m-Anisidine

Base Information

• Chemical Name: m-Anisidine
• CAS No.: 536-90-3
• Deprecated CAS: 918666-97-4
• Molecular Formula: C7H9NO
• Molecular Weight: 123.155
• Hs Code.: 29222200
• European Community (EC) Number: 208-651-4
• ICSC Number: 0375
• NSC Number: 7631
• UN Number: 2431
• UNII: JXA144KX2I
• DSSTox Substance ID: DTXSID8024529
• Nikkaji Number: J1.593H
• Wikipedia: M-Anisidine
• Wikidata: Q3296585
• Metabolomics Workbench ID: 123558
• ChEMBL ID: CHEMBL1500995
• Mol file: 536-90-3.mol

Synonyms:3-anisidine;m-anisidine

Chemical Property of m-Anisidine

Chemical Property:

• Appearance/Colour: Pale yellow oily liquid or dark red liquid
• Vapor Pressure: 0.0209mmHg at 25°C
• Melting Point: ?1-1 °C(lit.)
• Refractive Index: n20/D 1.581(lit.)
• Boiling Point: 251 °C at 760 mmHg
• PKA: 4.23(at 25℃)
• Flash Point: 109.6 °C
• PSA: 35.25000
• Density: 1.064 g/cm³
• LogP: 1.85860
• Storage Temp.: 2-8°C
• Sensitive.: Light Sensitive
• Solubility.: 18g/l
• Water Solubility.: <0.1 g/100 mL at 19℃
• XLogP3: 0.9
• 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%min ^*data from raw suppliers

m-Anisidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+, N, Xn
• Hazard Codes: Xn,N,T+
• Statements: 22-36/37/38-50/53-51/53-33-26/27/28
• Safety Statements: 26-60-61-45-36/37-28B

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Amines, Aromatic
• Canonical SMILES: COC1=CC=CC(=C1)N
• Recent EU Clinical Trials: A Phase 2, Single-Arm Study to Evaluate the Safety and Pharmacokinetics of Alefacept in Adolescent Subjects with Moderate to Severe Psoriasis
• Inhalation Risk: A harmful contamination of the air will not or will only very slowly be reached 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. Medical observation is indicated. The effects may be delayed.
• Uses: m-Anisidine is a highly poisonous monosubstituted aniline used as corrosion inhibitorsfor aluminum, copper and other metals in acidic solutions. The unusually large amount of dibromo product produced upon bromination of m-anisidine may be attributed to the two doubly activeated positions. The best enantioselectivity of 97 % ee was observed for the reaction of m-anisidine in organocatalytic asymmetric three-component cyclization of cinnamaldehydes and primary amines with 1, 3-Dicarbonyl Compounds. Evidence for the control of 2nd-harmonic generation activities from the x-ray crystal-structures of the complexes of l-tartaric acid with m-anisidine and p-toluidine was determined.

Technology Process of m-Anisidine

There total 105 articles about m-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: 99.0%

3-methoxyphenyl bromide (2398-37-0) → m-Anisidine (536-90-3,918666-97-4)

Guidance literature:

With bis(tri-ortho-tolylphosphine)palladium⁽⁰⁾; (R)-(-)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyl-di-tert-butylphosphine; ammonia; sodium t-butanolate; In 1,4-dioxane; at 80 ℃; for 5h; Inert atmosphere;

DOI:10.1021/ja903049z

Reference yield: 99.0%

1-chloro-3-methoxy-benzene (2845-89-8) → m-Anisidine (536-90-3,918666-97-4)

Guidance literature:

With bis(tri-ortho-tolylphosphine)palladium⁽⁰⁾; (R)-(-)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyl-di-tert-butylphosphine; ammonia; sodium t-butanolate; In 1,4-dioxane; at 100 ℃; for 12h; Inert atmosphere;

DOI:10.1021/ja903049z

Reference yield: 99.0%

carbonic acid dimethyl ester (616-38-6) + m-Hydroxyaniline (591-27-5) → m-Anisidine (536-90-3,918666-97-4)

Guidance literature:

With dimanganese decacarbonyl; at 180 ℃; for 1h;

DOI:10.1134/S1070428015030070

upstream raw materials:

3-nitroanisole

2-Chloroanisole

phenylsulfonyl azide

methoxybenzene

Downstream raw materials:

2-m-anisidino-ethanethiol

1-(3-methoxyphenyl)pyrrolidin-2-one

3-(3-methoxyphenyl)furan-2,5-dione

1-(3-Methoxy-phenyl)-dithiobiuret

Refernces

4-[(8-Alkyl-8-azabicyclo[3.2.1]octyl-3-yl)-3-arylanilino]-N,N-diethylbenz amides: High affinity, selective ligands for the delta opioid receptor illustrate factors important to antagonist activity

10.1016/S0960-894X(00)00209-2

The study focuses on the synthesis and evaluation of a series of tropane-derived compounds, specifically 4-[(8-alkyl-8-azabicyclo[3.2.1]octyl-3-yl)-3-arylanilino]-N,N-diethylbenzamides (denoted as 5a-d), which were designed to have high affinity and selectivity for the delta opioid receptor. These compounds are structurally similar to the piperidine-based compound 3 and were synthesized to test the hypothesis that limiting conformational flexibility could elicit antagonist activity in nitrogen-transposed compounds similar to 3. The chemicals used in the study include 3-tropanone, 3-methoxyaniline, butylated hydroxyanisole (BHA) ester of 4-fluorobenzoic acid, sodium methoxide, and various reagents for coupling and conversion reactions. The purpose of these chemicals was to synthesize the target compounds and assess their potential as selective ligands for the delta opioid receptor, with the aim of understanding the factors important to antagonist activity and potentially developing new opioid ligands with reduced side effects.