51867-83-5

Basic information

• Product Name: 5-Acetylamido-2-chloroaniline
• Synonyms: N-(3-Amino-4-chlorophenyl)acetamide;TIMTEC-BB SBB003719;3AC;3'-AMINO-4'-CHLOROACETANILIDE;3-AMINO-4-CHLORO-ACETANILIDE;5-ACETYLAMIDO-2-CHLOROANILINE;4-CHLORO-3-AMINO ACETANILIDE;3-Amino-4-Chloroacetoanilide
• CAS NO: 51867-83-5
• Molecular Formula: C₈H₉ClN₂O
• Molecular Weight: 184.62
• EINECS: 257-485-9
• Product Categories: Intermediates of Dyes and Pigments;NULL
• Mol File: 51867-83-5.mol
• Article Data: 5

Chemical Properties

• Melting Point: 172-176 °C(lit.)
• Boiling Point: 391.7 °C at 760 mmHg
• Flash Point: 190.7 °C
• Appearance: brown crystalline powder
• Density: 1.3264 (rough estimate)
• Vapor Pressure: 2.42E-06mmHg at 25°C
• Refractive Index: 1.5430 (estimate)
• PKA: 13.95±0.70(Predicted)
• CAS DataBase Reference: 5-Acetylamido-2-chloroaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Acetylamido-2-chloroaniline(51867-83-5)
• EPA Substance Registry System: 5-Acetylamido-2-chloroaniline(51867-83-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 51867-83-5(Hazardous Substances Data)

Usage

Description

5-Acetylamido-2-chloroaniline is an anilide that is N-phenylacetamide substituted by an amino group at position 3 and a chloro group at position 4. It is a brown crystalline powder with unique chemical properties that make it suitable for various applications.

Uses

Used in Chemical Synthesis:
5-Acetylamido-2-chloroaniline is used as an intermediate in the chemical synthesis of various organic compounds, particularly those involving the formation of amide and chloro groups. Its unique structure allows for the creation of a wide range of products with diverse applications.
Used in Pharmaceutical Industry:
5-Acetylamido-2-chloroaniline is used as a building block for the development of new pharmaceutical compounds. Its specific functional groups enable the design of molecules with potential therapeutic properties, making it a valuable asset in drug discovery and development.
Used in Dye Manufacturing:
5-Acetylamido-2-chloroaniline is used as a starting material in the production of various dyes and pigments. Its brown crystalline form can be further modified to create a range of colors, making it a versatile component in the dye manufacturing process.
Used in Research and Development:
5-Acetylamido-2-chloroaniline is used as a research compound for studying the properties and reactions of anilide derivatives. Its unique structure provides valuable insights into the behavior of similar compounds, contributing to the advancement of chemical knowledge and innovation.
Used in Analytical Chemistry:
5-Acetylamido-2-chloroaniline is used as a reference compound in analytical chemistry for the identification and quantification of related substances. Its distinct chemical properties make it an ideal candidate for calibration and quality control purposes in various analytical techniques.

InChI:InChI=1/C8H9ClN2O/c1-5(12)11-6-2-3-7(9)8(10)4-6/h2-4H,10H2,1H3,(H,11,12)

Upstream product

• 108-24-7 acetic anhydride 
• 97-00-7 1-chloro-2,4-dinitro-benzene 
• 635-22-3 4-Chloro-3-nitroaniline 
• 10199-85-6 1-chloro-2,4-dinitrochlorobenzene 
• 5540-60-3 N-(4-chloro-3-nitrophenyl)acetamide 

Downstream Products

• 149526-85-2 N-(3-azido-4-chlorophenyl)-N'-methyl-thiourea 
• 149526-84-1 N-(3-azido-4-chlorophenyl)-thiourea 
• 155593-82-1 3-azido-4-chlorophenylisothiocyanate 
• 155593-81-0 3-azido-4-chloroaniline 
• 155593-80-9 3-azido-4-chloroacetanilide 

Relevant articles and documents

Design, synthesis and biological evaluation of bis-aryl ureas and amides based on 2-amino-3-purinylpyridine scaffold as DFG-out B-Raf kinase inhibitors

By combining the scaffolds of UI-125 and Sorafenib, a series of bis-aryl ureas and amides based on 2-amino-3-purinylpyridine moiety were designed and synthesized as novel DFG-out B-RafV600E inhibitors. Among them, 20c-e, 20g and 21h displayed potent antiproliferative activities against melanoma A375 (B-RafV600E) cell lines with IC50 values of 3.190, 2.276, 1.856, 1.632 μM and 1.839 μM, respectively, comparable with the positive control Vemurafenib (IC50 Combining double low line 3.32 μM). Selected compounds were tested for the ERK inhibition in human melanoma A375 (B-RafV600E) and SK-MEL-2 (B-RafWT) cell lines by Western blot. The results revealed that our compounds inhibited the proliferation of melanoma A375 cells (B-RafV600E) through ERK pathway, without paradoxical activation of ERK in melanoma SK-MEL-2 cells (B-RafWT). Eventually, 20g and 21h were selected to confirm their inhibitory effects on tumor growth in A375 xenograft models in mice. Compound 20g exhibited equivalent antitumor efficacy in vivo (T/C Combining double low line 44.37%), compared to Sorafenib (T/C Combining double low line 37.35%), by 23-day repetitive administration of a single dose of 50 mg/kg without significant body weight loss.

One-pot reductive conversion of nitroarenes to N-arylacetamides mediated by metallic samarium

Nitroarenes can be reduced and then converted to N-arylacetamides by metallic samarium in the presence of acetic anhydride, acetic acid and methanol in excellent yields by a one pot-procedure.

Synthesis of N-(3-azido-4-chlorophenyl)-N'-[3H-methyl]thiourea, an efficient photoaffinity probe for the urea carrier

Starting from commercial 4-chloro-3-nitroaniline, through a 5 step synthesis, was prepared 3-azido-4-chlorophenylisothiocyanate 5 which was reacted with [3H]-methylamine. The latter was obtained by three methods: i- [3H]-LiAlT4 reduction of benzylcarbamate gave rise to [3H][-methylamine (S.A.: >70 Ci/mmol). ii- Catalytic reduction of HCN with 3H2 lead to [3H]-CH3NH2 (S.A.: 0.7 Ci/mmol). iii- Schmidt rearrangement of [3H]-sodium acetate gave [3H]-CH3NH2 (S.A.: 29 Ci/mmol). Compound 7 at the highest specific activity had a self radiolysis rate precluding its practical use in biological studies whilst 29 Ci/mmol [3H]-7 was satisfactory.