N-Hydroxy-5-methyl-5H-dibenzo[a,d]cycloheptene-5-amine

Base Information

• Chemical Name: N-Hydroxy-5-methyl-5H-dibenzo[a,d]cycloheptene-5-amine
• CAS No.: 89442-03-5
• Molecular Formula: C16H15 N O
• Molecular Weight: 237.301
• DSSTox Substance ID: DTXSID30538624
• Mol file: 89442-03-5.mol

Synonyms:89442-03-5;N-Hydroxy-5-methyl-5H-dibenzo[a,d]cycloheptene-5-amine;SCHEMBL10922159;DTXSID30538624;N-Hydroxy-5-methyl-5H-dibenzo[a,d][7]annulen-5-amine

Chemical Property of N-Hydroxy-5-methyl-5H-dibenzo[a,d]cycloheptene-5-amine

Chemical Property:

• PSA: 32.26000
• LogP: 3.80360
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 237.115364102
• Heavy Atom Count: 18
• Complexity: 299

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C2=CC=CC=C2C=CC3=CC=CC=C31)NO

Technology Process of N-Hydroxy-5-methyl-5H-dibenzo[a,d]cycloheptene-5-amine

There total 2 articles about N-Hydroxy-5-methyl-5H-dibenzo[a,d]cycloheptene-5-amine 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: 86.0%

5-hydroxy-5-methyl-5H-dibenzocycloheptene (18259-45-5) → 5-Hydroxylamino-5-methyl-5H-dibenzocycloheptene (89442-03-5)

Guidance literature:

With dichloro-acetic acid; hydroxylamine hydrochloride; sodium acetate; In dichloromethane; for 0.5h; Ambient temperature;

DOI:10.1021/jo00243a031

Reference yield:

dibenzosuberenon (2222-33-5) → 5-Hydroxylamino-5-methyl-5H-dibenzocycloheptene (89442-03-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / tetrahydrofuran; diethyl ether / 2 h / 15 - 20 °C

2: 86 percent / dichloroacetic acid, sodium acetate, hydroxylamine hydrochloride / CH₂Cl₂ / 0.5 h / Ambient temperature

With dichloro-acetic acid; hydroxylamine hydrochloride; sodium acetate; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/jo00243a031

Reference yield:

5-Hydroxylamino-5-methyl-5H-dibenzocycloheptene (89442-03-5) → 5-methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imine (70449-94-4)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium tert-butoxide / dimethylsulfoxide; toluene / 0.08 h / 55 °C

2: 90 percent / sodium acetate, H₂, 1.2 M HCl, glacial acetic acid / 5percent Pd/C / 3 h / 60 °C / 2068.6 Torr

With hydrogenchloride; potassium tert-butylate; hydrogen; sodium acetate; acetic acid; palladium on activated charcoal; In dimethyl sulfoxide; toluene;

DOI:10.1021/jo00243a031

upstream raw materials:

5-hydroxy-5-methyl-5H-dibenzocycloheptene

dibenzosuberenon

Downstream raw materials:

anti-12-hydroxy-5-methyl-10,11-dihydro-5H-dibenzocyclohepten-5,10-imine

5-methyl-5H-dibenzocycloheptene

5-methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imine

Refernces