4-(8-Methyl-9H-1,3-dioxolo(4,5-h)(2,3)benzodiazepin-5-yl)benzenamine

Base Information

• Chemical Name: 4-(8-Methyl-9H-1,3-dioxolo(4,5-h)(2,3)benzodiazepin-5-yl)benzenamine
• CAS No.: 102771-26-6
• Molecular Formula: C17H15 N3 O2
• Molecular Weight: 293.325
• European Community (EC) Number: 634-394-6
• UNII: 471V8NZ5X3
• DSSTox Substance ID: DTXSID40145500
• Nikkaji Number: J347.048B
• Wikipedia: GYKI_52466
• Wikidata: Q5515088
• Pharos Ligand ID: NMAU5VRG2B6S
• ChEMBL ID: CHEMBL275006
• Mol file: 102771-26-6.mol

Synonyms:1-(p-aminophenyl)-4-methyl-7,8-methylenedioxy-5H-2,3-benzodiazepine hydrochloride;GYKI 52466;GYKI-52466

Chemical Property of 4-(8-Methyl-9H-1,3-dioxolo(4,5-h)(2,3)benzodiazepin-5-yl)benzenamine

Chemical Property:

• Vapor Pressure: 4.15E-09mmHg at 25°C
• Boiling Point: 472.8°C at 760 mmHg
• PKA: 8.14±0.20(Predicted)
• Flash Point: 239.7°C
• PSA: 69.20000
• Density: 1.39
• LogP: 3.02130
• Storage Temp.: Desiccate at RT
• Solubility.: DMSO: 0.39 mg/mL
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 293.116426730
• Heavy Atom Count: 22
• Complexity: 482

Purity/Quality:

98%min ^*data from raw suppliers

GYKI 52466 dihydrochloride ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=NN=C(C2=CC3=C(C=C2C1)OCO3)C4=CC=C(C=C4)N
• Uses: 4-(8-Methyl-9H-1,3-dioxolo[4,5-h][2,3]benzodiazepin-5-yl)benzenamine is a non-competitive AMPA receptor antagonist and was found to have therapeutic potential for cocaine addiction treatment.

Technology Process of 4-(8-Methyl-9H-1,3-dioxolo(4,5-h)(2,3)benzodiazepin-5-yl)benzenamine

There total 6 articles about 4-(8-Methyl-9H-1,3-dioxolo(4,5-h)(2,3)benzodiazepin-5-yl)benzenamine 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: 80.0%

5-(4-nitrophenyl)-8-methyl-9H-1,3-dioxolo[4,5-h][2,3]benzodiazepine (102771-27-7) → 1-(4-aminophenyl)-4-methyl-7,8-methylenedioxy-5H-2,3-benzodiazepine (102771-26-6)

Guidance literature:

With tin(ll) chloride; In ethanol; at 70 ℃; for 1h;

DOI:10.1081/SCC-120002397

Reference yield:

palladium (7440-05-3) + 5-(4-nitrophenyl)-8-methyl-9H-1,3-dioxolo[4,5-h][2,3]benzodiazepine (102771-27-7) → 1-(4-aminophenyl)-4-methyl-7,8-methylenedioxy-5H-2,3-benzodiazepine (102771-26-6)

Guidance literature:

With hydrazine hydrate; pyrographite; In methanol; ethanol;

Reference yield:

1-allyl-3,4-methylenedioxybenzene (94-59-7) → 1-(4-aminophenyl)-4-methyl-7,8-methylenedioxy-5H-2,3-benzodiazepine (102771-26-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: Hg(OAc)2 / tetrahydrofuran / 1 h / 20 °C

1.2: 96 percent / NaBH₄; aq. NaOH / tetrahydrofuran / 1 h

2.1: 75 percent / pyridinium chlorochromate / CH₂Cl₂ / 20 °C

3.1: 60 percent / P₂O₅ / 1,2-dichloro-ethane / 8 h / 20 °C

4.1: 50 percent / hydrazine hydrate / ethanol / 2 h / 20 °C

5.1: 80 percent / SnCl₂ / ethanol / 1 h / 70 °C

With mercury(II) diacetate; phosphorus pentoxide; hydrazine hydrate; pyridinium chlorochromate; tin(ll) chloride; In tetrahydrofuran; ethanol; dichloromethane; 1,2-dichloro-ethane; 3.1: Friedel-Craft acylation;

DOI:10.1081/SCC-120002397

upstream raw materials:

5-(4-nitrophenyl)-8-methyl-9H-1,3-dioxolo[4,5-h][2,3]benzodiazepine

1-allyl-3,4-methylenedioxybenzene

β-oxy-α-(3',4'-methylenedioxyphenyl)propane

1-(1,3-benzodioxol-5-yl)-2-propanone

Downstream raw materials:

GYKI 52895

1-(4-Methylcarbamoylaminophenyl)-4-methyl-7,8-methylenedioxy-5H-2,3-benzodiazepine

Refernces

• 1、 -. "5H-2,3-benzodiazepine derivatives and pharmaceutical compositions containing the same". . . Retrieved 2008/06/13.