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4-Iodobenzyl bromide is an organic compound that exists as a light yellow adhering crystalline powder. It is characterized by its chemical structure, which includes a benzene ring with an iodine atom at the para position and a bromine atom attached to the benzyl group.

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  • 16004-15-2 Structure
  • Basic information

    1. Product Name: 4-Iodobenzyl bromide
    2. Synonyms: P-IODOBENZYL BROMIDE;4-IODOBENZYL BROMIDE;ALPHA-BROMO-4-IODOTOLUENE;1-BROMOMETHYL-4-IODO-BENZENE;4-Iodobenzyl Bromide p-Iodobenzyl Bromide;à-bromo-4-iodotoluene;4-Iodobenzyl bromide 97%;p-odobenzyl bromide
    3. CAS NO:16004-15-2
    4. Molecular Formula: C7H6BrI
    5. Molecular Weight: 296.93
    6. EINECS: N/A
    7. Product Categories: Fluorobenzene;Aromatic Halides (substituted);Methyl Halides;Phenyls & Phenyl-Het;Methyl Halides;Phenyls & Phenyl-Het;Halogenated Hydrocarbons;Aryl;C7;CMLLYL
    8. Mol File: 16004-15-2.mol
  • Chemical Properties

    1. Melting Point: 78-82 °C(lit.)
    2. Boiling Point: 140°C 15mm
    3. Flash Point: 140°C/15mm
    4. Appearance: Light yellow/Adhering Crystalline Powder
    5. Density: 2.0672 (rough estimate)
    6. Vapor Pressure: 0.0202mmHg at 25°C
    7. Refractive Index: 1.6500 (estimate)
    8. Storage Temp.: 2-8°C
    9. Solubility: N/A
    10. Water Solubility: Insoluble in water.
    11. Sensitive: Light Sensitive/Lachrymatory
    12. BRN: 2325160
    13. CAS DataBase Reference: 4-Iodobenzyl bromide(CAS DataBase Reference)
    14. NIST Chemistry Reference: 4-Iodobenzyl bromide(16004-15-2)
    15. EPA Substance Registry System: 4-Iodobenzyl bromide(16004-15-2)
  • Safety Data

    1. Hazard Codes: C,T
    2. Statements: 34-63-42/43-36/37/38
    3. Safety Statements: 26-36/37/39-45-23
    4. RIDADR: UN 3261 8/PG 2
    5. WGK Germany: 3
    6. RTECS:
    7. HazardClass: IRRITANT
    8. PackingGroup:
    9. Hazardous Substances Data: 16004-15-2(Hazardous Substances Data)

16004-15-2 Usage

Uses

Used in Organic Synthesis:
4-Iodobenzyl bromide is used as an organic chemical synthesis intermediate for various applications in the chemical and pharmaceutical industries. Its unique structure allows it to be a versatile building block in the synthesis of complex organic molecules, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-Iodobenzyl bromide is used as a key intermediate in the synthesis of various drugs and drug candidates. Its reactivity and functional groups make it suitable for the development of new therapeutic agents with potential applications in treating a wide range of diseases and medical conditions.
Used in Chemical Industry:
In the chemical industry, 4-Iodobenzyl bromide is utilized as an intermediate for the production of various specialty chemicals, such as dyes, pigments, and additives. Its unique properties enable it to be a valuable component in the formulation of these products, contributing to their performance and functionality.
Overall, 4-Iodobenzyl bromide is a versatile and valuable compound in the fields of organic synthesis, pharmaceuticals, and the chemical industry, serving as a crucial intermediate in the development of new and innovative products.

Check Digit Verification of cas no

The CAS Registry Mumber 16004-15-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,6,0,0 and 4 respectively; the second part has 2 digits, 1 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 16004-15:
(7*1)+(6*6)+(5*0)+(4*0)+(3*4)+(2*1)+(1*5)=62
62 % 10 = 2
So 16004-15-2 is a valid CAS Registry Number.
InChI:InChI=1/C7H6BrI/c8-5-6-1-3-7(9)4-2-6/h1-4H,5H2

16004-15-2 Well-known Company Product Price

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  • Alfa Aesar

  • (A18200)  4-Iodobenzyl bromide, 97%   

  • 16004-15-2

  • 5g

  • 931.0CNY

  • Detail
  • Alfa Aesar

  • (A18200)  4-Iodobenzyl bromide, 97%   

  • 16004-15-2

  • 25g

  • 3943.0CNY

  • Detail
  • Alfa Aesar

  • (A18200)  4-Iodobenzyl bromide, 97%   

  • 16004-15-2

  • 100g

  • 12855.0CNY

  • Detail

16004-15-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-Iodobenzyl Bromide

1.2 Other means of identification

Product number -
Other names 1-(bromomethyl)-4-iodobenzene

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:16004-15-2 SDS

16004-15-2Relevant articles and documents

Ethyl 2-formamido-2-(4-iodobenzyl)-3-(4-iodophenyl)propionate and ethyl 2-(3-bromobenzyl)-3-(3-bromophenyl)-2-formamidopropionate

Damodharan, Lakshminarasimhan,Pattabhi, Vasantha,Behera, Manoranjan,Kotha, Sambasivarao

, p. o216-o218 (2003)

The title compounds, C19H19I2NO3 and C19H19Br2NO3, are derivatives of α-aminoisobutyric acid with halogen substituents at the para and meta positions, respectively. The ethoxycarbonyl and formamide side chains attached to the Cαatom of the molecule adopt extended and folded conformations, respectively. The crystal structures are stabilized by N -H...O, C - H...O, C - Br...O and C - I...O interactions.

Design and synthesis of substituted (1-(benzyl)-1: H -1,2,3-triazol-4-yl)(piperazin-1-yl)methanone conjugates: Study on their apoptosis inducing ability and tubulin polymerization inhibition

Alvala, Mallika,Babu, Bathini Nagendra,Devi, Ganthala Parimala,Godugu, Chandraiah,Manasa, Kesari Lakshmi,Nagesh, Narayana,Sigalapalli, Dilep Kumar,Thatikonda, Sowjanya,Vuppaladadium, Sowmya

supporting information, p. 1295 - 1302 (2020/12/01)

A library of substituted (1-(benzyl)-1H-1,2,3-triazol-4-yl)(piperazin-1-yl)methanone derivatives were designed, synthesized and screened for their in vitro cytotoxic activity against BT-474, HeLa, MCF-7, NCI-H460 and HaCaT cells by employing 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Among all the synthesized analogues, compound 10ec displayed the highest cytotoxicity with the IC50 value of 0.99 ± 0.01 μM towards BT-474 cancer cell line. The target compound (10ec) was also evaluated for its tubulin polymerization inhibition study. Detailed biological studies such as acridine orange/ethidium bromide (AO/EB), DAPI and annexin V-FITC/propidium iodide staining assay suggested that compound 10ec induced the apoptosis of BT-474 cells. The clonogenic assay revealed that the inhibition of colony formation in BT-474 cells by 10ec in concentration-dependent manner. Moreover, the flow cytometric analysis revealed that 10ec induced apoptosis via cell cycle arrest at the sub-G1 and G2/M phase. In silico studies of sulfonyl piperazine-integrated triazole conjugates unveil that they possess drug-like properties. According to the molecular modelling studies, compound 10ec binds to the colchicine binding site of the tubulin.

Halogenation through Deoxygenation of Alcohols and Aldehydes

Chen, Jia,Lin, Jin-Hong,Xiao, Ji-Chang

supporting information, p. 3061 - 3064 (2018/05/28)

An efficient reagent system, Ph3P/XCH2CH2X (X = Cl, Br, or I), was very effective for the deoxygenative halogenation (including fluorination) of alcohols (including tertiary alcohols) and aldehydes. The easily available 1,2-dihaloethanes were used as key reagents and halogen sources. The use of (EtO)3P instead of Ph3P could also realize deoxy-halogenation, allowing for a convenient purification process, as the byproduct (EtO)3Pa?O could be removed by aqueous washing. The mild reaction conditions, wide substrate scope, and wide availability of 1,2-dihaloethanes make this protocol attractive for the synthesis of halogenated compounds.

Carbonylative Coupling of Alkyl Zinc Reagents with Benzyl Bromides Catalyzed by a Nickel/NN2 Pincer Ligand Complex

Andersen, Thomas L.,Donslund, Aske S.,Neumann, Karoline T.,Skrydstrup, Troels

supporting information, p. 800 - 804 (2017/12/26)

An efficient catalytic protocol for the three-component assembly of benzyl bromides, carbon monoxide, and alkyl zinc reagents to give benzyl alkyl ketones is described, and represents the first nickel-catalyzed carbonylative coupling of two sp3-carbon fragments. The method, which relies on the application of nickel complexed with an NN2-type pincer ligand and a controlled release of CO gas from a solid precursor, works well with a range of benzylic bromides. Mechanistic studies suggest the intermediacy of carbon-centered radicals.

A General Strategy to Enhance the Performance of Dye-Sensitized Solar Cells by Incorporating a Light-Harvesting Dye with a Hydrophobic Polydiacetylene Electrolyte-Blocking Layer

Desta, Mekonnen Abebayehu,Liao, Chia-Wei,Sun, Shih-Sheng

, p. 690 - 697 (2017/03/22)

A unique strategy to suppress charge recombination effectively and enhance light harvesting in dye-sensitized solar cells (DSSCs) is demonstrated by the design of a new dipolar organic dye functionalized with a diacetylene unit, which is capable of underg

Palladium-Catalyzed, ortho-Selective C-H Halogenation of Benzyl Nitriles, Aryl Weinreb Amides, and Anilides

Das, Riki,Kapur, Manmohan

, p. 1114 - 1126 (2018/06/18)

A palladium-catalyzed, ortho-selective C-H halogenation methodology is reported herein. The highlight of the work is the highly selective C(sp2)-H functionalization of benzyl nitriles in the presence of activated C(sp3)-H bond, which results in good yields of the halogenated products with excellent regioselectivity. Along with benzyl nitriles, aryl Weinreb amides and anilides have been evaluated for the transformation using aprotic conditions. Mechanistic studies yield interesting aspects with respect to the pathway of the reaction and the directing group abilities.

P(NMe2)3-Mediated Umpolung Alkylation and Nonylidic Olefination of α-Keto Esters

Wang, Sunewang Rixin,Radosevich, Alexander T.

supporting information, p. 3810 - 3813 (2015/08/18)

A commercial phosphorus-based reagent (P(NMe2)3) mediates umpolung alkylation of methyl aroylformates with benzylic and allylic bromides, leading to either Barbier-type addition or ylide-free olefination products upon workup. The reaction sequence is initiated by a two-electron redox addition of the tricoordinate phosphorus reagent with an α-keto ester compound (Kukhtin-Ramirez addition). A mechanistic rationale is offered for the chemoselectivity upon which the success of this nonmetal mediated C-C bond forming strategy is based.

Investigation of pyrolysis temperature in the one-step synthesis of L10 FePt nanoparticles from a FePt-containing metallopolymer

Dong, Qingchen,Li, Guijun,Wang, Hua,Wing-Tat Pong, Philip,Leung, Chi-Wah,Manners, Ian,Ho, Cheuk-Lam,Li, Hua,Wong, Wai-Yeung

, p. 734 - 741 (2015/07/27)

Ferromagnetic (L10 phase) FePt alloy nanoparticles (NPs) with extremely high magnetocrystalline anisotropy are considered to be very promising candidates for the next generation of ultrahigh-density data storage systems. The question of how to generate L10 FePt NPs with high coercivity, controllable size, and a narrow size distribution is a challenge. We report here a single-step fabrication of L10 FePt NPs by employing one of the two new polyferroplatinyne bimetallic polymers as precursors. The influence of the pyrolysis temperature on the size and magnetic properties of the resulting FePt alloy NPs has been investigated in detail.

A scalable procedure for light-induced benzylic brominations in continuous flow

Cantillo, David,De Frutos, Oscar,Rincon, Juan A.,Mateos, Carlos,Oliver Kappe

supporting information, p. 223 - 229 (2014/01/17)

A continuous-flow protocol for the bromination of benzylic compounds with N-bromosuccinimide (NBS) is presented. The radical reactions were activated with a readily available household compact fluorescent lamp (CFL) using a simple flow reactor design based on transparent fluorinated ethylene polymer (FEP) tubing. All of the reactions were carried out using acetonitrile as the solvent, thus avoiding hazardous chlorinated solvents such as CCl4. For each substrate, only 1.05 equiv of NBS was necessary to fully transform the benzylic starting material into the corresponding bromide. The general character of the procedure was demonstrated by brominating a diverse set of 19 substrates containing different functional groups. Good to excellent isolated yields were obtained in all cases. The novel flow protocol can be readily scaled to multigram quantities by operating the reactor for longer time periods (throughput 30 mmol h-1), which is not easily possible in batch photochemical reactors. The bromination protocol can also be performed with equal efficiency in a larger flow reactor utilizing a more powerful lamp. For the bromination of phenylacetone as a model, a productivity of 180 mmol h -1 for the desired bromide was achieved.

One-pot transformation of methylarenes into aromatic aldehydes under metal-free conditions

Tabata, Masayuki,Moriyama, Katsuhiko,Togo, Hideo

, p. 3402 - 3410 (2014/06/09)

On the basis of studies of the transformation of benzylic bromides into the corresponding aromatic aldehydes by treatment with N-methylmorpholine N-oxide, various methylarenes were treated either with DBDMH in the presence of AIBN in acetonitrile at reflux (Method A) or with NBS in CCl4 under irradiation with a tungsten lamp at 30 °C (Method B), followed by treatment with N-methylmorpholine N-oxide to provide aromatic aldehydes in good yields. These methods could be adopted in one-pot transformations of methylarenes into aromatic aldehydes under conditions free of less toxic reagents and transition metals. Copyright

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