17201-43-3

Basic information

• Product Name: 4-Cyanobenzyl bromide
• Synonyms: 4-(bromomethyl)-benzonitril;Benzonitrile, 4-(bromomethyl)-;Benzonitrile, p-(bromomethyl)-;p-(Bromomethyl)benzonitrile;p-Tolunitrile, alpha-bromo-;p-Toluonitrile, alpha-bromo-;P-CYANOBENZYL BROMIDE;CYANOBENZYLBROMIDE(P-)
• CAS NO: 17201-43-3
• Molecular Formula: C₈H₆BrN
• Molecular Weight: 196.04
• EINECS: 241-246-0
• Product Categories: Aromatic Halides (substituted);Organics;Miscellaneous;Aromatics Compounds;Aromatics;Building Blocks;C8 to C9;Chemical Synthesis;Cyanides/Nitriles;Nitrogen Compounds;Organic Building Blocks
• Mol File: 17201-43-3.mol

Chemical Properties

• Melting Point: 115-117 °C(lit.)
• Boiling Point: 143 °C / 12mmHg
• Flash Point: 125.1 ºC
• Appearance: Clear colorless to yellow/Liquid
• Density: 1.5466 (rough estimate)
• Vapor Pressure: 0.00321mmHg at 25°C
• Refractive Index: 1.6550 (estimate)
• Storage Temp.: Store at 0-5°C
• Water Solubility: Soluble in chloroform and methanol. Insoluble in water.
• BRN: 636717
• CAS DataBase Reference: 4-Cyanobenzyl bromide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Cyanobenzyl bromide(17201-43-3)
• EPA Substance Registry System: 4-Cyanobenzyl bromide(17201-43-3)

Safety Data

• Hazard Codes: C
• Statements: 34-42/43
• Safety Statements: 22-26-36/37/39-45-28A
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• F: 10-19-21
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 17201-43-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Cyanobenzyl bromide is used as an intermediate for the synthesis of a series of piperidine-linked aromatic diimidazolines. These compounds have been synthesized as conformationally restricted congeners of the anti-Pneumocystis carinii (PCP) drug, Pentamidine, which is used for the treatment of PCP infections.
Used in Agriculture:
As a benzyl halide, 4-Cyanobenzyl bromide is utilized as a postemergence herbicide. It helps control the growth of unwanted plants and weeds in agricultural fields, ensuring better crop yield and quality.
Used in Chemical Synthesis:
4-Cyanobenzyl bromide is used in the synthesis of ligands containing a chelating pyrazolyl-pyridine group with a pendant aromatic nitrile. These ligands are essential in various chemical reactions and processes, contributing to the development of new compounds and materials.
Used in Synthesis of 4-[(2H-tetra-zol-2-yl)methyl]benzonitrile:
4-(Bromomethyl)benzonitrile can be used in the preparation of 4-[(2H-tetra-zol-2-yl)methyl]benzonitrile by reacting with 2H-tetrazole in the presence of potassium hydroxide (KOH). 4-Cyanobenzyl bromide has potential applications in various chemical and pharmaceutical processes.

InChI:InChI=1/C8H6BrN/c9-5-7-1-3-8(6-10)4-2-7/h1-4H,5H2

Upstream product

• 7726-95-6 bromine 
• 104-85-8 para-methylbenzonitrile 
• 94-36-0 dibenzoyl peroxide 
• 827-58-7 2-p-tolyl-1,3,4-oxadiazole 
• 10406-25-4 4-aminobenzyl cyanide 
• 874-89-5 4-Cyanobenzyl alcohol 
• 106-38-7 para-bromotoluene 
• 105-07-7 4-cyanobenzaldehyde 

Downstream Products

• 105-07-7 4-cyanobenzaldehyde 
• 28487-61-8 2,3-bis-(4-cyano-phenyl)-propionitrile 
• 849133-34-2 4-((4-nitrophenoxy)methyl)benzonitrile 
• 854626-60-1 4-p-tolyloxymethyl-benzonitrile 
• 168028-51-1 4-(methylthiomethyl)benzonitrile 
• 146781-27-3 4-ethoxymethyl-benzonitrile 
• 57928-75-3 4-(phenoxymethyl)benzonitrile 
• 34403-48-0 methyl-4-cyanobenzylamine 
• 1552-41-6 diethyl [(4-cyanophenyl)methyl]phosphonate 
• 6232-88-8 4-bromomethylbenzoic Acid 
• 1642-81-5 p-(chloromethyl)benzoic acid 
• 57042-60-1 1-p-Cyanobenzyl-4-methylpyridinium bromide 
• 160032-27-9 3-thienyl-4-cyanobenzylsulfide 
• 98300-08-4 N-(4-cyanobenzyl)-3-cyanopyridin-1-ium bromide 

Relevant articles and documents

Deconjugative α-Alkylation of Cyclohexenecarboxaldehydes: An Access to Diverse Terpenoids

A general and efficient method for the deconjugative α-alkylation of α,β-unsaturated aldehydes promoted by a synergistic effect between tBuOK and NaH, which considerably increases the reaction rate under mild conditions, is reported. The β,γ-unsaturated aldehyde, resulting from the α-alkylation, is transformed in high yield into the corresponding allyl acetate via a lead(IV) acetate-mediated oxidative fragmentation. This strategy could be used for the construction of the carbon skeleton of a wide variety of alkyl or arylterpenoids.

[1,3]-Claisen rearrangement via removable functional group mediated radical stabilization

A thermal O-to-C [1,3]-rearrangement of α-hydroxy acid derived enol ethers was achieved under mild conditions. The 2-aminothiophenol protection of carboxylic acids facilitates formation of the [1,3] precursor and its thermal rearrangement via stabilization of a radical intermediate. Experimental and theoretical evidence for dissociative radical pair formation, its captodative stability via aminothiophenol, and a unique solvent effect are presented. The aminothiophenol was deprotected from rearrangement products as well as after derivatization to useful synthons.

Carbocation Catalyzed Bromination of Alkyl Arenes, a Chemoselective sp3 vs. sp2 C?H functionalization.

The versatility of the trityl cation (TrBF4) as a highly efficient Lewis acid organocatalyst is demonstrated in a light induced benzylic brominaion of alkyl-arenes under mild conditions. The reaction was conducted at ambient temperature under common hood light (55 W fluorescent light) with catalyst loadings down to 2.0 mol% using N-bromosuccinimide (NBS) as the brominating agent. The protocol is applicable to an extensive number of substrates to give benzyl bromides in good to excellent yields. In contrast to most previously reported strategies, this protocol does not require any radical initiator or extensive heating. For electron-rich alkyl-arenes, the trityl ion catalyzed bromination could be easily switched between benzylic sp3 C?H functionalization and arene sp2 C?H functionalization by simply alternating the solvent. This chemoselective switch allows for high substrate control and easy preparation of benzyl bromides and bromoarenes, respectively. The chemoselective switch was also applied in a one-pot reaction of 1-methylnaphthalene for direct introduction of both sp3 C?Br and sp2 C?Br functionality. (Figure presented.).

Visible-Light-Driven Oxidative Mono- and Dibromination of Benzylic sp 3 C-H Bonds with Potassium Bromide/Oxone at Room Temperature

Benzylic sp 3 C-H bonds have been successfully brominated with potassium bromide by using Oxone as an oxidant in water/dichloromethane under visible light at room temperature. Toluene, ethylbenzene and other alkylbenzenes bearing an electron-withdrawing group, such as Br, Cl, COMe, CO 2 Et, CO 2 H, CN or NO 2, provide the corresponding benzylic monobromides in good to excellent yields in this reaction. Dibromides can also be produced in the presence of excess potassium bromide in a prolonged reaction time. Control of the illuminance of visible light (~500 lux) is crucial to achieving both high yield and high selectivity in these brominations. Mono- and difluorides can be conveniently prepared through nucleophilic substitutions of the benzylic bromides with potassium fluoride.

Substituent Dependent Optical Properties of p-phenyl Substituted ethenyl-E-thiophenes

Various electron donor and acceptor substituted (NO2, CN, Cl, H, OCH3, NH2) p-phenyl ethenyl-E- thiophenes (1–6) were synthesized and substituent dependent optical properties (dipole moment, transition dipole moment, oscillator strength, optical band gap, hyperpolarizability) were studied using Solvatochromism and Density functional theory. It is shown that thiophene acts as a weak electron donor in presence of an electron withdrawing p-phenyl substituent (NO2, CN, Cl), whereas thiophene acts as a weak electron acceptor in presence of an electron donating p-phenyl substituent (OCH3, NH2). In comparison to ethenyl thiophene 4, the HOMO-LUMO energy band gap is decreased upon increasing the electron donating or electron withdrawing capacity of p-phenyl substituent. From the excited state dipole moment calculation, it is shown that the excited state is highly dipolar for nitro and amino compounds 1 and 6, whereas compounds 2–5 show a non-polar excited state. As compared to the ethenyl thiophene 4, the first hyperpolarizability (β) increases upon substitution either with a strong electron withdrawing or strong electron donating p-phenyl substituent. A large β value is found for p-nitro phenyl ethenyl-E-thiophene and p-amino phenyl ethenyl-E- thiophene. Overall, these studies provide useful information in understanding the optical properties of phenyl and heterocyclic based ethenyl systems.

One-pot synthesis of α,β-epoxy ketones through domino reaction between alkenes and aldehydes catalyzed by proline based chiral organocatalysts

Proline based metal free organocatalysts were developed by using a new approach for the synthesis of epoxide derivatives through a domino reaction. This domino reaction (oxidative coupling) allows a direct access to epoxides from various alkenes and aldehydes through C-H functionalization and C-C/C-O bond formation. The catalytic efficiencies of the newly synthesized organocatalysts were also determined by domino reaction in the presence of various functional groups containing aldehyde and alkene derivatives with very good yields (up to 95%) and ee's (up to 99%).

Benzylsulfanyl benzo-heterocycle amides and hydrazones as new agents against drug-susceptible and resistant: Mycobacterium tuberculosis

A series of benzylsulfanyl benzo-heterocycle amides and hydrazones were synthesized and evaluated for anti-tubercular activities. The isonicotinyl hydrazone derivatives 12d, 12e and 12f exhibited good anti-tubercular activity against Mycobacterium tuberculosis H37Rv (ATCC #27294) with MIC values of 0.23, 0.24 and 0.24 μM, respectively, and were also active against SDR-TB, MDR-TB and XDR-TB. More importantly, compound 12e also showed low cytotoxicity and good metabolic stability, and could significantly reduce the mycobacterial burden in a mouse model infected with autoluminescent H37Ra strain, which may serve as a lead compound for further development.

An efficient and selective method for the iodination and bromination of alcohols under mild conditions

A straightforward and effective procedure for the conversion of a variety of alcohols into the corresponding alkyl iodides and bromides is described using KX/P2O5 (X = I, Br). The reactions were easily carried out in acetonitrile under mild conditions. Using this method, the selective conversion of benzylic alcohols in the presence of aliphatic alcohols was achieved.

One-Step Synthesis of Substituted Benzofurans from ortho- Alkenylphenols via Palladium-Catalyzed C=H Functionalization

A dehydrogenative oxygenation of C(sp2)=H bonds with intramolecular phenolic hydroxy groups has been developed, which provides a straightforward and concise access to structurally diversely benzofurans from ortho-alkenylphenols. The reaction is catalyzed by palladium on carbon (Pd/C) without any oxidants and sacrificing hydrogen acceptors.

Palladium-catalyzed silylation reaction between benzylic halides and silylboronate

An efficient Pd-catalyzed silylation reaction of benzylic halides with silylboronate is reported. In this reaction, primary and secondary benzylic halides could react well with silylboronates to afford benzylic silanes. This reaction accommodates a broad substrate scope and proceeds smoothly under very mild reaction conditions. The corresponding products could be obtained in moderate to high yields and with stereospecificity.