(2,3-Dihydrobenzo[b][1,4]dioxin-2-yl)methanamine

Base Information

• Chemical Name: (2,3-Dihydrobenzo[b][1,4]dioxin-2-yl)methanamine
• CAS No.: 4442-59-5
• Molecular Formula: C9H11NO2
• Molecular Weight: 165.192
• Hs Code.: 2932990090
• European Community (EC) Number: 224-671-6
• NSC Number: 116045
• DSSTox Substance ID: DTXSID801305746
• Nikkaji Number: J205.827H
• Mol file: 4442-59-5.mol

Synonyms:2-aminomethyl-1,4-benzodioxane

Chemical Property of (2,3-Dihydrobenzo[b][1,4]dioxin-2-yl)methanamine

Chemical Property:

• Vapor Pressure: 0.00885mmHg at 25°C
• Melting Point: 184-188 °C
• Refractive Index: n20/D 1.5594
• Boiling Point: 266 °C at 760 mmHg
• PKA: 8.88±0.29(Predicted)
• Flash Point: 124.1 °C
• PSA: 44.48000
• Density: 1.154 g/cm³
• LogP: 1.48540
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility.: Chloroform, Ethyl Acetate
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 165.078978594
• Heavy Atom Count: 12
• Complexity: 152

Purity/Quality:

97% ^*data from raw suppliers

2-Aminomethyl-1,4-benzodioxane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 34-41-37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1C(OC2=CC=CC=C2O1)CN
• Uses: 2-Aminomethyl-1,4-benzodioxane is used in the synthesis of N-substituted (dihydrobenzodioxinyl)methylamine derivatives as D2 antagonists/5-HT1A partial agonists with potential as atypical antipsychotic agents in relation to affinity for α1 adrenoceptors.

Technology Process of (2,3-Dihydrobenzo[b][1,4]dioxin-2-yl)methanamine

There total 6 articles about (2,3-Dihydrobenzo[b][1,4]dioxin-2-yl)methanamine 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: 87.0%

2-hydroxymethyl-2,3-dihydrobenzo[1,4]dioxin (3663-82-9) → (2,3-dihydrobenzo[1,4]dioxin-2-ylmethyl)amine (4442-59-5)

Guidance literature:

2-hydroxymethyl-2,3-dihydrobenzo[1,4]dioxin; In dichloromethane; cooling;

With dibenzyl azodicarboxylate; In dichloromethane; cooling;

With trifluoroacetic acid; In dichloromethane; Further stages.;

DOI:10.1016/j.tetlet.2007.09.034

Reference yield: 83.0%

2-cyano-1,4-benzodioxane (1008-92-0) → (2,3-dihydrobenzo[1,4]dioxin-2-ylmethyl)amine (4442-59-5)

Guidance literature:

With hydrogenchloride; hydrogen; platinum(IV) oxide; In methanol; at 20 ℃; for 36h; under 760 Torr;

DOI:10.1016/S0223-5234(00)00164-1

Reference yield:

2-azidomethyl-2,3-dihydro-1,4-benzodioxine (128318-80-9) → (2,3-dihydrobenzo[1,4]dioxin-2-ylmethyl)amine (4442-59-5)

Guidance literature:

With hydrogen; palladium on activated charcoal;

DOI:10.1016/S0960-894X(01)00456-5

upstream raw materials:

2-chloromethyl-1,4-benzodioxane

2-cyano-1,4-benzodioxane

2-azidomethyl-2,3-dihydro-1,4-benzodioxine

2-hydroxymethyl-2,3-dihydrobenzo[1,4]dioxin

Downstream raw materials:

1-[N-(2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)-glycyl]-piperidine

4-[N-(2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)-glycyl]-morpholine

1-[N-(2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)-β-alanyl]-piperidine

N-(2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)-β-alanine-cyclohexylamide

Refernces

New Ras CAAX mimetics: Design, synthesis, antiproliferative activity, and RAS prenylation inhibition

10.1016/j.bmcl.2009.07.065

The research focuses on the design, synthesis, and biological evaluation of new Ras CAAX mimetics. These compounds were designed by replacing cysteine in the Ras protein's C-terminal CAAX tetrapeptide with 2-hydroxymethylbenzodioxane or 2-aminomethylbenzodioxane, and using pluri-substituted biphenyl systems as internal spacers and AA dipeptide bioisosteres. The resultant compounds were linked to the methyl ester of L-methionine, glycine, or L-leucine by an amide bond. The synthesized compounds were tested for their antiproliferative effects on human aortic smooth muscle cells (SMCs) and their ability to inhibit Ras prenylation. The most potent compound was found to be the methionine derivative with a methyleneoxy linker between benzodioxane and 2-methylbiphenyl, which demonstrated significant antiproliferative activity and direct interference with Ras prenylation. The study highlights the importance of the linker between the dioxane and biphenyl core and the o-substitution on the biphenyl core for the observed biological activities.