Salicylamide

Base Information

• Chemical Name: Salicylamide
• CAS No.: 65-45-2
• Molecular Formula: C7H7NO2
• Molecular Weight: 137.138
• Hs Code.: 2924.29
• European Community (EC) Number: 200-609-3
• NSC Number: 757318,3115
• UNII: EM8BM710ZC
• DSSTox Substance ID: DTXSID3021726
• Nikkaji Number: J1.408G
• Wikipedia: Salicylamide
• Wikidata: Q2496906
• NCI Thesaurus Code: C80566
• RXCUI: 9518
• Metabolomics Workbench ID: 43714
• ChEMBL ID: CHEMBL27577
• Mol file: 65-45-2.mol

Synonyms:salicylamide;salicylamide sodium;salicylamide sulfate;salicylamide, 3H-labeled;salicylamide, calcium (2:1) salt;salicylamide, monosodium salt

Chemical Property of Salicylamide

Chemical Property:

• Appearance/Colour: white or light pink crystals or powder
• Vapor Pressure: 0.000195mmHg at 25°C
• Melting Point: 140-144 °C(lit.)
• Refractive Index: 1.612
• Boiling Point: 318.3 °C at 760 mmHg
• PKA: pKa 8.13(H2O t = 37) (Uncertain)
• Flash Point: 146.3 °C
• PSA: 63.32000
• Density: 1.286 g/cm³
• LogP: 1.19140
• Storage Temp.: Refrigerator
• Solubility.: methanol: 0.1 g/mL, clear
• Water Solubility.: <0.1 g/100 mL at 20℃
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 137.047678466
• Heavy Atom Count: 10
• Complexity: 136

Purity/Quality:

99% ^*data from raw suppliers

Salicylamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38-20/21/22
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C(=C1)C(=O)N)O
• Description: Salicylamide is less acidic (pKa 8.2) than other salicylic acid derivatives. Although poorly soluble in water, stable solutions can be formed at pH 9 through ionization of the phenolic group. It is absorbed from the GI tract on oral administration and is rapidly metabolized to inactive metabolites by intestinal mucosa, but not by hydrolysis. Activity appears to reside in the intact molecule. Salicylamide is approximately 40 to 55% plasma protein bound, and it competes with other salicylates and acetaminophen for glucuronide conjugation, decreasing the extent of conjugation of these other drugs.
• Uses: Medicine (analgesic). salicylamide is an analgesic, fungicide, and anti-inflammatory ingredient used to soothe the skin. Salicylamide is an aromatic amide. Salicylamide is used in combination with both aspirin and caffeine in the over-the-counter pain remedies. It is used as an analgesic and as an antipyretic.
• Clinical Use: Whereas salicylamide is reported to be as effective as aspirin as an analgetic/antipyretic and is effective in relieving pain associated with arthritic conditions, it does not appear to possess useful anti-inflammatory activity. Thus, indications for the treatment of arthritic disease states are unwarranted, and its use is restricted to the relief of minor aches and pain at a dosage of 325 to 650 mg three or four times per day. Its effects in humans are not reliable, however, and its use is not widely recommended.

Technology Process of Salicylamide

There total 125 articles about Salicylamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 50.0%

2-Cyanophenylboronic acid (138642-62-3) → salicylonitrile (611-20-1) + salicylamide (65-45-2)

Guidance literature:

With menadione; sodium hydrogencarbonate; sodium L-ascorbate; In ethanol; water; at 20 ℃; for 24h; under 760.051 Torr; pH=8.5; Overall yield = 94 %; Darkness; Green chemistry;

DOI:10.1039/c5cc01519g

Reference yield: 35.0%

benzamide (55-21-0,27208-38-4) → 3-hydroxybenzamide (618-49-5) + p-hydroxybenzamide (619-57-8) + 2-benzoylaminobenzamide (18543-22-1) + salicylamide (65-45-2)

Guidance literature:

With (difluoroboryl)dimethylglyoximatocobalt(II) bis(acetonitrile); water; 3-cyano-1-methylquinolinium cation; In acetonitrile; at 20 ℃; for 5h; Inert atmosphere; Irradiation; Green chemistry;

Reference yield: 18.0%

1-cyanobenzene oxide-oxepin (73654-43-0) → salicylonitrile (611-20-1) + salicylamide (65-45-2) + phenol (108-95-2,27073-41-2)

Guidance literature:

In tetrahydrofuran; water; for 48h; Heating; pH=7;

DOI:10.1021/jo00317a036

upstream raw materials:

1,3-benzoxazine-2,4-dione

aniline

2-methyl-2,3-dihydro-4H-1,3-benzoxazin-4-one

2-isopropyl-2,3-dihydro-4H-benzo[e][1,3]oxazin-4-one

Downstream raw materials:

2-hydroxy-N-morpholin-4-ylmethyl-benzamide

O-acetylsalicylamide

salacetamide

2-hydroxy-N-(2-hydroxybenzoyl)benzamide

Refernces

• 1、 Wang, Dengfeng,Zhang, Xuelan,Wei, Wei,Sun, Yuhan. "Mg/Al mixed oxides: Heterogeneous basic catalysts for the synthesis of salicylamide from urea and phenol". . p. 159 - 162. Retrieved 2012.
• 2、 Bahreininejad, Mohammad Hasan,Moeinpour, Farid. "Green and efficient Beckmann rearrangement by Cu(II) contained nano-silica triazine based dendrimer in water". . p. 893 - 901. Retrieved 2021/01/12.
• 3、 Vyas, Komal M.,Mandal, Poulami,Singh, Rinky,Mobin, Shaikh M.,Mukhopadhyay, Suman. "Arene-ruthenium(II)-phosphine complexes: Green catalysts for hydration of nitriles under mild conditions". . . Retrieved 2019/12/11.