(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:

98%,99%, ^*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

• 1、 Congreve, Miles S.,Kay, Corinne,Scicinski, Jan J.,Ley, Steven V.,Williams, Geoffrey,Murray, Peter J.,McKeown, Stephen C.,Watson, Stephen P.. "Versatile solid-phase synthesis of secondary amines from alcohols. Development of an N-Boc-(o-nitrobenzene)sulfonamide linker". . p. 4153 - 4156. Retrieved 2007/10/03.
• 2、 Sanchez, Isabel,Dolors Pujol, Maria,Guillaumet, Gerald,Massingham, Roy,Monteil, Andre,Dureng, Georges,Winslow, Eileen. "Design and synthesis of substituted compounds containing the 1,4- benzodioxin subunit. New potential calcium antagonists". . p. 663 - 676. Retrieved 2007/10/03.