1(2H)-Phthalazinone supplier

Name
1(2H)-Phthalazinone
EINECS 204-319-8
CAS No. 119-39-1
Article Data69
CAS DataBase
Density 1.318 g/cm³
Solubility In soluble in water
Melting Point 183-185 °C
Formula C₈H₆N₂O
Boiling Point 423.4 °C at 760 mmHg
Molecular Weight 146.148
Flash Point 209.9 °C
Transport Information
Appearance Off-white to pale yellow crystalline powder
Safety 22-24/25-36/37/39-26
Risk Codes 22-36/37/38-68
Molecular Structure
Hazard Symbols Xn
Synonyms 1-Hydroxyphthalazine;1-Oxophthalazine;1-Phthalazinol;ICX 56225770;NSC 10432;Phthalazin-1-one;Phthalazinone;Phthalazone;Benzo[d]pyridazin-1(2H)one;
PSA 45.75000
LogP 0.92310

Synthetic route

: 119-67-5
o-carboxybenzaldehyde

: 119-39-1
phthalazone

Conditions

Conditions	Yield
With sodium acetate; hydrazinium sulfate In water	100%
With tert-butylbenzene; hydrogen; platinum; hydrazine In 1,4-dioxane at 80℃; under 750.075 Torr; for 0.5h; Sealed tube;	99%
With hydrazine at 95℃; for 0.666667h; Large scale;	96.36%

: 62551-42-2
2-dibromomethyl-benzoic acid

: 119-39-1
phthalazone

Conditions

Conditions	Yield
With hydrazine hydrate In ethanol	88%

: 65349-12-4
2-((2-benzoylhydrazono)methyl)benzoic acid

A: 119-39-1
phthalazone

B: 65-85-0
benzoic acid

Conditions

Conditions	Yield
With tin(ll) chloride In 1,4-dioxane for 15h; Reflux;	A 84% B 77%

: 55294-87-6
N-2-(3'-phthalide-yl)phthalazin-1-one

: 119-39-1
phthalazone

Conditions

Conditions	Yield
With hydrazine hydrate In ethanol for 2h; hydrazinolysis; Heating;	73.2%

: 201230-82-2
carbon monoxide

: 19820-56-5
2-formylphenyl tosylate

: 119-39-1
phthalazone

Conditions

Conditions	Yield
With palladium(II) trifluoroacetate; t-butoxycarbonylhydrazine; 1,3-bis-(diphenylphosphino)propane; magnesium sulfate; potassium carbonate In acetonitrile at 140℃; under 7500.75 Torr; for 21h; Autoclave;	68%

: 97694-83-2
2,3-Dihydro-9bH-oxazolo[2,3-a]isoindol-5-one

: 119-39-1
phthalazone

Conditions

Conditions	Yield
With hydrazine hydrate In ethanol for 50h; Heating;	48%

: 6940-49-4
3-Bromophthalide

: 119-39-1
phthalazone

Conditions

Conditions	Yield
Stage #1: 3-Bromophthalide With hydrogenchloride In water for 2h; Reflux; Stage #2: With hydrazine In water at 20℃; for 2h;	47%
With ethanol; hydrazine hydrate
Multi-step reaction with 2 steps 1: benzene; ammonia 2: aqueous N2H4 View Scheme

: 253-52-1
PHTHALAZINE

: 119-39-1
phthalazone

Conditions

Conditions	Yield
With benzonitrile oxide In benzene for 3h; Heating;	45%
Stage #1: PHTHALAZINE With aldehyde oxidase In aq. phosphate buffer for 0.166667h; pH=7.4; Stage #2: In dimethyl sulfoxide Solvent; Enzymatic reaction;
With human aldehyde oxidase isoform 1 In aq. buffer at 37℃; for 0.0833333h; pH=7.4; Kinetics; Reagent/catalyst;

: 480-91-1
oxisoindole

: 119-39-1
phthalazone

Conditions

Conditions	Yield
With hydrazine hydrate at 200℃;

: 5784-45-2
1-chlorophthalazine

: 119-39-1
phthalazone

Conditions

Conditions	Yield
With sodium hydroxide
With hydrogenchloride

: 4752-10-7
1,4-dichlorophthalazine

A: 253-52-1
PHTHALAZINE

B: 119-39-1
phthalazone

Conditions

Conditions	Yield
With phosphorus; hydrogen iodide

: 16824-02-5
3-ethoxy-3H-isobenzofuran-1-one

: 119-39-1
phthalazone

Conditions

Conditions	Yield
With sulfuric acid; water; sodium acetate; hydrazine

: 3260-44-4
4-oxo-3,4-dihydrophthalazine-1-carboxylic acid

: 119-39-1
phthalazone

Conditions

Conditions	Yield
With nitrobenzene at 250℃;

: 3260-44-4
4-oxo-3,4-dihydrophthalazine-1-carboxylic acid

A: 119-39-1
phthalazone

B: 15719-64-9, 15719-76-3, 97762-63-5
methylammonium carbonate

: 100541-62-6
2-carboxybenzaldehydeisonicotinoylhydrazone

A: 55-22-1
pyridine-4-carboxylic acid

B: 119-39-1
phthalazone

Conditions

Conditions	Yield
at 190 - 200℃;

: 347309-96-0
2-((2-carbamoylhydrazono)methyl)benzoic acid

: 119-39-1
phthalazone

Conditions

Conditions	Yield
With acetic acid

: 347309-96-0
2-((2-carbamoylhydrazono)methyl)benzoic acid

: 64-19-7
acetic acid

: 119-39-1
phthalazone

: 26486-93-1
3-hydroxy-2,3-dihydro-isoindol-1-one

: 119-39-1
phthalazone

Conditions

Conditions	Yield
With hydrazine hydrate

: 119-67-5
o-carboxybenzaldehyde

: 1752-30-3
Acetone thiosemicarbazone

: 119-39-1
phthalazone

Conditions

Conditions	Yield
With acetic acid; chloroacetic acid

: 7335-65-1
hydrazinium monoacetate

: 119-67-5
o-carboxybenzaldehyde

: 119-39-1
phthalazone

Conditions

Conditions	Yield
With water

: 328-50-7
α-ketoglutaric acid

: 304-20-1
hydralazine hydrochloride

: 119-39-1
phthalazone

Conditions

Conditions	Yield
With phosphate buffer In water at 37℃; pH=7.4, dark, several week;

: 304-20-1
hydralazine hydrochloride

A: 54687-66-0
3-hydroxymethyl-s-triazolo-<3,4-a>phthalazine

B: 234-80-0
1,2,4-triazolo[3,4-a]phthalazine

C: 20062-41-3
3-methyl-s-triazolo<3,4-a>phthalazine

D: 119-39-1
phthalazone

E: 65846-18-6
4-(2-acetylhydrazino)-phthalazinone

Conditions

Conditions	Yield
metabolism studies;

...Expand

: 304-20-1
hydralazine hydrochloride

: 67-64-1
acetone

: 119-39-1
phthalazone

Conditions

Conditions	Yield
With phosphate buffer In water at 37℃; pH=7.4, dark, several week;

: 253-52-1
PHTHALAZINE

A: 87-41-2
2-benzofuran-1(3H)-one

B: 119-39-1
phthalazone

C: 91-15-6
phthalonitrile

D: 643-79-8
o-phthalic dicarboxaldehyde

Conditions

Conditions	Yield
With dihydrogen peroxide; sodium oxalate; iron(II) sulfate Kinetics; Further Variations:; Reagents; Oxidation; Photolysis;

...Expand

: 7647-01-0
hydrogenchloride

: 5784-45-2
1-chlorophthalazine

: 119-39-1
phthalazone

3-amino-phthalide: 3-amino-phthalide

: 119-39-1
phthalazone

Conditions

Conditions	Yield
With ethanol; hydrazine hydrate

: 6940-49-4
3-Bromophthalide

: 64-17-5
ethanol

: 7803-57-8
hydrazine hydrate

: 119-39-1
phthalazone

...Expand

: 64-17-5
ethanol

: 65543-72-8
3,3'-oxy-di-phthalide

: 7803-57-8
hydrazine hydrate

: 119-39-1
phthalazone

...Expand

: 5784-45-2
1-chlorophthalazine

aqueous NaOH: aqueous NaOH

: 119-39-1
phthalazone

: 119-39-1
phthalazone

: 1044569-46-1
1-hydrazinophthalazine

Conditions

Conditions	Yield
With hydrazine at 0 - 25℃; for 24h; Product distribution / selectivity;	99%
With hydrazine In isopropyl alcohol at 0 - 25℃; for 24h; Product distribution / selectivity;	86%
Multi-step reaction with 2 steps 1: trichlorophosphate / 0.03 h 2: hydrazine hydrate / ethanol / 1 h View Scheme
Multi-step reaction with 2 steps 1: trichlorophosphate / 0.03 h 2: hydrazine hydrate / ethanol / 1 h View Scheme

: 119-39-1
phthalazone

: 169457-73-2
tert-butyl 4-(2-bromoethyl)piperidine-1-carboxylate

: 2-(2-(1-tert-butoxycarbonylpiperidin-4-yl)ethyl)phthalazin-1(2H)-one

Conditions

Conditions	Yield
Stage #1: phthalazone With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 1h; Stage #2: tert-butyl 4-(2-bromoethyl)piperidine-1-carboxylate In N,N-dimethyl-formamide; mineral oil at 20℃;	99%

: 119-39-1
phthalazone

: 336107-47-2
3-(biphenyl-4-yloxymethyl)-pent-4-en-1-ol

: 336107-54-1
2-[3-(biphenyl-4-yloxymethyl)-pent-4-enyl]-2H-phthalazin-1-one

Conditions

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; Mitsunobu reaction;	95%

: 50-00-0
formaldehyd

: 119-39-1
phthalazone

: 941-95-7
2-(hydroxymethyl)phthalazin-1(2H)-one

Conditions

Conditions	Yield
In ethanol; water for 7h; Reflux;	91%

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

: 119-39-1
phthalazone

: tert-butyl 1-oxophthalazine-2(1H)-carboxylate

Conditions

Conditions	Yield
With dmap In tetrahydrofuran at 20℃;	91%

: 119-39-1
phthalazone

: 5784-45-2
1-chlorophthalazine

Conditions

Conditions	Yield
With trichlorophosphate at 130℃; for 1.5h;	90%
With trichlorophosphate at 80℃; for 0.5h; Product distribution / selectivity;	85%
With trichlorophosphate at 70 - 80℃; for 0.5h; Product distribution / selectivity;	85%

: 22445-41-6
3,5-dimethylphenyl iodide

: 119-39-1
phthalazone

: 2-(3,5-dimethylphenyl)phthalazin-1(2H)-one

Conditions

Conditions	Yield
With copper(l) iodide; (S,S)-1,2-diaminocyclohexane; caesium carbonate In 1,4-dioxane; dodecane at 110℃; for 24h;	90%

: 119-39-1
phthalazone

: 186191-19-5
m-(2-bromoethyloxy)benzaldehyde

: 3-[2-[1-oxo-2(1H)-phthalazinyl]ethoxy]benzaldehyde

Conditions

Conditions	Yield
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 80℃; for 5h;	90%

: 588-72-7
[(E)-2-bromoethenyl]benzene

: 119-39-1
phthalazone

: (E)-2-styrylphthalazin-1(2H)-one

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 23h; Heating;	89%

: 50-00-0
formaldehyd

: 119-39-1
phthalazone

: 879-16-3
N-chloromethylphthalazin-1(2H)-one

Conditions

Conditions	Yield
Stage #1: formaldehyd; phthalazone In water Heating; Stage #2: With thionyl chloride In dichloromethane; N,N-dimethyl-formamide at 20℃; Further stages.;	87%

: 6032-29-7
(+/-)-2-pentanol

: 119-39-1
phthalazone

: 2-(pentan-2-yl)phthalazin-1(2H)-one

Conditions

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at -20 - 20℃; for 25h; Mitsunobu Displacement; Inert atmosphere;	85%

: 119-39-1
phthalazone

: 52191-15-8
4-(2-bromoethyloxy)benzaldehyde

: 214282-14-1
4-[2-[1-oxo-1,2-dihydrophthalazin-2-yl]ethoxy]benzaldehyde

Conditions

Conditions	Yield
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 80℃; for 5h;	84%
Stage #1: phthalazone With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 0.5h; Stage #2: 4-(2-bromoethyloxy)benzaldehyde In N,N-dimethyl-formamide at 65 - 70℃; for 24h;	44%

: 119-39-1
phthalazone

: 56894-29-2
1-(3-chloropropyl)-2-methyl-5-nitro-1H-imidazole

: 2-[3-(2-methyl-5-nitro-1H-imidazol-1-yl)propyl]phthalazin-1(2H)-one

Conditions

Conditions	Yield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 20℃; for 48h;	82%

: 591-50-4
iodobenzene

: 119-39-1
phthalazone

: 6266-49-5
2-phenylphthalazin-1-one

Conditions

Conditions	Yield
With copper(l) iodide; L-methionine; potassium carbonate In N,N-dimethyl-formamide at 100℃; for 24h; Reagent/catalyst; Inert atmosphere; chemoselective reaction;	81%
With copper(l) iodide; potassium carbonate In N,N-dimethyl-formamide at 150℃; for 6h;	78%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; potassium carbonate In triethylamine; N,N-dimethyl-formamide at 110℃; for 12h; Inert atmosphere;	21%

: 17739-45-6, 59146-56-4
2-(2-bromoethoxy)tetrahydropyran

: 119-39-1
phthalazone

: 1,2-Dihydro-1-oxo-2-(tetrahydropyran-2-ylethoxy)-phthalazine

Conditions

Conditions	Yield
With potassium hydroxide In water; dimethyl sulfoxide	80%

: 17739-45-6, 59146-56-4
2-(2-bromoethoxy)tetrahydropyran

: 119-39-1
phthalazone

: 131952-80-2
2-{2-[(Tetrahydro-2-pyranyl)oxy]ethyl}-1-oxophthalazine

Conditions

Conditions	Yield
With potassium hydroxide In water; dimethyl sulfoxide	80%

: 1591-31-7
4-iodo-biphenyl

: 119-39-1
phthalazone

: 1394916-71-2
2-([1,1'-biphenyl]-4-yl)phthalazin-1(2H)-one

Conditions

Conditions	Yield
With bis(tetrapropylammonium) tetraiododicuprate(I); trans-1,2-cyclohexanediamine methanesulfonic acid; caesium carbonate In 1,4-dioxane at 130℃; for 24h; Inert atmosphere;	80%

: 119-39-1
phthalazone

: 19064-73-4
4-bromo-2H-phthalazin-1-one

Conditions

Conditions	Yield
Stage #1: phthalazone With potassium carbonate In N,N-dimethyl-formamide for 0.0833333h; Inert atmosphere; Stage #2: With benzyltrimethylazanium tribroman-2-uide In N,N-dimethyl-formamide at 40℃; for 5h; Inert atmosphere; regioselective reaction;	79%
With bromine; potassium bromide In water at 20℃; for 31h; pH=5.8; Heating;	66%
With bromine; potassium bromide

: 119-39-1
phthalazone

: 158407-04-6
tert-butyl 4-(bromomethyl)piperidine-1-carboxylate

: 2-(1-tert-butoxycarbonylpiperidin-4-ylmethyl)phthalazin-1(2H)-one

Conditions

Conditions	Yield
Stage #1: phthalazone With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 1h; Stage #2: tert-butyl 4-(bromomethyl)piperidine-1-carboxylate In N,N-dimethyl-formamide; mineral oil at 20℃;	78%

: 300-57-2
allylbenzene

: 119-39-1
phthalazone

: 2-cinnamylphthalazin-1(2H)-one

Conditions

Conditions	Yield
With 2,6-dimethyl-1,4-benzoquinone; palladium dichloride In dimethyl sulfoxide at 100℃; for 24h; chemoselective reaction;	76%

: 14258-40-3
2-(2-chloroethoxy)ethyl ethanoate

: 119-39-1
phthalazone

: 2-[2-(2-acetoxyethoxy)ethyl]-1(2H)-phthalazinone

Conditions

Conditions	Yield
Stage #1: phthalazone With sodium hydride In N,N-dimethyl-formamide at 100℃; for 1h; Metallation; Stage #2: 2-(2-chloroethoxy)ethyl ethanoate In N,N-dimethyl-formamide at 100℃; for 5h; Alkylation;	73%

: 119-39-1
phthalazone

: 78-92-2, 15892-23-6
iso-butanol

: 2-(butan-2-yl)phthalazin-1(2H)-one

Conditions

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at -20 - 20℃; for 25h; Mitsunobu Displacement; Inert atmosphere;	72%

: 1-benzyl-4-(3-bromopropyl)piperidine

: 119-39-1
phthalazone

: 3-(N-benzylpiperidin-4-yl)propylphthalazin-1(2H)-one

Conditions

Conditions	Yield
Stage #1: phthalazone With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; Stage #2: 1-benzyl-4-(3-bromopropyl)piperidine In N,N-dimethyl-formamide; mineral oil at 20℃;	70%

: 119-39-1
phthalazone

2-Cl-6-F-C6H3CH2-Y: 2-Cl-6-F-C6H3CH2-Y

: 2-(2-chloro-6-fluoro-benzyl)-2H-phthalazin-1-one

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide Alkylation; Irradiation;	65%

1(2H)-Phthalazinone Consensus Reports

Reported in EPA TSCA Inventory.

1(2H)-Phthalazinone Specification

1(2H)-Phthalazinone is an organic compound with the formula C₈H₆N₂O, and its systematic name is the same with the product name. With the CAS registry number 119-39-1, it is also named as Benzo[d]pyridazin-1(2H)one. It belongs to the product categories of Miscellaneous; Aldehyde. Its EINECS number is 204-319-8. In addition, the molecular weight is 146.15. This chemical is used as biochemical reagents. Its classification code is Mutation data. It can be used as Hydralazine hydrochloride intermediate.

Physical properties of 1(2H)-Phthalazinone are: (1)ACD/LogP: 0.75; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.75; (4)ACD/LogD (pH 7.4): 0.75; (5)ACD/BCF (pH 5.5): 2.19; (6)ACD/BCF (pH 7.4): 2.19; (7)ACD/KOC (pH 5.5): 60.95; (8)ACD/KOC (pH 7.4): 60.95; (9)#H bond acceptors: 3; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 41.46 Å²; (13)Index of Refraction: 1.667; (14)Molar Refractivity: 41.272 cm³; (15)Molar Volume: 110.881 cm³; (16)Polarizability: 16.362×10^-24cm³; (17)Surface Tension: 52.7 dyne/cm; (18)Density: 1.318 g/cm³; (19)Flash Point: 209.9 °C; (20)Enthalpy of Vaporization: 70.39 kJ/mol; (21)Boiling Point: 423.4 °C at 760 mmHg; (22)Vapour Pressure: 9.11E-08 mmHg at 25°C.

Preparation of 1(2H)-Phthalazinone: this chemical can be prepared by 2-formyl-benzoic acid. This reaction will need reagents hydrazine sulfate, sodium acetate and solvent H₂O. The yield is about 100%.

1(2H)-Phthalazinone can be prepared by 2-formyl-benzoic acid

Uses of 1(2H)-Phthalazinone: it can be used to produce 1-bromo-phthalazine at the temperature of 130 °C. It will need reagent POBr₃ with the reaction time of 30 min. The yield is about 58%.

1(2H)-Phthalazinone can be used to produce 1-bromo-phthalazine at the temperature of 130 °C

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. It is harmful if swallowed. It has a possible risk of irreversible effects. You should not breathe dust. 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 must avoid contact with skin and eyes.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C1c2ccccc2\C=N/N1
(2)Std. InChI: InChI=1S/C8H6N2O/c11-8-7-4-2-1-3-6(7)5-9-10-8/h1-5H,(H,10,11)
(3)Std. InChIKey: IJAPPYDYQCXOEF-UHFFFAOYSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intravenous	180mg/kg (180mg/kg)		U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#00139,
rat	LD50	oral	370mg/kg (370mg/kg)		Industrial Hygiene Foundation of America, Chemical and Toxicological Series, Bulletin. Vol. 6, Pg. 1, 1967.

Product Name

1(2H)-Phthalazinone

Synthetic route

1(2H)-Phthalazinone Consensus Reports

1(2H)-Phthalazinone Specification

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