Isoquinolin-3-amine supplier | CasNO.25475-67-6

Name
ISOQUINOLIN-3-AMINE
EINECS
CAS No. 25475-67-6
Article Data14
CAS DataBase
Density 1.21 g/cm³
Solubility
Melting Point 154-156 °C
Formula C₉H₈N₂
Boiling Point 331.2 °C at 760 mmHg
Molecular Weight 144.176
Flash Point 180.4 °C
Transport Information
Appearance
Safety 26-36/37/39-24/25
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi,Xn
Synonyms Isoquinoline,3-amino- (6CI,7CI,8CI);3-Aminoisoquinoline;Isoquinolin-3-ylamine;NSC 218383;
PSA 38.91000
LogP 2.39820

Synthetic route

: tert-butyl 2-(2-(1,3-dioxolan-2-yl)phenyl)-2-cyanoacetate

: 25475-67-6
isoquinolin-3-amine

Conditions

Conditions	Yield
Stage #1: tert-butyl 2-(2-(1,3-dioxolan-2-yl)phenyl)-2-cyanoacetate In ethanol; water at 90℃; for 18h; Sealed tube; Stage #2: With ammonium chloride In ethanol; water at 90℃; for 3h;	86%

: 135737-14-3
2-(2-formylphenyl)acetonitrile

: 25475-67-6
isoquinolin-3-amine

Conditions

Conditions	Yield
With ammonia; trifluoroacetic acid In methanol for 4h; Heating;	69%

: 150-30-1
Phenylalanine

: 10321-49-0
3-amino-4-bromoisoquinoline

A: 25475-67-6
isoquinolin-3-amine

B: C18H17N3O

C: 2-benzylpyrazino[2,3-c]isoquinolin-3-ol

Conditions

Conditions	Yield
With copper(I) oxide; potassium phosphate In dimethyl sulfoxide at 90℃; for 40h; Inert atmosphere;	A n/a B 0.47 g C 18%

...Expand

: 19493-45-9
3-chloroisoquinoline

: 25475-67-6
isoquinolin-3-amine

Conditions

Conditions	Yield
With ammonium hydroxide; copper(II) sulfate at 140℃;

: 34784-02-6
3-bromoisoquinoline

: 25475-67-6
isoquinolin-3-amine

Conditions

Conditions	Yield
With ammonium hydroxide; copper(II) sulfate at 140℃;

: 50458-77-0
isoquinoline-3(S)-carboxamide

: 25475-67-6
isoquinolin-3-amine

Conditions

Conditions	Yield
With potassium hydroxide; bromine
With potassium hydroxide; bromine Hofmann degradation; Cooling;

: 66729-00-8
3-amino-4-chloroisoquinoline

: 25475-67-6
isoquinolin-3-amine

Conditions

Conditions	Yield
With methanol; sodium methylate at 200℃;

: 6624-49-3
isoquinoline-3-carboxylic acid

: 25475-67-6
isoquinolin-3-amine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: methanol; diazomethane; diethyl ether / Behandeln des Reaktionsprodukts in Methanol mit NH3 2: bromine; aqueous KOH View Scheme

: 3336-49-0
4-isoquinolinol

: 25475-67-6
isoquinolin-3-amine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: sulfuric acid; potassium nitrate 2: phosphoryl chloride 3: palladium/charcoal; ethanol / Hydrogenation 4: sodium methylate; methanol / 200 °C View Scheme

: 101860-70-2
4-chloro-3-nitroisoquinoline

: 25475-67-6
isoquinolin-3-amine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: palladium/charcoal; ethanol / Hydrogenation 2: sodium methylate; methanol / 200 °C View Scheme

: 36718-46-4
3-nitro-isoquinolin-4-ol

: 25475-67-6
isoquinolin-3-amine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: phosphoryl chloride 2: palladium/charcoal; ethanol / Hydrogenation 3: sodium methylate; methanol / 200 °C View Scheme

: 86-94-2
isoquinoline-1,3-diol

: 25475-67-6
isoquinolin-3-amine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: phosphorus (III)-bromide 2: acetic acid; aqueous hydriodic acid; red phosphorus 3: CuSO4; aqueous NH3 / 140 °C View Scheme

: 53987-60-3
1,3-dibromoisoquinoline

: 25475-67-6
isoquinolin-3-amine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid; aqueous hydriodic acid; red phosphorus 2: CuSO4; aqueous NH3 / 140 °C View Scheme

: 13130-79-5
3-amino-1-bromoisoquinoline

: 25475-67-6
isoquinolin-3-amine

Conditions

Conditions	Yield
With palladium on activated charcoal; hydrogen

: 25475-67-6
isoquinolin-3-amine

: 40532-06-7
2-isothiocyanato-1,4-dimethoxybenzene

: N-(3H-[1,2,4]thiadiazolo[4,3-b]isoquinolin-3-ylidene)-2,5-dimethoxyaniline

Conditions

Conditions	Yield
With montmorillonite K10 Clay In acetonitrile at 20℃; for 1h;	96%

: 25475-67-6
isoquinolin-3-amine

: 577-19-5
2-nitrophenyl bromide

: 1370708-46-5
N-(2-nitrophenyl)isoquinolin-3-amine

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane for 5h; Buchwald-Hartwig Coupling; Inert atmosphere;	94%

: 25475-67-6
isoquinolin-3-amine

: 102368-13-8
1,1'-Thiocarbonyldi-2(1H)-pyridone

: 769960-94-3
3-isothiocyanatoisoquinoline

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 2h;	93%
In dichloromethane at 20℃; for 2h;	93%
In dichloromethane at 20℃; for 18h;	85%

: 25475-67-6
isoquinolin-3-amine

: 103-72-0
phenyl isothiocyanate

: N-(3H-[1,2,4]thiadiazolo[4,3-b]isoquinolin-3-ylidene)aniline

Conditions

Conditions	Yield
With montmorillonite K10 Clay In acetonitrile at 20℃; for 2h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature;	93%

: 25475-67-6
isoquinolin-3-amine

: 98-86-2
acetophenone

: 70845-68-0
2-Phenyl-imidazo<2,1-a>isochinolin

Conditions

Conditions	Yield
With indium(III) triflate; copper(l) iodide; oxygen In 1-methyl-pyrrolidin-2-one at 100℃; under 760.051 Torr; for 30h; Schlenk technique;	92%

: 25475-67-6
isoquinolin-3-amine

: 622-59-3
1-isothiocyanato-4-methylbenzene

: N-(3H-[1,2,4]thiadiazolo[4,3-b]isoquinolin-3-ylidene)-4-methylaniline

Conditions

Conditions	Yield
With montmorillonite K10 Clay In acetonitrile at 20℃; for 1h;	92%

: 25475-67-6
isoquinolin-3-amine

: 4637-24-5
N,N-dimethyl-formamide dimethyl acetal

: N'-hydroxy-N-(isoquinolin-3-yl)formimidamide

Conditions

Conditions	Yield
Stage #1: isoquinolin-3-amine; N,N-dimethyl-formamide dimethyl acetal In isopropyl alcohol at 80℃; for 3h; Inert atmosphere; Stage #2: With hydroxylamine hydrochloride In isopropyl alcohol at 50℃; for 12h; Inert atmosphere;	92%

: 25475-67-6
isoquinolin-3-amine

: 108-37-2
1-bromo-3-chlorobenzene

: 1370708-39-6
N-(3-chlorophenyl)isoquinolin-3-amine

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); johnphos; sodium t-butanolate In toluene for 5h; Buchwald-Hartwig Coupling; Inert atmosphere;	91%

: 25475-67-6
isoquinolin-3-amine

: 89007-45-4
4-isopropylphenyl isothiocyanate

: N-(3H-[1,2,4]thiadiazolo[4,3-b]isoquinolin-3-ylidene)-4-isopropylaniline

Conditions

Conditions	Yield
With montmorillonite K10 Clay In acetonitrile at 20℃; for 2h;	91%

: 25475-67-6
isoquinolin-3-amine

: 2131-55-7
4-Chlorophenyl isothiocyanate

: N-(3H-[1,2,4]thiadiazolo[4,3-b]isoquinolin-3-ylidene)-4-chloroaniline

Conditions

Conditions	Yield
With montmorillonite K10 Clay In acetonitrile at 20℃; for 3h;	89%

: 25475-67-6
isoquinolin-3-amine

: 83939-28-0
3,4-isoquinolinedione 4-oxime

Conditions

Conditions	Yield
With sodium nitrite In sulfuric acid 1.) 5-10 deg C, 45 min; 2.) 3-7 deg C, 2.5 h;	88%

: 25475-67-6
isoquinolin-3-amine

: 108-86-1
bromobenzene

: N-phenylisoquinolin-3-amine

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane for 46h; Buchwald-Hartwig reaction; Inert atmosphere; Reflux;	87%
With tris-(dibenzylideneacetone)dipalladium(0); johnphos; sodium t-butanolate In toluene for 5h; Buchwald-Hartwig Coupling; Inert atmosphere;	87%
With tris-(dibenzylideneacetone)dipalladium(0); johnphos; sodium t-butanolate In toluene at 110℃; for 5h; Buchwald-Hartwig arylation; Inert atmosphere;	85%

: 25475-67-6
isoquinolin-3-amine

: 2131-61-5
p-nitrophenyl isothiocyanate

: N-(3H-[1,2,4]thiadiazolo[4,3-b]isoquinolin-3-ylidene)-4-nitroaniline

Conditions

Conditions	Yield
With montmorillonite K10 Clay In acetonitrile at 20℃; for 3h;	87%

: 25475-67-6
isoquinolin-3-amine

: 504-02-9
1,3-cylohexanedione

: 3-(isoquinolin-3-ylamino)cyclohex-2-en-1-one

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In water; toluene for 4h; Dean-Stark; Reflux; Inert atmosphere;	87%

: 25475-67-6
isoquinolin-3-amine

: 52913-14-1
O-tosylhydroxylamine

: 75949-14-3
2,3-diamino-isoquinolinium 4-methylbenzenesulfonate

Conditions

Conditions	Yield
In dichloromethane at 25℃; for 1h;	85%

: 25475-67-6
isoquinolin-3-amine

: 106-38-7
para-bromotoluene

: 1373873-57-4
N-p-tolylisoquinolin-3-amine

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); johnphos; sodium t-butanolate In toluene at 110℃; for 5h; Buchwald-Hartwig arylation; Inert atmosphere;	85%

: 25475-67-6
isoquinolin-3-amine

: 24398-88-7
ethyl 3-bromobenzoate

: 1370708-53-4
ethyl 3-(isoquinolin-3-ylamino)benzoate

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane for 6h; Buchwald-Hartwig Coupling; Inert atmosphere;	84%

: 25475-67-6
isoquinolin-3-amine

: 6630-33-7
ortho-bromobenzaldehyde

: 1370708-55-6
2-(isoquinolin-3-ylamino)benzaldehyde

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane for 2h; Buchwald-Hartwig Coupling; Inert atmosphere;	84%

: 25475-67-6
isoquinolin-3-amine

: 74-88-4
methyl iodide

: 3-(N,N-dimethylamino)isoquinoline

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 0℃; Inert atmosphere;	84%

: 25475-67-6
isoquinolin-3-amine

: 66729-00-8
3-amino-4-chloroisoquinoline

Conditions

Conditions	Yield
With N-chloro-succinimide In methanol at 20℃; for 3h;	84%
With 1-chloro-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one In N,N-dimethyl-formamide at 20℃; for 12h; regioselective reaction;	66%
With 1,3-dichloro-5,5-dimethylhydantoin; Isopropyl acetate at -10℃; for 16h; Reagent/catalyst; Temperature;	20.52 g

: 25475-67-6
isoquinolin-3-amine

: 1885-14-9
phenyl chloroformate

: isoquinolin-3-ylcarbamic acid phenyl ester

Conditions

Conditions	Yield
With pyridine In acetonitrile at 23℃; for 1h;	83%
With pyridine In acetonitrile at 20℃; for 1h;	83%
at 0 - 20℃;

: 25475-67-6
isoquinolin-3-amine

: 5798-75-4
Ethyl 4-bromobenzoate

: 1370708-54-5
ethyl 4-(isoquinolin-3-ylamino)benzoate

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane for 6h; Buchwald-Hartwig Coupling; Inert atmosphere;	83%

: 25475-67-6
isoquinolin-3-amine

: 542-85-8
Ethyl isothiocyanate

: N-(3H-[1,2,4]thiadiazolo[4,3-b]isoquinolin-3-ylidene)ethanamine

Conditions

Conditions	Yield
With montmorillonite K10 Clay In acetonitrile at 20℃; for 3h;	83%

: 25475-67-6
isoquinolin-3-amine

: AuOH(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)

: 1522372-36-6
(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)(isoquinolin-3-ylamino)gold

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃; for 20h;	82%

: 25475-67-6
isoquinolin-3-amine

: 56601-42-4
cyclopropyl isothiocyanate

: N-(3H-[1,2,4]thiadiazolo[4,3-b]isoquinolin-3-ylidene)cyclopropanamine

Conditions

Conditions	Yield
With montmorillonite K10 Clay In acetonitrile at 20℃; for 2h;	82%

: 25475-67-6
isoquinolin-3-amine

: 590-42-1
tert-butyl isothiocyanate

: N-(3H-[1,2,4]thiadiazolo[4,3-b]isoquinolin-3-ylidene)-2-methylpropan-2-amine

Conditions

Conditions	Yield
With montmorillonite K10 Clay In acetonitrile at 20℃; for 2h;	82%

: 25475-67-6
isoquinolin-3-amine

: 1-(2-ethylphenyl)-5-methyl-1H-pyrazole-4-carboxylic acid

: 1-(2-ethylphenyl)-N-(isoquinolin-3-yl)-5-methyl-1H-pyrazole-4-carboxamide

Conditions

Conditions	Yield
With chloro-N,N,N',N'-bis(tetramethylene)formamidinium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In 1,2-dichloro-ethane at 80℃;	82%

: 25475-67-6
isoquinolin-3-amine

: 30626-03-0
(3E)-4-(4-chlorophenyl)-3-buten-2-one

: 1505454-53-4
(E)-2-(4-chlorostyryl)imidazo[2,1-a]isoquinoline

Conditions

Conditions	Yield
With indium(III) triflate; copper(l) iodide; oxygen In 1-methyl-pyrrolidin-2-one at 100℃; under 760.051 Torr; for 30h; Schlenk technique;	81%

: 25475-67-6
isoquinolin-3-amine

: 10321-49-0
3-amino-4-bromoisoquinoline

Conditions

Conditions	Yield
With N-Bromosuccinimide; ammonium acetate In acetonitrile at 20℃; for 0.0833333h; regioselective reaction;	80%
With N-Bromosuccinimide In ethanol; dichloromethane at 5 - 20℃;	75%
With N-Bromosuccinimide In ethanol; dichloromethane at 5 - 20℃; for 2.33h;	75%

Isoquinolin-3-amine Specification

The 3-Isoquinolinamine, with the CAS registry number 25475-67-6, is also known as Isoquinolin-3-ylamine. It belongs to the product categories of Amines; Quinolines, Isoquinolines&Quinoxalines; Quinoline&Isoquinoline; Heterocyclic Compounds; Quinolines, Isoquinolines & Quinoxalines; Building Blocks; Isoquinoline. This chemical's molecular formula is C₉H₈N₂ and molecular weight is 144.17. What's more, its systematic name is Isoquinolin-3-amine.

Physical properties of 3-Isoquinolinamine are: (1)ACD/LogP: 1.85; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.72; (4)ACD/LogD (pH 7.4): 1.85; (5)ACD/BCF (pH 5.5): 11.03; (6)ACD/BCF (pH 7.4): 14.87; (7)ACD/KOC (pH 5.5): 178.04; (8)ACD/KOC (pH 7.4): 239.97; (9)#H bond acceptors: 2; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 16.13 Å²; (13)Index of Refraction: 1.708; (14)Molar Refractivity: 46.42 cm³; (15)Molar Volume: 119 cm³; (16)Polarizability: 18.4×10^-24cm³; (17)Surface Tension: 59.8 dyne/cm; (18)Density: 1.21 g/cm³; (19)Flash Point: 180.4 °C; (20)Enthalpy of Vaporization: 57.38 kJ/mol; (21)Boiling Point: 331.2 °C at 760 mmHg; (22)Vapour Pressure: 0.000159 mmHg at 25°C.

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need wear suitable protective clothing, gloves and eye/face protection and you should avoid contact with skin and eyes.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C1=CC=C2C=NC(=CC2=C1)N
(2)InChI: InChI=1S/C9H8N2/c10-9-5-7-3-1-2-4-8(7)6-11-9/h1-6H,(H2,10,11)
(3)InChIKey: VYCKDIRCVDCQAE-UHFFFAOYSA-N

Product Name

ISOQUINOLIN-3-AMINE

Synthetic route

Isoquinolin-3-amine Specification

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