542-69-8 Usage
Chemical Description
1-Iodobutane and allyl bromide are alkyl halides used in organic synthesis.
Description
1-Iodobutane, also known as butyl iodide, is an organic compound with the chemical formula C4H9I. It is a colorless liquid that is soluble in chloroform, miscible with ethanol and ether, and insoluble in water. 1-Iodobutane exhibits unique thermal chemistry and undergoes changes when exposed to light or left for an extended period.
Uses
1. Used in Chemical Synthesis:
1-Iodobutane is used as a reagent in the synthesis of various organic compounds, such as S-alkylated 5-(2-, 3-, and 4-methoxyphenyl)-4H-1,2,4-triazole-3-thiol and 5-(2-, 3-, and 4-methoxyphenyl)-4-phenyl-4H-1,2,4-triazole-3-thiol. Its ability to participate in chemical reactions makes it a valuable component in the creation of new molecules with potential applications in various fields.
2. Used in Pharmaceutical Industry:
1-Iodobutane is utilized as a pharmaceutical intermediate, playing a crucial role in the development and production of various medications. Its versatility in chemical reactions allows for the creation of different drug compounds that can address a wide range of health issues.
3. Used in Medical Applications:
In the medical field, 1-Iodobutane is employed in a wide range of applications, including the development of new treatments and therapies. Its unique properties make it suitable for use in various medical procedures and the creation of innovative medical products.
4. Used in Animal Nutrition Products:
1-Iodobutane is also used in the animal nutrition industry, where it contributes to the development of products that promote the health and well-being of animals. Its role in this industry highlights its versatility and the potential benefits it can provide to both humans and animals.
5. Used in LCD Chemicals:
In the electronics industry, 1-Iodobutane is used in the production of polarizing films for Liquid Crystal Display (LCD) chemicals. Its properties make it an essential component in the creation of high-quality displays that are used in various electronic devices, such as televisions, computer monitors, and smartphones.
Preparation
1-Iodobutane is obtained by reacting n-butanol with iodine in the presence of phosphorus.
Synthesis Reference(s)
The Journal of Organic Chemistry, 44, p. 2048, 1979 DOI: 10.1021/jo01326a042Synthesis, p. 114, 1976
Purification Methods
Dry the iodide with MgSO4 or P2O5, fractionally distil it through a column packed with glass helices, taking the middle fraction and storing over calcium or mercury in the dark. Alternatively purify it by prior passage through activated alumina or by shaking with conc H2SO4 then washing with Na2SO3 solution. It has also been treated carefully with sodium to remove free HI and H2O, before distilling through a column containing copper turnings at the top. Another purification procedure consisted of treatment with bromine, followed by extraction of free halogen with Na2S2O3, washing with H2O, drying and fractionally distilling. [Beilstein 1 IV 271.]
Check Digit Verification of cas no
The CAS Registry Mumber 542-69-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,4 and 2 respectively; the second part has 2 digits, 6 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 542-69:
(5*5)+(4*4)+(3*2)+(2*6)+(1*9)=68
68 % 10 = 8
So 542-69-8 is a valid CAS Registry Number.
InChI:InChI=1/C4H9I/c1-2-3-4-5/h2-4H2,1H3
542-69-8Relevant articles and documents
EXCHANGE OF BROMINE AND CHLORINE BY IODINE IN ALIPHATIC HALIDES CATALYZED BY IRON PENTACARBONYL
Amriev, R. A.,Velichko, F. K.,Freidlina, R. Kh.
, p. 213 - 215 (1985)
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Cox, Philip J.,Doidge-Harrison, Solange M. S. V.,Howie, R. Alan,Nowell, Ian W.,Taylor, Oonah J.,Wardell, James L.
, (1989)
MeLi + LiCl in THF: One Heterodimer and no tetramers
Lecachey, Baptiste,Oulyadi, Hassan,Lameiras, Pedro,Harrison-Marchand, Anne,Gerard, Helene,Maddaluno, Jacques
, p. 5976 - 5983 (2010)
The structure of the aggregates formed when mixing methyllithium and lithium chloride in THF has been studied by multinuclear magnetic resonance at 170 K. The data suggest that only one new entity is observed, that is the dimer [(MeLi)(LiCl)], in equilibrium (K ≈ 0.6) with [MeLi]4 and [LiCl]2. NMR diffusion measurements lead to the conclusion that this dimer is trisolvated in THF at 170 K, a solvation scheme in agreement with DFT computations.
Visible-light-mediated multicomponent reaction for secondary amine synthesis
Wang, Xiaochen,Zhu, Binbing,Dong, Jianyang,Tian, Hao,Liu, Yuxiu,Song, Hongjian,Wang, Qingmin
supporting information, p. 5028 - 5031 (2021/05/28)
The widespread presence of secondary amines in agrochemicals, pharmaceuticals, natural products, and small-molecule biological probes has inspired efforts to streamline the synthesis of molecules with this functional group. Herein, we report an operationally simple, mild protocol for the synthesis of secondary amines by three-component alkylation reactions of imines (generated in situ by condensation of benzaldehydes and anilines) with unactivated alkyl iodides catalyzed by inexpensive and readily available Mn2(CO)10. This protocol, which is compatible with a wide array of sensitive functional groups and does not require a large excess of the alkylating reagent, is a versatile, flexible tool for the synthesis of secondary amines.
Halogen-Imparted Reactivity in Lithium Carbenoid Mediated Homologations of Imine Surrogates: Direct Assembly of bis-Trifluoromethyl-β-Diketiminates and the Dual Role of LiCH2I
Castoldi, Laura,Holzer, Wolfgang,Ielo, Laura,Lombino, Jessica,Pace, Vittorio,Prandi, Cristina,Roller, Alexander,Touqeer, Saad
supporting information, p. 20852 - 20857 (2020/09/12)
The selective formal insertion (homologation) of a carbon unit bridging the two trifluoroacetamidoyl chlorides (TFAICs) units is reported. The tactic is levered on a highly chemoselective homologation–metalation–acyl nucleophilic substitution sequence which precisely enables to assemble novel trifluoromethylated β-diketiminates within a single synthetic operation. Unlike previous homologations conducted with LiCH2Cl furnishing aziridines, herein we exploit the unique capability of iodomethyllithium to act contemporaneously as a C1 source (homologating effect) and metalating agent. The mechanistic rationale grounded on experimental evidences supports the hypothesized proposal and, the structural analysis gathers key aspects of this class of valuable ligands in catalysis.
HALIDE-MEDIATED DEALKYLATION OF PHOSPHOTRIESTERS
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Paragraph 0010; 0012; 0051, (2018/02/03)
In one embodiment, a method includes contacting a phosphotriester and a halogen salt in a polar solvent. In another embodiment, a method for dealkylating tributylphosphate includes contacting tributylphosphate and a halogen salt in a polar solvent.