40247-40-3

Basic information

• Product Name: 5,8-dihydro-5,8-epoxyisoquinoline
• Synonyms: 5,8-dihydro-5,8-epoxyisoquinoline
• CAS NO: 40247-40-3
• Molecular Formula: C₉H₇NO
• Molecular Weight: 145.16
• Mol File: 40247-40-3.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 105 °C(Press: 4 Torr)
• Appearance: /
• Density: 1.289±0.06 g/cm3(Predicted)
• PKA: 5.75±0.20(Predicted)
• CAS DataBase Reference: 5,8-dihydro-5,8-epoxyisoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 5,8-dihydro-5,8-epoxyisoquinoline(40247-40-3)
• EPA Substance Registry System: 5,8-dihydro-5,8-epoxyisoquinoline(40247-40-3)

Safety Data

• Hazardous Substances Data: 40247-40-3(Hazardous Substances Data)

Upstream product

• 110-00-9 furan 
• 694-52-0 4-fluoropyridine 
• 77332-79-7 3-chloro-4-iodopyridine 
• 112921-55-8 3-bromo-4-pyridyl phenyl sulfoxide 
• 93772-12-4 3-(3',3'-dimethyltriazene-1-yl)pyridine-4-carboxylic acid 
• 134391-67-6 3-bromo-4-(trimethylsilyl)pyridine 
• 134391-69-8 3-Brom-2,4-bis(trimethylsilyl)pyridin 
• 79698-59-2 chloro-3-di(trimethylsilyl)-2,4-pyridine 
• 204459-37-0 4-(triethylsilyl)pyridin-3-yl trifluoromethanesulfonate 
• 626-60-8 3-Chloropyridine 
• 51581-40-9 3-pyridyl diethylcarbamate 
• 1001004-63-2 4-(triethylsilyl)pyridin-3-ol 
• 141811-93-0 4-(triethylsilyl)pyridin-3-yl diethylcarbamate 
• 7579-20-6 3-Aminopyridine-4-carboxylic acid 

Downstream Products

• 1274655-44-5 7-(dibenzylamino)-7,8-dihydro-isoquinolin-8-ol 
• 1274655-33-2 6-(dibenzylamino)-5,6-dihydroisoquinolin-5-ol 

Relevant articles and documents

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Rh(I)-catalyzed ring-opening of hetaryne-furan diels-alder adducts: Rapid access to stereochemically defined heterocyclic scaffolds

Probing the nucleophilic ring-opening of various bicyclic [2.2.1] hetaryne-furan Diels-Alder adducts revealed that efficient reactivity could be observed with heteroatom nucleophiles by using a cationic Rh(I) complex in combination with a chiral Josiphos-

Substituted 3,4-pyridynes: Clean cycloadditions

The stabilisation of 3,4-pyridyne (1) by an alkoxy group adjacent to the ring nitrogen is reported. The regioselective lithiation of 2-ethoxy- (14), 2-methoxy- (18), 2-isopropoxy- (19) and 6-isopropoxy- (26) -3-chloropyridines with tertbutyllithium at low temperatures, followed by elimination of lithium chloride affords 2- and 6-alkoxy-3,4-pyridynes. These species are trapped m situ with furan in a Diels-Alder reaction to give 5-8 in 66-89% yield, and do not give products typical of polymerisation or nucleophilic addition to the 3,4-pyridyne intermediates. As a comparison treatment of 3-chloropyridine with furan and LDA gives only 19% of adduct (4). We also report the novel use of the isopropoxy (rather than methoxy) group in these systems, which can act as a heteroatomic electron donating group which inhibits a-lithiation by tert-butyllithium because of its increased steric bulk. The Royal Society of Chemistry 2000.