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Basic Information

Molecular Structure:
CAS No.:	123-33-1
Name:	3,6-Dihydroxypyridazine
Article Data:	44

Formula:	C₄H₄N₂O₂
Molecular Weight:	112.088
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;
EINECS:	204-619-9
Density:	1.321 g/cm³
Melting Point:	299-301 °C (dec.)(lit.)
Boiling Point:	477.2 °C at 760 mmHg
Flash Point:	242.4 °C
Solubility:	6 g/L
Appearance:	Crystalline
Hazard Symbols:	Xn,Xi
Risk Codes:	36/37/38-40
Safety:	26-36-45-36/37/39
Transport Information:	UN 3077 9/PG 3
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

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Chemistry

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

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.

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.

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.

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).

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