55-21-0 Usage
Description
Benzamide, also known as a carbonic acid amide of benzoic acid, is an aromatic amide that consists of benzene bearing a single carboxamido substituent. It appears as off-white crystals or powder and exhibits an angle of about 15° with the plane of the amide group, indicating that the benzamide molecule is not flat. Benzamide is combustible, slightly soluble in water, and soluble in many organic solvents. It is the parent of the class of benzamides and has a freezing/melting point of 132-133°C.
Uses
1. Used in Semiconductor Research:
Benzamide is used as a study material to understand the mechanism of photocatalytic decomposition of aqueous solutions of acetic acid, acetamide, and acetonitrile in the presence of semiconductors.
2. Used as a Nicotinamide-Mimic PARP Inhibitor and Neuroprotectant:
Benzamide serves as a nictoinamide-mimic PARP inhibitor and neuroprotectant, playing a role in the development of pharmaceuticals for various applications.
3. Used in Biotransformation Studies:
Benzamide is employed to develop a robust screening method to study biotransformations using (+)-gamma-lactamase enzyme.
4. Used in the Determination of Glycine:
Benzamide is utilized in the determination of glycine, an important amino acid.
5. Used as an Intermediate in Organic Synthesis:
Benzamide is used as an intermediate in organic synthesis, contributing to the production of various compounds.
6. Used in Pharmaceutical Production:
Benzamide is employed in the production of pharmaceuticals, including radioiodinated benzamides for potential therapeutic applications in patients with metastatic malignant melanoma.
7. Used in Dye Production:
Benzamide is also used in the production of dyes, showcasing its versatility in different industries.
Safety Profile
Moderately toxic by ingestion andintraperitoneal routes. When heated to decomposition itemits toxic fumes of NOx.
Preparation
Take a mixture of 5 ml concentrated ammonia and 5 ml water in a conical flask with a well-fitting cork. Add 2 ml (2.4 g.) benzoyl chloride, cork the flask and shake vigorously. Heat generates due to the reaction, hence hold the cork securely during shaking. After 15 min not even a trace of oily benzoyl chloride remains. Filter the fine flakes, wash with cold water and recrystallise from hot water: yield, 1-5 g. Colourless crystals of benzamide.
Preparation of benzamide from benzoyl chloride
Synthesis Reference(s)
The Journal of Organic Chemistry, 59, p. 4114, 1994 DOI: 10.1021/jo00094a021Chemical and Pharmaceutical Bulletin, 39, p. 1152, 1991 DOI: 10.1248/cpb.39.1152Synthetic Communications, 20, p. 1445, 1990 DOI: 10.1080/00397919008052860
Reactivity Profile
Benzamide reacts with azo and diazo compounds to generate toxic gases. Forms flammable gases with strong reducing agents. Mixing with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. Combustion generates toxic mixed oxides of nitrogen (NOx).
Hazard
Depresses the central nervous system;
toxic.
Fire Hazard
Flash point data for Benzamide are not available, however Benzamide is probably combustible.
Biochem/physiol Actions
Inhibits poly(ADP-ribose) polymerase (PARP).
Clinical Use
Benzamide on radioiodination by different labeling procedures results in large-scale production of radioiodinated benzamides having potential therapeutic application for patients with metastatic malignant melanoma.
Potential Exposure
Benzamide is used in organic
synthesis.
Purification Methods
Crystallise it from hot water (about 5mL/g), EtOH or 1,2-dichloroethane, and dry it in air. It has also been crystallised from dilute aqueous NH3, H2O, Me2CO, then *C6H6 using a Soxhlet extractor. Dry it in an oven at 110o for 8hours and store in a desiccator over 99% H2SO4. [Bates & Hobbs J Am Chem Soc 73 2151 1951, Beilstein 9 IV 725.]
Check Digit Verification of cas no
The CAS Registry Mumber 55-21-0 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 5 respectively; the second part has 2 digits, 2 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 55-21:
(4*5)+(3*5)+(2*2)+(1*1)=40
40 % 10 = 0
So 55-21-0 is a valid CAS Registry Number.
InChI:InChI=1/C7H7NO/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H2,8,9)
55-21-0Relevant articles and documents
Nitrogen Atom Transfer Catalysis by Metallonitrene C?H Insertion: Photocatalytic Amidation of Aldehydes
Schmidt-R?ntsch, Till,Verplancke, Hendrik,Lienert, Jonas N.,Demeshko, Serhiy,Otte, Matthias,Van Trieste, Gerard P.,Reid, Kaleb A.,Reibenspies, Joseph H.,Powers, David C.,Holthausen, Max C.,Schneider, Sven
supporting information, (2022/01/20)
C?H amination and amidation by catalytic nitrene transfer are well-established and typically proceed via electrophilic attack of nitrenoid intermediates. In contrast, the insertion of (formal) terminal nitride ligands into C?H bonds is much less developed and catalytic nitrogen atom transfer remains unknown. We here report the synthesis of a formal terminal nitride complex of palladium. Photocrystallographic, magnetic, and computational characterization support the assignment as an authentic metallonitrene (Pd?N) with a diradical nitrogen ligand that is singly bonded to PdII. Despite the subvalent nitrene character, selective C?H insertion with aldehydes follows nucleophilic selectivity. Transamidation of the benzamide product is enabled by reaction with N3SiMe3. Based on these results, a photocatalytic protocol for aldehyde C?H trimethylsilylamidation was developed that exhibits inverted, nucleophilic selectivity as compared to typical nitrene transfer catalysis. This first example of catalytic C?H nitrogen atom transfer offers facile access to primary amides after deprotection.
Amide bond formation in aqueous solution: Direct coupling of metal carboxylate salts with ammonium salts at room temperature
Nielsen, John,Tung, Truong Thanh
supporting information, p. 10073 - 10080 (2021/12/10)
Herein, we report a green, expeditious, and practically simple protocol for direct coupling of carboxylate salts and ammonium salts under ACN/H2O conditions at room temperature without the addition of tertiary amine bases. The water-soluble coupling reagent EDC·HCl is a key component in the reaction. The reaction runs smoothly with unsubstituted/substituted ammonium salts and provides a clean product without column chromatography. Our reaction tolerates both carboxylate (which are unstable in other forms) and amine salts (which are unstable/volatile when present in free form). We believe that the reported method could be used as an alternative and suitable method at the laboratory and industrial scales. This journal is
A mild and selective Cu(II) salts-catalyzed reduction of nitro, azo, azoxy, N-aryl hydroxylamine, nitroso, acid halide, ester, and azide compounds using hydrogen surrogacy of sodium borohydride
Kalola, Anirudhdha G.,Prasad, Pratibha,Mokariya, Jaydeep A.,Patel, Manish P.
supporting information, p. 3565 - 3589 (2021/10/12)
The first mild, in situ, single-pot, high-yielding well-screened copper (II) salt-based catalyst system utilizing the hydrogen surrogacy of sodium borohydride for selective hydrogenation of a broad range of nitro substrates into the corresponding amine under habitancy of water or methanol like green solvents have been described. Moreover, this catalytic system can also activate various functional groups for hydride reduction within prompted time, with low catalyst-loading, without any requirement of high pressure or molecular hydrogen supply. Notably, this system explores a great potential to substitute expensive traditional hydrogenation methodologies and thus offers a greener and simple hydrogenative strategy in the field of organic synthesis.