4442-59-5

Basic information

• Product Name: 2,3-DIHYDRO-1,4-BENZODIOXIN-2-YLMETHYLAMINE
• Synonyms: CHEMBRDG-BB 4100090;BUTTPARK 36\04-10;C-(2,3-DIHYDRO-BENZO[1,4]DIOXIN-2-YL)-METHYLAMINE;(2,3-DIHYDROBENZO[B][1,4]DIOXIN-2-YL)METHANAMINE;2,3-DIHYDRO-1,4-BENZODIOXIN-2-YLMETHYLAMINE;2-(AMINOMETHYL)BENZODIOXAN;2-AMINOMETHYL-2,3-DIHYDRO-BENZO[1,4]DIOXINE;2-AMINOMETHYL-1,4-BENZODIOXAN
• CAS NO: 4442-59-5
• Molecular Formula: C₉H₁₁NO₂
• Molecular Weight: 165.19
• EINECS: 224-671-6
• Mol File: 4442-59-5.mol
• Article Data: 7

Chemical Properties

• Melting Point: 184-188 °C
• Boiling Point: 105-110 °C/3 mmHg
• Flash Point: 124.1 °C
• Appearance: /
• Density: 1.1679 g/mL at 25 °C
• Vapor Pressure: 0.00885mmHg at 25°C
• Refractive Index: n20/D 1.5594
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility: Chloroform, Ethyl Acetate
• PKA: 8.88±0.29(Predicted)
• CAS DataBase Reference: 2,3-DIHYDRO-1,4-BENZODIOXIN-2-YLMETHYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-DIHYDRO-1,4-BENZODIOXIN-2-YLMETHYLAMINE(4442-59-5)
• EPA Substance Registry System: 2,3-DIHYDRO-1,4-BENZODIOXIN-2-YLMETHYLAMINE(4442-59-5)

Safety Data

• Hazard Codes: Xi
• Statements: 34-41-37/38
• Safety Statements: 26-36/37/39
• RIDADR: 2735
• WGK Germany: 3
• RTECS: DF3676000
• HazardClass: IRRITANT
• Hazardous Substances Data: 4442-59-5(Hazardous Substances Data)

Usage

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.

InChI:InChI=1/C9H11NO2/c10-5-7-6-11-8-3-1-2-4-9(8)12-7/h1-4,7H,5-6,10H2/p+1/t7-/m1/s1

Upstream product

• 1008-92-0 2-cyano-1,4-benzodioxane 
• 128318-80-9 2-azidomethyl-2,3-dihydro-1,4-benzodioxine 
• 1094-91-3 2-(toluene-4-sulfonyloxymethyl)-2,3-dihydro-benzo[1,4]dioxine 
• 3663-82-9 2-hydroxymethyl-2,3-dihydrobenzo[1,4]dioxin 
• 2164-33-2 2-chloromethyl-1,4-benzodioxane 

Downstream Products

• 101997-49-3 1-[N-(2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)-glycyl]-piperidine 
• 3562-90-1 4-[N-(2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)-glycyl]-morpholine 
• 102071-89-6 1-[N-(2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)-β-alanyl]-piperidine 
• 110356-88-2 N-(2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)-β-alanine-cyclohexylamide 
• 119750-12-8 PCM-0102881 
• 74398-46-2 3-[(2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)-amino]-propan-1-ol 
• 95110-13-7 1,4-benzodioxane-2-carboxyamide 
• 116210-76-5 N-(cyclohexylphenylmethyl)-2-{[(2,3-dihydro-1,4-benzodioxin-2-yl)methyl]amino}acetamide 
• 87780-21-0 N-(2,3-Dihydro-benzo[1,4]dioxin-2-ylmethyl)-benzamide 
• 138803-89-1 1-[(2,3-Dihydro-benzo[1,4]dioxin-2-ylmethyl)-amino]-3-(6-phenyl-pyridazin-3-yloxy)-propan-2-ol 
• 95110-11-5 2,6-dimethoxyphenoxymethylcarboxy N-(1,4-benzodioxane-2-ylmethyl) amide 
• 87780-22-1 N-(2,3-Dihydro-benzo[1,4]dioxin-2-ylmethyl)-2-phenyl-acetamide 
• 87780-23-2 N-(2,3-Dihydro-benzo[1,4]dioxin-2-ylmethyl)-3-phenyl-propionamide 

Relevant articles and documents

Efficient conversion of primary and secondary alcohols to primary amines

A convenient single-vessel conversion of primary and secondary alcohols to primary amines is reported. Use of this method results in substantially cleaner crude products than similar procedures reported in the literature. A simple work-up also makes this procedure ideal for parallel synthesis.

N-Hydroxyl derivatives of guanidine based drugs as enzymatic NO donors

Recent research suggests that NO may play a role in the physiological effects of some guanidine-containing drugs. In this report, three guanidine-containing drugs (guanadrel, guanoxan, and guanethidine) together with their N-hydroxyl derivatives were synthesized and their NO-releasing abilities catalyzed by nitric oxide synthases (NOSs) and horseradish peroxidase were evaluated. The guanidine containing compounds could not release NO in the presence of NOS or peroxidase. The corresponding N-hydroxyl compounds exhibited weak NO-releasing ability under the catalyzed of NOS and good NO-releasing ability under the oxidation by horseradish peroxidase in the presence of H2O2. These compounds also displayed vasodilatory activity. Elsevier Science Ltd. All rights reserved.

N-substituted (2,3-dihydro-1,4-benzodioxin-2-yl)methylamine derivatives as 92 antagonists/5-HT(1A) partial agonists with potential as atypical antipsychotic agents

A series of N-substituted 1-(2,3-dihydro-1,4-benzodioxin-2- yl)methylamine derivatives with D2 antagonist/5-HT(1A) partial agonist activity has been prepared as potential atypical antipsychotic agents. Optimization of in vitro receptor binding activity and in vivo activity in rodent models of psychosis has led to compound 24, which showed good affinities for human D2, D3, and 5-HT(1A) receptors but significantly less affinity for human α1 adrenoceptors and rat H1 and muscarinic receptors. In rodents, 24 showed functional D2-like antagonism and 5-HT(1A) partial agonism. After oral dosing, 24 showed good activity in rodent antipsychotic tests and very little potential to cause extrapyramidal side effects (EPS), as measured by its ability to induce catalepsy in rats only at very high doses. In the light of this promising profile of activity, 24 has been selected for clinical investigation as a novel antipsychotic agent with a predicted low propensity to cause EPS.