628-21-7

Basic information

• Product Name: 1,4-Diiodobutane
• Synonyms: 1,4-DIIODOBUTANE;TETRAMETHYLENE IODIDE;TETRAMETHYLENE DIIODIDE;1,4-diiodo-butan;1,4-Dijodbutan;1,4-Diodobutane;Butane,1,4-diiodo-;α,ω-Diiodobutane
• CAS NO: 628-21-7
• Molecular Formula: C₄H₈I₂
• Molecular Weight: 309.92
• EINECS: 211-032-1
• Product Categories: Iodine Compounds
• Mol File: 628-21-7.mol

Chemical Properties

• Melting Point: 6 °C(lit.)
• Boiling Point: 147-152 °C26 mm Hg(lit.)
• Flash Point: 108-110°C/10mm
• Appearance: clear brownish liquid
• Density: 2.35 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0434mmHg at 25°C
• Refractive Index: n20/D 1.621(lit.)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Water Solubility: insoluble
• Sensitive: Light Sensitive
• BRN: 1098276
• CAS DataBase Reference: 1,4-Diiodobutane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Diiodobutane(628-21-7)
• EPA Substance Registry System: 1,4-Diiodobutane(628-21-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• RIDADR: 2810
• WGK Germany: 3
• RTECS: EJ9200000
• F: 8-10
• TSCA: Yes
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 628-21-7(Hazardous Substances Data)

Usage

Uses

1. Used in the Solar Energy Industry:
1,4-Diiodobutane is used as an additive to enhance the performance of perovskite solar cells. Its incorporation into the perovskite layer improves the stability and efficiency of the solar cells by reducing defects and optimizing the charge transport properties.
2. Used in the Membrane Technology Industry:
1,4-Diiodobutane is used as a crosslinking agent for the synthesis of anion exchange membranes from cellulose. The crosslinking process involving 1,4-Diiodobutane enhances the mechanical, thermal, and chemical stability of the resulting membranes, making them more suitable for applications in fuel cells, water treatment, and other electrochemical processes.

InChI:InChI=1/C4H8I2/c5-3-1-2-4-6/h1-4H2

Upstream product

• 109-99-9 tetrahydrofuran 
• 67-64-1 acetone 
• 74-88-4 methyl iodide 
• 6940-78-9 4-chlorobutyl bromide 
• 110-56-5 1,4-dichlorobutane 
• 4731-62-8 dimethylphosphinous iodide 
• 109019-49-0 dicyclohexylphosphinous iodide 
• 110-63-4 Butane-1,4-diol 
• 96-41-3 Cyclopentanol 
• 925-90-6 ethylmagnesium bromide 
• 3710-30-3 1,7-Octadiene 
• 105472-90-0 tetrakis(tetrahydrofuran)triiodolanthanum 
• 16029-98-4 trimethylsilyl iodide 
• 20549-72-8 4-phenoxybutyl iodide 

Downstream Products

• 45650-35-9 5-azonia-spiro[4.4]nonane; iodide 
• 15394-33-9 methyl 4-(methylsulfanyl)butyl sulfide 
• 628-67-1 butane-1,4-diol diacetate 
• 5457-30-7 4-phthalimido-1-iodobutane 
• 19224-27-2 1,4-bis(benzoyloxy)butane 
• 109260-27-7 N,N,N',N'-tetraethyl-N,N'-bis-[2-(2-benzyl-phenoxy)-ethyl]-N,N'-butanediyl-di-ammonium; diiodide 
• 124-04-9 Adipic acid 
• 111-69-3 hexanedinitrile 
• 109-99-9 tetrahydrofuran 
• 110-01-0 thiophene 
• 1647-16-1 1,10-decadiene 
• 4286-49-1 1,4-dinitrobutane 
• 119251-02-4 1,1'-dibenzyl-1,1'-butanediyl-bis-pyrrolidinium; diiodide 
• 7335-06-0 1-ethylpyrrolidine 

Relevant articles and documents

Continuous method for preparation of dihalogenated alkane from diol compound

The invention discloses a continuous method for preparation of dihalogenated alkane from a diol compound. A diol compound and haloid acid are used as the substrate, a microchannel reactor is utilizedto synthesize dihalogenated alkane continuously. Synthesis of the dihalogenated alkane includes the steps of: inputting the diol compound and haloid acid into a mixer respectively by a metering pump at room temperature, conducting premixing, then sending the mixture into a high-temperature section of the microchannel reactor at for reaction, and controlling the reaction temperature by an externalcirculating heat exchange system; at the end of the reaction, letting the product flow out from an outlet of the microchannel reactor and enter a cooling section, letting the cooled material enter a liquid separation kettle for standing and liquid separation, and collecting an organic layer; and preheating the organic layer, then feeding the preheated organic layer into a rectifying tower by a metering pump, controlling the temperature and reflux ratio of a reboiler, and collecting fractions at a specific temperature, thus obtaining the target product in a product collecting tank. The method provided by the invention has the characteristics of high reaction efficiency, safety, environmental protection, convenience and rapidity.

Catalytic Iodination of the Aliphatic C-F Bond by YbI3(THF)3: Mechanistic Insight and Synthetic Utility

A facile iodination protocol of unactivated alkyl fluorides using catalytic amounts of YbI3(THF)3 in the presence of iodotrimethylsilane as a stoichiometric fluoride trapping agent is presented. 1H NMR spectroscopy demonstrates a two-step catalytic cycle where TMSI regenerates active YbI3(THF)3. Finally, the catalytic reaction is extended into a one-pot procedure to demonstrate a potential application of the method. Overall, the findings present a distinct strategy for C-F bond transformations in the presence of catalytic YbI3(THF)3.

Conformationally constrained κ receptor agonists: Stereoselective synthesis and pharmacological evaluation of 6,8-diazabicyclo[3.2.2]nonane Derivatives

Three sets of stereoisomeric bicyclic κ agonists with defined orientation of the pharmacophoric elements pyrrolidine and dichlorophenylacetamide were stereoselectively prepared and pharmacologically evaluated. Stereoselective reduction, reductive amination, and Mitsunobu inversions were the key steps for the establishment of the desired stereochemistry. The κ affinity decreased in the following order depending on the N-substituent: CO2CH3 > benzyl > COCH 2CH3. Bicyclic derivatives with (1S,2R,5R)-configuration showed the highest κ receptor affinity, which led to dihedral angles of 97° and 45° for the N(pyrrolidine)-C-C-N(phenylacetamide) structural element. The most potent κ agonist of this series was (+)-methyl (1S,2R,5R)-8-[2-(3,4-dichlorophenyl)acetyl]-2-(pyrrolidin-1-yl)-6, 8-diazabicyclo[3.2.2]nonane-6-carboxylate (ent-23, WMS-0121) with an K i value of 1.0 nM. ent-23 revealed high selectivity against the other classical opioid receptors and related receptor systems. In the [ 35S]GTPγS-binding assay at human κ-opioid receptors, ent-23 was proved to be a full agonist with the same EC50 value (87 nM) as the prototypical full agonist U-69,593 (EC50 = 80 nM).

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.

The versatile behavior of the PdCl2/Et3SiH system. Conversion of alcohols to the corresponding halides and alkanes

The versatility of the palladium(II) chloride/triethylsilane system has been tested in the transformation of alcohols. The conversion to the corresponding halides and alkanes has been achieved in good yields and in the absence of solvent for a variety of substrates.

Reaction of tert-Butyl- and Phenyldiiodophosphines with Tetrahydrofuran

tert-Butyl- and phenyldiiodophosphines react with tetrahydrofuran, yielding tetraorganylcyclotetraphosphine, 1,4-diiodobutane, and oxygen-containing phosphorus compounds. The reaction proceeds via the stage of phosphine - phosphonium dimer formation with subsequent self-reduction of the latter by the halogenophilic mechanism yielding compounds with a P-P bond, diorganyldiiododisphosphines which are further converted to the final products under the action of tetrahydrofuran.

Stoichiometric Reactions of Nonconjugated Dienes with Zirconocene Derivatives. Further Delineation of the Scope of Bicyclization and Observation of Novel Multipositional Alkene Regioisomerization

The reaction of n-Bu2ZrCp2 with nonconjugated dienes containing substituted vinyl groups can lead to either bicyclization or the formation of conjugated diene-zirconocenes via multipositional regioisomerization.

Photoinduced Molecular Transformations. Part 154. On the Mechanism of the Formation of the 5-Iodopentyl Formate in the Photolysis of Cyclopentanol Hypoiodite in Solution in the Presence of Mercury(II) Oxide-Iodine.

(18)O-labelling experiments established that the formation of 5-iodopentyl formate in the photolysis of cyclopentanol hypoiodite in the presence of excess mercury(II) oxide-iodine in benzene involves the following pathway: a) a β-scission of a cyclopentyloxy radical to rearrange to a primary 5-oxopentyl radical, which generates the corresponding carbocation by a metal ionassisted one-electron oxidation; b) an intramolecular addition of the 5-oxopentyl cation to the formyl oxygen to generate a tetrahydropyranyl cation; c) a combination of the tetrahydropyranyl cation with diiodine oxide (I2O) to form a lactol hypoiodite; d) generation of a carbon-centred radical by a selective β-scission of a carbon-carbon bond of an alkoxyl radical generated from the lactol hypoiodite; e) abstraction of an iodine by the carbon-centred radical from an iodine molecule to form the 5-iodopentyl formate. 5-Iodopentyl formate is also produced by prolonged irradiation of a solution of 5-iodopentanal in the presence of mercury(II) oxide and iodine in benzene with Pyrex-filtered light.The formate in this case should be formed through the generation of the 5-oxopentyl cation (mentioned above) by mercury-assisted ionization of its carbon-iodine bond, followed by the same pathway as that mentioned above.

Cleavage of ethers and geminal diacetates using the boron triiodide-N,N-diethylaniline complex

The boron triiodide-N,N-diethylaniline complex, generated in situ from borane:N,N-diethylaniline and iodine cleaves ethers and regenerates carbox-aldehydes from the corresponding geminal diacetate derivatives under mild conditions in good yields. Recently a simple procedure for the preparation of alkyl and alkenyl iodides in good yields using boron triiodide-N,N-diethylaniline complex and acetic acid was reported.1 This prompted us to report our results on the cleavage of ethers and regeneration of aldehydes from geminal diacetates using the boron triiodide-N,N-diethylaniline reagent.