58059-31-7

Basic information

• Product Name: 3-CHLORO-6-(4-METHOXYPHENYL)-PYRIDAZINE
• Synonyms: SALOR-INT L480835-1EA;3-CHLORO-6-(4-METHOXYPHENYL)-PYRIDAZINE;3-Chloro-6-(p-Methoxyphenyl)pyridazine
• CAS NO: 58059-31-7
• Molecular Formula: C₁₁H₉ClN₂O
• Molecular Weight: 220.65
• Product Categories: Aromatics;Heterocycles;Intermediates
• Mol File: 58059-31-7.mol
• Article Data: 10

Chemical Properties

• Melting Point: 160 °C
• Boiling Point: 407.764 °C at 760 mmHg
• Flash Point: 200.409 °C
• Appearance: /
• Density: 1.246 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.576
• Solubility: Chloroform, Dichloromethane, Ethyl Acetate
• PKA: 0.58±0.10(Predicted)
• CAS DataBase Reference: 3-CHLORO-6-(4-METHOXYPHENYL)-PYRIDAZINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CHLORO-6-(4-METHOXYPHENYL)-PYRIDAZINE(58059-31-7)
• EPA Substance Registry System: 3-CHLORO-6-(4-METHOXYPHENYL)-PYRIDAZINE(58059-31-7)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 58059-31-7(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Synthesis Reference(s)

Synthetic Communications, 16, p. 543, 1986 DOI: 10.1080/00397918608078770

InChI:InChI=1/C11H9ClN2O/c1-15-9-4-2-8(3-5-9)10-6-7-11(12)14-13-10/h2-7H,1H3

Synthetic route

6-(4-methoxyphenyl)-2H-pyridazin-3-one (2166-33-8) → 3-chloro-6-(4-methoxyphenyl)pyridazine (58059-31-7)

Conditions	Yield
With isocyanate de chlorosulfonyle In acetonitrile at 60 - 65℃; for 3.5h;	82%
With trichlorophosphate at 85 - 95℃; for 4h;
With trichlorophosphate Heating;

tris(4-methoxyphenyl)bismuth (33397-21-6) + 3-chloro-6-iodopyridazine (135034-10-5) → 3-chloro-6-(4-methoxyphenyl)pyridazine (58059-31-7)

Conditions	Yield
With palladium diacetate; triphenylphosphine In N,N-dimethyl-formamide at 90℃; for 4h; Catalytic behavior; Reagent/catalyst; Inert atmosphere; chemoselective reaction;	82%

4-methoxyphenylboronic acid (5720-07-0) + 3-chloro-6-iodopyridazine (135034-10-5) → 3,6-bis-(4-methoxyphenyl)-pyridazine (2166-07-6) + 3-chloro-6-(4-methoxyphenyl)pyridazine (58059-31-7)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In 1,4-dioxane Suzuki Coupling; Heating; Inert atmosphere; chemoselective reaction;	A 15% B 70%

3,6-dichlorpyridazine (141-30-0) + 4-methoxyphenylboronic acid (5720-07-0) → 3-chloro-6-(4-methoxyphenyl)pyridazine (58059-31-7)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In 1,4-dioxane Suzuki Coupling; Heating; Inert atmosphere; chemoselective reaction;	58%
With potassium phosphate tribasic trihydrate; (2-mesityl-1H-inden-3-yl)dicyclohexyl phosphine; palladium diacetate; Aliquat 336 In water at 20 - 100℃; for 8h; Suzuki-Miyaura Coupling; Inert atmosphere;	43%
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; water; toluene at 80℃; for 16h;

3,6-dichlorpyridazine (141-30-0) + tris(4-methoxyphenyl)bismuth (33397-21-6) → 4,4'-Dimethoxybiphenyl (2132-80-1) + 3-chloro-6-(4-methoxyphenyl)pyridazine (58059-31-7)

Conditions	Yield
With palladium diacetate; triphenylphosphine; cesium fluoride In N,N-dimethyl-formamide at 90℃; Inert atmosphere; chemoselective reaction;	A 17 %Chromat. B 43%

6-(4-methoxy-phenyl)-2H-pyridazin-3-one (2166-33-8) → 3-chloro-6-(4-methoxyphenyl)pyridazine (58059-31-7)

Conditions	Yield
With trichlorophosphate at 0℃; for 6h; Heating / reflux;	40%

3,6-dichlorpyridazine (141-30-0) + 4-methoxyphenylzinc chloride (93296-09-4) → 3,6-bis-(4-methoxyphenyl)-pyridazine (2166-07-6) + 3-chloro-6-(4-methoxyphenyl)pyridazine (58059-31-7)

Conditions	Yield
tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 20℃; for 24h;

3,6-dichlorpyridazine (141-30-0) + tris(4-methoxyphenyl)bismuth (33397-21-6) → 3-chloro-6-(4-methoxyphenyl)pyridazine (58059-31-7)

Conditions	Yield
With palladium diacetate; triphenylphosphine; cesium fluoride In N,N-dimethyl-formamide at 90℃; Reagent/catalyst; Inert atmosphere; chemoselective reaction;

C11H12N2O2 → 3-chloro-6-(4-methoxyphenyl)pyridazine (58059-31-7)

Conditions	Yield
With trichlorophosphate

1-(4-methoxyphenyl)ethanone (100-06-1) → 3-chloro-6-(4-methoxyphenyl)pyridazine (58059-31-7)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: acetic acid / Reflux 1.2: 2 h / Reflux 2.1: trichlorophosphate / Heating View Scheme

phenylzinc(II) bromide (38111-44-3) + 3-chloro-6-(4-methoxyphenyl)pyridazine (58059-31-7) → 3-(4-methoxyphenyl)-6-phenylpyridazine (2166-04-3)

Conditions	Yield
tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 60℃;	80%

3-HYDROXYPYRIDINE (109-00-2) + 3-chloro-6-(4-methoxyphenyl)pyridazine (58059-31-7) → 3-hydroxy-1-<6-(4-methoxyphenyl)-3-pyridazinyl>pyridinium chloride

Conditions	Yield
In butan-1-ol for 4h; Heating;	79.4%

4-HYDROXYPIPERIDINE (5382-16-1) + 3-chloro-6-(4-methoxyphenyl)pyridazine (58059-31-7) → 3-(4-hydroxypiperidino)-6-(4-methoxyphenyl)pyridazine (93181-98-7)

Conditions	Yield
In butan-1-ol for 3h; Heating;	75%

1H-imidazole (288-32-4) + 3-chloro-6-(4-methoxyphenyl)pyridazine (58059-31-7) → 3-(1H-imidazol-1-yl)-6-(4-methoxyphenyl)pyridazine

Conditions	Yield
Stage #1: 1H-imidazole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 1h; Stage #2: 3-chloro-6-(4-methoxyphenyl)pyridazine In N,N-dimethyl-formamide; mineral oil at 100℃; for 6h;	60%

acetic acid hydrazide (1068-57-1) + 3-chloro-6-(4-methoxyphenyl)pyridazine (58059-31-7) → 6-(4-Methoxy-phenyl)-3-methyl-[1,2,4]triazolo[4,3-b]pyridazine (76970-05-3)

Conditions	Yield
In butan-1-ol for 48h; Heating;	51%

formic acid hydrazide (624-84-0) + 3-chloro-6-(4-methoxyphenyl)pyridazine (58059-31-7) → 6-(4-methoxyphenyl)-1,2,4-triazolo<4,3-b>pyridazine (117979-38-1)

Conditions	Yield
With triethylamine hydrochloride In xylene for 2h; Heating / reflux;	27%

3-chloro-6-(4-methoxyphenyl)pyridazine (58059-31-7) + 4-(2-hydroxy-ethoxy)-benzaldehyde (22042-73-5) → 4-{2-[6-(4-methoxy-phenyl)-pyridazin-3-yloxy]-ethoxy}-benzaldehyde (935692-89-0)

Conditions	Yield
Stage #1: 4-(2-hydroxy-ethoxy)-benzaldehyde With sodium In tetrahydrofuran at 60℃; for 2h; Stage #2: 3-chloro-6-(4-methoxyphenyl)pyridazine In tetrahydrofuran for 10h; Heating / reflux;	9%

3-chloro-6-(4-methoxyphenyl)pyridazine (58059-31-7) → 3-hydrazino-6-(p-methoxyphenyl)pyridazine (18772-76-4)

Conditions	Yield
With hydrazine hydrate In butan-1-ol at 100℃; for 6h;

3-chloro-6-(4-methoxyphenyl)pyridazine (58059-31-7) → 6-endo-cyano-8-<6-(4-methoxyphenyl)-3-pyridazinyl>-8-azabicyclo<3.2.1>oct-3-en-2-one

Conditions	Yield
Multi-step reaction with 3 steps 1: 79.4 percent / butan-1-ol / 4 h / Heating 2: Et3N 3: 45 percent / hydroquinone / acetonitrile / 48 h / Heating View Scheme

3-chloro-6-(4-methoxyphenyl)pyridazine (58059-31-7) → 6-endo-phenyl-8-<6-(4-methoxyphenyl)-3-pyridazinyl>-8-azabicyclo<3.2.1>oct-3-en-2-one

Conditions	Yield
Multi-step reaction with 2 steps 1: 79.4 percent / butan-1-ol / 4 h / Heating 2: 40 percent / Et3N, hydroquinone / 48 h / Heating View Scheme

3-chloro-6-(4-methoxyphenyl)pyridazine (58059-31-7) → (1R,2S,6R,7R)-3,11-Bis-[6-(4-methoxy-phenyl)-pyridazin-3-yl]-3,11-diaza-tricyclo[5.3.1.12,6]dodeca-4,9-diene-8,12-dione

Conditions	Yield
Multi-step reaction with 2 steps 1: 79.4 percent / butan-1-ol / 4 h / Heating 2: Et3N View Scheme

3-chloro-6-(4-methoxyphenyl)pyridazine (58059-31-7) → 3-hydroxy-1-<6-(4-methoxyphenyl)-3-pyridazinyl>pyridinium maleate

Conditions	Yield
Multi-step reaction with 3 steps 1: 79.4 percent / butan-1-ol / 4 h / Heating 2: Et3N 3: 91 percent / tetrahydrofuran / 14 h / Heating View Scheme

3-chloro-6-(4-methoxyphenyl)pyridazine (58059-31-7) → 3-hydroxy-1-<6-(4-methoxyphenyl)-3-pyridazinyl>pyridinium fumarate

Conditions	Yield
Multi-step reaction with 3 steps 1: 79.4 percent / butan-1-ol / 4 h / Heating 2: Et3N 3: 85 percent / dioxane / 14 h / Heating View Scheme

3-chloro-6-(4-methoxyphenyl)pyridazine (58059-31-7) → 2-(3-carboxypropyl)-3-amino-6-(4-methoxyphenyl)pyridazinium bromide (104104-50-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: hydrazine hydrate / butan-1-ol / 6 h / 100 °C 2: H2 / Raney Ni / methanol / 20 °C / 760 Torr 3: dimethylformamide / 8 h / 80 °C 4: 48percent HBr / acetic acid / 10 h / 100 °C View Scheme

3-chloro-6-(4-methoxyphenyl)pyridazine (58059-31-7) → 6-Amino-1-(3-ethoxycarbonyl-propyl)-3-(4-methoxy-phenyl)-pyridazin-1-ium; bromide (105538-31-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrazine hydrate / butan-1-ol / 6 h / 100 °C 2: H2 / Raney Ni / methanol / 20 °C / 760 Torr 3: dimethylformamide / 8 h / 80 °C View Scheme

3-chloro-6-(4-methoxyphenyl)pyridazine (58059-31-7) → 3-amino-6-(4'-methoxyphenyl)pyridazine (4776-87-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrazine hydrate / butan-1-ol / 6 h / 100 °C 2: H2 / Raney Ni / methanol / 20 °C / 760 Torr View Scheme

3-chloro-6-(4-methoxyphenyl)pyridazine (58059-31-7) → 3-chloro-6-(4-hydroxyphenyl)pyridazine (99708-46-0)

Conditions	Yield
With boron tribromide In dichloromethane at 20℃; for 16h;

3,4,5-trimethoxybenzohydrazide (3291-03-0) + 3-chloro-6-(4-methoxyphenyl)pyridazine (58059-31-7) → 3-(3,4,5-trimethoxyphenyl)-6-(4-methoxyphenyl)-[1,2,4]triazolo[4,3-b]pyridazine

Conditions	Yield
In butan-1-ol Heating; Microwave irradiation;

C10H14N2O4 (1153791-73-1) + 3-chloro-6-(4-methoxyphenyl)pyridazine (58059-31-7) → 3-(2,3,4-trimethoxyphenyl)-6-(4-methoxyphenyl)-[1,2,4]triazolo[4,3-b]pyridazine

Conditions	Yield
In butan-1-ol Heating; Microwave irradiation;

Upstream product

• 141-30-0 3,6-dichlorpyridazine 
• 93296-09-4 4-methoxyphenylzinc chloride 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 33397-21-6 tris(4-methoxyphenyl)bismuth 
• 5720-07-0 4-methoxyphenylboronic acid 
• 135034-10-5 3-chloro-6-iodopyridazine 
• 2166-33-8 6-(4-methoxy-phenyl)-2H-pyridazin-3-one 
• 2166-33-8 6-(4-methoxyphenyl)-2H-pyridazin-3-one 

Downstream Products

• 935692-89-0 4-{2-[6-(4-methoxy-phenyl)-pyridazin-3-yloxy]-ethoxy}-benzaldehyde 
• 117979-38-1 6-(4-methoxyphenyl)-1,2,4-triazolo<4,3-b>pyridazine 
• 99708-46-0 3-chloro-6-(4-hydroxyphenyl)pyridazine 
• 4776-87-8 3-amino-6-(4'-methoxyphenyl)pyridazine 
• 105538-31-6 6-Amino-1-(3-ethoxycarbonyl-propyl)-3-(4-methoxy-phenyl)-pyridazin-1-ium; bromide 
• 104104-50-9 2-(3-carboxypropyl)-3-amino-6-(4-methoxyphenyl)pyridazinium bromide 
• 2166-04-3 3-(4-methoxyphenyl)-6-phenylpyridazine 
• 18772-76-4 3-hydrazino-6-(p-methoxyphenyl)pyridazine 
• 76970-05-3 6-(4-Methoxy-phenyl)-3-methyl-[1,2,4]triazolo[4,3-b]pyridazine 
• 93181-98-7 3-(4-hydroxypiperidino)-6-(4-methoxyphenyl)pyridazine 

Relevant articles and documents

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An easily available Pd(OAc)2/(2-mesitylindenyl) dicyclohexylphosphine/Me(octyl)3N+Cl-/K 3PO4·3H2O catalytic system was developed and it shows high catalytic activity in the Suzuki-Miyaura cross-coupling reaction of a diverse array of aryl and heteroaryl chlorides in water. Notably, this catalytic system also works with ultra-low loading of the catalyst with high turnover numbers.