20074-80-0

Basic information

• Product Name: 5-chloropentanal
• Synonyms: 5-chloropentanal;Pentanal, 5-chloro-;5-Chlorovaleraldehyde
• CAS NO: 20074-80-0
• Molecular Formula: C5H9ClO
• Molecular Weight: 120.5774
• Mol File: 20074-80-0.mol

Chemical Properties

• Boiling Point: 172℃
• Flash Point: 67℃
• Appearance: /
• Density: 1.006
• Vapor Pressure: 1.36mmHg at 25°C
• Refractive Index: 1.419
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• CAS DataBase Reference: 5-chloropentanal(CAS DataBase Reference)
• NIST Chemistry Reference: 5-chloropentanal(20074-80-0)
• EPA Substance Registry System: 5-chloropentanal(20074-80-0)

Safety Data

• Hazardous Substances Data: 20074-80-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-chloropentanal is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to undergo multiple chemical reactions, contributing to the development of new drugs and medicinal compounds.
Used in Agrochemical Industry:
In the agrochemical sector, 5-chloropentanal is utilized as an intermediate in the production of pesticides and other agrochemicals, enhancing the effectiveness of these products in agricultural applications.
Used in Organic Chemistry Research:
5-chloropentanal is employed as a reagent in organic chemistry reactions, facilitating the synthesis of a wide range of chemical products through its versatile transformation capabilities. This makes it an indispensable tool in advancing chemical research and development.

InChI:InChI=1/C5H9ClO/c6-4-2-1-3-5-7/h5H,1-4H2

Upstream product

• 113832-57-8 N-ethylidenecyclohexylamine 
• 109-70-6 1.3-chlorobromopropane 
• 26939-18-4 2,4,4,6-tetramethyl-5,6-dihydro-4H-1,3-oxazine 
• 928-50-7 5-chloropent-1-ene 
• 5259-98-3 5-chloropentan-1-ol 
• 78999-24-3 5-benzyloxy-1-pentanal 
• 20395-28-2 5-chloropentyl acetate 
• 142-68-7 TETRAHYDROPYRANE 
• 14267-92-6 1-chloro-4-pentyne 
• 194920-87-1 5-chloro-2-ethenylpentanoic acid 
• 96-41-3 Cyclopentanol 
• 6280-87-1 δ-chlorovaleronitrile 
• 14273-86-0 methyl 5-chloropentanoate 
• 19141-74-3 5?chloro?1,2?epoxypentane 

Downstream Products

• 98736-98-2 5-chloro-2-(phenylselenenyl)pentanal 
• 3105-95-1 pipecolinic acid 
• 392692-65-8 C₆₃H₉₆BClO₁₁Si 
• 392692-67-0 C₆₂H₉₄Cl₂O₁₂Si₂ 
• 392692-68-1 C₆₃H₉₆Cl₂O₁₁Si₂ 
• 392692-66-9 1-[6-[[4-(tert-butyl-dimethyl-silanyloxy)-6-(4-chloro-butyl)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-(4-methoxy-benzyloxy)-methyl]-3,4-bis-(4-methoxy-benzyloxy)-5-methyl-tetrahydro-pyran-2-yl]-7-chloro-4-hydroxy-octa-5,7-dien-2-one 
• 392692-64-7 1-[(2R,3R,4R,5R,6R)-6-[(S)-[(2R,4S,5S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-(4-chloro-butyl)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-(4-methoxy-benzyloxy)-methyl]-3,4-bis-(4-methoxy-benzyloxy)-5-methyl-tetrahydro-pyran-2-yl]-propan-2-one 
• 392692-62-5 (1S,4S,5R,6R)-10-chloro-4-hydroxy-1-(p-methoxybenzyloxy)-1-[4,5-(R,R)-bis(p-methoxybenzyloxy)-3-(R)-methyl-6-(R)-(2-methylallyl)-tetrahydropyran-2-(R)-yl]-5-methyl-6-(triethylsiloxy)-decan-2-one 
• 862509-67-9 (2R,4S,5R)-9-chloro-5-triethylsiloxy-2-(p-methoxybenzyloxy)-4-methyl-nonan-3-one 
• 1903-22-6 ethyl cyclopentylideneacetate 

Relevant articles and documents

Building polyfunctional piperidines: A stereoselective strategy of a three-component Mannich reaction inspired by biosynthesis and applications in the synthesis of natural alkaloids (+)-241D; (-)-241D; isosolenopsin A and (-)-epimyrtine

A general method to assemble multi-substituted chiral piperidines was developed, inspired by the biosynthesis of piperidine natural products. In biosynthesis, Δ1-piperideine 4 plays a key role as a common intermediate giving rise to a variety of piperidine-based natural alkaloids. Nature uses l-lysine as a building block, enzymatically transforming it into a δ-amino carbonyl intermediate 3 as the precursor to cyclize into Δ1-piperideine 4. We envisioned that such a process could be accomplished by a vinylogous type Mannich reaction if a functionalized dienolate was employed. A stereoselective three-component vinylogous Mannich-type reaction (VMR) of 1,3-bis-trimethylsily enol ether 7 was therefore investigated and was found to give cyclized chiral dihydropyridinone compound 9 as an adduct. Like Δ1-piperideine in biosynthesis, the chiral 2,3-dihydropyridinone compound 9 from VMR is a versatile intermediate for building a variety of new chiral piperidine compounds. The method was showcased by concise two-step approaches in the synthesis of the bioactive natural alkaloids (+)-241D; (-)-241D and isosolenopsin A. Furthermore, when properly functionalized substrate aldehyde 24 was employed, the corresponding dihydropyridinone adduct 25 cyclized to form a second piperidine ring, leading to a chiral polyfunctional quinolizidine enaminone 27. This versatile intermediate was used to prepare a variety of new chiral quinolizidine compounds, including natural alkaloid (-)-epimyrtine.

Palladium/Copper-catalyzed Oxidation of Aliphatic Terminal Alkenes to Aldehydes Assisted by p-Benzoquinone

The development of an anti-Markovnikov Wacker-type oxidation for simple aliphatic alkenes is a significant challenge. Herein, a variety of aldehydes can be selectively obtained from various unbiased aliphatic terminal alkenes using PdCl2(MeCN)2/CuCl in the presence of p-benzoquinone (BQ) under mild reaction conditions. Isomerization of the terminal alkene to the internal alkene was suppressed via slow addition of the starting material to the reaction mixture. In addition to the Pd catalyst, CuCl and BQ were essential in order to obtain the anti-Markovnikov product with high selectivity. Terminal alkenes bearing a halogen substituent afforded their corresponding aldehydes with high anti-Markovnikov selectivity. The halogen acts as a directing group in the reaction. DFT calculations indicate that a μ-chloro Pd(II)?Cu(I) bimetallic species with BQ coordinated to Cu is the catalytically active species in the case of a terminal alkene without a directing group.

A Two-Directional Synthesis of (+)-β-Isosparteine

A two-directional synthesis of (+)-β-isosparteine is described in five steps from glutaric acid, where the entire carbon and nitrogen backbone of the alkaloid, possessing the requisite relative and absolute stereochemistry at its four stereogenic centers, is assembled using a double imino-aldol reaction.

Cascade oxime formation, cyclization to a nitrone, and intermolecular dipolar cycloaddition

Simple haloaldehydes, including enolisable aldehydes, were found to be suitable for the formation of cyclic products by cascade (domino) condensation, cyclisation, dipolar cycloaddition chemistry. This multi-component reaction approach to heterocyclic compounds was explored by using hydroxylamine, a selection of aldehydes, and a selection of activated dipolarophiles. Initial condensation gives intermediate oximes that undergo cyclisation with displacement of halide to give intermediate nitrones; these nitrones undergo in situ intermolecular dipolar cycloaddition reactions to give isoxazolidines. The cycloadducts from using dimethyl fumarate were treated with zinc/acetic acid to give lactam products and this provides an easy way to prepare pyrrolizinones, indolizinones, and pyrrolo[2,1-a]isoquinolinones. The chemistry is illustrated with a very short synthesis of the pyrrolizidine alkaloid macronecine and a formal synthesis of petasinecine.

Bioinspired aerobic oxidation of alcohols with a bifunctional ligand based on bipyridine and TEMPO

A novel bioinspired bifunctional ligand incorporating metal-binding site and stable free radical has been synthesized. The catalytic system obtained from the bifunctional ligand with copper(i) iodide in the presence of N-methylimidazole is highly efficient for the oxidation of a broad range of primary benzylic, allylic, alkynyl, aliphatic alcohols and secondary benzylic alcohols to the corresponding aldehydes and ketones in good to excellent yields. The catalyst system exhibits broad functional-group compatibility. The reaction is carried out in acetonitrile as solvent under air balloon at room temperature. The catalyst system features excellent activity for primary aliphatic alcohol oxidation and a high chemoselective oxidation of primary alcohols over the secondary alcohols. This oxidation process is readily amenable to larger-scale application. The interaction of the different components in the reaction mixtures was studied by UV-visible spectroscopy. The data indicated that Cu(i) existed throughout the reaction. A plausible mechanism of the catalytic cycle is proposed.

Stereoconvergent negishi arylations of racemic secondary alkyl electrophiles: Differentiating between a CF3 and an alkyl group

In this report, we establish that a readily available nickel/bis(oxazoline) catalyst accomplishes a wide array of enantioconvergent cross-couplings of arylzinc reagents with CF3-substituted racemic secondary alkyl halides, a process that necessitates that the chiral catalyst be able to effectively distinguish between a CF3 and an alkyl group in order to provide good ee. We further demonstrate that this method can be applied without modification to the catalytic asymmetric synthesis of other families of fluorinated organic compounds.

Chemoenzymatic synthesis of phosphonic acid analogues of L-lysine, L-proline, L-ornithine, and L-pipecolic acid of 99 % ee - Assignment of absolute configuration to (-)-proline

(±)-ω-Halo-α-(chloroacetoxy)phosphonates were kinetically resolved by use of a protease (Chirazyme P-2). The esters recovered at levels of conversion between 56 and 72 % furnished (S)-alcohols of 99 % ee. These were converted via azides into the phosphonic acid analogues of L-lysine, L-proline, L-ornithine and L-pipecolic acid. (-)-Phosphaproline was transformed into crystalline ureas derived from (R)- and (S)-1-phenylethyl isocyanate. X-ray structure analyses revealed that the levorotary phosphaproline has the R configuration, contrary to earlier reports. Copyright

Total syntheses of (-) epilupinine and (-)-tashiromine using imino-aldol reactions

Short routes to enantiomerically pure indolizidine and quinolizidine alkaloids have been developed using imino-aldol reactions of enolates derived from phenyl 5-chlorovalerate. High levels of syn selectivity (dr ～13-16:1) were obtained using lithium enolates of phenyl esters in combination with tert-butylsulfinyl imines. The imino-aldol adducts were deprotected and cyclized to afford (-)-epilupinine ((-)-2) and (-)-tashiromine ((-)-1) in two further steps.

Design and synthesis of resin-conjugated Tamiflu analogs for affinity chromatography

Two types of resin-conjugated Tamiflu analogs were synthesized by modifying our original synthetic route of oseltamivir phosphate (Tamiflu). The prepared resins bound to influenza virus neuraminidase, the main target of Tamiflu. The resins will be useful for isolating and identifying presumed endogenous vertebrate proteins that interact with Tamiflu, which might relate to the rarely observed abnormal behavior exhibited by some influenza patients treated with Tamiflu.

NOVEL MACROCYCLIC INHIBITORS OF HEPATITIS C VIRUS REPLICATION

The embodiments provide compounds of the general Formula I, as well as compositions, including pharmaceutical compositions, comprising a subject compound. The embodiments further provide treatment methods, including methods of treating a hepatitis C virus infection and methods of treating liver fibrosis, the methods generally involving administering to an individual in need thereof an effective amount of a subject compound or composition.