olefins were converted to corresponding target molecules under solvent-free conditions catalyzed by two novel multi-SO3H functionalized multi heteropolyanion-based ionic hybrids through one-pot consecutive addition esterification and hydrolysis reactions. This approach has several advantages, including high yield, simple workup and simple purification.

Method for preparing formate-type compound

The invention discloses a method for preparing a formate-type compound. The method comprises the following steps of: adopting an alcohol-type compound and 1,3-dihydroxyacetone as reaction raw materials, and under the existence of a composite catalyst and an oxidant, reacting for 2-48 hours in a reaction medium in a reactor at a reaction temperature of 25-100 DEG C so as to obtain the formate-typecompound. The method disclosed by the invention is simple, and is mild in reaction condition, and by the method, a target product can be obtained by low cost and high yield; the used catalyst has highcatalytic activity, and is easily separated from a reaction system to be repeatedly used; the whole process is environment-friendly, and the reaction raw material (1,3-dihydroxyacetone) is easily converted from a side product (glycerol) of biodiesel, so that the utilization of the glycerol is promoted.

Method of using swelling-able acidic poly(ionic liquid) to catalyze esterification between formic acid and alkenes to prepare formate

The invention discloses a method of using swelling-able acidic poly(ionic liquid) to catalyze esterification between formic acid and alkenes to prepare formate. According to the method, an acidic poly(ionic liquid) that can swell in formic acid is synthesized at first; 1-vinyl-3-alkyl imidazolium bromine salt ionic liquid and sodium acrylate are taken as the copolymerization monomers, and throughfree radical polymerization and acidification that uses an acid with an equal molar weight, the poly(ionic liquid) is prepared. The poly(ionic liquid) is taken as a catalyst to catalyze the esterification reactions between formic acid and alkenes; the catalytic activity of the poly(ionic liquid) is equal to that of a homogeneous catalyst and the selectivity is higher than that of a homogeneous catalyst or a heterogeneous catalyst. The swelling-able acidic poly(ionic liquid) is used to catalyze the esterification reactions between formic acid and alkenes, the characteristic that the poly(ionicliquid) can swell in formic acid is utilized, the poly(ionic liquid) is fully dispersed in the substrate, at the same time, the active centers of the acid are immobilized on the poly(ionic liquid), thus the active centers can fully contact with the substrate, and the catalytic efficiency is largely improved.

Hypervalent λ3-bromane strategy for Baeyer-Villiger oxidation: Selective transformation of primary aliphatic and aromatic aldehydes to formates, which is missing in the classical Baeyer-Villiger oxidation

A conceptually distinct, modern strategy for Baeyer-Villiger oxidation (BVO) was developed. Our novel method involves initial hydration of water to carbonyl compounds, followed by ligand exchange of hypervalent aryl-λ3-bromane on bromane(III) with the resulting hydrate, yielding a new type of activated Criegee intermediate. The intermediate undergoes BV rearrangement and produces an ester via facile reductive elimination of an aryl-λ3-bromanyl group, because of the hypernucleofugality. The novel strategy makes it possible to induce selectively the BV rearrangement of straight chain primary aliphatic as well as aromatic aldehydes, which is missing in the classical BVO: for instance, octanal and benzaldehyde afforded rearranged formate esters with high selectivity (>95%) under our conditions, while the attempted classical BVO produced only carboxylic acids. This firmly establishes the powerful nature of new methodology for BVO.

Dual behavior of alcohols in iodine-catalyzed esterification under solvent-free reaction conditions

The dual behavior phenomenon of alcohols in iodine-catalyzed esterification under solvent-free reaction conditions (SFRCs) is described; the governing factor is the stability of the carbonium ion generated from the alcohol; high concentration reaction conditions (HCRCs) or dilute solutions are much less suitable. In the case of benzylic alcohols, loss of optical activity was noted, whereas alkyl alcohols furnished a product with retention of stereochemistry.

Compounds, Compositions and methods for insect control

Rapidly acting compositions having vapor phase insecticidal activity comprise natural products or natural product-based materials. Further, these materials are non-petroleum based, are typically 100% biodegradable, and typically do not persist in the environment, unlike traditional pesticides. The compositions kill susceptible insects on contact in seconds, even the notoriously hardy peripleneta species. The compositions also kill insects behind cracks and crevices and when sprayed onto absorbent surfaces such as wood and plasterboard, where traditional contact insecticides work poorly or not at all. New methods of testing insecticides can be used to quantify these effects.

Reactions of 5-(alkyl)thianthrenium and other sulfonium salts with nucleophiles

A series of 5-(alkyl)thianthrenium triflates (3a-d, g-i) with alkyl (R) groups Me (a), Et (b), isoPr (c), 2-Bu (d), cyclopentyl (g), cyclohexyl (h) and cycloheptyl (i) were prepared by alkylation of thianthrene (Th) with alkyl formate and trifluoromethanesulfonic (triflic) acid. Benzylation (3f) was achieved with benzyl bromide and silver triflate. 5-(Neopentyl)thianthrenium perchlorate (3e) was prepared by reaction of thianthrene cation radical perchlorate with dineopentyl mercury. Methyl- (4a) and cyclohexyldiphenylsulfonium triflate (4b) were made by alkylation of diphenyl sulfide. Benzyldimethyl- (5a), dibenzylmethyl- (5b) and benzylmethylphenylsulfonium perchlorate (5c) were prepared in standard ways. Reactions of these sulfonium salts with iodide ion and thiophenoxide ion were studied for comparison with our earlier reported reactions of comparable 5-(alkoxy)thianthrenium and methoxydiphenylsulfonium salts. It is deduced that reactions of 3-5 with nucleophiles (Nu-) I- and PhS- follow traditional SN2 and E2C paths. Thus, the salts 3a-c, e and f gave virtually quantitative yields of RNu and Th, while small amounts of butene(s) were obtained from 3d. The cycloalkyl salts 3g-i gave amounts of cycloalkylNu and cycloalkene typical of competition of SN2 and E2C routes in the classical reactions of cycloalkyl halides and tosylates with I- and PhS- ions. Whereas 4a gave only SN2 products, 4b gave SN2 and E2C products typical of SN2/E2C competition. Among the salts 5a-c displacement of the benzyl group was dominant (5a) or exclusive (5b, c), thus exhibiting the preferential displacement of a benzyl group that has been fully documented in earlier studies of SN2 reactions. Qualitative comparison showed that 3a (methyl) reacted much faster than 3e (neopentyl) with PhS-. Unlike alkoxysulfonium salts, the salts 3-5 do not appear to undergo reactions at the sulfonium sulfur atom. Copyright