513-48-4

Basic information

• Product Name: 2-Iodobutane
• Synonyms: 2-IODOBUTANE;S-BUTYL IODIDE;SEC-BUTYL IODIDE;2-Butyl Iodide;2-Butyliodide;2-Iodbutan;2-iodo-butan;2-Jodbutan
• CAS NO: 513-48-4
• Molecular Formula: C₄H₉I
• Molecular Weight: 184.02
• EINECS: 208-163-1
• Product Categories: Organics;Iodine Compounds
• Mol File: 513-48-4.mol
• Article Data: 23

Chemical Properties

• Melting Point: -104 °C
• Boiling Point: 119-120 °C(lit.)
• Flash Point: 75 °F
• Appearance: liquid
• Density: 1.598 g/mL at 25 °C(lit.)
• Vapor Pressure: 18.6mmHg at 25°C
• Refractive Index: n20/D 1.499(lit.)
• Storage Temp.: Flammables area
• Solubility: alcohol: soluble(lit.)
• Water Solubility: Insoluble in water. Soluble in alcohol and diethyl ether.
• Sensitive: Light Sensitive
• Stability: Stable. Flammable. Incompatible with strong oxidizing agents. Light sensitive.
• Merck: 14,1574
• BRN: 1718777
• CAS DataBase Reference: 2-Iodobutane(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Iodobutane(513-48-4)
• EPA Substance Registry System: 2-Iodobutane(513-48-4)

Safety Data

• Hazard Codes: Xi,F
• Statements: 10-36/37/38
• Safety Statements: 26-36
• RIDADR: UN 2390 3/PG 2
• WGK Germany: 3
• RTECS: EK4410000
• F: 8
• TSCA: Yes
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 513-48-4(Hazardous Substances Data)

Usage

Chemical Properties

liquid

Uses

It is used as a solvent organic synthesis and as pharmaceutical intermediate.

General Description

2-iodobutane is a colorless liquid. Less dense than water. Vapors heavier than air. Used to make other chemicals and as a solvent.

Air & Water Reactions

Highly flammable. Slightly soluble in water.

Reactivity Profile

Halogenated aliphatic compounds, such as 2-Iodobutane, are moderately or very reactive. Reactivity generally decreases with increased degree of substitution of halogen for hydrogen atoms. Low molecular weight haloalkanes are highly flammable and can react with some metals to form dangerous products. Materials in this group are incompatible with strong oxidizing and reducing agents. Also, they are incompatible with many amines, nitrides, azo/diazo compounds, alkali metals, and epoxides.

Health Hazard

May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.

Fire Hazard

HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.

Purification Methods

Purify the iodide by shaking with conc H2SO4, then washing it with water, aqueous Na2SO3 and again with water. Dry (MgSO4) and distil. Alternatively, pass it through a column of activated alumina before distillation, or treat with bromine, followed by extraction of the free halogen with aqueous Na2S2O3, thoroughly washing with water, drying and distilling. It is stored over silver powder and distilled before use. [Beilstein 1 IV 272.]

InChI:InChI=1/C4H9I/c1-3-4(2)5/h4H,3H2,1-2H3/t4-/m0/s1

Upstream product

• 106-98-9 1-butylene 
• 107-01-7 butene-2 
• 909878-64-4 meso-erythritol 
• 691-88-3 di-sec-butyl mercury 
• 78-92-2 iso-butanol 
• 2314-97-8 iodotrifluoromethane 
• 590-18-1 (Z)-2-Butene 
• 78-86-4 s-butyl chloride 
• 63866-84-2 sec-Butyldiphenylarsanoxid 
• 2348-55-2 sec-Butyl-Radikal 
• 693-02-7 hex-1-yne 
• 106-97-8 n-butane 
• 1825-66-7 sec-butoxytrimethylsilane 
• 1708-29-8 2,5-dihydrofuran 

Downstream Products

• 25991-45-1 1-(1-methylpropyl)piperidine 
• 105-46-4 sec-Butyl acetate 
• 583-48-2 3,4-dimethylhexane 
• 107-01-7 butene-2 
• 513-53-1 1-methyl-1-propanethiol 
• 600-24-8 2-nitrobutane 
• 924-52-7 2-butyl nitrate 
• 74-98-6 propane 
• 626-26-6 sec-butyl sulfide 
• 78-92-2 iso-butanol 
• 106-97-8 n-butane 
• 857004-42-3 toluene-4-sulfonic acid-[N-sec-butyl-4-(4-nitro-phenylsulfanyl)-anilide] 
• 924-43-6 sec-butyl nitrite 
• 22921-59-1 2-(1-methylpropyloxy)benzaldehyde 

Relevant articles and documents

Photoinduced Palladium-Catalyzed Dicarbofunctionalization of Terminal Alkynes

Herein, a conceptually distinct approach was developed that allowed for the dicarbofunctionalization of alkynes at room temperature using simple, bench-stable alkyl iodides and a second molecule of alkyne as coupling partner. Specifically, the photochemical activation of palladium complexes enabled this strategic dicarbofunctionalization via addition of alkyl radicals from secondary and tertiary alkyl iodides and formation of an intermediate palladium vinyl complex that could undergo subsequent Sonogashira reaction with a second alkyne molecule. This alkylation–alkynylation sequence allowed the one-step synthesis of 1,3-enynes including heteroarenes and biologically active compounds with high efficiency without exogenous photosensitizers or oxidants and now opens up pathways towards cascade reactions via photochemical palladium catalysis.

A mild and highly chemoselective iodination of alcohol using polymer supported DMAP

The synthesis of organic compounds using polymer supported catalysts and reagents, where the required product is always in solution, has been of great interest in recent years, both in industries and academia especially in pharmaceutical research. Here, a simple and efficient method for conversion of alcohols into their iodides in high yield using polymer supported 4-(Dimethylamino)pyridine (DMAP) is described. Polymer supported DMAP is used in catalytic amount and is recovered and reused several times. Additionally, this method is highly chemoselective. [Figure not available: see fulltext.]

Iodination of alcohols over Keggin-type heteropoly compounds: A simple, selective and expedient method for the synthesis of alkyl iodides

Different catalysts derived from Keggin-type heteropoly compounds were prepared and their catalytic activities have been compared in the iodination of benzyl alcohol with KI under mild reaction conditions. A high catalytic activity was found over tungstophosphoric acid supported on silica and titania. The effect of catalyst loading, iodine source and the nature of substituents on the aromatic ring of benzyl alcohol were investigated. Finally, several competitive reactions were studied between structurally diverse alcohols. This protocol provides a mild and expedient way for the conversion of various alcohols to their corresponding alkyl iodides with high selectivity.