3-aminoquinoline

H302 (10.9%): Harmful if swallowed [Warning Acute toxicity, oral]

H312 (10.9%): Harmful in contact with skin [Warning Acute toxicity, dermal]

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H332 (10.9%): Harmful if inhaled [Warning Acute toxicity, inhalation]

H335 (13%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 46 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Chemical shift

Nuclear magnetic resonance

Spin-spin coupling constant

CSL00129

3-AMINOQUINOLINE + SODIUM ETHYLXANTHATE

I was attempting to prepare 3-[ethoxy(thiocarbonyl)thio]quinoline by reacting the diazonium salt of 3-aminoquinine with potassium ethyl xanthate when an explosion occurred. Thankfully, the injury I received was minor. I was following the procedure described in the Journal of the Chemical Society, Part III [3, 2384 (1959)] on twice their scale. Jerry March's book "Advanced Organic Chemistry: Reactions, Mechanisms, Structure" (New York: John Wiley & Sons, 1992, 4th edition, page 670) lists the procedure as a customary route for the desired aryl xanthate ester and a convenient method for producing thiophenols. The same procedure is also described in "Organic Syntheses, Collective Volume III" (New York: John Wiley & Sons, page 809), which contains a cautionary note about a reported explosion, although the editors found no unusual reactivity. Since diazo esters were present, the explosion most likely resulted from the diazo ester's tendency to decompose explosively. It is unclear whether the diazo ester is a precursor of the desired product or whether the diazo ester forms through a competitive reaction. The reaction proceeded without event. But unlike the literature preparations, precipitation occurred during product extraction with diethyl ether and was isolated by filtration. A 1H NMR of the wet cake was consistent with the desired structure. The solid was air-dried overnight and weighed 17 g. The detonation occurred when a metal spatula was inserted into the solid. Related work in Tetrahedron Letters [26, 6365 (1985)] successfully demonstrated the safe preparation of diaryl sulfides. However, this was done at 25 ºC (mine at 45 ºC) with care taken to avoid heat, since a reference is cited of an explosion at 60 ºC. Also, the disappearance of the suspected diazo sulfide was monitored by thin layer chromatography, and sluggish reactions were not pushed to conversion. Instead, chromatography was used to remove any intermediates.

Explosive

M (up to 100g)

http://pubs.acs.org/cen/safety/20010709.html

CSL00205

3-[Ethoxylthiocarbonylthio]quinoline; Carbonodithioic acid, O-ethyl S-3-quinolinyl ester + Potassium ethylxanthate + 3-Aminoquinoline

I was attempting to prepare 3-[ethoxy(thiocarbonyl)thio]quinoline by reacting the diazonium salt of 3-aminoquinine with potassium ethyl xanthate when an explosion occurred. Thankfully, the injury I received was minor. I was following the procedure described in the Journal of the Chemical Society, Part III [3, 2384 (1959)] on twice their scale. Jerry March's book "Advanced Organic Chemistry: Reactions, Mechanisms, Structure" (New York: John Wiley & Sons, 1992, 4th edition, page 670) lists the procedure as a customary route for the desired aryl xanthate ester and a convenient method for producing thiophenols. The same procedure is also described in "Organic Syntheses, Collective Volume III" (New York: John Wiley & Sons, page 809. DOI: 10.15227/orgsyn.027.0081), which contains a cautionary note about a reported explosion, although the editors found no unusual reactivity. Since diazo esters were present, the explosion most likely resulted from the diazo ester's tendency to decompose explosively. It is unclear whether the diazo ester is a precursor of the desired product or whether the diazo ester forms through a competitive reaction. The reaction proceeded without event. But unlike the literature preparations, precipitation occurred during product extraction with diethyl ether and was isolated by filtration. A 1H NMR of the wet cake was consistent with the desired structure. The solid was air-dried overnight and weighed 17 g. The detonation occurred when a metal spatula was inserted into the solid. Related work in Tetrahedron Letters [26, 6365 (1985)] successfully demonstrated the safe preparation of diaryl sulfides. However, this was done at 25 ºC (mine at 45 ºC) with care taken to avoid heat, since a reference is cited of an explosion at 60 ºC. Also, the disappearance of the suspected diazo sulfide was monitored by thin layer chromatography, and sluggish reactions were not pushed to conversion. Instead, chromatography was used to remove any intermediates." (reprint of full text)

Not Available

In the safety letter above, one substance name - - 3-aminoquinine- may be misspelled. The correct name is 3-Aminoquinoline. See Discussion section of: Cragoe, Edward J., Jr.; Robb, Charles M. 3-Hydroxyquinoline. Org. Synth. 1960, 40, 54. DOI: 10.15227/orgsyn.040.0054

10.1021/cen-v079n028.p006

Literature Reference

10/22/2022