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9-Julolidinecarboxaldehyde
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Name

9-Julolidinecarboxaldehyde

 EINECS N/A
CAS No. 33985-71-6 Density 1.18 g/cm3
PSA 20.31000 LogP 2.26290
Solubility N/A Melting Point 83 °C
Formula C13H15NO Boiling Point 404.8 °C at 760 mmHg
Molecular Weight 201.268 Flash Point 173.5 °C
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 33985-71-6 (2,3,6,7-Tetrahydro-1H,5H-benzo[ij]quinolizine-9-carboxaldehyde) Hazard Symbols N/A
Synonyms

2,3,6,7-Tetrahydro-1H,5H-pyrido[3,2,1-ij]quinoline-9-carbaldehyde;9-Formyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizine;9-Formyljulolidine;9-Julolidinal;9-Julolidinecarboxaldehyde;9-Julolidinylcarboxaldehyde;NSC159999;

Article Data 25

9-Julolidinecarboxaldehyde Synthetic route

N-[(1,2,3,5,6,7-hexahydropyrido[3,2,1-ij]quinolin-9-yl)methylene]-N-methylmethanaminium tetrafluoroborate

33985-71-6

9-julolidinecarboxaldehyde

Conditions
ConditionsYield
With sodium hydroxide In methanol; water pH=Ca. 8 - 9;98%
479-59-4

julolidine

68-12-2, 33513-42-7

N,N-dimethyl-formamide

33985-71-6

9-julolidinecarboxaldehyde

Conditions
ConditionsYield
Stage #1: N,N-dimethyl-formamide With trichlorophosphate at 20℃; for 0.5h; Vilsmeier-Haack Formylation; Inert atmosphere;
Stage #2: julolidine at 90℃; for 4.5h; Vilsmeier-Haack Formylation; Inert atmosphere;		94%
Stage #1: N,N-dimethyl-formamide With trichlorophosphate at 2℃; for 0.5h;
Stage #2: julolidine at 90℃; for 4h;		93%
With trichlorophosphate Vilsmeier reaction;92%
479-59-4

julolidine

33985-71-6

9-julolidinecarboxaldehyde

Conditions
ConditionsYield
Stage #1: N,N-dimethyl-formamide With trichlorophosphate at 0℃; for 1.25h;
Stage #2: julolidine for 1.16667h; Vilsmeier Formylation;		91%
479-59-4

julolidine

93-61-8

N-methyl-N-phenylformamide

33985-71-6

9-julolidinecarboxaldehyde

Conditions
ConditionsYield
With diethyl ether; trichlorophosphate
83646-41-7

1,2,3,5,6,7-hexahydropyrido[3,2,1-ij]quinoline hydrobromide

33985-71-6

9-julolidinecarboxaldehyde

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: trichlorophosphate / 0.75 h / 0 °C
1.2: 0 - 40 °C
2.1: sodium hydroxide / water; methanol / pH Ca. 8 - 9
View Scheme
504-29-0

2-aminopyridine

33985-71-6

9-julolidinecarboxaldehyde

119072-55-8, 7188-38-7

tert-butylisonitrile

N-(tert-butyl)-2-(2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-9-yl)imidazo[1,2-a]pyridin-3-amine

Conditions
ConditionsYield
With chloroacetic acid In methanol at 100℃; for 1h; Sealed tube;98%
33985-71-6

9-julolidinecarboxaldehyde

5217-47-0

N,N'-diethyl-2-thiobarbituric acid

julolidinyl-n-N,N'-diethylthiobarbituric acid

Conditions
ConditionsYield
In ethanol for 6h; Ambient temperature;97%
33985-71-6

9-julolidinecarboxaldehyde

2-(4-methylthiazol-2(5H)-ylidene)malononitrile

2-{4-methyl-5-[(2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1.ij]quinolin-9-yl)methylene]thiazol-2(5H)-ylidene}malononitrile

Conditions
ConditionsYield
With acetic anhydride at 90℃; for 8h; Knoevenagel Condensation;97%
33985-71-6

9-julolidinecarboxaldehyde

2-(4-phenyl-5H-thiazol-2-ylidene)malononitrile

(Z)-2-{5-[(1,2,3,5,6,7-hexahydropyrido[3,2,1-ij]quinolin-9-yl)methylene]-4-phenylthiazol-2(5H)-ylidene}malononitrile

Conditions
ConditionsYield
With acetic anhydride at 90℃; for 8h; Knoevenagel Condensation;97%
33985-71-6

9-julolidinecarboxaldehyde

6,7,13-trimethyl-4,5,8,9-tetrahydroisoquinolino[1,2-a]pyrido[1,2-k][2,9]phenanthroline-3,10-diium trifluoromethanesulfonate

(rac)-(E)-13-(2-(1,2,3,5,6,7-hexahydropyrido[3,2,1-ij]quinolin-9-yl)vinyl)-6,7-dimethyl-4,5,8,9-tetrahydroisoquinolino[1,2-a]pyrido[1,2-k][2,9]phenanthroline-3,10-diium trifluoromethanesulfonate

Conditions
ConditionsYield
With pyrrolidine In methanol at 20℃; for 4h; Knoevenagel Condensation; Darkness; Schlenk technique; Inert atmosphere;97%

9-Julolidinecarboxaldehyde Specification

The cas register number of 9-Julolidinecarboxaldehyde is 33985-71-6. It also can be called as 2,3,6,7-Tetrahydro-1H,5H-benzo[ij]quinolizine-9-carboxaldehyde and the Systematic name about this chemical is 2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinoline-9-carbaldehyde.

Physical properties about 9-Julolidinecarboxaldehyde are: (1)ACD/LogP: 2.74; (2)ACD/LogD (pH 5.5): 2.74; (3)ACD/LogD (pH 7.4): 2.74; (4)ACD/BCF (pH 5.5): 70.8; (5)ACD/BCF (pH 7.4): 71.1; (6)ACD/KOC (pH 5.5): 733.35; (7)ACD/KOC (pH 7.4): 736.53; (8)#H bond acceptors: 2; (9)#Freely Rotating Bonds: 1; (10)Polar Surface Area: 20.31Å2; (11)Index of Refraction: 1.614; (12)Molar Refractivity: 59.28 cm3; (13)Molar Volume: 169.9 cm3; (14)Polarizability: 23.5x10-24cm3; (15)Surface Tension: 51.3 dyne/cm; (16)Enthalpy of Vaporization: 65.63 kJ/mol; (17)Boiling Point: 404.8 °C at 760 mmHg; (18)Vapour Pressure: 9.2E-07 mmHg at 25°C.

Uses of 9-Julolidinecarboxaldehyde: it can be used to produce (E)-3-(9-julolidinyl)-1-phenyl-2-propen-1-one with 1-phenyl-ethanone at temperature of 20 ℃. This reaction is a kind of Condensation. It will need reagent NaOH and H2O with reaction time of 20 hours. The yield is about 61.5%.

You can still convert the following datas into molecular structure:
(1)SMILES: O=Cc1cc3c2c(c1)CCCN2CCC3
(2)InChI: InChI=1/C13H15NO/c15-9-10-7-11-3-1-5-14-6-2-4-12(8-10)13(11)14/h7-9H,1-6H2
(3)InChIKey: XIIVBURSIWWDEO-UHFFFAOYAS
(4)Std. InChI: InChI=1S/C13H15NO/c15-9-10-7-11-3-1-5-14-6-2-4-12(8-10)13(11)14/h7-9H,1-6H2
(5)Std. InChIKey: XIIVBURSIWWDEO-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 5600ug/kg (5.6mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#08343,

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