46049-48-3

Basic information

• Product Name: (R)-2,3-dihydro-1,4-Benzodioxin-2-methanamine
• Synonyms: (R)-2,3-dihydro-1,4-Benzodioxin-2-methanamine;(R)-(2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanamine
• CAS NO: 46049-48-3
• Molecular Formula: C₉H₁₁NO₂
• Molecular Weight: 165.19
• Mol File: 46049-48-3.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 266 °C at 760 mmHg
• Flash Point: 124.1 °C
• Appearance: /
• Density: 1.154 g/cm³
• Vapor Pressure: 0.00885mmHg at 25°C
• Refractive Index: 1.545
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• CAS DataBase Reference: (R)-2,3-dihydro-1,4-Benzodioxin-2-methanamine(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2,3-dihydro-1,4-Benzodioxin-2-methanamine(46049-48-3)
• EPA Substance Registry System: (R)-2,3-dihydro-1,4-Benzodioxin-2-methanamine(46049-48-3)

Safety Data

• Hazardous Substances Data: 46049-48-3(Hazardous Substances Data)

Usage

General Description

(R)-2,3-dihydro-1,4-Benzodioxin-2-methanamine is a chemical compound with the molecular formula C9H11NO2. It is a chiral amine with a benzodioxin ring structure and a methanamine group attached to carbon 2. (R)-2,3-dihydro-1,4-Benzodioxin-2-methanamine has potential use in pharmaceutical and chemical synthesis due to its chiral nature and unique ring structure. It may also have applications in organic chemistry as a building block for the synthesis of other compounds. Additionally, its chiral nature makes it a candidate for use as a ligand in asymmetric catalysis reactions. Note: The chemical "2,3-dihydro-1,4-Benzodioxin-2-methanamine" does not exist in chemical databases.

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

Upstream product

• 71084-44-1 2-[(R)-1-(2,3-Dihydro-benzo[1,4]dioxin-2-yl)methyl]-isoindole-1,3-dione 
• 4442-59-5 (2,3-dihydrobenzo[1,4]dioxin-2-ylmethyl)amine 
• 3663-79-4 methyl 2,3-dihydrobenzo[b][1,4]dioxine-2-carboxylate 
• 950725-72-1 (S)-1,4-benzodioxane-2-carboxamide 
• 62703-32-6 (R)-3-(2-benzyloxyphenoxy)-1,2-propanediol acetonide 
• 753022-86-5 (R)-3-(2-hydroxyphenoxy)-1,2-bis(tosyloxy)propane 
• 753022-89-8 (R)-2-((azido)methyl)-1,4-benzodioxane 
• 164515-27-9 (2S)-1-(2'-benzyloxyphenoxy)-2-tosyloxy-3-benzyloxypropane 
• 164515-26-8 (2S)-1-(2'-benzyloxyphenoxy)-3-benzyloxy-2-propanol 
• 62501-71-7 (R)-2-benzyloxymethyl-2,3-dihydrobenzodioxane 
• 62501-72-8 (R)-2-hydroxymethyl-1,4-benzodioxane 
• 62501-73-9 (2S)-2-(hydroxymethyl)-1,4-benzodioxan tosylate 
• 650597-69-6 (S)-2-((mesyloxy)methyl)-1,4-benzodioxane 
• 119702-00-0 (S)-3-(2-benzyloxyphenoxy)-1,2-propanediol 

Downstream Products

• 81602-24-6 (R)-WB-4101 
• 62501-72-8 (R)-2-hydroxymethyl-1,4-benzodioxane 
• 650597-66-3 (S)‐methyl 1,4‐benzodioxane‐2‐carboxylate 
• 1191886-13-1 C₂₅H₂₃NO₅ 
• 1191886-14-2 C₂₅H₂₃NO₆ 

Relevant articles and documents

Crystallization-based resolution of 1,4-benzodioxane-2-carboxylic acid enantiomers via diastereomeric 1-phenylethylamides

Unlike the diastereomeric 1-phenylethylammonium salts, the diastereomeric N-1-phenylethylamides of (S)- and (R)-1,4-benzodioxane-2-carboxylic acid show significant differences in fusibility and solubility so as to be efficiently resolved by precipitation of the less soluble diastereomer (>98% de), while chromatographic purification of the unprecipitated fraction affords the more soluble one (>99% de). Overall, 95% of the former and 80% of the latter are recovered. The hydrolysis of the two resolved amides provides the two acid enantiomers and the resolving amine in quantitative yield and with unchanged stereoisomeric purity.

Structure-affinity studies for a novel series of homochiral naphtho and tetrahydronaphtho analogues of α1 antagonist WB-4101

A number of enantiomeric pairs of naphthodioxane, tetrahydronaphthodioxane and naphthoxy analogues of WB-4101 (1) were designed and synthesized in order to improve the selectivity profile of the parent compound, hopefully in favour of the α1a-AR with respect to the other two α1 subtypes and the 5-HT1A receptor. The new compounds 2-8 and, in addition, the two enantiomers of 1 were tested in binding assays on the α1a-AR, α1b-AR, α1d-AR, and the 5-HT1A receptor. Two of them, namely the naphtho- and tetrahydronaphthodioxane derivatives (S)-2 and (S)-3, showed lower, but significantly more specific α1a affinity than (S)-1, while the two enantiomers of the 2-methoxy-1-naphthoxy analogue 6 maintained most of the very high α1a affinity of (S)-1 and its α1a versus α1b selectivity slightly increasing the α1a/α1d and α1a/5HT 1A affinity ratios. The SAR data were evaluated in the light of known α1 subtype pharmacophores and of the α1a-AR binding mode of WB-4101 resultant from literature mutagenesis studies disclosing some interesting consonances with these models.