4740-24-3

Basic information

• Product Name: 4-(BUTYLAMINO)BENZOIC ACID
• Synonyms: LABOTEST-BB LT00000179;4-(BUTYLAMINO)BENZOIC ACID;4-n-butylaminobenzoic acid;4-(ButylaMino)benzoic acid 97%;262412_ALDRICH;Benzoic acid, 4-(butylamino)-;CBDivE_002387;MLS000776796
• CAS NO: 4740-24-3
• Molecular Formula: C₁₁H₁₅NO₂
• Molecular Weight: 193.24
• Product Categories: Aromatic Amino Acids;Peptide Synthesis;Unnatural Amino Acid Derivatives
• Mol File: 4740-24-3.mol
• Article Data: 11

Chemical Properties

• Melting Point: 149-151 °C(lit.)
• Boiling Point: 353.5°Cat760mmHg
• Flash Point: 167.6°C
• Appearance: /
• Density: 1.13g/cm³
• Vapor Pressure: 1.32E-05mmHg at 25°C
• Refractive Index: 1.577
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 4-(BUTYLAMINO)BENZOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(BUTYLAMINO)BENZOIC ACID(4740-24-3)
• EPA Substance Registry System: 4-(BUTYLAMINO)BENZOIC ACID(4740-24-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 4740-24-3(Hazardous Substances Data)

Usage

Description

4-(Butylamino)benzoic acid, also known as N-Butyl-4-aminobenzoic acid, is an organic compound derived from 4-aminobenzoic acid with a butyl group substitution on the nitrogen atom. This modification enhances its chemical properties and makes it a versatile intermediate for various applications.

Uses

Used in Pharmaceutical Industry:
4-(Butylamino)benzoic acid is used as an intermediate for the synthesis of 5-nitrothiophene derivatives, which possess antimicrobial activity. These derivatives are particularly effective against multidrug-resistant strains of Staphylococcus aureus, a significant concern in the medical field due to its resistance to many common antibiotics.
Used in Chemical Synthesis:
As an intermediate, 4-(Butylamino)benzoic acid can be utilized in the synthesis of various other compounds with different applications in the chemical industry. Its unique structure allows for further functionalization and modification, making it a valuable building block for the development of new materials and products.

InChI:InChI=1/C11H15NO2/c1-2-3-8-12-10-6-4-9(5-7-10)11(13)14/h4-7,12H,2-3,8H2,1H3,(H,13,14)

Upstream product

• 109-69-3 n-Butyl chloride 
• 150-13-0 4-amino-benzoic acid 
• 586-76-5 4-Bromobenzoic acid 
• 109-73-9 N-butylamine 
• 74-11-3 para-chlorobenzoic acid 
• 94-09-7 p-aminoethylbenzoate 
• 123-72-8 butyraldehyde 
• 62-23-7 4-nitro-benzoic acid 
• 109-65-9 1-bromo-butane 
• 111098-25-0 4-(1-Benzotriazol-1-yl-butylamino)-benzoic acid 
• 136-47-0 tetracaine hydrochloride 
• 94-32-6 ethyl 4-(N-butylamino)benzoate 

Downstream Products

• 93959-20-7 4-butylamino-benzoyl chloride 
• 1126-78-9 N-(n-butyl)aniline 
• 71839-12-8 N-(n-butyl)-4-methoxycarbonylaniline 
• 1012103-36-4 C₁₆H₂₆N₂O₂ 
• 1012103-37-5 C₁₇H₂₈N₂O₂ 
• 244623-81-2 C₁₈H₃₀N₂O₂ 
• 1012103-35-3 C₂₁H₃₆N₂O₂ 
• 1012103-38-6 C₂₂H₃₈N₂O₂ 
• 1012103-39-7 C₂₃H₄₀N₂O₂ 
• 3772-42-7 4-butylamino-benzoic acid-(2-diethylamino-ethyl ester) 
• 136-47-0 tetracaine hydrochloride 
• 97022-62-3 4-(butylamino)-N-(2-(dimethylamino)ethyl)benzamide 
• 1312300-91-6 4-(butylamino)-N-(2-(dimethylamino)ethyl)benzothioamide 

Relevant articles and documents

N-Trifluoromethyl Amines and Azoles: An Underexplored Functional Group in the Medicinal Chemist's Toolbox

Introducing trifluoromethyl groups is a common strategy to improve the properties of biologically active compounds. However, N-Trifluoromethyl moieties on amines and azoles are very rarely used. To evaluate their suitability in drug design, we synthesized a series of N-Trifluoromethyl amines and azoles, determined their stability in aqueous media, and investigated their properties. We show that N-Trifluoromethyl amines are prone to hydrolysis, whereas N-Trifluoromethyl azoles have excellent aqueous stability. Compared to their N-methyl analogues, N-Trifluoromethyl azoles have a higher lipophilicity and can show increased metabolic stability and Caco-2 permeability. Furthermore, N-Trifluoromethyl azoles can serve as bioisosteres of N-iso-propyl and N-Tert-butyl azoles. Consequently, we suggest that N-Trifluoromethyl azoles are valuable substructures to be considered in medicinal chemistry.

Design, synthesis and biological activity evaluation of benzoate compounds as local anesthetics

Tetracaine and pramocaine were used as the lead compounds to design benzoate compounds. The combination principle was used to design the target molecule, and the target molecule was modified by bioisostere formation and modification with alkyl groups. In this research, a total of 16 compounds were designed and synthesized. In the process of synthesis, we selected a route with high total yields, mild conditions and simple operation. Three steps were used in the synthesis of the new target compounds, namely, alkylation, esterification and alkylation. The newly designed target compounds were evaluated via surface anesthesia, infiltration anesthesia, block anesthesia and acute toxicity tests. The results of biological activity experiments showed that compounds 4d, 4g, 4j, 4k, 4n, and 4o had a good local anesthetic effect, and the results of acute toxicity tests showed that the target compounds had low toxicity.

Cyclic nucleotide-gated channel block by hydrolysis-resistant tetracaine derivatives

To meet a pressing need for better cyclic nucleotide-gated (CNG) channel antagonists, we have increased the biological stability of tetracaine-based blockers by synthesizing amide and thioamide linkage substitutions of tetracaine (1) and a higher affinity