5-Chloro-2-nitroaniline

Base Information

• Chemical Name: 5-Chloro-2-nitroaniline
• CAS No.: 1635-61-6
• Molecular Formula: C6H5ClN2O2
• Molecular Weight: 172.571
• Hs Code.: 29214210
• European Community (EC) Number: 216-661-5
• NSC Number: 400866
• UNII: 656XJM4CON
• DSSTox Substance ID: DTXSID20167604
• Nikkaji Number: J140.783J
• Wikidata: Q27263839
• Mol file: 1635-61-6.mol

Synonyms:5-Chloro-2-nitroaniline;1635-61-6;Benzenamine, 5-chloro-2-nitro-;2-Nitro-5-chloroaniline;3-Chloro-6-nitroaniline;Aniline, 5-chloro-2-nitro-;5-chloro-2-nitrobenzenamine;5-Chloro-2-nitrobenzeneamine;2-Amino-4-chloro-nitrobenzene;5-chloro-2-nitro-aniline;5-chloro-2-nitrophenylamine;CCRIS 8934;EINECS 216-661-5;UNII-656XJM4CON;NSC 400866;656XJM4CON;2-amino-4-chloro-1-nitrobenzene;MFCD00007776;NSC-400866;5-chlor-2-nitroanilin;5-CHLORO-2-NITRO-PHENYLAMINE;NSC400866;5-chloro-2nitroaniline;3-chloro-6-nitro-aniline;2-amino4-chloronitrobenzene;SCHEMBL112538;3-amino-4-nitro-chlorobenzene;4-chloro-2-amino-nitrobenzene;amino-4-chloro-1-nitrobenzene;5-Chloro-2-nitroaniline, 97%;DTXSID20167604;5-CHLORO,2-NITRO-ANILINE;CHLORO-2-NITROANILINE, 5-;STR03184;2-AMINO-4-CHLORONITROBENZENE;3-AMINO-4-NITROCHLOROBENZENE;STL183336;AKOS000120351;AKOS025395588;AC-2574;AM61791;CCG-302569;CS-W009030;PS-4582;1-NITRO-2-AMINO-4-CHLOROBENZENE;LS-165037;A3632;FT-0612061;EN300-19792;AE-562/40245919;W-107952;Q27263839;5-Chloro-2-nitroaniline, technical, >=98.0% (HPLC);F2190-0502;Z104475410

Chemical Property of 5-Chloro-2-nitroaniline

Chemical Property:

• Appearance/Colour: yellow to orange powder
• Vapor Pressure: 8.7E-07mmHg at 25°C
• Melting Point: 125-129 °C (dec.)(lit.)
• Refractive Index: 1.628
• Boiling Point: 323.4 °C at 760 mmHg
• PKA: -1.46±0.25(Predicted)
• Flash Point: 149.4 °C
• PSA: 71.84000
• Density: 1.494 g/cm³
• LogP: 2.93480
• Storage Temp.: Store below +30°C.
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 172.0039551
• Heavy Atom Count: 11
• Complexity: 159

Purity/Quality:

98%, ^*data from raw suppliers

5-Chloro-2-nitroaniline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+,N,T
• Hazard Codes: T+,N,T
• Statements: 26/27/28-33-51/53
• Safety Statements: 28-36/37-45-61-28A

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1Cl)N)[N+](=O)[O-]
• Description: 2-Nitro-5-chloroaniline is an important pharmaceutical and veterinary drug intermediate. It has been applied in the upgraded product of veterinary drug albendazole-fenbendazole, and has a broad market prospect.
• Uses: 5-Chloro-2-nitroaniline is a useful synthetic intermediate. It can be used as a reagent to synthesize benzamide derivatives as histone deacetylase inhibitors. It is an intermediate used to synthesize 1-Nitro Febantel a Febantel impurity. 5-Chloro-2-nitroaniline was used in the synthesis of 5-(4-substituted piperazin-1-yl)-2-nitroanilines and 5-(4-substituted piperazin-1-yl)benzimidazole-2-carbamates.

Technology Process of 5-Chloro-2-nitroaniline

There total 34 articles about 5-Chloro-2-nitroaniline 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%

methanol (67-56-1) + N-(5-chloro-2-nitrophenyl)acetamide (5443-33-4) + sodium methylate (124-41-4) → 5-chloro-2-nitroaniline (1635-61-6)

Guidance literature:

for 3h; Heating / reflux;

Reference yield: 86.0%

4-chlorobenzonitrile (100-00-5) → 5-chloro-2-nitroaniline (1635-61-6)

Guidance literature:

With O-Methylhydroxylamin; potassium tert-butylate; copper(l) chloride; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1039/a901537j

Reference yield: 71.0%

6-chlorobenzo[c][1,2,5]oxadiazole 1-oxide (39060-31-6) → 5-chloro-2-nitroaniline (1635-61-6) + 5-chlorobenzo[c][1,2,5]oxadiazole (19155-86-3)

Guidance literature:

With 2,3-dimethyl-2,3-butane diol; bis(N,N-dimethylformamide)dichloridodioxidomolybdenum(VI); In N,N-dimethyl acetamide; at 120 ℃; for 0.416667h; chemoselective reaction; Microwave irradiation; Sealed tube; Green chemistry;

DOI:10.1002/adsc.201700071

upstream raw materials:

2,4-dichloronitrobenzene

3-Chloroacetanilide

N-(5-chloro-2-nitrophenyl)acetamide

(5-chloro-2-nitro-phenyl)-phenyl sulfone

Downstream raw materials:

5-(4-methylpiperazine-1-yl)-2-nitroaniline

ethyl N¹-(2-nitro-5-chlorophenyl)hydrazono-N²-chloroacetate

5-chloro-2-nitro-N-trifluoroacetylaniline

4-Chloro-1,2-phenylenediamine

Refernces

• 1、 Fuson et al.. "-". . p. 799,804. Retrieved 1947.
• 2、 Gupta, Sampa,Ansari, Alisha,Sashidhara, Koneni V.. "Base promoted peroxide systems for the efficient synthesis of nitroarenes and benzamides". supporting information. . Retrieved 2019/09/07.
• 3、 Rubio-Presa, Rubén,Fernández-Rodríguez, Manuel A.,Pedrosa, María R.,Arnáiz, Francisco J.,Sanz, Roberto. "Molybdenum-Catalyzed Deoxygenation of Heteroaromatic N-Oxides and Hydroxides using Pinacol as Reducing Agent". supporting information. p. 1752 - 1757. Retrieved 2017/05/22.