N-Hydroxy-2-toluidine

Base Information

• Chemical Name: N-Hydroxy-2-toluidine
• CAS No.: 611-22-3
• Molecular Formula: C7H9 N O
• Molecular Weight: 123.155
• European Community (EC) Number: 612-088-3
• UNII: L90UBW6LOA
• DSSTox Substance ID: DTXSID00209975
• Nikkaji Number: J29.542F
• Wikidata: Q26840953
• Mol file: 611-22-3.mol

Synonyms:N-hydroxy-2-toluidine;N-hydroxy-o-toluidine

Chemical Property of N-Hydroxy-2-toluidine

Chemical Property:

• Vapor Pressure: 0.0545mmHg at 25°C
• Melting Point: 44°C
• Refractive Index: 1.5380 (estimate)
• Boiling Point: 223.6°C at 760 mmHg
• PKA: 9.02±0.70(Predicted)
• Flash Point: 111°C
• PSA: 32.26000
• Density: 1.159g/cm³
• LogP: 1.86910
• Storage Temp.: -20°C Freezer
• Solubility.: Dichloromethane; Ethyl Acetate
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 123.068413911
• Heavy Atom Count: 9
• Complexity: 85

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=CC=C1NO
• Uses: N-(o-Tolyl)hydroxylamine is an intermediate in the synthesis of Pyrametostrobin (P847010), a novel fungicide. Also, it is derived from 1-Methyl-2-nitrobenzene (N572306), which is a toxic pollutant of the environment because of its large scale use in the production of explosives. It is a useful synthetic intermediate. It shows carcinogenic activity in rats.

Technology Process of N-Hydroxy-2-toluidine

There total 22 articles about N-Hydroxy-2-toluidine 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: 99.0%

1-methyl-2-nitrobenzene (88-72-2) → N-(o-tolyl)hydroxylamine (611-22-3)

Guidance literature:

With hydrazine hydrate; In ethanol; water; 1,2-dichloro-ethane; at 45 ℃; for 2h; Temperature; Catalytic behavior;

Reference yield:

1-methyl-2-nitrobenzene (88-72-2) → o-toluidine (95-53-4) + N-(o-tolyl)hydroxylamine (611-22-3)

Guidance literature:

In ethanol; water; at 25 ℃; Rate constant; Mechanism; Product distribution; polarographic reduction; potential-dependent rate constants k_f,h, αn_a; pH = 1.81-11.00;

Reference yield:

N-o-tolylbenzohydroxamic acid (1143-74-4) → benzoic acid (65-85-0,8013-63-6) + N-(o-tolyl)hydroxylamine (611-22-3)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; water; at 55 ℃; Further Variations:; Reagents; Kinetics;

DOI:10.1524/zpch.218.5.563.30505

upstream raw materials:

1-methyl-2-nitrobenzene

2-nitrosotoluene

acetic acid

o-toluidine

Downstream raw materials:

(E)-di-o-tolyl-diazene-N-oxide

2,2'-dimethylazoxybenzene

N,N'-Di-o-tolyl-diazene N-oxide

2-methyl-4-methoxyaniline

Refernces

• 1、 Liu, Shi Juan,Wang, Yan Hua,Hao, Yuan Ping,Jiang, Jing Yang. "Promoting effect of ethanol on the synthesis of N-(2-methylphenyl) hydroxylamine from o-nitrotoluene in Zn/H2O/CO2 system". . p. 221 - 224. Retrieved 2011.
• 2、 Yan, Ziqiang,Xie, Xiaoyu,Song, Qun,Ma, Fulei,Sui, Xinyu,Huo, Ziyu,Ma, Mingming. "Tandem selective reduction of nitroarenes catalyzed by palladium nanoclusters". supporting information. p. 1301 - 1307. Retrieved 2020/03/11.
• 3、 Ishida, Yasuhiro,Nakamura, Itaru,Tashiro, Hiroki,Terada, Masahiro. "Synthesis of meta-substituted anilines via copper-catalyzed [1,3]-methoxy rearrangement". supporting information. p. 3794 - 3798. Retrieved 2020/06/08.