1008-92-0

Basic information

• Product Name: 2,3-DIHYDRO-1,4-BENZODIOXINE-2-CARBONITRILE
• Synonyms: 2,3-Dihydrobenzo[1,4]dioxine-2-carbonitrile;2,3-Dihydro-1,4-benzodioxin-2-carbonitrile;1,4-Benzodioxin-2-carbonitrile, 2,3-dihydro-;2,3-Dihydro-1,4-benzodioxine-2-carbonitrile 95%;2-Cyano-2,3-dihydro-1,4-benzodioxine, 2-Cyano-1,4-benzodioxane;2,3-Dihydro-1,4-benzodioxine-2-carbonitrile95%
• CAS NO: 1008-92-0
• Molecular Formula: C₉H₇NO₂
• Molecular Weight: 161.1616
• EINECS: 200-258-5
• Product Categories: Aromatics;Heterocycles
• Mol File: 1008-92-0.mol
• Article Data: 17

Chemical Properties

• Melting Point: NA
• Boiling Point: 310.7 °C at 760 mmHg
• Flash Point: 136.2 °C
• Appearance: /
• Density: 1.26 g/cm³
• Vapor Pressure: 0.000589mmHg at 25°C
• Refractive Index: 1.574
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2,3-DIHYDRO-1,4-BENZODIOXINE-2-CARBONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-DIHYDRO-1,4-BENZODIOXINE-2-CARBONITRILE(1008-92-0)
• EPA Substance Registry System: 2,3-DIHYDRO-1,4-BENZODIOXINE-2-CARBONITRILE(1008-92-0)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 1008-92-0(Hazardous Substances Data)

Usage

Chemical Properties

Pale Yellow Low-Melting Solid

InChI:InChI=1/C9H7NO2/c10-5-7-6-11-8-3-1-2-4-9(8)12-7/h1-4,7H,6H2

Upstream product

• 4554-16-9 2,3-dibromopropionitrile 
• 120-80-9 benzene-1,2-diol 
• 3663-80-7 1,4-benzodioxane-2-carboxylic acid 
• 22821-76-7 4-(methylsulfonyl)benzonitrile 
• 493-09-4 benzo-1,4-dioxane 
• 172876-96-9 3-oxo-1λ³-benzo[d][1,2]iodaoxole-1(3H)-carbonitrile 
• 1616377-88-8 rac-2-N,N-dichloroaminomethyl-1,4-benzodioxane 
• 4442-59-5 (2,3-dihydrobenzo[1,4]dioxin-2-ylmethyl)amine 
• 920-37-6 2-Chloroacrylonitrile 

Downstream Products

• 4442-59-5 (2,3-dihydrobenzo[1,4]dioxin-2-ylmethyl)amine 
• 33070-04-1 rac-1,4-benzodioxane-2-carboxamide 
• 64179-67-5 rac-1,4-benzodioxane-2-carboxaldehyde 
• 1011-48-9 2-acetyl-2,3-dihydro-1,4-benzodioxin 
• 1014-18-2 2-bromo-1-(2,3-dihydrobenzo[b][1,4]dioxin-2-yl)ethanone 
• 1269604-13-8 (4R)-4-(N-benzyloxycarbonyl-2-aminoethyl)-2-(2,3-dihydro-1,4-benzodioxan-2-yl)imidazoline 
• 1269488-18-7 (4R)-4-(N-benzyloxycarbonyl-2-aminoethyl)-2-(2,3-dihydro-1,4-benzodioxan-2-yl)imidazoline hydrochloride 
• 1269604-12-7 (4S)-4-(N-benzyloxycarbonyl-2-aminoethyl)-2-(2,3-dihydro-1,4-benzodioxan-2-yl)imidazoline 
• 1269488-17-6 (4S)-4-(N-benzyloxycarbonyl-2-aminoethyl)-2-(2,3-dihydro-1,4-benzodioxan-2-yl)imidazoline hydrochloride 
• 79944-56-2 Idazoxan hydrochloride 
• 130482-64-3 N-(2-Morpholin-4-yl-ethyl)-2,3-dihydro-benzo[1,4]dioxine-2-carboxamidine; hydrochloride 

Relevant articles and documents

Decarboxylative alkynylation and cyanation of carboxylic acids using photoredox catalysis and hypervalent iodine reagents

Alkynes and nitriles are important functional groups that serve as versatile building blocks in organic synthesis and find applications in material and medicinal sciences. A convenient and straightforward access to both classes of compounds under mild conditions is, therefore, highly desirable. Herein, we disclose the decarb-oxylative alkynylation and cyanation of broadly available carboxylic acids using photoredox catalysis and hyper-valent iodine reagents. Choices of both catalysts and reagents were crucial. Computational and experimental studies revealed two different possible mechanisms that are dictated by the oxidation potential of the reagents: radical for alkynylation, ionic for cyanation.

From 2-aminomethyl-1,4-benzodioxane enantiomers to unichiral 2-cyano- and 2-carbonyl-substituted benzodioxanes via dichloroamine

2-Substituted 1,4-benzodioxanes, such as 2-cyano-, 2-methoxycarbonyl-, 2-aminocarbonyl-, and 2-formyl-1,4-benzodioxane, are key synthons that for the most part are never described as enantiomers or are inadequately characterized for enantiomeric purity. They were prepared by quantitative N,N-dichlorination of (R)- and (S)-2-aminomethyl-1,4-benzodioxane and successive functional group conversions in high yields without any racemization of the stereogenic benzodioxane C(2).

Synthesis and biological activity of novel carbacyclins having bicyclic substituents on the ω-chain

A number of carbacyclins having bicyclic substituents on the ω-chain have been synthesized and tested for antiplatelet aggregation activity in vitro (against collagen-induced aggregation of rat platelet), for reduction of systemic blood pressure in vivo (ability to reduce the blood pressure in anesthetized rat by iv injection), and for cytoprotective activity (protection against ethanol-induced rat gastric lesion). The most effective compound for each activity was [3aS-[2E,3aα,4α(3R),5β,6aα]]-5-[hexahydro-5-hydroxy-4-[3-hydroxy-3-(2- indanyl)-1-propynyl]-2(1H)-pentalenylidene]pentanoic acid (compound 11a), while some 1,4-benzodioxan analogues had selectivity for organ-protective activity, and indan analogues showed selectivity in their antiaggregation activity.

Decarboxylative Cyanation of Aliphatic Carboxylic Acids via Visible-Light Flavin Photocatalysis

An operationally simple method is disclosed for the decarboxylative cyanation of aliphatic carboxylic acids at room temperature. Riboflavin tetraacetate, which is an inexpensive organic photocatalyst, promotes the oxidation of carboxylic acids upon visible-light activation. After decarboxylation, the generated radicals are trapped by TsCN, yielding the desired nitriles without any further additive, in a redox-neutral process. Importantly, this protocol can be adapted to flow conditions.