3145-86-6

Basic information

• Product Name: P-NITROBENZYL IODIDE
• Synonyms: P-NITROBENZYL IODIDE;alpha-iodo-p-nitrotoluene;4-NitrobenzylIodide,>99%;1-(Iodomethyl)-4-nitrobenzene;1-Iodomethyl-4-nitrobenzene;1-Nitro-4-(iodomethyl)benzene;4-(Iodomethyl)-1-nitrobenzene;4-Nitrobenzyl iodide
• CAS NO: 3145-86-6
• Molecular Formula: C₇H₆INO₂
• Molecular Weight: 263.03
• EINECS: 221-557-8
• Mol File: 3145-86-6.mol

Chemical Properties

• Melting Point: 124 °C
• Boiling Point: 327.5°Cat760mmHg
• Flash Point: 151.9°C
• Appearance: /
• Density: 1.928g/cm³
• CAS DataBase Reference: P-NITROBENZYL IODIDE(CAS DataBase Reference)
• NIST Chemistry Reference: P-NITROBENZYL IODIDE(3145-86-6)
• EPA Substance Registry System: P-NITROBENZYL IODIDE(3145-86-6)

Safety Data

• Hazardous Substances Data: 3145-86-6(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
P-Nitrobenzyl iodide is used as a reagent in organic synthesis for its ability to facilitate the formation of a wide range of organic compounds. Its versatility in this application is crucial for the development of new chemical entities.
Used in Pharmaceutical Production:
In the pharmaceutical industry, P-Nitrobenzyl iodide is used as a precursor for the production of various pharmaceuticals. Its role in the synthesis of medicinal compounds is vital for the creation of new drugs and the improvement of existing ones.
Used in Agrochemical Synthesis:
P-Nitrobenzyl iodide is also utilized in the synthesis of agrochemicals, contributing to the development of new pesticides and other agricultural chemicals that are essential for crop protection and yield enhancement.
Used in Dye Production:
In the dye industry, P-Nitrobenzyl iodide serves as a precursor for the production of various dyes. Its involvement in dye synthesis is important for the creation of new colorants used in textiles, printing, and other applications.
Used in Chemical Protection:
P-Nitrobenzyl iodide is used as a protecting agent for alcohols and amines in organic chemistry reactions. This application is crucial for preventing unwanted side reactions, thereby ensuring the successful synthesis of target compounds.

Upstream product

• 99-99-0 1-methyl-4-nitrobenzene 
• 64-17-5 ethanol 
• 100-14-1 4-nitrobenzyl chloride 
• 14856-73-6 4-nitrobenzyl trimethylsilyl ether 
• 500-11-8 4-nitrobenzyl fluoride 
• 104-03-0 4-nitrobenzeneacetic acid 
• 139884-17-6 1-((methoxymethoxy)methyl)-4-nitrobenzene 
• 1058649-42-5 4-nitro-1-[(ethoxymethoxy)methyl]benzene 
• 555-16-8 4-nitrobenzaldehdye 
• 70207-45-3 (4-nitrobenzyl)phosphoric acid diethyl ester 
• 18483-99-3 2-(4-nitrobenzyloxy)tetrahydro-2H-pyran 
• 29540-08-7 tert-butyl p-nitrophenylperacetate 
• 1950-78-3 p-toluenesulfonyl iodide 
• 100-11-8 1-bromomethyl-4-nitro-benzene 

Downstream Products

• 109771-12-2 dimethyl (2R,3R)-2-O-(p-nitrobenzyl)tartrate 
• 7409-30-5 p-nitrobenzylamine 
• 555-16-8 4-nitrobenzaldehdye 
• 619-93-2 (Z)-4,4'-dinitrostilbene 
• 736-31-2 trans-4,4'-dinitrostilbene 
• 56679-04-0 bis(p-nitrobenzyl)ether 
• 14688-37-0 cis-p,p'-dinitrostilbene oxide 
• 100-11-8 1-bromomethyl-4-nitro-benzene 
• 100-14-1 4-nitrobenzyl chloride 
• 99-99-0 1-methyl-4-nitrobenzene 
• 118643-64-4 (4-Nitro-benzyl)-phenyl-phosphinic acid (2S,3R)-4-iodo-2,3-dimethoxy-butyl ester 
• 118643-68-8 (4-Nitro-benzyl)-phenyl-phosphinic acid (4S,5R)-5-iodomethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester 
• 143784-71-8 di(p-nitrobenzyl) methoxycarbonylphosphonate 
• 136794-71-3 4'-O-demethyl-4β-[(4''-nitrobenzyl)amino]-4-desoxypodophyllotoxin 

Relevant articles and documents

Solvent-free conversion of alcohols into iodides with NaI supported on KSF clay

A variety of allylic, benzylic, primary, and secondary saturated alcohols have been converted into the corresponding iodides using NaI supported on KSF clay. Selective conversion of allylic and benzylic alcohols in the presence of primary and secondary saturated alcohols has also been demonstrated. Copyright Taylor & Francis, Inc.

Iminophosphorane-mediated regioselective umpolung alkylation reaction of α-iminoesters

Umpolung reactions of imines, especially the asymmetric reactions, have been extensively studied as they provide access to important chiral amines in an efficient manner. The reactions studied range from simple Michael reactions to several kinds of other reactions such as the aza-benzoin reaction, aza-Stetter reaction, addition with MBH carbonate, and Ir-catalysed allylation. Herein, we report the first umpolung alkylation reaction of α-iminoesters with alkyl halides mediated by iminophosphorane as an organic superbase. The desired products were obtained in up to 82% yield with almost perfect regioselectivities. The key to the regioselectivity of this reaction was the use of 4-trifluoromethyl benzyl imines as a substrate. The products were successfully derivatised into the more functionalised molecules in good yields.

Selective iodination of alcohols with NaI/Amberlyst 15 in acetonitrile

A simple and effective procedure for conversion of primary, secondary, allylic and benzylic alcohols into the corresponding iodides is described using NaI/Amberlyst 15 in acetonitrile at room temperature. Selective conversion of benzylic alcohols in the presence of saturated alcohols into the corresponding benzylic iodides is achieved under these conditions.

Enhancing the leaving group ability of alkyl fluorides: I/F exchange reactions mediated by LiI

The carbon–fluorine (C–F) bond is one of the strongest bonds in organic chemistry and generally inert toward nucleophilic substitution reactions. To overcome the relative inertness of the C–F bond, this work focused on the ability of simple lithium salts

Preparation method of benzyl iodide and derivatives thereof

The invention discloses a preparation method of benzyl iodide and derivatives thereof. The preparation method comprises the following steps: under the reduction action of sodium borohydride, a benzylalcohol compound shown as a formula I reacts with elemental iodine to obtain benzyl iodide shown as a formula II and derivatives thereof; in the formula I and the formula II, R represents one or moresubstituents on a benzene ring and is selected from at least one of aryl, substituted or unsubstituted alkyl, halogen and nitro. The preparation method of benzyl iodide and derivatives thereof is scientific and reasonable, sodium borohydride which is mild in reactivity, low in price and easily available is used as a reducing agent, and elemental iodine is convenient and easily available; in addition, the preparation method has the characteristics of simplicity and convenience in operation, high synthesis yield, easiness in product purification, environmental friendliness and the like.

Rhodium-Catalyzed Generation of Anhydrous Hydrogen Iodide: An Effective Method for the Preparation of Iodoalkanes

The preparation of anhydrous hydrogen iodide directly from molecular hydrogen and iodine using a rhodium catalyst is reported for the first time. The anhydrous hydrogen iodide generated was proven to be highly active in the transformations of alkenes, phenyl aldehydes, alcohols, and cyclic ethers to the corresponding iodoalkanes. Therefore, the present methodology not only has provided convenient access to anhydrous hydrogen iodide but also offers a practical preparation method for various iodoalkanes in excellent atom economy.

Catalytic Halogen Bond Activation in the Benzylic C-H Bond Iodination with Iodohydantoins

This letter presents the side-chain iodination of electron-deficient benzylic hydrocarbons at rt using N-hydroxyphthalimide (NHPI) as radical initiator and 1,3-diiodo-5,5-dimethylhydantoin and 3-iodo-1,5,5-trimethylhydantoin (3-ITMH) as iodine source. Addition of a carboxylic acid increased the reactivity due to complex formation with and activation of 3-ITMH by proton transfer and halogen bond formation. No SEAr reactions were observed under the employed reaction conditions. Our method enables convenient product isolation and gives 50-72% yields of isolated products.

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.]

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-Pot Transformation of Aliphatic Carboxylic Acids into N-Alkylsuccin-imides with NIS and NCS/NaI

Primary aliphatic carboxylic acids were treated with N-iodosuccinimide (NIS) in 1,2-dichloroethane to form the corresponding alkyl iodides under warming conditions. Based on these results, those aliphatic carboxylic acids were treated with NIS, followed by the reaction with K2CO3to give the corresponding N-alkylsuccinimides in good yields in one pot. Moreover, those aliphatic carboxylic acids were treated with N-chlorosuccinimide (NCS) and NaI, followed by the reaction with K2CO3to provide the corresponding N-alkylsuccinimides in good to moderate yields in one pot. By using the present method, successive treatment of primary aliphatic carboxylic acids (10 mmol) with NIS, K2CO3, and then hydrazine provided the corresponding decarboxylated primary amines in good yield.