3,6-Dihydroxypyridazine supplier

Name
3,6-Dihydroxypyridazine
EINECS 204-619-9
CAS No. 123-33-1
Article Data44
CAS DataBase
Density 1.321 g/cm³
Solubility 6 g/L
Melting Point 299-301 °C (dec.)(lit.)
Formula C₄H₄N₂O₂
Boiling Point 477.2 °C at 760 mmHg
Molecular Weight 112.088
Flash Point 242.4 °C
Transport Information UN 3077 9/PG 3
Appearance Crystalline
Safety 26-36-45-36/37/39
Risk Codes 36/37/38-40
Molecular Structure
Hazard Symbols Xn,Xi
Synonyms 3(2H)-Pyridazinone,6-hydroxy- (6CI,7CI);1,2-Dihydro-3,6-pyridazinedione;3,6-Dioxopyridazine;3,6-Pyridazinediol;6-Hydroxy-3(2H)-pyridazinone;Antergon;Antyrost;MAH;MH;Sorbatran;SuperDe-Sprout;Yadi;Yake;MH (hydrazide);Maleic acid cyclic hydrazide;Maleic cyclic hydrazide;Maleic hydrazide;Malepin;Malzid;Mazide;NSC 13892;NSC 234167;NSC 48832;NSC 8823;Regulox 36;Royal Slo-Gro;
PSA 65.72000
LogP -0.93680

Synthetic route

: 108-31-6
maleic anhydride

: 123-33-1
Maleic hydrazide

Conditions

Conditions	Yield
With hydrazine hydrate; sulfuric acid; lanthanum(lll) triflate In water at 30 - 120℃; for 10.5h; Temperature; Reagent/catalyst;	97.2%
With hydrazine hydrate In water at 100℃; for 3h;	92%
With hydrogenchloride; hydrazine hydrate In water Cooling with ice; Reflux;	86%

: 110-16-7
maleic acid

: 123-33-1
Maleic hydrazide

Conditions

Conditions	Yield
With hydrazine hydrate In water at 95℃; for 3h; Reagent/catalyst; Time;	90%
With water; hydrazine

: 18259-51-3
1-oxy-2H-pyridazin-3-one

: 123-33-1
Maleic hydrazide

Conditions

Conditions	Yield
With acetic anhydride

: 5343-00-0, 15189-88-5
N,N'-bis-(3c-carboxy-acryloyl)-hydrazine

: 123-33-1
Maleic hydrazide

Conditions

Conditions	Yield
With water

: 108-31-6
maleic anhydride

: 7803-57-8
hydrazine hydrate

: 64-19-7
acetic acid

: 123-33-1
Maleic hydrazide

Conditions

Conditions	Yield
Verb. 1 = 1 Mol;

...Expand

: 108-31-6
maleic anhydride

: hydrazine hydrate

: 123-33-1
Maleic hydrazide

Conditions

Conditions	Yield
In acetic acid for 3h; Reflux;

: 123-33-1
Maleic hydrazide

: 502-95-4
tetrahydropyridazine-3,6-dione

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol	95%
With ethanol; platinum at 100℃; under 2942.03 Torr; Hydrogenation;
With ethanol; aluminium amalgam

: 123-33-1
Maleic hydrazide

: 459-57-4
4-fluorobenzaldehyde

: 126-81-8
dimedone

: 11-(4-fluorophenyl)-3,4-dihydro-3,3-dimethyl-2H-pyridazino[1,2-a]indazole-1,6,9(11H)-trione

Conditions

Conditions	Yield
With 1-methyl-2-pyrrolidinone hydrosulfate In neat (no solvent) at 85℃; for 0.05h; Green chemistry;	94%

...Expand

: 123-33-1
Maleic hydrazide

: 104-88-1
4-chlorobenzaldehyde

: 126-81-8
dimedone

: 1091592-75-4
11-(4-chlorophenyl)-3,3-dimethyl-11-3,4-dihydro-1H-pyridazino[1,2-a]indazole-1,6,9(2H,11H)-trione

Conditions

Conditions	Yield
With 1-methyl-2-pyrrolidinone hydrosulfate In neat (no solvent) at 85℃; for 0.0833333h; Green chemistry;	93%
With toluene-4-sulfonic acid at 80℃; for 0.333333h; neat (no solvent);	49%

...Expand

: 123-33-1
Maleic hydrazide

: 555-16-8
4-nitrobenzaldehdye

: 126-81-8
dimedone

: 1091592-76-5
3,3-dimethyl-11-(4-nitrophenyl)-2,3,4,11-tetrahydro-1H-pyridazino[1,2-a]indazole-1,6,9-trione

Conditions

Conditions	Yield
With 1-methyl-2-pyrrolidinone hydrosulfate In neat (no solvent) at 85℃; for 0.05h; Green chemistry;	93%
With toluene-4-sulfonic acid at 80℃; for 0.416667h; neat (no solvent);	48%

...Expand

: 123-33-1
Maleic hydrazide

: 1108-03-8, 2418-45-3, 2874-25-1, 3957-39-9, 57760-54-0, 60018-28-2, 78148-63-7, 125225-12-9
ergosta-5,7,22-trien-3β-yl acetate

: 41238-06-6
C34H48N2O4

Conditions

Conditions	Yield
With lead(IV) acetate In methanol; chloroform	92%

: 123-33-1
Maleic hydrazide

: 89-98-5
2-chloro-benzaldehyde

: 126-81-8
dimedone

: 1091592-77-6
11-(2-chlorophenyl)-3,3-dimethyl-3,4-dihydro-1H-pyridazino[1,2-a]indazole-1,6,9(2H,11H)-trione

Conditions

Conditions	Yield
With 1-methyl-2-pyrrolidinone hydrosulfate In neat (no solvent) at 85℃; for 0.0833333h; Green chemistry;	92%
With toluene-4-sulfonic acid at 80℃; for 0.666667h; neat (no solvent);	55%

...Expand

: 123-33-1
Maleic hydrazide

: 126-81-8
dimedone

: 552-89-6
2-nitro-benzaldehyde

: 3,4-dihydro-3,3-dimethyl-11-(2-nitrophenyl)-2H-pyridazino[1,2-a]indazole-1,6,9(11H)-trione

Conditions

Conditions	Yield
With 1-methyl-2-pyrrolidinone hydrosulfate In neat (no solvent) at 85℃; for 0.0833333h; Green chemistry;	92%

...Expand

: 123-33-1
Maleic hydrazide

: ethyl 5-(5-methoxy-2-(phenylethynyl)phenyl)-5-oxopenta-2,3-dienoate

: ethyl 2-(3-methoxy-5,8,11-trioxo-13-phenyl-6,6a,8,11-tetrahydro-5H-benzo[e]pyridazino[1,2-a]indazol-6a-yl)acetate

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 80℃;	92%

: 123-33-1
Maleic hydrazide

: 555-16-8
4-nitrobenzaldehdye

: 109-77-3
malononitrile

: 3-amino-1-(4-nitrophenyl)-5,8-dioxo-5,8-dihydro-1H-pyrazolo-[1,2-a]pyridazine-2-carbonitrile

Conditions

Conditions	Yield
With acetic acid at 100℃; for 3h; Temperature; Green chemistry;	92%

...Expand

: 123-33-1
Maleic hydrazide

: 3132-99-8
m-bromobenzoic aldehyde

: 126-81-8
dimedone

: 1091592-78-7
11-(3-bromophenyl)-3,3-dimethyl-3,4-dihydro-1H-pyridazino[1,2-a]indazole-1,6,9(2H,11H)-trione

Conditions

Conditions	Yield
With 1-methyl-2-pyrrolidinone hydrosulfate In neat (no solvent) at 85℃; for 0.1h; Green chemistry;	91%
With toluene-4-sulfonic acid at 80℃; for 0.333333h; neat (no solvent);	54%

...Expand

: 123-33-1
Maleic hydrazide

: 100-52-7
benzaldehyde

: 126-81-8
dimedone

: 1091592-74-3
3,3-dimethyl-11-phenyl-2,3,4,11-tetrahydro-1H-pyridazino[1,2-a]indazole-1,6,9-trione

Conditions

Conditions	Yield
With 1-methyl-2-pyrrolidinone hydrosulfate In neat (no solvent) at 85℃; for 0.1h; Catalytic behavior; Solvent; Temperature; Green chemistry;	91%
With toluene-4-sulfonic acid at 80℃; for 0.5h; neat (no solvent);	50%

...Expand

: 123-33-1
Maleic hydrazide

: 126-81-8
dimedone

: 66-99-9
β-naphthaldehyde

: 3,4-dihydro-3,3-dimethyl-11-(naphthalen-3-yl)-2H-pyridazino[1,2-a]indazole-1,6,9(11H)-trione

Conditions

Conditions	Yield
With 1-methyl-2-pyrrolidinone hydrosulfate In neat (no solvent) at 85℃; for 0.1h; Green chemistry;	90%

...Expand

: 123-33-1
Maleic hydrazide

: 99-61-6
3-nitro-benzaldehyde

: 109-77-3
malononitrile

: 3-amino-1-(3-nitrophenyl)-5,8-dioxo-5,8-dihydro-1H-pyrazolo-[1,2-a]pyridazine-2-carbonitrile

Conditions

Conditions	Yield
With acetic acid at 100℃; for 4h; Green chemistry;	90%
With triethanolamine In water at 60℃; for 1.16667h; Knoevenagel Condensation; Sonication; Green chemistry;	55%

...Expand

: 123-33-1
Maleic hydrazide

: ethyl 5-(2-((4-ethylphenyl)ethynyl)phenyl)-5-oxopenta-2,3-dienoate

: ethyl 2-(13-(4-ethylphenyl)-5,8,11-trioxo-6,6a,8,11-tetrahydro-5H-benzo[e]pyridazino[1,2-a]indazol-6a-yl)acetate

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 80℃;	90%

: 123-33-1
Maleic hydrazide

: 587-04-2
3-Chlorobenzaldehyde

: 109-77-3
malononitrile

: 3-amino-1-(3-chlorophenyl)-5,8-dioxo-5,8-dihydro-1H-pyrazolo[1,2-a]pyridazine-2-carbonitrile

Conditions

Conditions	Yield
With acetic acid at 100℃; for 5h; Green chemistry;	89%
With triethanolamine In water at 60℃; for 1.08333h; Knoevenagel Condensation; Sonication; Green chemistry;	55%

...Expand

: 123-33-1
Maleic hydrazide

: C21H14Cl2O3

: ethyl 2-(3-chloro-13-(4-chlorophenyl)-5,8,11-trioxo-6,6a,8,11-tetrahydro-5H-benzo[e]pyridazino[1,2-a]indazol-6a-yl)acetate

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 80℃;	89%

: 123-33-1
Maleic hydrazide

: 6361-23-5
2,5-dichloro-benzaldehyde

: 109-77-3
malononitrile

: C14H8Cl2N4O2

Conditions

Conditions	Yield
With acetic acid at 100℃; for 4.5h; Green chemistry;	89%

...Expand

: 123-33-1
Maleic hydrazide

: 123-11-5
4-methoxy-benzaldehyde

: 126-81-8
dimedone

: 3,4-dihydro-11-(4-methoxyphenyl)-3,3-dimethyl-2H-pyridazino[1,2-a]indazole-1,6,9(11H)-trione

Conditions

Conditions	Yield
With 1-methyl-2-pyrrolidinone hydrosulfate In neat (no solvent) at 85℃; for 0.166667h; Green chemistry;	88%

...Expand

: 123-33-1
Maleic hydrazide

: 89-98-5
2-chloro-benzaldehyde

: 109-77-3
malononitrile

: 3-amino-1-(2-chlorophenyl)-5,8-dioxo-5,8-dihydro-1H-pyrazolo-[1,2-a]pyridazine-2-carbonitrile

Conditions

Conditions	Yield
With acetic acid at 100℃; for 5h; Green chemistry;	88%
With triethanolamine In water at 60℃; for 0.433333h; Knoevenagel Condensation; Sonication; Green chemistry;	73%

...Expand

: 123-33-1
Maleic hydrazide

: ethyl 5-oxo-5-(2-(phenylethynyl)phenyl)penta-2,3-dienoate

: ethyl 2-(5,8,11-trioxo-13-phenyl-6,6a,8,11-tetrahydro-5H-benzo[e]pyridazino[1,2-a]indazol-6a-yl)acetate

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 80℃;	87%

: 123-33-1
Maleic hydrazide

: 104-87-0
4-methyl-benzaldehyde

: 126-81-8
dimedone

: 1091592-80-1
3,3-dimethyl-11-(4-methylphenyl)-3,4-dihydro-1H-pyridazino[1,2-a]indazole-1,6,9(2H,11H)-trione

Conditions

Conditions	Yield
With 1-methyl-2-pyrrolidinone hydrosulfate In neat (no solvent) at 85℃; for 0.166667h; Green chemistry;	86%
With toluene-4-sulfonic acid at 80℃; for 0.5h; neat (no solvent);	46%

...Expand

: 123-33-1
Maleic hydrazide

: 141-30-0
3,6-dichlorpyridazine

Conditions

Conditions	Yield
Stage #1: Maleic hydrazide With trichlorophosphate at 90℃; for 4h; Stage #2: With sodium hydrogencarbonate In water Cooling with ice;	85%
With trichlorophosphate for 5h; Heating;	67%
With trichlorophosphate

: 123-33-1
Maleic hydrazide

: 173382-69-9
1,2-bis-(3-bromo-1-propynyl)benzene

: 14-oxa-1,19-diaza-tricyclo[13.3.1.05,10]nonadeca-5(10),6,8,15(19),16-pentaene-3,11-diyn-18-one

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 12h;	85%

: 123-33-1
Maleic hydrazide

: 100-52-7
benzaldehyde

: 109-77-3
malononitrile

: 3-amino-5,8-dioxo-1-phenyl-5,8-dihydro-1H-pyrazolo[1,2-a]pyridazine-2-carbonitrile

Conditions

Conditions	Yield
With acetic acid at 100℃; for 6h; Green chemistry;	85%
With triethanolamine In water at 60℃; for 1.5h; Catalytic behavior; Solvent; Knoevenagel Condensation; Sonication; Green chemistry;	40%

...Expand

: 1120-71-4
1,3-propanesultone

: 123-33-1
Maleic hydrazide

: disodium 3-[6-oxo-3-(3-sulfonatopropoxy)-1,6-dihydro-1-pyridazinyl]propanesulfonate

Conditions

Conditions	Yield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In benzene for 1h; Heating;	84.1%

: 123-33-1
Maleic hydrazide

: 434-16-2
7-dehydrocholesterol

: 81126-46-7
C31H46N2O3

Conditions

Conditions	Yield
With lead(IV) acetate In dichloromethane; isopropyl alcohol	84%

3,6-Dihydroxypyridazine Chemical Properties

1,2-DIHYDROPYRIDAZINE-3,6-DIONE(123-33-1) is the chemical compound with the formula C₄H₄N₂O₂.Its molar weight is 112.09g/mol.
1,2-DIHYDROPYRIDAZINE-3,6-DIONE(123-33-1) is also named 1,2-dihydro-6-pyridazinedione;3(2H)-Pyridazinone, 6-hydroxy-;3,6-Dihydroxypridazine;3,6-Dioxopyridazine;3,6-Pyridazinedione, 1,2-dihydro-;6-Hydroxy-2H-pyridazin-2-one;6-hydroxy-3(2h)-pyridazinon.
Melting point: 299-301 ^oC (dec.)(lit.)
Density: 1.6 g/cm³
Flash Point: 300^oC
Boiling Point: 477.2 ^oC at 760 mmHg
Storage temp.: 0-6^oC
Water Solubility: 6 g/L
Index of Refraction: 1.501
Molar Refractivity: 25 cm³
Molar Volume: 84.8 cm³
Surface Tension: 41.3 dyne/cm
Enthalpy of Vaporization: 76.93 kJ/mol
Vapour Pressure: 9.9E-10 mmHg at 25^oC
The chemical structure of 1,2-DIHYDROPYRIDAZINE-3,6-DIONE(123-33-1) is

3,6-Dihydroxypyridazine Uses

1,2-DIHYDROPYRIDAZINE-3,6-DIONE(123-33-1) is used as a herbicide and plant-growth inhibitor. It is used to control suckering of tobacco, for weed control and as a sugar content stabilizer in beets.

3,6-Dihydroxypyridazine Toxicity Data With Reference

1.	cyt-grh-orl 5 mg	CYTOAN Cytologia. 37 (1972),345.
2.	mma-sat 50 µL/plate	MUREAV Mutation Research. 66 (1979),247.
3.	dns-esc 30 µmol/L	ZKKOBW Zeitschrift fuer Krebsforschung und Klinische Onkologie. 92 (1978),177.
4.	sln-dmg-orl 4000 ppm	MUREAV Mutation Research. 55 (1978),15.
5.	sln-dmg-par 4000 ppm	NATUAS Nature. 207 (1965),439.
6.	cyt-mus-ipr 5000 ppm	CISCB7 CIS, Chromosome Information Service. 20 (1976),28.
7.	orl-rat LD50:3800 mg/kg	WRPCA2 World Review of Pest Control. 9 (1970),119.

3,6-Dihydroxypyridazine Consensus Reports

IARC Cancer Review: Group 3 IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 ,1987,p. 56.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 4 ,1974,p. 173.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . Reported in EPA TSCA Inventory.

3,6-Dihydroxypyridazine Safety Profile

Moderately toxic by ingestion. Questionable carcinogen with experimental tumorigenic data. Mutation data reported. Can cause chronic liver damage and acute central nervous system effects. When heated to decomposition it emits highly toxic fumes of NO_x. See also HYDRAZINE.
Hazard Codes:

Xi,Xn
Risk Statements: 36/37/38-40
36/37/38: Irritating to eyes, respiratory system and skin
40: Limited evidence of a carcinogenic effect
Safety Statements: 26-36-45-36/37/39
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36: Wear suitable protective clothing
45: In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
36/37/39: Wear suitable protective clothing, gloves and eye/face protection
RIDADR: UN 3077 9/PG 3
WGK Germany: 2
RTECS: UR5950000
HS Code: 29339990
Hazardous Substances Data: 123-33-1(Hazardous Substances Data).

Product Name

3,6-Dihydroxypyridazine

Synthetic route

3,6-Dihydroxypyridazine Chemical Properties

3,6-Dihydroxypyridazine Uses

3,6-Dihydroxypyridazine Toxicity Data With Reference

3,6-Dihydroxypyridazine Consensus Reports

3,6-Dihydroxypyridazine Safety Profile

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