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
• Article Data: 27

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

General Description

3-Iodobenzamide is a chemical compound with the molecular formula C7H6INO that is commonly used in the synthesis of various pharmaceutical and agrochemical compounds. It is a white to yellow crystalline solid that is soluble in organic solvents. 3-Iodobenzamide is often utilized as a building block in the production of biologically active molecules, and it is also a useful intermediate in the preparation of various heterocyclic compounds. Additionally, it has potential applications in the field of medicinal chemistry, particularly in the development of new drugs for the treatment of a range of diseases. Overall, 3-Iodobenzamide is a versatile and important chemical reagent with a variety of uses in the pharmaceutical and chemical industries.

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

Upstream product

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

Downstream Products

• 106748-26-9 3-iodothiobenzamide 
• 1262882-24-5 3-(6-methoxy-1H-indol-2-yl)benzamide 
• 69113-59-3 3-iodobenzonitrile 
• 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 

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.

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.

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.

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.