10388-19-9

Basic information

• Product Name: 3-IODOBENZAMIDE
• Synonyms: 3-IODOBENZAMIDE;3-iodo-benzamid;m-iodo-benzamid
• CAS NO: 10388-19-9
• Molecular Formula: C₇H₆INO
• Molecular Weight: 247.03
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Anilines, Amides & Amines;Iodine Compounds
• Mol File: 10388-19-9.mol

Chemical Properties

• Melting Point: 187 °C
• Boiling Point: 322.5 °C at 760 mmHg
• Flash Point: 148.9 °C
• Appearance: /
• Density: 1.897 g/cm³
• Vapor Pressure: 0.000278mmHg at 25°C
• Refractive Index: 1.66
• Storage Temp.: 2-8°C
• Solubility: soluble in Dimethylformamide
• CAS DataBase Reference: 3-IODOBENZAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-IODOBENZAMIDE(10388-19-9)
• EPA Substance Registry System: 3-IODOBENZAMIDE(10388-19-9)

Safety Data

• Hazardous Substances Data: 10388-19-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Iodobenzamide is used as a key intermediate for the synthesis of various pharmaceutical compounds. Its role in the production of biologically active molecules makes it an essential component in the development of new drugs for the treatment of a range of diseases.
Used in Agrochemical Industry:
In the agrochemical sector, 3-Iodobenzamide is employed as a building block in the synthesis of agrochemical compounds. Its contribution to the creation of effective agrochemicals is vital for agricultural productivity and pest control.
Used in Medicinal Chemistry:
3-Iodobenzamide is used as a research tool in medicinal chemistry, where it aids in the exploration and development of novel drug candidates. Its versatility as a chemical reagent is crucial for advancing the field and discovering new therapeutic options.

InChI:InChI=1/C7H6INO/c8-6-3-1-2-5(4-6)7(9)10/h1-4H,(H2,9,10)

Upstream product

• 55-21-0 benzamide 
• 57-13-6 urea 
• 618-51-9 3-Iodobenzoic acid 
• 625-95-6 3-Iodotoluene 
• 696-40-2 3-iodobenzylamine 
• 3544-24-9 3-Aminobenzamide 
• 79-37-8 oxalyl dichloride 
• 100-47-0 benzonitrile 
• 1711-10-0 3-iodobenzoyl chloride 
• 60-29-7 diethyl ether 
• 696-41-3 m-iodobenzaldehyde 

Downstream Products

• 269411-42-9 ethyl (E)-3-(3-carbamoylphenyl)acrylate 
• 106748-26-9 3-iodothiobenzamide 
• 1262882-24-5 3-(6-methoxy-1H-indol-2-yl)benzamide 
• 269411-81-6 3-[2-(methoxy-methyl-carbamoyl)-vinyl]benzamide 
• 69113-59-3 3-iodobenzonitrile 
• 52059-68-4 5-(3-Iodphenyl)-1,3,4-oxathiazol-2-on 
• 138385-43-0 3-<1-deoxy-2,3-O-(1-methyl-1,1-ethanediyl)-β-D-ribofuranosyl>benzamide 
• 1270044-34-2 10-([1,1′-biphenyl]-4-yl)benzo[h]quinoline 
• 331-28-2 m-[(trifluoromethyl)thio]benzamide 

Relevant articles and documents

Rapid microwave promoted Sonogashira coupling reactions on solid phase

A microwave-enhanced, rapid, and efficient solid-phase version of the Sonogashira reaction is presented. It has been applied to the coupling of aryl iodides and bromides with various acetylene derivatives giving excellent yields in 15-25 min. The scopes of homogeneous, solventless, and solid-phase conditions for Sonogashira coupling of aryl halides are compared.

Tetraalkylammonium dichloroiodates as iodinating agents: Absence of activity in solid phases and superelectrophilic activity in sulfuric acid

In contrast to published results, tetraalkylammonium dichloroiodates (Alk4N+ICl2-) cannot be iodinating reagents for arenes in solvent-free conditions. Nevertheless, tetraalkylammonium dichloroiodates in sulfuric acid solutions or in the presence of Ag 2SO4 in H2SO4 possess superelectrophilic properties and act as very convenient and efficient iodinating agents for deactivated arenes. Georg Thieme Verlag Stuttgart.

Transition metal-free synthesis of primary amides from aldehydes and hydroxylamine hydrochloride

Primary aromatic amides can be synthesized from aldehydes and hydroxylamine hydrochloride in the presence of Cs2CO3. Various aromatic aldehydes (include some heteroaromatic aldehydes) are able to generate the corresponding aromatic amides in moderate to excellent yields.

Visible light-mediated synthesis of amides from carboxylic acids and amine-boranes

Here, a photocatalytic deoxygenative amidation protocol using readily available amine-boranes and carboxylic acids is described. This approach features mild conditions, moderate-to-good yields, easy scale-up, and up to 62 examples of functionalized amides with diverse substituents. The synthetic robustness of this method was also demonstrated by its application in the late-stage functionalization of several pharmaceutical molecules.

Efficient nitriding reagent and application thereof

The invention discloses an efficient nitriding reagent and application thereof, wherein the nitriding reagent comprises nitrogen oxide, an active agent, a reducing agent and an organic solvent. By applying the nitriding reagent, nitrogen-containing compounds such as amide, nitrile and the like can be produced, and the method is simple in condition, low in waste discharge amount and simple in reaction equipment.

Nitromethane as a nitrogen donor in Schmidt-type formation of amides and nitriles

The Schmidt reaction has been an efficient and widely used synthetic approach to amides and nitriles since its discovery in 1923. However, its application often entails the use of volatile, potentially explosive, and highly toxic azide reagents. Here, we report a sequence whereby triflic anhydride and formic and acetic acids activate the bulk chemical nitromethane to serve as a nitrogen donor in place of azides in Schmidt-like reactions. This protocol further expands the substrate scope to alkynes and simple alkyl benzenes for the preparation of amides and nitriles.

Transamidation for the Synthesis of Primary Amides at Room Temperature

Various primary amides have been synthesized using the transamidation of various tertiary amides under metal-free and mild reaction conditions. When (NH4)2CO3 reacts with a tertiary amide bearing an N-electron-withdrawing substituent, such as sulfonyl and diacyl, in DMSO at 25 °C, the desired primary amide product is formed in good yield with good funcctional group tolerance. In addition, N-tosylated lactam derivatives afforded their corresponding N-tosylamido alkyl amide products via a ring opening reaction.

Chemoselective Synthesis of Aryl Ketones from Amides and Grignard Reagents via C(O)-N Bond Cleavage under Catalyst-Free Conditions

Conversion of a wide range of N-Boc amides to aryl ketones was achieved with Grignard reagents via chemoselective C(O)-N bond cleavage. The reactions proceeded under catalyst-free conditions with different aryl, alkyl, and alkynyl Grignard reagents. α-Ketoamide was successfully converted to aryl diketones, while α,β-unsaturated amide underwent 1,4-addition followed by C(O)-N bond cleavage to provide diaryl propiophenones. N-Boc amides displayed higher reactivity than Weinreb amides with Grignard reagents. A broad substrate scope, excellent yields, and quick conversion are important features of this methodology.

Base promoted peroxide systems for the efficient synthesis of nitroarenes and benzamides

A useful and efficient approach for the synthesis of nitroarenes from several aromatic amines (including heterocycles) using peroxide and base has been developed. This oxidative reaction is very easy to handle and afforded the products in good yields. Formation of benzamides from benzylamine was also successfully carried out with this metal-free catalytic system in good to excellent yields.

Direct Transformation of Arylamines to Aryl Halides via Sodium Nitrite and N-Halosuccinimide

A one-pot universal approach for transforming arylamines to aryl halides via reaction with sodium nitrite (NaNO2) and N-halosuccinimide (NXS) in DMF at room temperature under metal- and acid-free condition is described. This new protocol that is complementary to the Sandmeyer reaction, is suggested to involve the in situ generation of nitryl halide induce nitrosylation of aryl amine to form the diazo intermediate which is halogenated to furnish the aryl halide.