4-Acetamidobenzoic acid

Base Information

• Chemical Name: 4-Acetamidobenzoic acid
• CAS No.: 556-08-1
• Molecular Formula: C9H9NO3
• Molecular Weight: 179.175
• Hs Code.: 29242995
• European Community (EC) Number: 209-114-7
• NSC Number: 760374,4002
• UNII: 04Z20NMK31
• DSSTox Substance ID: DTXSID5024392
• Nikkaji Number: J95.026B
• Wikipedia: Acedoben
• Wikidata: Q2823222
• NCI Thesaurus Code: C74109
• Metabolomics Workbench ID: 56651
• ChEMBL ID: CHEMBL112687
• Mol file: 556-08-1.mol

Synonyms:4-acetamidobenzoic acid;4-acetamidobenzoic acid, sodium salt;Acedoben;acetyl-p-aminobenzoic acid;Fibroderm;p-acetamidobenzoic acid;PACBA;para-acetamidobenzoic acid

Chemical Property of 4-Acetamidobenzoic acid

Chemical Property:

• Appearance/Colour: white to beige in colour crystalline powder
• Vapor Pressure: 1.66E-08mmHg at 25°C
• Melting Point: 259-262 °C (dec.)(lit.)
• Refractive Index: 1.5600 (estimate)
• Boiling Point: 439.6 °C at 760 mmHg
• PKA: pK1: 4.28 (25°C)
• Flash Point: 219.7 °C
• PSA: 66.40000
• Density: 1.326 g/cm³
• LogP: 1.41620
• Storage Temp.: Store below +30°C.
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: <0.1 g/100 mL at 21℃
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 179.058243149
• Heavy Atom Count: 13
• Complexity: 207

Purity/Quality:

99% ^*data from raw suppliers

Acedoben ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Aminobenzoic Acids
• Canonical SMILES: CC(=O)NC1=CC=C(C=C1)C(=O)O
• Uses: immune stimulant (component) Acedoben is the acetylated derivative of p-aminobenzoic acid (PABA). Acedoben is a metabolite of the anesthetic Benzocaine (B202970).
• Therapeutic Function: Antiviral

Technology Process of 4-Acetamidobenzoic acid

There total 66 articles about 4-Acetamidobenzoic acid 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: 98.0%

para-acetamidobenzaldehyde (122-85-0) → p-(acetylamino)benzoic acid (556-08-1)

Guidance literature:

With sodium chlorite; sodium dihydrogenphosphate; dihydrogen peroxide; In methanol; water; acetonitrile; at 10 ℃; for 1h;

DOI:10.1021/jo00354a037

Reference yield: 97.9%

4-Methylacetanilide (103-89-9) → p-(acetylamino)benzoic acid (556-08-1)

Guidance literature:

With oxygen; cobalt(II) acetate; sodium bromide; In acetic acid; at 90 ℃; for 1h; Product distribution; Kinetics; var. concentration of reagents, var. temperature, var. time;

Reference yield: 91.0%

4-amino-benzoic acid (150-13-0,159246-81-8,8014-65-1) + acetyl chloride (75-36-5) → p-(acetylamino)benzoic acid (556-08-1)

Guidance literature:

In N,N-dimethyl-formamide; for 3h; Heating;

DOI:10.1016/0223-5234(96)88270-5

upstream raw materials:

N-[4-(chloroacetyl)phenyl]acetamide

acetic acid-[4-(trans-2-chloro-vinyl)-anilide]

acetic acid-(4-trichloroacetyl-anilide)

acetic anhydride

Downstream raw materials:

4-methoxycarbonyl aniline

p-aminoethylbenzoate

1,4-dihydrobenzoic acid

3-nitro-4-acetamidobenzoic acid

Refernces

• 1、 Tel'nov et al.. "-". . . Retrieved 1975.
• 2、 Zeynizadeh, Behzad,Mohammad Aminzadeh, Farkhondeh,Mousavi, Hossein. "Chemoselective reduction of nitroarenes, N-acetylation of arylamines, and one-pot reductive acetylation of nitroarenes using carbon-supported palladium catalytic system in water". . p. 3289 - 3312. Retrieved 2021/05/11.
• 3、 Kim, Seongwoo,Lee, Ha-Eun,Suh, Jong-Min,Lim, Mi Hee,Kim, Min. "Sequential Connection of Mutually Exclusive Catalytic Reactions by a Method Controlling the Presence of an MOF Catalyst: One-Pot Oxidation of Alcohols to Carboxylic Acids". supporting information. p. 17573 - 17582. Retrieved 2020/12/22.