541-28-6

Basic information

• Product Name: Isoamyl iodide
• Synonyms: ISOPENTYL IODIDE;ISOAMYL IODIDE;Iodo-isopentane;1-IODO-3-METHYLBUTANE;1-iodo-3-methyl-butan;1-Jod-3-methylbutan;3-Methyl-1-iodobutane;3-Methylbutyliodide
• CAS NO: 541-28-6
• Molecular Formula: C₅H₁₁I
• Molecular Weight: 198.05
• EINECS: 208-773-8
• Product Categories: Miscellaneous;Iodine Compounds
• Mol File: 541-28-6.mol
• Article Data: 12

Chemical Properties

• Melting Point: -85.6°C (estimate)
• Boiling Point: 149 °C(lit.)
• Flash Point: 115 °F
• Appearance: clear slightly yellow to pink liquid
• Density: 1.497 g/mL at 25 °C(lit.)
• Vapor Pressure: 5.82mmHg at 25°C
• Refractive Index: n20/D 1.492(lit.)
• Storage Temp.: Flammables area
• Water Solubility: Insoluble in water. Soluble in most common organic solvents.
• Sensitive: Light Sensitive
• Merck: 14,5120
• BRN: 1730990
• CAS DataBase Reference: Isoamyl iodide(CAS DataBase Reference)
• NIST Chemistry Reference: Isoamyl iodide(541-28-6)
• EPA Substance Registry System: Isoamyl iodide(541-28-6)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 10-22
• Safety Statements: 16
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• RTECS: EK4412000
• F: 1-8-9
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 541-28-6(Hazardous Substances Data)

Usage

Chemical Properties

clear slightly yellow to pink liquid

Uses

1-Iodo-3-methylbutane can be used for organic synthesis or used as solvents.

Preparation

Synthesis of 1-Iodo-3-methylbutane: Bromo-3-methylbutane (30.2 g, 0.20 mol) was added dropwise to a mixture of NaI (44.97g, 0.30 mol) and acetone (500 mL). The mixture was refluxed overnight. The mixture was filtrated and the filter cake was washed with (2 x 50 mL) acetone. The acetone was evaporated under reduced pressure. 1-Iodo-3-methylbutane was distilled under vacuum to give 13.8g (35 %) (b.p. 25 - 35°C, 15 mmHg).

InChI:InChI=1/C5H11I/c1-5(2)3-4-6/h5H,3-4H2,1-2H3

Upstream product

• 544-01-4 isopentyl ether 
• 507-02-8 acetyl iodide 
• 628-04-6 1-ethoxy-3-methyl-butane 
• 618-38-2 benzoyl iodide 
• 123-92-2 3-methyl-1-butyl acetate 
• 7553-56-2 iodine 
• 5337-70-2 orthoformic acid triisopentyl ester 
• 4237-74-5 isoamylmagnesium chloride 
• 107-84-6 1-chloro-3-methylbutane 
• 107-82-4 i-pentyl bromide 
• 123-51-3 i-Amyl alcohol 

Downstream Products

• 4462-09-3 N-isopentylpiperidine 
• 54899-89-7 N-(isopentyl)-quinolinium iodide 
• 17071-48-6 3-methyl-1-propoxy-butane 
• 94319-01-4 1-isopentyl-4-methyl-quinolinium; iodide 
• 5398-08-3 diethyl isopentylmalonate 
• 45173-31-7 triisoamylphosphine 
• 5424-26-0 tetra-i-pentylammonium iodide 
• 543-50-0 isopentylsulfanyl cyanate 
• 97042-13-2 bis-(4-isopentyloxy-phenyl)-sulfone 
• 119987-34-7 diphenyl(isopentyl)phosphine sulphide 
• 857005-76-6 toluene-4-sulfonic acid-[N-isopentyl-4-(4-nitro-phenylsulfanyl)-anilide] 
• 874514-24-6 toluene-4-sulfonic acid-[4-(2-benzyloxy-4-nitro-phenylsulfanyl)-N-isopentyl-anilide] 
• 544-01-4 isopentyl ether 
• 563-45-1 3-Methyl-1-butene 

Relevant articles and documents

Scalable and Phosphine-Free Conversion of Alcohols to Carbon-Heteroatom Bonds through the Blue Light-Promoted Iodination Reaction

One of the fundamental and highly valuable transformations in organic chemistry is the nucleophilic substitution of alcohols. Traditionally, these reactions require strategies that employ stoichiometric hazardous reagents and are associated with difficulty in purification of the by-products. To overcome these challenges, here, we report a simple route toward the diverse conversion of alcohols via an SN2 pathway, in which blue light-promoted iodination is used to form alkyl iodide intermediates from simple unreactive alcohols. The scope of the process tolerates a range of nucleophiles to construct C-N, C-O, C-S, and C-C bonds. Furthermore, we also demonstrate that this method can be used for the preparation and late-stage functionalization of pharmaceuticals, as highlighted by the syntheses of thiocarlide, butoxycaine, and pramoxine.

Visible-Light-Promoted Remote C-H Functionalization of o-Diazoniaphenyl Alkyl Sulfones

Visible-light irradiation of ortho-diazoniaphenyl alkyl sulfones in the presence of Ru(bpy)32+ results in remote Csp3-H functionalization. Key mechanistic steps in these processes involve intramolecular hydrogen atom transfer from Csp3-H bonds to aryl radicals to generate alkyl/benzyl radicals. Subsequent polar crossover occurs by single-electron oxidation of the alkyl/benzyl radicals to carbenium ions that then intercept nucleophiles. We have developed remote hydroxylations, etherifications, an amidation, and C-C bond formation processes using this strategy.

Iodination of alcohols using triphenylphosphine/iodine in ionic liquid under solvent-free conditions

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