o-Anisidine

Base Information

• Chemical Name: o-Anisidine
• CAS No.: 90-04-0
• Molecular Formula: C7H9NO
• Molecular Weight: 123.155
• Hs Code.: 2922.29 Oral rat LD50: 2 gm/kg
• European Community (EC) Number: 201-963-1
• ICSC Number: 0970
• NSC Number: 3122
• UN Number: 2431
• UNII: NUX042F201
• DSSTox Substance ID: DTXSID5023877
• Nikkaji Number: J3.551C
• Wikipedia: O-Anisidine
• Wikidata: Q3295808
• ChEMBL ID: CHEMBL1612004
• Mol file: 90-04-0.mol

Synonyms:o-Anisidine;o-Anisidine(8CI);1-Amino-2-methoxybenzene;2-Aminoanisole;2-Aminomethoxybenzene;2-Methoxy-1-aminobenzene;2-Methoxyaniline;2-Methoxybenzenamine;2-Methoxyphenylamine;NSC 3122;o-Aminoanisole;o-Aminomethoxybenzene;o-Methoxyaniline;o-Methoxyphenylamine;

Chemical Property of o-Anisidine

Chemical Property:

• Appearance/Colour: light red or light yellow oily liquid
• Vapor Pressure: 0.0885mmHg at 25°C
• Melting Point: 3-6 °C
• Refractive Index: 1.573
• Boiling Point: 225 °C
• PKA: 4.52(at 25℃)
• Flash Point: 107 °C
• PSA: 35.25000
• Density: 1.092 g/cm³
• LogP: 1.85860
• Storage Temp.: Refrigerator
• Sensitive.: Light Sensitive
• Solubility.: 14g/l
• Water Solubility.: 13 g/L (20 ºC)
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 123.068413911
• Heavy Atom Count: 9
• Complexity: 85
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

o-Anisidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,Xi
• Hazard Codes: T,Xi
• Statements: 45-23/24/25-68
• Safety Statements: 53-45

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Amines, Aromatic
• Canonical SMILES: COC1=CC=CC=C1N
• Inhalation Risk: A harmful contamination of the air can be reached rather quickly on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: The substance may cause effects on the blood. This may result in the formation of methaemoglobin. Exposure could cause haemolysis. This may result in haemolytic anaemia. The effects may be delayed. Medical observation is indicated.
• Effects of Long Term Exposure: The substance may have effects on the blood. This may result in the formation of methaemoglobin and anaemia. This substance is possibly carcinogenic to humans.
• Description: o-Anisidine was produced commercially in the United States from the 1920s until late 1950s. By 2009, worldwide only six industries manufactured o-anisidine, but none produced hydrochloride salt. o-Anisidine was available from 44 suppliers, including 20 US suppliers, and the hydrochloride salt was available from eight suppliers, including five US suppliers. US imports of o-anisidine and its hydrochloride salt are reported in the category ‘o-anisidines, p-anisidines, and p-phenetidine,’ and US exports are reported in the category ‘anisidines, dianisidines, phenetidines, and their salts.’ From 1989 to 2008, imports ranged from a high of over 4.6 million kg in 1996 to zero in 2007 and 2008, and exports ranged from zero to 262 000 kg. Reports filed under the US Environmental Protection Agency’s (EPA) Toxic Substances Control Act Inventory Up Rule indicated that United States production plus imports of o-anisidine totaled 500 000 lb–1 million lb in 1986, 1990, and 2006; 1 million–10 million lb in 1990 and 1998; and 10 000–500 000 lb in 2002.
• Physical properties: Colorless, yellow to reddish liquid with an amine-like odor. Becomes brown on exposure to air.
• Uses: Similar to other aromatic amines, o-anisidine may cause methemglobinemia and cancer in humans. It is used mainly as an intermediate for the production of azo dyes and pigments. Other industrial uses of o-anisidine include synthesis of other dyes and pharmaceuticals, as a corrosion inhibitor for steel, and as an antioxidant for polymercaptan resins (IARC, 1999; HSDB, 2012). Intermediate for azo dyes and for guaiacol. In the preparation of azo dyes; corrosion inhibitor; chemical intermediate It is primarily used as a chemical intermediate in the production of pigments, dyes, pharmaceuticals, and fragrances. o-Anisidine hydrochloride is used as a chemical intermediate in the production of numerous azo and triphenylmethane dyes and pigments (e.g., C.I. direct red 72, disperse orange 29, direct yellow 44, direct red 24, and acid red 4); in the production of pharmaceuticals, including the expectorant guaiacol; as a corrosion inhibitor for steel; and as an antioxidant for polymercaptan resins.

Technology Process of o-Anisidine

There total 150 articles about o-Anisidine 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%

2-Chloroanisole (766-51-8) → 2-methoxy-phenylamine (90-04-0)

Guidance literature:

With tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; lithium hexamethyldisilazane; CyJohnPhos; 1,1,1-triphenylsilylamine; In toluene; at 100 ℃; for 17h;

DOI:10.1021/ol0166808

Reference yield: 95.0%

4-iodoanisol (529-28-2) → 2-methoxy-phenylamine (90-04-0)

Guidance literature:

With ammonium hydroxide; In water; at 20 ℃; for 9h; Green chemistry;

DOI:10.1039/c9nj04981a

Reference yield: 90.0%

2-methoxyacetanilide (93-26-5) → ethanol (64-17-5) + 2-methoxy-phenylamine (90-04-0)

Guidance literature:

With hydrogen; In toluene; at 160 ℃; for 15h; under 45004.5 Torr; Catalytic behavior; Autoclave;

DOI:10.1039/c9cy02128k

upstream raw materials:

diazomethane

2-amino-phenol

2-Nitroanisole

1,3-bis-(2-methoxy-phenyl)-thiourea

Downstream raw materials:

2-((2-methoxyphenyl)amino)ethan-1-ol

2-[2-hydroxyethyl-(2-methoxyphenyl)amino]ethanol

2-(2-methoxy-phenyl)-pyridine

3-(2-methoxyphenyl)pyridine

Refernces

• 1、 Wang, Jiaqing,Ge, Danhua,Cao, Xueqin,Tang, Minghua,Pan, Yue,Gu, Hongwei. "A facile synthesis of Pt@Ir zigzag bimetallic nanocomplexes for hydrogenation reactions". . p. 9216 - 9219. Retrieved 2015.
• 2、 Carswell. "-". . p. 2417. Retrieved 1931.
• 3、 Dong, Zhenhua,Pan, Hongguo,Gao, Pengwei,Xiao, Yongmei,Fan, Lulu,Chen, Jing,Wang, Wentao. "Palladium Immobilized on a Polyimide Covalent Organic Framework: An Efficient and Recyclable Heterogeneous Catalyst for the Suzuki–Miyaura Coupling Reaction and Nitroarene Reduction in Water". . p. 299 - 306. Retrieved 2021/05/10.
• 4、 Ammaiyappan, Yuvaraj,Darcel, Christophe,Tongdee, Satawat,Wu, Jiajun. "A Concise Route to Cyclic Amines from Nitroarenes and Ketoacids under Iron-Catalyzed Hydrosilylation Conditions". . p. 3859 - 3865. Retrieved 2021/07/12.