5,6,7,8-Tetrahydro-1,6-naphthyridine supplier

Name
2-P-TOLYL-4,5,6,7-TETRAHYDRO-OXAZOLO[5,4-C]PYRIDINE
EINECS
CAS No. 80957-68-2
Article Data10
CAS DataBase
Density 1.069 g/cm³
Solubility
Melting Point
Formula C₈H₁₀N₂
Boiling Point 47.62 °C at 760 mmHg
Molecular Weight 134.181
Flash Point 103.557 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 5,6,7,8-Tetrahydro-1,6-naphthyridine;
PSA 24.92000
LogP 1.05610

Synthetic route

: 625100-00-7
3-bromo-5,6,7,8-tetrahydro-1,6-naphthyridine

: 80957-68-2
5,6,7,8-tetrahydro-1,6-naphthyridine

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In ethanol under 2844.39 Torr; for 3.5h;	100%
With palladium 10% on activated carbon; hydrogen In ethanol under 2844.39 Torr; for 3.5h;	0.5 g

: 75510-02-0
6-benzyl-5,6,7,8-tetrahydro-1,6-naphthyridine

: 80957-68-2
5,6,7,8-tetrahydro-1,6-naphthyridine

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In acetic acid at 50 - 60℃;	94%
With palladium on activated charcoal; hydrogen; acetic acid under 2585.81 Torr; for 48h;	64%
With hydrogen; palladium 10% on activated carbon In acetic acid at 50 - 60℃; under 760.051 Torr; for 2h;	60%
With hydrogen; acetic acid; palladium on activated charcoal at 50 - 60℃; for 2h;

: 3612-20-2
1-phenylmethyl-4-piperidone

: 80957-68-2
5,6,7,8-tetrahydro-1,6-naphthyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Et3N; pyridinium acetate / 22 h / 120 °C 2: H2; AcOH / Pd/C / 2 h / 50 - 60 °C View Scheme
Multi-step reaction with 2 steps 1: 37 percent / Et3N, piperidinium acetate / 24 h / 120 °C 2: 94 percent / H2 / Pd-C / acetic acid / 50 - 60 °C View Scheme
Multi-step reaction with 2 steps 1: sodium tetrachloroaurate(III) dihydrate / ethanol / 8 h / 90 °C / Sealed tube 2: palladium on activated charcoal; hydrogen; acetic acid / 48 h / 2585.81 Torr View Scheme

: 65719-09-7
methyl 2-methylnicotinate

: 80957-68-2
5,6,7,8-tetrahydro-1,6-naphthyridine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 16 h / 90 °C / Inert atmosphere 2.1: tetrabutyl ammonium fluoride / acetonitrile / 16 h / 0 - 30 °C / Inert atmosphere 3.1: hydrogen / methanol; water / 16 h / 50 °C / 2585.81 Torr 4.1: dimethylsulfide borane complex / tetrahydrofuran; dichloromethane / 16 h / 0 - 90 °C 4.2: 0.25 h / 30 °C 4.3: 3 h / 0 - 90 °C View Scheme

Yield

Multi-step reaction with 4 steps
1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 16 h / 90 °C / Inert atmosphere
2.1: tetrabutyl ammonium fluoride / acetonitrile / 16 h / 0 - 30 °C / Inert atmosphere
3.1: hydrogen / methanol; water / 16 h / 50 °C / 2585.81 Torr
4.1: dimethylsulfide borane complex / tetrahydrofuran; dichloromethane / 16 h / 0 - 90 °C
4.2: 0.25 h / 30 °C
4.3: 3 h / 0 - 90 °C
View Scheme

: 116986-08-4
methyl 2-(bromomethyl)pyridine-3-carboxylate

: 80957-68-2
5,6,7,8-tetrahydro-1,6-naphthyridine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: tetrabutyl ammonium fluoride / acetonitrile / 16 h / 0 - 30 °C / Inert atmosphere 2.1: hydrogen / methanol; water / 16 h / 50 °C / 2585.81 Torr 3.1: dimethylsulfide borane complex / tetrahydrofuran; dichloromethane / 16 h / 0 - 90 °C 3.2: 0.25 h / 30 °C 3.3: 3 h / 0 - 90 °C View Scheme

: methyl 2-(cyanomethyl)nicotinate

: 80957-68-2
5,6,7,8-tetrahydro-1,6-naphthyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: hydrogen / methanol; water / 16 h / 50 °C / 2585.81 Torr 2.1: dimethylsulfide borane complex / tetrahydrofuran; dichloromethane / 16 h / 0 - 90 °C 2.2: 0.25 h / 30 °C 2.3: 3 h / 0 - 90 °C View Scheme

: 155058-02-9
7,8-Dihydro-1,6-Naphthyridine-5(6H)-one

: 80957-68-2
5,6,7,8-tetrahydro-1,6-naphthyridine

Conditions

Conditions	Yield
Stage #1: 7,8-Dihydro-1,6-Naphthyridine-5(6H)-one With dimethylsulfide borane complex In tetrahydrofuran; dichloromethane at 0 - 90℃; for 16h; Stage #2: In methanol at 30℃; for 0.25h; Stage #3: With hydrogenchloride In 1,4-dioxane at 0 - 90℃; for 3h;

: 38749-79-0
3-bromo-2-picoline

: 80957-68-2
5,6,7,8-tetrahydro-1,6-naphthyridine

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: triethylamine; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) / 16 h / 80 °C / 2585.81 Torr 2.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 16 h / 90 °C / Inert atmosphere 3.1: tetrabutyl ammonium fluoride / acetonitrile / 16 h / 0 - 30 °C / Inert atmosphere 4.1: hydrogen / methanol; water / 16 h / 50 °C / 2585.81 Torr 5.1: dimethylsulfide borane complex / tetrahydrofuran; dichloromethane / 16 h / 0 - 90 °C 5.2: 0.25 h / 30 °C 5.3: 3 h / 0 - 90 °C View Scheme

Yield

Multi-step reaction with 5 steps
1.1: triethylamine; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) / 16 h / 80 °C / 2585.81 Torr
2.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 16 h / 90 °C / Inert atmosphere
3.1: tetrabutyl ammonium fluoride / acetonitrile / 16 h / 0 - 30 °C / Inert atmosphere
4.1: hydrogen / methanol; water / 16 h / 50 °C / 2585.81 Torr
5.1: dimethylsulfide borane complex / tetrahydrofuran; dichloromethane / 16 h / 0 - 90 °C
5.2: 0.25 h / 30 °C
5.3: 3 h / 0 - 90 °C
View Scheme

: 19125-34-9
1-phenylpiperidin-4-one

: 80957-68-2
5,6,7,8-tetrahydro-1,6-naphthyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium tetrachloroaurate(III) dihydrate / ethanol / Reflux 2: hydrogen; palladium on activated charcoal / acetic acid / 2 h / 60 °C View Scheme

: 6-phenyl-5,6,7,8-tetrahydro-1,6-naphthyridine

: 80957-68-2
5,6,7,8-tetrahydro-1,6-naphthyridine

Conditions

Conditions	Yield
With palladium on activated charcoal; hydrogen In acetic acid at 60℃; for 2h;

: 1253378-59-4
6-chloro-4-methyl-3-nitro-2-pyrrolidin-1-yl-pyridine

: 80957-68-2
5,6,7,8-tetrahydro-1,6-naphthyridine

: 1253378-62-9
6-(4-methyl-5-nitro-6-pyrrolidin-1-yl-pyridin-2-yl)-5,6,7,8-tetrahydro-[1,6]-naphthyridine

Conditions

Conditions	Yield
With triethylamine In dimethyl sulfoxide at 110℃; for 8h; Microwave irradiation;	100%

: 80957-68-2
5,6,7,8-tetrahydro-1,6-naphthyridine

: 1430218-32-8
7,8-dihydro-1,6-naphthyridine

Conditions

Conditions	Yield
With manganese(IV) oxide In dichloromethane; dimethyl sulfoxide at 20℃; for 24h;	100%

: 1323408-40-7
4-((4-(bromomethyl)benzyl)oxy)-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione

: 80957-68-2
5,6,7,8-tetrahydro-1,6-naphthyridine

: 1323403-44-6
4-((4-((7,8-DIHYDRO-1,6-NAPHTHYRIDIN-6(5H)-YL)METHYL) BENZYL)OXY)-2-(2,6-DIOXOPIPERIDIN-3-YL)ISOINDOLINE-1,3-DIONE

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 17h;	99%

: 7623-09-8
2-chloropropionyl chloride

: 80957-68-2
5,6,7,8-tetrahydro-1,6-naphthyridine

: 95395-45-2
6-(2-chloropropionyl)-5,6,7,8-tetrahydro-1,6-naphthyridine

Conditions

Conditions	Yield
With triethylamine In chloroform Ambient temperature;	89%

: 1323407-86-8
3-[4-[[4-(bromomethyl)phenyl]methoxy]-1-oxo-isoindolin-2-yl]piperidine-2,6-dione

: 80957-68-2
5,6,7,8-tetrahydro-1,6-naphthyridine

: 1323403-58-2
3-(4-((4-((7,8-DIHYDRO-1,6-NAPHTHYRIDIN-6(5H)-YL)METHYL) BENZYL)OXY)-1-OXOISOINDOLIN-2-YL)PIPERIDINE-2,6-DIONE

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 1h;	88%

: 625-35-4, 3488-22-0, 10487-71-5
trans-chrotonyl chloride

: 80957-68-2
5,6,7,8-tetrahydro-1,6-naphthyridine

: 95395-49-6
6-crotonoyl-5,6,7,8-tetrahydro-1,6-naphthyridine

Conditions

Conditions	Yield
With pyridine In chloroform 1.) 2 h, 5 deg C; 2.) r.t.;	84%

: 80957-68-2
5,6,7,8-tetrahydro-1,6-naphthyridine

: 540-51-2
2-bromoethanol

: 95395-56-5
6-(2-hydroxyethyl)-5,6,7,8-tetrahydro-1,6-naphthyridine

Conditions

Conditions	Yield
With triethylamine In ethanol for 9.5h; Heating;	69%

: 95395-48-5
1-(2-chloropropionyl)-4-(2-methoxyphenyl)piperazine

: 80957-68-2
5,6,7,8-tetrahydro-1,6-naphthyridine

: 95395-47-4
6-<2-<4-(2-methoxyphenyl)-1-piperazinyl>-1-methyl-2-oxoethyl>-5,6,7,8-tetrahydro-1,6-naphthyridine

Conditions

Conditions	Yield
With triethylamine In ethanol Heating;	60%

: 80957-68-2
5,6,7,8-tetrahydro-1,6-naphthyridine

: 75-36-5
acetyl chloride

: 90781-15-0
6-Acetyl-5,6,7,8-tetrahydro-1,6-naphthyridine

Conditions

Conditions	Yield
With triethylamine In dichloromethane	58%

: 80957-68-2
5,6,7,8-tetrahydro-1,6-naphthyridine

: 627-18-9
1-bromo-3-propanol

: 75510-13-3
6-(3-hydroxypropyl)-5,6,7,8-tetrahydro-1,6-naphthyridine

Conditions

Conditions	Yield
With triethylamine In ethanol Heating;	56%

: 24424-99-5
di-tert-butyl dicarbonate

: 80957-68-2
5,6,7,8-tetrahydro-1,6-naphthyridine

: 259809-44-4
7,8-dihydro-5H-[1,6]naphthyridine-6-carboxylic acid tert-butyl ester

Conditions

Conditions	Yield
With sodium hydroxide In water; toluene for 0.333333h;	55%
With sodium hydroxide In toluene for 0.166667h;	981 mg

: 7677-24-9
trimethylsilyl cyanide

: 80957-68-2
5,6,7,8-tetrahydro-1,6-naphthyridine

: 5,6,7,8-tetrahydro-1,6-naphthyridine-6-nitrile

Conditions

Conditions	Yield
With potassium fluoride; tetrabutylammomium bromide In acetonitrile at 20℃; for 3h;	47%

: 2-(5-amino-2-(furan-2-yl)-7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-7-yl)-2-phenylacetic acid

: 80957-68-2
5,6,7,8-tetrahydro-1,6-naphthyridine

: 2-(5-amino-2-(furan-2-yl)-7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-7-yl)-1-(7,8-dihydro-1,6-naphthyridin-6 (5H)-yl)-2-phenylethan-1-one

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 16h;	44%

: C16H13ClFN5

: 80957-68-2
5,6,7,8-tetrahydro-1,6-naphthyridine

: C24H22FN7

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine at 120℃; Sealed tube;	39%

: C17H15ClFN5

: 80957-68-2
5,6,7,8-tetrahydro-1,6-naphthyridine

: C25H24FN7

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine Sealed tube;	39%

: C16H12ClF2N5

: 80957-68-2
5,6,7,8-tetrahydro-1,6-naphthyridine

: C24H21F2N7

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine at 130℃; for 8h;	39%

: C16H10ClFN4

: 80957-68-2
5,6,7,8-tetrahydro-1,6-naphthyridine

: C26H21FN6

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine at 130℃; for 12h;	38%

: 80957-68-2
5,6,7,8-tetrahydro-1,6-naphthyridine

: 762-04-9
phosphonic acid diethyl ester

: diethyl (5,6,7,8-tetrahydro-1,6-napthyridin-5-yl)phosphonate

Conditions

Conditions	Yield
With sodium acetate; lithium perchlorate In acetonitrile at 20℃; for 6h; Electrolysis;	38%

: C17H14ClFN4

: 80957-68-2
5,6,7,8-tetrahydro-1,6-naphthyridine

: C25H23FN6

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine at 120℃; Sealed tube;	35%

: 1616059-77-8
1-methyl-6-(3-(oxiran-2-ylmethoxy)phenyl)-1H-benzo[d]imidazole

: 80957-68-2
5,6,7,8-tetrahydro-1,6-naphthyridine

: 1-(7,8-dihydro-1,6-naphthyridin-6(5H)-yl)-3-(3-(1-methyl-1H-benzo[d]imidazol-6-yl)phenoxy)propan-2-ol

Conditions

Conditions	Yield
In ethanol at 80℃; for 5h;	25.4%

: N-(2-hydroxy-3-iodopropyl)-2-(quinolin-8-yloxy)acetamide

: 80957-68-2
5,6,7,8-tetrahydro-1,6-naphthyridine

: N-[2-hydroxy-3-(5,6,7,8-tetrahydro-1,6-naphthyridin-6-yl)propyl]-2-(quinolin-8-yloxy)acetamide

Conditions

Conditions	Yield
In methanol at 80℃; for 24h;	19%

: 1616059-87-0
tert-butyl cyclopentyl(3-(oxiran-2-ylmethoxy)benzyl)carbamate

: 80957-68-2
5,6,7,8-tetrahydro-1,6-naphthyridine

: tert-butyl cyclopentyl(3-(3-(7,8-dihydro-1,6-naphthyridin-6(5H)-yl)-2-hydroxypropoxy)benzyl)carbamate

Conditions

Conditions	Yield
In ethanol at 100℃; for 0.5h; Microwave irradiation;	8.7%

: 96743-74-7
4-methacryloyl-4-(2-methoxyphenyl)piperazine

: 80957-68-2
5,6,7,8-tetrahydro-1,6-naphthyridine

: 95395-52-1
6-<3-<4-(2-methoxyphenyl)-1-piperazinyl>-2-methyl-3-oxopropyl>-5,6,7,8-tetrahydro-1,6-naphthyridine

Conditions

Conditions	Yield
With N-benzyl-trimethylammonium hydroxide In ethanol Heating;

: 95395-50-9
1-crotonoyl-4-(2-methoxyphenyl)piperazine

: 80957-68-2
5,6,7,8-tetrahydro-1,6-naphthyridine

: 95395-51-0
6-<3-<4-(2-methoxyphenyl)-1-piperazinyl>-1-methyl-3-oxopropyl>-5,6,7,8-tetrahydro-1,6-naphthyridine

Conditions

Conditions	Yield
With N-benzyl-trimethylammonium hydroxide In ethanol Heating;

: 80957-68-2
5,6,7,8-tetrahydro-1,6-naphthyridine

: 1057855-79-4
5,6,7,8-tetrahydro-[1,6]naphthyridine-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 981 mg / aq. NaOH / toluene / 0.17 h 2: 98 percent / m-chloroperbenzoic acid / CH2Cl2 / 0.5 h / 0 °C 3: 88 percent / N,N-dimethylcarbamyl chloride / CH2Cl2 / 41 h / 20 °C 4: aq. HCl / 3 h / 100 °C View Scheme

: 80957-68-2
5,6,7,8-tetrahydro-1,6-naphthyridine

: 259809-45-5
6-(tert-butoxycarbonyl)-5,6,7,8-tetrahydro-1,6-naphthyridine-1-oxide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 981 mg / aq. NaOH / toluene / 0.17 h 2: 98 percent / m-chloroperbenzoic acid / CH2Cl2 / 0.5 h / 0 °C View Scheme

5,6,7,8-Tetrahydro-1,6-naphthyridine Specification

The systematic name of 5,6,7,8-Tetrahydro-1,6-naphthyridine is 5,6,7,8-tetrahydro-1,6-naphthyridine. With the CAS registry number 80957-68-2, it is also named as 1,6-Naphthyridine,5,6,7,8-tetrahydro-. The product's category is chiral chemicals. Besides, its molecular formula is C₈H₁₀N₂ and its molecular weight is 134.18.

The other characteristics of 5,6,7,8-Tetrahydro-1,6-naphthyridine can be summarized as: (1)ACD/LogP: 0.15; (2)# of Rule of 5 Violations: 0; (3)ACD/BCF (pH 5.5): 1; (4)ACD/BCF (pH 7.4): 1; (5)ACD/KOC (pH 5.5): 1; (6)ACD/KOC (pH 7.4): 3; (7)H bond acceptors: 2; (8)H bond donors: 1; (9)Freely Rotating Bonds: 0; (10)Polar Surface Area: 24.92 Å²; (11)Index of Refraction: 1.548; (12)Molar Refractivity: 39.866 cm³; (13)Molar Volume: 125.52 cm³; (14)Polarizability: 15.804×10^-24cm³; (15)Surface Tension: 42.485 dyne/cm; (16)Density: 1.069 g/cm³; (17)Flash Point: 103.557 °C; (18)Enthalpy of Vaporization: 48.478 kJ/mol; (19)Boiling Point: 247.62 °C at 760 mmHg; (20)Vapour Pressure: 0.025 mmHg at 25 °C.

People can use the following data to convert to the molecule structure.
(1)SMILES:c1ccnc2CCNCc12
(2)InChI:InChI=1/C8H10N2/c1-2-7-6-9-5-3-8(7)10-4-1/h1-2,4,9H,3,5-6H2
(3)InChIKey:FPEAARFNXIWCTP-UHFFFAOYAZ
(4)Std. InChI:InChI=1S/C8H10N2/c1-2-7-6-9-5-3-8(7)10-4-1/h1-2,4,9H,3,5-6H2
(5)Std. InChIKey:FPEAARFNXIWCTP-UHFFFAOYSA-N

Product Name

2-P-TOLYL-4,5,6,7-TETRAHYDRO-OXAZOLO[5,4-C]PYRIDINE

Synthetic route

5,6,7,8-Tetrahydro-1,6-naphthyridine Specification

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