10297-05-9

Basic information

• Product Name: 1-CHLORO-4-IODOBUTANE
• Synonyms: 1-chloro-4-iodo-butan;Butane, 1-chloro-4-iodo-;TETRAMETHYLENE CHLOROIODIDE;1-CHLORO-4-IODOBUTANE;1-IODO-4-CHLOROBUTANE;4-Chlorobutyl iodide;1-Chloro-4-iodobutane (stabilized with Copper chip);4-Iodobutyl chloride, 4-Chlorobutyl iodide
• CAS NO: 10297-05-9
• Molecular Formula: C₄H₈ClI
• Molecular Weight: 218.46
• EINECS: 233-669-4
• Product Categories: Alkyl;Halogenated Hydrocarbons;Organic Building Blocks
• Mol File: 10297-05-9.mol

Chemical Properties

• Melting Point: 93 °C
• Boiling Point: 88-89 °C19 mm Hg(lit.)
• Flash Point: 200 °F
• Appearance: clear yellow to brown liquid
• Density: 1.785 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.643mmHg at 25°C
• Refractive Index: n20/D 1.54(lit.)
• Storage Temp.: 2-8°C(protect from light)
• Solubility: Chloroform, Ethyl Acetate
• Sensitive: Light Sensitive
• BRN: 1361365
• CAS DataBase Reference: 1-CHLORO-4-IODOBUTANE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-CHLORO-4-IODOBUTANE(10297-05-9)
• EPA Substance Registry System: 1-CHLORO-4-IODOBUTANE(10297-05-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 10297-05-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
1-Chloro-4-iodobutane is utilized as a reagent in the synthesis of alkyl chromones and quinolones via cyclization and alkylation of enaminones. It serves as an essential intermediate in various pharmaceutical synthesis processes, contributing to the development of new drugs and therapeutic agents.
Used in Chemical Research:
1-CHLORO-4-IODOBUTANE is also employed in several research studies, including:
1. Preparation of 6-hendecenoic acid, which may have potential applications in the chemical and pharmaceutical industries.
2. Catalytic asymmetric synthesis of levobupivacaine, a local anesthetic used in medical procedures.
3. Synthesis of alkaloids such as deoxyvasicinone and mackinazolinone, which are organic compounds with potential applications in the pharmaceutical and chemical industries.

InChI:InChI=1/C4H8ClI/c5-3-1-2-4-6/h1-4H2

Upstream product

• 26910-61-2 4-chlorobutyl methanesulfonate 
• 110-56-5 1,4-dichlorobutane 
• 20999-32-0 4-chlorobutyl 4-methylbenzenesulfonate 
• 111-13-7 hexyl-methyl-ketone 
• 41049-30-3 2-(4-iodobutoxy)tetrahydropyran 
• 109-69-3 n-Butyl chloride 
• 928-51-8 4-Chloro-1-butanol 

Downstream Products

• 10297-06-0 1-chloro-5-hexyne 
• 54377-34-3 1-chloro-5-decyne 
• 63401-07-0 C₉H₁₈N₂O 
• 67257-59-4 (5-Chloro-1-{[1-phenyl-meth-(E)-ylidene]-amino}-pentyl)-phosphonic acid diethyl ester 
• 14860-82-3 1-chloro-4-propoxybutane 
• 129378-52-5 2-tert-butyldimethylsilyl-N,N-dimethylimidazole-1-sulfonamide 
• 149647-72-3 1-(N,N-dimethylsulfamoyl)-2-(tert-butyldimethylsilyl)-5-(4-chlorobutyl)imidazole 
• 143037-77-8 4-(4-chlorobutyl)-4,5-dihydro-5-methyl-3-methylene-5-phenyl-2(3H)-furanone 
• 94012-71-2 trimethyl(6-iodo-1-hexynyl)silane 
• 113964-33-3 (6-chlorohex-1-yn-1-yl)trimethylsilane 
• 71673-28-4 (Z)-1-chloro-5-decene 
• 170642-32-7 (S,S)-pseudoephedrine D-pipecolinamide 
• 182635-00-3 1-chloro-4-(phenylselanyl)butane 
• 203710-61-6 (2S,3S,7S,8aR)-7-(4-Chloro-butyl)-3-methoxymethyl-8a-methyl-2-phenyl-hexahydro-oxazolo[3,2-a]pyridin-5-one 

Related news

Transformation of OH-adduct of 1-CHLORO-4-IODOBUTANE (cas 10297-05-9) into intra-molecular radical cation in neutral aqueous solution07/27/2019

The iodine centered OH-adduct formed on reaction of ⋅OH radicals with 1-chloro-4-iodobutane in neutral aqueous solution transforms (k=5.4×105 s−1) to an intra-molecular radical cation (Download full-size image). The unfavorable structural conformation of solute radical cation generated on react...detailed

Relevant articles and documents

Transformation of OH-adduct of 1-chloro-4-iodobutane into intra-molecular radical cation in neutral aqueous solution

The iodine centered OH-adduct formed on reaction of OH radicals with 1-chloro-4-iodobutane in neutral aqueous solution transforms (k=5.4×105 s-1) to an intra-molecular radical cation (). The unfavorable structural conformation of solute radical cation generated on reaction of OH radicals with 1-chloro-5-iodopentane does not allow the transformation of OH-adduct into an intra-molecular radical and instead a dimer radical cation () is formed.

Aliphatic C-H Bond Iodination by a N-Iodoamide and Isolation of an Elusive N-Amidyl Radical

Contrary to C-H chlorination and bromination, the direct iodination of alkanes represents a great challenge. We reveal a new N-iodoamide that is capable of a direct and efficient C-H bond iodination of various cyclic and acyclic alkanes providing iodoalkanes in good yields. This is the first use of N-iodoamide for C-H bond iodination. The method also works well for benzylic C-H bonds, thereby constituting the missing version of the Wohl-Ziegler iodination reaction. Mechanistic details were elucidated by DFT computations, and the N-centered radical derived from the used N-iodoamide, which is the key intermediate in this process, was matrix-isolated in a solid argon matrix and characterized by UV-vis as well as IR spectroscopy.

PROCESS FOR THE PREPARATION OF N-IODOAMIDES

The present invention provides new stable crystalline N-iodoamides - 1-iodo- 3,5,5-trimethylhydantoin (1-ITMH) and 3-iodo-4,4-dimethyl-2-oxazolidinone (IDMO). The present invention further provides a process for the preparation of organic iodides using N-iodoamides of this invention and recovery of the amide co-products from waste water.

Epiquinamide: A Poison That Wasn't from a Frog That Was

In 2003, we reported the isolation, structure elucidation, and pharmacology of epiquinamide (1), a novel alkaloid isolated from an Ecuadoran poison frog, Epipedobates tricolor. Since then, several groups, including ours, have undertaken synthetic efforts to produce this compound, which appeared initially to be a novel, β2-selective nicotinic acetylcholine receptor agonist. Based on prior chiral GC analysis of synthetic and natural samples, the absolute structure of this alkaloid was established as (15,9aS)-1-acetamidoquinolizidine. We have synthesized the (1.R*,9aS*)-isomer (epiepiquinamide) using an iminium ion nitroaldol reaction as the key step. We have also synthesized ent-1 semisynthetically from (-)-lupinine. Synthetic epiquinamide is inactive at nicotinic receptors, in accord with recently published reports. We have determined that the activity initially reported is due to cross-contamination from co-occurring epibatidine in the isolated material.

Synthesis of enantiopure bicyclic α,α-disubstituted spirolactams via asymmetric Birch reductive alkylation

The synthesis of enantiopure bicyclic α,α-disubstituted spirolactams is described using a diastereoselective Birch reductive alkylation as the key step. Hydrogenation of the resultant alkylated cyclohexadienes followed by intramolecular cyclization provides access to enantiopure 8-azaspiro[5.6]dodecan-7-ones.

One-step conversion of protected alcohols into alkyl halides using dimethylphosgeniminium salt

Efficient conversion of tetrahydro-2-pyranyl (THP)protected alcohols into the corresponding halides using dichlorophosgeniminium chloride in the presence of tetraalkylammonium halide.

Divalent Lanthanide Derivatives in Organic Synthesis. 1. Mild Preparation of SmI2 and YbI2 and Their Use as Reducing or Coupling Agents

The facile synthesis of SmI2 and YbI2 from corresponding metals in THF is described.The reactivity of these potentially powerful reducing agents toward a variety functional groups is tested.Epoxides and sulfoxides are deoxygenated.Aldehydes are selectively reduced in presence of ketones.Alkyl halides or tosylates are converted into alkanes.Only coupling products are obtained from benzylic or allylic halides.In the presence of a SmI2-THF solution, tertiary alcohols are easily obtained from reactions between ketones and alkyl halides.In a similar manner, SmI2 promotes straightforward alkylation of ketones by alkyl sulfonates.Selective addition of polyfunctional halides or tosylates to ketones may be performed.In these reactions, catalytic amounts of FeCl3 enhance the reactivity.