1,2,3,4-Tetrahydroquinoline supplier

Name
1,2,3,4-Tetrahydroquinoline
EINECS 211-237-6
CAS No. 635-46-1
Article Data226
CAS DataBase
Density 1.006 g/cm³
Solubility <1 g/L (20 °C) in water
Melting Point 9-14 °C(lit.)
Formula C₉H₁₁N
Boiling Point 250.775 °C at 760 mmHg
Molecular Weight 133.193
Flash Point 100.6 °C
Transport Information
Appearance clear pale yellow to yellow liquid
Safety 26-36/37-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Kusol;1.2.3.4-tetra-hydroquinoline;Quinoline, 1,2,3,4-tetrahydro-;1,2,3,4-Hydroquinoline;1.2.3.4-tetra- hydroquinoline;1,2,3,4－tetrahydroquinolines;1,2,3,4-Tetrahydro-quinoline;
PSA 12.03000
LogP 2.18270

Synthetic route

: 91-22-5
quinoline

: 635-46-1
1,2,3,4-tetrahydroisoquinoline

Conditions

Conditions	Yield
With hydrogen; Wilkinson's catalyst In benzene at 85℃; under 16031.6 Torr; for 60h;	100%
With hydrogen; polymer incarcerated palladium In tetrahydrofuran at 20℃; for 24h;	100%
With hydrogen; Pd-containing polymer micelles In tetrahydrofuran at 20℃; under 760 Torr; for 24h;	100%

: 2739-16-4
3,4-dihydro-2H-quinoline-1-carbaldehyde

: 635-46-1
1,2,3,4-tetrahydroisoquinoline

Conditions

Conditions	Yield
With sodium hydroxide In ethanol; water	99%
With sodium hydroxide In ethanol for 6h; Hydrolysis; Heating;	93%
With hydrogenchloride

: 182565-33-9
1-(4-nitrobenzenesulfonyl)-1,2,3,4-tetrahydroquinoline

: 635-46-1
1,2,3,4-tetrahydroisoquinoline

Conditions

Conditions	Yield
With potassium carbonate; thiophenol In acetonitrile for 24h;	99%

: 3,4-dihydro-2H-quinoline-1-carboxylic acid allyl ester

: 635-46-1
1,2,3,4-tetrahydroisoquinoline

Conditions

Conditions	Yield
With titanium(IV) isopropylate; chloro-trimethyl-silane; magnesium In tetrahydrofuran at 50℃; for 24h;	99%
Multi-step reaction with 2 steps 1: aminomethyl resin-supported N-propylbarbituric acid / Pd(PPh3)4 / tetrahydrofuran / 1 h / 20 - 40 °C 2: 86 percent / aminomethyl resin-supported N-propylbarbituric acid / Pd(PPh3)4 / tetrahydrofuran / 40 °C View Scheme

: C13H13NO2

: 635-46-1
1,2,3,4-tetrahydroisoquinoline

Conditions

Conditions	Yield
With titanium(IV) isopropylate; chloro-trimethyl-silane; magnesium In tetrahydrofuran at 50℃; for 12h;	99%

: 4964-71-0
5-bromoquinoline

: 635-46-1
1,2,3,4-tetrahydroisoquinoline

Conditions

Conditions	Yield
With hydrogen In water at 20℃; for 24h; regioselective reaction;	97%

: 5344-90-1
2-Aminobenzyl alcohol

: 64-17-5
ethanol

: 635-46-1
1,2,3,4-tetrahydroisoquinoline

Conditions

Conditions	Yield
With layered double hydroxide supported NiAl at 20 - 125℃; for 24h; Reagent/catalyst;	97%

: 553-03-7
3,4-dihydro-2(1H)-quinolone

: 635-46-1
1,2,3,4-tetrahydroisoquinoline

Conditions

Conditions	Yield
With [RuCl2(N-heterocyclic carbene)(bis[2-(diphenylphosphino)ethyl]amine)]; hydrogen; caesium carbonate In toluene; butan-1-ol at 120℃; under 22502.3 Torr; for 6h; Catalytic behavior; Solvent; Reagent/catalyst; Schlenk technique; Autoclave;	96%
With borane-ammonia complex; boron trifluoride diethyl etherate; tris(pentafluorophenyl)borate In 1,2-dichloro-ethane at 60℃; for 16h;	90%
With tetra(n-butyl)ammonium borohydride In dichloromethane for 10h; Heating;	86%

: 18655-48-6
3-(2-chlorophenyl)-1-propanamine

: 635-46-1
1,2,3,4-tetrahydroisoquinoline

Conditions

Conditions	Yield
With bis(acetylacetonate)nickel(II); sodium t-butanolate; 1,3-bis[2,6-bis(1-methylethyl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene monohydrochloride In 1,4-dioxane at 100℃; for 4h;	96%
With sodium hydride; tert-butyl alcohol; 1,3-bis[2,6-bis(1-methylethyl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene monohydrochloride; palladium diacetate In 1,4-dioxane for 3h;

: 580-22-3
2-aminoquinoline

: 635-46-1
1,2,3,4-tetrahydroisoquinoline

Conditions

Conditions	Yield
With iridium(IV) oxide tetrahydrate; hydrogen In methanol at 20℃; for 24h; regioselective reaction;	96%

: 5434-99-1
1-((4-nitrophenyl)sulfonyl)-1,2,3,4-tetrahydroquinoline

: 635-46-1
1,2,3,4-tetrahydroisoquinoline

Conditions

Conditions	Yield
With magnesium; lithium tert-butoxide In tetrahydrofuran at 20℃; for 12h; Product distribution; Further Variations:; Reagents;	94%

: 1,2,3,4-tetrahydroquinolinetrimethylmethanesulfonamide

: 635-46-1
1,2,3,4-tetrahydroisoquinoline

Conditions

Conditions	Yield
With trifluorormethanesulfonic acid; methoxybenzene In dichloromethane at 0℃; desulfonation;	93%

: 326899-59-6
1-(mesitylsulfonyl)-1,2,3,4-tetrahydroquinoline

: 635-46-1
1,2,3,4-tetrahydroisoquinoline

Conditions

Conditions	Yield
With titanium(IV) isopropylate; chloro-trimethyl-silane; magnesium In tetrahydrofuran at 50℃; for 12h; Inert atmosphere;	93%

: 4169-19-1
1-acetyl-1,2,3,4-tetrahydroquinoline

A: 635-46-1
1,2,3,4-tetrahydroisoquinoline

B: 64-17-5
ethanol

Conditions

Conditions	Yield
With hydrogen In toluene at 160℃; under 45004.5 Torr; for 15h; Catalytic behavior; Autoclave;	A 93% B 89 %Chromat.
With {Ru(H)(BH4)(CO)(3-(di-tert-butylphosphino)-N-((1-methyl-1H-imidazol-2-yl)methyl)propylamine)}; hydrogen In isopropyl alcohol at 120℃; under 22502.3 Torr; for 18h; Autoclave;	A 99 %Chromat. B 99 %Chromat.
With C16H25MnN3O3P(1+)*Br(1-); potassium tert-butylate; hydrogen In cyclohexane at 100℃; under 22502.3 Torr; for 16h; Inert atmosphere; Autoclave;	A 88 %Chromat. B 85 %Chromat.

: 91-22-5
quinoline

: 455-19-6
4-Trifluoromethylbenzaldehyde

A: 635-46-1
1,2,3,4-tetrahydroisoquinoline

B: 1611478-22-8
1-(4-(trifluoromethyl)benzyl)-1,2,3,4-tetrahydroquinoline

Conditions

Conditions	Yield
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; (meta-(trifluoromethyl)phenyl)boronic acid In 1,2-dichloro-ethane at 60℃; for 12h; Kinetics; Reagent/catalyst;	A n/a B 93%

...Expand

: 91-22-5
quinoline

A: 10500-57-9
5,6,7,8-tetrahydroquinoline

B: 635-46-1
1,2,3,4-tetrahydroisoquinoline

Conditions

Conditions	Yield
With 5% Ru/MgO; hydrogen In tetrahydrofuran at 150℃; under 38002.6 Torr; for 0.7h; Time; Concentration; Pressure;	A 7% B 92%
With hydrogen; platinum(IV) oxide In trifluoroacetic acid	A 80% B 6%
With Cp*Rh(2-(2-pyridyl)phenyl)H; hydrogen In tetrahydrofuran at 80℃; under 3040.2 Torr; for 48h; Catalytic behavior; Glovebox;	A 58% B 14%

: N-(trichloroethoxy carbonyl)-tetrahydroquinoline

: 635-46-1
1,2,3,4-tetrahydroisoquinoline

Conditions

Conditions	Yield
With ammonium acetate; 10% Cd/Pd In tetrahydrofuran; water for 0.75h;	92%

: 3,4-dihydro-2H-quinoline-1-carboxylic acid allyl ester

A: 635-46-1
1,2,3,4-tetrahydroisoquinoline

B: 80574-15-8
1-allyl-1,2,3,4-tetrahydroquinoline

Conditions

Conditions	Yield
With aminomethyl resin-supported N-propylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 20 - 40℃; for 1h;	A 92% B n/a

: 68253-35-0, 100485-57-2, 3349-60-8
indan-1-one oxime

: 635-46-1
1,2,3,4-tetrahydroisoquinoline

Conditions

Conditions	Yield
Stage #1: indan-1-one oxime With diisobutylaluminium hydride In hexane; dichloromethane at 0 - 20℃; Inert atmosphere; Stage #2: With sodium fluoride In hexane; dichloromethane; water at 0℃; for 0.5h;	92%
Stage #1: indan-1-one oxime With diisobutylaluminium hydride In hexane; dichloromethane at 0 - 20℃; Inert atmosphere; Stage #2: With water; sodium fluoride In hexane; dichloromethane at 0℃; for 0.5h; Inert atmosphere; regioselective reaction;	92%
With dichloroaluminum hydride In cyclopentyl methyl ether at 0 - 20℃;	69%
Multi-step reaction with 2 steps 1.1: hydrogenchloride; sodium cyanoborohydride / methanol / 0 - 20 °C 2.1: diisobutylaluminium hydride / hexane; dichloromethane / 3.5 h / 0 °C / Inert atmosphere 2.2: 0.5 h / 0 °C / Inert atmosphere View Scheme

: 1613-37-2
Quinoline N-oxide

: 635-46-1
1,2,3,4-tetrahydroisoquinoline

Conditions

Conditions	Yield
Stage #1: Quinoline N-oxide With H2SiEt2; tris(pentafluorophenyl)borate In chloroform at 65℃; for 12h; Inert atmosphere; Stage #2: With hydrogenchloride In diethyl ether at 20℃; for 1h;	91%
With ammonium formate; 10percent palladium on carbon In methanol at 20℃; for 16h;	87%
With hydrogen In toluene at 120℃; under 15001.5 Torr; for 48h; Autoclave;	90 %Chromat.
With hydrogen In water; isopropyl alcohol Heating; High pressure; chemoselective reaction;	68 %Chromat.

: 57591-47-6
3-(2-aminophenyl)-1-propanol

: 635-46-1
1,2,3,4-tetrahydroisoquinoline

Conditions

Conditions	Yield
With C36H35IrN2P(1+)*C32H12BF24(1-); potassium tert-butylate In diethylene glycol dimethyl ether at 60℃; for 24h; Inert atmosphere;	91%
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; potassium carbonate In toluene at 111℃; for 17h;	96 % Chromat.

: 91-22-5
quinoline

: 64-18-6
formic acid

A: 635-46-1
1,2,3,4-tetrahydroisoquinoline

B: 2739-16-4
3,4-dihydro-2H-quinoline-1-carbaldehyde

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 130℃; for 0.166667h; Reagent/catalyst;	A 91% B 7%
With triethylamine In N,N-dimethyl-formamide at 130℃; for 2h; chemoselective reaction;

...Expand

: 24310-24-5
1-(Toluene-4-sulfonyl)-1,2,3,4-tetrahydro-quinoline

: 635-46-1
1,2,3,4-tetrahydroisoquinoline

Conditions

Conditions	Yield
With naphthalene; tetraethylammonium bromide In N,N-dimethyl-formamide at 0℃; Inert atmosphere; Electrolysis;	90%
With titanium(IV) isopropylate; chloro-trimethyl-silane; magnesium In tetrahydrofuran at 50℃; for 12h; Inert atmosphere;	79%
With sodium hydride In N,N-dimethyl acetamide at 60℃; for 8h; Inert atmosphere;	32%

: 251980-46-8
1-indanone O-(tert-butyldimethylsilyl)oxime

: 635-46-1
1,2,3,4-tetrahydroisoquinoline

Conditions

Conditions	Yield
With borane-THF at 60℃; Reduction;	88%
With dimethylsulfide borane complex; boron trifluoride diethyl etherate at 20℃;

: 91-22-5
quinoline

: 67-63-0
isopropyl alcohol

A: 635-46-1
1,2,3,4-tetrahydroisoquinoline

B: 21863-25-2
1-(1-methylethyl)-1,2,3,4-tetrahydroquinoline

Conditions

Conditions	Yield
With palladium 10% on activated carbon; zinc at 150℃; for 24h; Autoclave;	A 88% B 11%
With perchloric acid; bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] In water for 17h; Heating;	A 69 % Chromat. B n/a

...Expand

: 79476-07-6
3-Iodoquinoline

A: 91-22-5
quinoline

B: 635-46-1
1,2,3,4-tetrahydroisoquinoline

Conditions

Conditions	Yield
With 2,6-dimethylpyridine; phenylsilane; indium(III) acetate In ethanol at 20℃; for 120h;	A 88% B 8%
With 2,6-dimethylpyridine; phenylsilane; indium(III) acetate In ethanol at 20℃; for 48h;	A 29% B 48%

: 198218-85-8
1-(2-nitrobenzyl)-1,2,3,4-tetrahydroquinoline

: 635-46-1
1,2,3,4-tetrahydroisoquinoline

Conditions

Conditions	Yield
With hydrazine In 1,4-dioxane; water for 0.333333h; Inert atmosphere; UV-irradiation;	88%

: 5825-44-5
N-nitroso-1,2,3,4-tetrahydroquinoline

: 635-46-1
1,2,3,4-tetrahydroisoquinoline

Conditions

Conditions	Yield
With sodium tetrahydroborate; titanium tetrachloride In 1,2-dimethoxyethane for 14h; Ambient temperature;	87%

: 80639-72-1
1,3,4,5-tetrahydrobenzo<1,2-c>thiazepine 2,2-dioxide

: 635-46-1
1,2,3,4-tetrahydroisoquinoline

Conditions

Conditions	Yield
at 650℃; under 0.005 Torr;	86.9%
at 650℃; under 0.005 Torr; Mechanism; flash vacuum pyrolyses (flow system);	86.9%

: 635-46-1
1,2,3,4-tetrahydroisoquinoline

: 506-68-3
bromocyane

: 1530-84-3
N-cyano-tetrahydro quinoline

Conditions

Conditions	Yield
	100%
With benzene

: 635-46-1
1,2,3,4-tetrahydroisoquinoline

: 625-36-5
2-chloropropionyl chloride

: 57369-31-0
1,2,6,7-tetrahydropyrido<3,2,1-i,j>quinolin-3(5H)-one

Conditions

Conditions	Yield
Stage #1: 1,2,3,4-tetrahydroisoquinoline; 2-chloropropionyl chloride In acetone for 1h; Inert atmosphere; Reflux; Stage #2: With aluminum (III) chloride; sodium chloride at 150℃; for 1h; Inert atmosphere;	100%
Stage #1: 1,2,3,4-tetrahydroisoquinoline; 2-chloropropionyl chloride In acetone for 1h; Reflux; Stage #2: With aluminum (III) chloride; sodium chloride at 150℃; for 0.5h;	88%
With acetone Erhitzen des Reaktionsprodukts mit Aluminiumchlorid;
With aluminium trichloride 1.) acetone, reflux, 2 h, 2.) heating; Multistep reaction;

: 635-46-1
1,2,3,4-tetrahydroisoquinoline

: 124-38-9
carbon dioxide

: 121565-21-7
1,2,3,4-tetrahydroquinolin-1-carboxylic acid lithium salt

Conditions

Conditions	Yield
Stage #1: 1,2,3,4-tetrahydroisoquinoline With n-butyllithium In diethyl ether; hexane at -78 - 20℃; for 2h; Stage #2: carbon dioxide In diethyl ether; hexane at -78℃;	100%
Stage #1: 1,2,3,4-tetrahydroisoquinoline With n-butyllithium In diethyl ether at -78 - 20℃; Cooling with acetone-dry ice; Inert atmosphere; Stage #2: carbon dioxide In diethyl ether at -78℃; Cooling with ethanol-dry ice;	100%
Stage #1: 1,2,3,4-tetrahydroisoquinoline With n-butyllithium In diethyl ether at -78℃; for 17h; Schlenk technique; Inert atmosphere; Stage #2: carbon dioxide In diethyl ether at -78 - 20℃; Schlenk technique;	100%
With n-butyllithium 1) THF, hexane, -78 deg C, 2) room temp.; Multistep reaction;
Stage #1: 1,2,3,4-tetrahydroisoquinoline With n-butyllithium In hexane; tert-butyl methyl ether at -20 - 20℃; Schlenk technique; Stage #2: carbon dioxide In tetrahydrofuran; diethyl ether; hexane; tert-butyl methyl ether at -78 - 20℃; Schlenk technique;

: 635-46-1
1,2,3,4-tetrahydroisoquinoline

: 407-25-0
trifluoroacetic anhydride

: 79066-90-3
1-(3,4-dihydroquinolin-1(2H)-yl)-2,2,2-trifluoroethanone

Conditions

Conditions	Yield
With triethylamine In diethyl ether at 0 - 20℃; for 5h;	100%
With triethylamine In diethyl ether at 20℃; for 5h;	100%
With triethylamine In diethyl ether at 0 - 20℃;	98%

: 635-46-1
1,2,3,4-tetrahydroisoquinoline

: 5825-44-5
N-nitroso-1,2,3,4-tetrahydroquinoline

Conditions

Conditions	Yield
With sulfuric acid; sodium chloride; sodium nitrite In dichloromethane	100%
With sulfuric acid; sodium nitrite In dichloromethane for 1.5h;	100%
With sodium nitrite In water; acetic acid; ethyl acetate	96%

: 635-46-1
1,2,3,4-tetrahydroisoquinoline

: 100-47-0
benzonitrile

: 28748-92-7
phenyl(1,2,3,4-tetrahydroquinolin-8-yl)methanone

Conditions

Conditions	Yield
Stage #1: 1,2,3,4-tetrahydroisoquinoline; benzonitrile With aluminum (III) chloride; water; boron trichloride In dichloromethane; toluene at 110℃; Stage #2: With hydrogenchloride; water In dichloromethane; toluene at 80℃; for 1h;	100%
Stage #1: 1,2,3,4-tetrahydroisoquinoline; benzonitrile With aluminum (III) chloride; boron trichloride In dichloromethane; toluene at 0 - 110℃; Stage #2: With hydrogenchloride; water at 80℃; for 1h;	100%
With aluminium trichloride; boron trichloride In 1,2-dichloro-ethane Acylation;

: 635-46-1
1,2,3,4-tetrahydroisoquinoline

: 98-09-9
benzenesulfonyl chloride

: 5434-99-1
1-((4-nitrophenyl)sulfonyl)-1,2,3,4-tetrahydroquinoline

Conditions

Conditions	Yield
With pyridine at 20℃; for 1h;	100%
With pyridine at 50℃; Inert atmosphere;	97%
With pyridine at 60 - 80℃; Inert atmosphere;	87%

: 635-46-1
1,2,3,4-tetrahydroisoquinoline

: 6160-65-2
1,1'-Thiocarbonyldiimidazole

: 1-(1H-imidazol-1-ylcarbonothioyl)-1,2,3,4-tetrahydroquinoline

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 2h;	100%

: diethyl (piperidin-1-yl)ethynephosphonate

: 635-46-1
1,2,3,4-tetrahydroisoquinoline

: diethyl (E)-2-(piperidin-1-yl)-2-(1,2,3,4-tetrahydroquinolin-1-yl)ethenephosphonate

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In tetrachloromethane at 60℃;	100%

: 635-46-1
1,2,3,4-tetrahydroisoquinoline

: 19519-59-6
2-chloroacetylenephosphonic acid dimethyl ester

: 1105013-11-3
dimethyl (1,2,3,4-tetrahydroqunolyl)ethynylphosphonate

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile for 2h; Heating;	100%

: 635-46-1
1,2,3,4-tetrahydroisoquinoline

: 109-72-8, 29786-93-4
n-butyllithium

: 124-38-9
carbon dioxide

: 121565-21-7
1,2,3,4-tetrahydroquinolin-1-carboxylic acid lithium salt

Conditions

Conditions	Yield
Stage #1: 1,2,3,4-tetrahydroisoquinoline; n-butyllithium In diethyl ether at -78 - 20℃; for 2h; Cooling with acetone-dry ice; Stage #2: carbon dioxide In diethyl ether at -78 - 20℃; Cooling with acetone-dry ice;	100%

...Expand

: 635-46-1
1,2,3,4-tetrahydroisoquinoline

: 1126-09-6
4-carbethoxypiperidine

: 503-38-8
trichloromethyl chloroformate

: 1000211-89-1
ethyl 1-(3,4-dihydroquinolin-1(2H)-ylcarbonyl)piperidine-4-carboxylate

Conditions

Conditions	Yield
Stage #1: 1,2,3,4-tetrahydroisoquinoline; trichloromethyl chloroformate With triethylamine In dichloromethane Stage #2: 4-carbethoxypiperidine In dichloromethane	100%

...Expand

: 104-53-0
3-phenyl-propionaldehyde

: 635-46-1
1,2,3,4-tetrahydroisoquinoline

: 1-(3-phenylpropyl)-1,2,3,4-tetrahydroquinoline

Conditions

Conditions	Yield
With sodium tris(acetoxy)borohydride In 2-methyltetrahydrofuran at 18℃; for 1h; Solvent; Reagent/catalyst; Green chemistry;	100%

: 635-46-1
1,2,3,4-tetrahydroisoquinoline

: 563-76-8
α-bromopropionyl bromide

: 118484-79-0
2-bromo-1-(3,4-dihydroquinolin-1(2H)-yl)propan-1-one

Conditions

Conditions	Yield
With pyridine In dichloromethane at -78 - 20℃; for 1.75h;	100%

: 635-46-1
1,2,3,4-tetrahydroisoquinoline

: 14273-90-6
methyl 6-bromohexanoate

: N-methoxycarbonylpentyl-1,2,3,4-tetrahydroquinoline

Conditions

Conditions	Yield
With potassium carbonate; potassium iodide In acetonitrile at 100℃; for 21h; Inert atmosphere;	100%
With potassium carbonate; potassium iodide In acetonitrile for 38h; Inert atmosphere; Reflux;	91%
With sodium carbonate; sodium iodide In acetonitrile for 48h; Reflux; Inert atmosphere;	81%
With potassium carbonate; potassium iodide In acetonitrile at 100℃; for 30h; Inert atmosphere;	76%
With potassium carbonate; potassium iodide In acetonitrile at 100℃; for 30h; Inert atmosphere;	76%

: 98-01-1
furfural

: 635-46-1
1,2,3,4-tetrahydroisoquinoline

: trans-4,5-bis(dihydroquinoline)cyclopent-2-enone

Conditions

Conditions	Yield
With copper(II) bis(trifluoromethanesulfonate) In water at 20℃; for 0.0166667h;	100%

: 635-46-1
1,2,3,4-tetrahydroisoquinoline

: 110-46-3
isopentyl nitrite

: 5825-44-5
N-nitroso-1,2,3,4-tetrahydroquinoline

Conditions

Conditions	Yield
With 4-(1,1-dimethylethyl)benzoic acid In dichloromethane at 20℃; for 24h; Inert atmosphere; Schlenk technique; Glovebox;	100%

: 635-46-1
1,2,3,4-tetrahydroisoquinoline

: 124-38-9
carbon dioxide

: C10H10NO2(1-)*Li(1+)

Conditions

Conditions	Yield
Stage #1: 1,2,3,4-tetrahydroisoquinoline In diethyl ether at -78℃; for 0.5h; Schlenk technique; Stage #2: With n-butyllithium In diethyl ether for 2h; Inert atmosphere; Stage #3: carbon dioxide In diethyl ether at -78 - 20℃;	100%

: 635-46-1
1,2,3,4-tetrahydroisoquinoline

: 124-38-9
carbon dioxide

: C9H11N*2Li(1+)*CO3(2-)

Conditions

Conditions	Yield
Stage #1: 1,2,3,4-tetrahydroisoquinoline With n-butyllithium In diethyl ether at -78℃; for 2h; Schlenk technique; Inert atmosphere; Stage #2: carbon dioxide In diethyl ether at -78℃; Schlenk technique; Inert atmosphere;	100%

: 635-46-1
1,2,3,4-tetrahydroisoquinoline

: 33735-01-2
lithium 1,2,3,4-tetrahydroquinolide

Conditions

Conditions	Yield
Stage #1: 1,2,3,4-tetrahydroisoquinoline In diethyl ether at -78℃; for 0.5h; Schlenk technique; Cooling with acetone-dry ice; Stage #2: With n-butyllithium In diethyl ether for 2h; Inert atmosphere;	100%

: 635-46-1
1,2,3,4-tetrahydroisoquinoline

: 1-phenyl-3-methyl-1H-pyrazole-5-carbonyle chloride

: C20H19N3O

Conditions

Conditions	Yield
With pyridine In dichloromethane at 25℃; for 0.5h;	99.7%

: 635-46-1
1,2,3,4-tetrahydroisoquinoline

: 64-18-6
formic acid

: 2739-16-4
3,4-dihydro-2H-quinoline-1-carbaldehyde

Conditions

Conditions	Yield
Stage #1: formic acid With acetic anhydride at 70℃; for 1h; Inert atmosphere; Stage #2: 1,2,3,4-tetrahydroisoquinoline at 50℃; Inert atmosphere;	99%
With iodine at 70℃;	96%

: 635-46-1
1,2,3,4-tetrahydroisoquinoline

: 91-22-5
quinoline

Conditions

Conditions	Yield
With oxygen In para-xylene at 110℃; for 3.5h;	99%
With pyridine at 20℃; for 2h; Catalytic behavior; Reagent/catalyst; Irradiation;	99%
With 1,10-Phenanthroline; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium tert-butylate; oxygen; nickel dibromide In tert-Amyl alcohol at 95℃; for 24h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature;	99%

: 635-46-1
1,2,3,4-tetrahydroisoquinoline

: 16174-75-7
2-[2-(p-tolylsulfanyl)phenyl]acetic acid

: 207349-81-3
1-(3,4-Dihydro-2H-quinolin-1-yl)-2-(2-p-tolylsulfanyl-phenyl)-ethanone

Conditions

Conditions	Yield
With oxalyl dichloride; N,N-dimethyl-formamide In benzene for 2h; Ambient temperature;	99%

: 673-32-5
1-Phenylprop-1-yne

: 635-46-1
1,2,3,4-tetrahydroisoquinoline

: 1-[(2E)-3-phenylprop-2-en-1-yl]-1,2,3,4-tetrahydroquinoline

Conditions

Conditions	Yield
With benzoic acid; DavePhos; tris(dibenzylideneacetone)dipalladium(0) chloroform complex In toluene at 50℃;	99%
With chlorobis(cyclooctene)rhodium(I) dimer; 1,3-bis-(diphenylphosphino)propane; benzene-1,2-dicarboxylic acid In tetrahydrofuran at 70℃; for 18h; Glovebox; enantioselective reaction;	99%
With tetrakis(triphenylphosphine) palladium(0); benzoic acid; CyJohnPhos In water at 100℃; for 24h; Sealed tube; Inert atmosphere; regioselective reaction;	98%

: 635-46-1
1,2,3,4-tetrahydroisoquinoline

: 79-22-1
methyl chloroformate

: 94567-78-9
3,4-dihydro-2H-quinoline-1-carboxylic acid methyl ester

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 0 - 50℃; for 6h;	99%
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 6h; Cooling with ice; Inert atmosphere;
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 5.16667h; Cooling with ice;

1,2,3,4-Tetrahydroquinoline Chemical Properties

Molecular Structure of 1,2,3,4-Tetrahydroquinoline (CAS NO.635-46-1):

IUPAC Name: 1,2,3,4-tetrahydroquinoline
Molecular Formula: C₉H₁₁N
Molecular Weight: 133.19
H bond acceptors: 1
H bond donors: 1
Freely Rotating Bonds: 0
Polar Surface Area: 3.24Å²
Index of Refraction: 1.544
Molar Refractivity: 41.77 cm³
Molar Volume: 132.2 cm³
Surface Tension: 37 dyne/cm
Density: 1.006 g/cm³
Flash Point: 100.6 °C
Enthalpy of Vaporization: 48.81 kJ/mol
Boiling Point: 250.8 °C at 760 mmHg
Vapour Pressure: 0.0212 mmHg at 25°C
Melting point: 15-17^oC
EINECS: 211-237-6
Water Solubility: <1 g/L (20 ºC)
BRN: 116149
InChI
InChI=1/C9H11N/c1-2-6-9-8(4-1)5-3-7-10-9/h1-2,4,6,10H,3,5,7H2
Smiles
N1c2c(cccc2)CCC1
Product Categories: Quinoline&Isoquinoline; Building Blocks; Heterocyclic Building Blocks; Isoquinolines; Quinolines; Alphabetical Listings; Flavors and Fragrances; Q-Z

1,2,3,4-Tetrahydroquinoline Safety Profile

Hazard Codes: Irritant Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36/37-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37:Wear suitable protective clothing and gloves.
S36:Wear suitable protective clothing.
WGK Germany: 3
HS Code: 29334990

1,2,3,4-Tetrahydroquinoline Specification

1,2,3,4-Tetrahydroquinoline , with CAS number of 635-46-1, can be called Kusol ; 1.2.3.4-tetra-hydroquinoline ; Quinoline, 1,2,3,4-tetrahydro- ; 1,2,3,4-Hydroquinoline ; 1.2.3.4-tetra- hydroquinoline ; 1,2,3,4－tetrahydroquinolines ; 1,2,3,4-Tetrahydro-quinoline . It is a clear pale yellow to yellow liquid.

Product Name

1,2,3,4-Tetrahydroquinoline

Synthetic route

1,2,3,4-Tetrahydroquinoline Chemical Properties

1,2,3,4-Tetrahydroquinoline Safety Profile

1,2,3,4-Tetrahydroquinoline Specification

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