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Synthetic route

(1-phenylethylidene)hydrazine
13466-30-3

(1-phenylethylidene)hydrazine

moist air

moist air

A

hydrazine hydrate
7803-57-8

hydrazine hydrate

B

acetophenonazine
729-43-1

acetophenonazine

hydrogenchloride
7647-01-0

hydrogenchloride

formaldehyd
50-00-0

formaldehyd

hydrazinecarbodithioic acid methyl ester
5397-03-5

hydrazinecarbodithioic acid methyl ester

A

5-methylsulfanyl-[1,3,4]thiadiazole-3-carbodithioic acid methyl ester

5-methylsulfanyl-[1,3,4]thiadiazole-3-carbodithioic acid methyl ester

B

hydrazine hydrate
7803-57-8

hydrazine hydrate

sulfuric acid
7664-93-9

sulfuric acid

bis-[1-(6-hydroxy-[2]naphthyl)-ethylidene]-hydrazine

bis-[1-(6-hydroxy-[2]naphthyl)-ethylidene]-hydrazine

acetic acid
64-19-7

acetic acid

A

hydrazine hydrate
7803-57-8

hydrazine hydrate

B

6-aceto-naphthol-(2)

6-aceto-naphthol-(2)

N-amino-N',N''-diphenyl-guanidine
56004-08-1

N-amino-N',N''-diphenyl-guanidine

A

hydrazine hydrate
7803-57-8

hydrazine hydrate

B

aniline
62-53-3

aniline

C

triphenylguanazole

triphenylguanazole

Conditions
ConditionsYield
at 180℃;
hydroxide

hydroxide

hypochlorite
14380-61-1

hypochlorite

urea
57-13-6

urea

A

chloride
16887-00-6

chloride

B

carbonate(2-)
3812-32-6

carbonate(2-)

C

hydrazine hydrate
7803-57-8

hydrazine hydrate

Conditions
ConditionsYield
In not given in alk. soln.;
sodium hydrazide
13598-47-5

sodium hydrazide

A

hydrazine hydrate
7803-57-8

hydrazine hydrate

B

sodium hydroxide
1310-73-2

sodium hydroxide

Conditions
ConditionsYield
With ethanol; water In benzene byproducts: sodium alcoholate; decompn. of NaNH*NH2 without explosion: pouring greater amounts of dry benzene over NaNH*NH2 under N2 atmosphere, then addn. of small amounts of alcoholic benzene by shaking until solid substance has reacted; addn. of water;;
water
7732-18-5

water

butan-2-one azine
5921-54-0

butan-2-one azine

hydrazine hydrate
7803-57-8

hydrazine hydrate

Conditions
ConditionsYield
at 160 - 190℃; under 7500.75 - 8250.83 Torr; pH=8.2 - 8.5; Inert atmosphere; Industrial scale;
nitrogen
7727-37-9

nitrogen

A

ammonia
7664-41-7

ammonia

B

hydrazine hydrate
7803-57-8

hydrazine hydrate

Conditions
ConditionsYield
With potassium hydroxide In water at 20℃; under 760.051 Torr; Reagent/catalyst; Electrochemical reaction;
nitrogen
7727-37-9

nitrogen

water
7732-18-5

water

A

ammonia
7664-41-7

ammonia

B

hydrazine hydrate
7803-57-8

hydrazine hydrate

Conditions
ConditionsYield
With lithium perchlorate at 20℃; for 10h; pH=6.5; Reagent/catalyst; Electrochemical reaction;
nitrogen
7727-37-9

nitrogen

water
7732-18-5

water

hydrogen
1333-74-0

hydrogen

A

ammonia
7664-41-7

ammonia

B

hydrazine hydrate
7803-57-8

hydrazine hydrate

Conditions
ConditionsYield
With hydrogenchloride pH=1; Reagent/catalyst; Electrochemical reaction;
4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

hydrazine hydrate
7803-57-8

hydrazine hydrate

Conditions
ConditionsYield
With hydrogenchloride In ethanol; water for 0.166667h;
nickel(II) chloride hexahydrate

nickel(II) chloride hexahydrate

hydrazine hydrate
7803-57-8

hydrazine hydrate

sodium hydroxide
1310-73-2

sodium hydroxide

nickel
7440-02-0

nickel

Conditions
ConditionsYield
In water N2H4*H2O (80%) added to aq. soln. of NiCl2*6H2O (temp. increased to 65°C) under vigorous stirring, cooling to 50°C, aq. NaOH (50%)added (temp. increased to 54°C), 1 h; ppt. washed with water and dried at room temp. for 16 h;100%
In water; ethylene glycol byproducts: N2, H2O; other Radiation; soln. of Ni compd. in ethylene glycol treated with hydrazine hydrate andNaOH under external magnetic field (0.13-0.35 T) with vigorous stirring , react at 60°C; pptd., septd., washed (ethanol), dried (vac., 40°C, 24 h), SEM, XRD;
praseodymium(III)-bis(octaethylporphyrinate)

praseodymium(III)-bis(octaethylporphyrinate)

hydrazine hydrate
7803-57-8

hydrazine hydrate

PrH(OEP)2

PrH(OEP)2

Conditions
ConditionsYield
In dichloromethane byproducts: N2; stirring at room temp. for 3 h; solvent and the excess of hydrazine hydrate evapd. (vac.); residue dried (50°C, 1 d);100%
(+)-(1S,11R)-[1-(2'-Aethylallyloxy)-2,2,3,3,7,7,8,8,11,12,12,13,13,17,17,18,18-heptadecamethyl-10,20-diaza-decahydroporphinato(2-)]-nickel

(+)-(1S,11R)-[1-(2'-Aethylallyloxy)-2,2,3,3,7,7,8,8,11,12,12,13,13,17,17,18,18-heptadecamethyl-10,20-diaza-decahydroporphinato(2-)]-nickel

hydrazine hydrate
7803-57-8

hydrazine hydrate

(+)-(1S,11R,2'RS)-[1-(2'-Methyl-1'-butoxy)-2,2,3,3,7,7,8,8,11,12,12,13,13,17,17,18,18-heptadecamethyl-10,20-diaza-decahydroporphinato(2-)]-nickel

(+)-(1S,11R,2'RS)-[1-(2'-Methyl-1'-butoxy)-2,2,3,3,7,7,8,8,11,12,12,13,13,17,17,18,18-heptadecamethyl-10,20-diaza-decahydroporphinato(2-)]-nickel

Conditions
ConditionsYield
With dihydrogen peroxide; copper(II) sulfate In tetrahydrofuran 30 % H2O2-soln. added for 20 min to Ni-complex, hydrazine monohydrate, CuSO4*5H2O in THF at 40°C; addn. of hexane, washing, filtration, evapn., drying at room temp., 0.01 Torr for 24 h;100%
[Zn(C20H2N4(CH3)4(C6H4OCH2CH2SCOCH3)2((CH2)5CH3)4)]
850620-67-6

[Zn(C20H2N4(CH3)4(C6H4OCH2CH2SCOCH3)2((CH2)5CH3)4)]

hydrazine hydrate
7803-57-8

hydrazine hydrate

[Zn(C20H2N4(CH3)4(C6H4OCH2CH2SH)2((CH2)5CH3)4)]
850620-58-5

[Zn(C20H2N4(CH3)4(C6H4OCH2CH2SH)2((CH2)5CH3)4)]

Conditions
ConditionsYield
In dichloromethane at 25°C;100%
(pS)-1-phthalimido-2-methylferrocene
1350636-34-8

(pS)-1-phthalimido-2-methylferrocene

hydrazine hydrate
7803-57-8

hydrazine hydrate

(pS)-1-amino-2-methylferrocene
1350890-19-5, 31760-79-9

(pS)-1-amino-2-methylferrocene

Conditions
ConditionsYield
In ethanol under Ar; N2H4 added via syringe to stirring soln. of Fe compd., refluxed for 2 h; added H2O, mixt. transferred into separatory funnel contg. H2O and (C2H5)2O, org. layer sepd., aq. layer extd. with addnl. (C2H5)2O, combined org. fractions dried over anhyd. Na2SO4 for 2 h, filtered, solvent removed(vac.);100%
methyl 2-(2,4-dimethyl-6-(pyridin-4-yl)phenoxy)acetate
1572184-86-1

methyl 2-(2,4-dimethyl-6-(pyridin-4-yl)phenoxy)acetate

hydrazine hydrate
7803-57-8

hydrazine hydrate

2-(2,4-dimethyl-6-(pyridin-3-yl)phenoxy)acetohydrazide
1572184-81-6

2-(2,4-dimethyl-6-(pyridin-3-yl)phenoxy)acetohydrazide

Conditions
ConditionsYield
In ethanol at 100℃; for 12h;100%
salicylaldehyde
90-02-8

salicylaldehyde

hydrazine hydrate
7803-57-8

hydrazine hydrate

benzil
134-81-6

benzil

cobalt(II) bromide

cobalt(II) bromide

nickel dibromide

nickel dibromide

Co2Ni((C6H4OCHN2(C6H5)C)2)2Br2(H2O)4*H2O
171201-92-6

Co2Ni((C6H4OCHN2(C6H5)C)2)2Br2(H2O)4*H2O

Conditions
ConditionsYield
In ethanol refluxing (2+1+1 h); cooling (room temp.), NaOH addn., pptn., filtration, washing (ethanol), drying; elem. anal.;99%
salicylaldehyde
90-02-8

salicylaldehyde

hydrazine hydrate
7803-57-8

hydrazine hydrate

benzil
134-81-6

benzil

copper(ll) bromide
7789-45-9

copper(ll) bromide

nickel dibromide

nickel dibromide

Cu2Ni((C6H4OCHN2(C6H5)C)2)2Br2(H2O)4*1.5H2O

Cu2Ni((C6H4OCHN2(C6H5)C)2)2Br2(H2O)4*1.5H2O

Conditions
ConditionsYield
In ethanol refluxing (2+1+1 h); cooling (room temp.), NaOH addn., pptn., filtration, washing (ethanol), drying; elem. anal.;99%
salicylaldehyde
90-02-8

salicylaldehyde

hydrazine hydrate
7803-57-8

hydrazine hydrate

benzil
134-81-6

benzil

nickel dibromide

nickel dibromide

Ni3((C6H4OCHN2(C6H5)C)2)2Br2
171201-89-1

Ni3((C6H4OCHN2(C6H5)C)2)2Br2

Conditions
ConditionsYield
In ethanol refluxing (2+1+1 h); cooling (room temp.), NaOH addn., pptn., filtration, washing (ethanol), drying; elem. anal.;99%
salicylaldehyde
90-02-8

salicylaldehyde

hydrazine hydrate
7803-57-8

hydrazine hydrate

benzil
134-81-6

benzil

cobalt(II) chloride
7646-79-9

cobalt(II) chloride

nickel dichloride

nickel dichloride

Co2Ni((C6H4OCHN2(C6H5)C)2)2Cl2(H2O)4*H2O
171201-91-5

Co2Ni((C6H4OCHN2(C6H5)C)2)2Cl2(H2O)4*H2O

Conditions
ConditionsYield
In ethanol refluxing (2+1+1 h); cooling (room temp.), NaOH addn., pptn., filtration, washing (ethanol), drying; elem. anal.;99%
salicylaldehyde
90-02-8

salicylaldehyde

hydrazine hydrate
7803-57-8

hydrazine hydrate

benzil
134-81-6

benzil

copper dichloride

copper dichloride

nickel dichloride

nickel dichloride

Cu2Ni((C6H4OCHN2(C6H5)C)2)2Cl2(H2O)4*1.5H2O

Cu2Ni((C6H4OCHN2(C6H5)C)2)2Cl2(H2O)4*1.5H2O

Conditions
ConditionsYield
In ethanol refluxing (2+1+1 h); cooling (room temp.), NaOH addn., pptn., filtration, washing (ethanol), drying; elem. anal.;99%
salicylaldehyde
90-02-8

salicylaldehyde

hydrazine hydrate
7803-57-8

hydrazine hydrate

benzil
134-81-6

benzil

nickel dichloride

nickel dichloride

Ni3((C6H4OCHN2(C6H5)C)2)2Cl2
171201-88-0

Ni3((C6H4OCHN2(C6H5)C)2)2Cl2

Conditions
ConditionsYield
In ethanol refluxing (2+1+1 h); cooling (room temp.), NaOH addn., pptn., filtration, washing (ethanol), drying; elem. anal.;99%
[((C5H5)Fe(C5H4C6H4N))2C6H4]

[((C5H5)Fe(C5H4C6H4N))2C6H4]

hydrazine hydrate
7803-57-8

hydrazine hydrate

[((C5H5)Fe(C5H4C6H4NH))2C6H4]*H2O

[((C5H5)Fe(C5H4C6H4NH))2C6H4]*H2O

Conditions
ConditionsYield
In not given99%
N-methyl-4-(methylamino)-3-nitro-N-phenylbenzene sulfonamide
1095501-93-1

N-methyl-4-(methylamino)-3-nitro-N-phenylbenzene sulfonamide

hydrazine hydrate
7803-57-8

hydrazine hydrate

3-amino-N-methyl-4-(methylamino)-N-phenylbenzene sulfonamide
1095501-96-4

3-amino-N-methyl-4-(methylamino)-N-phenylbenzene sulfonamide

Conditions
ConditionsYield
With activated charcoal; iron(III) chloride hexahydrate In isopropyl alcohol for 8h; boiling;99%
ammonium sulfate

ammonium sulfate

hydrazine hydrate
7803-57-8

hydrazine hydrate

magnesium
7439-95-4

magnesium

hydrazinium magnesium sulfate

hydrazinium magnesium sulfate

Conditions
ConditionsYield
byproducts: NH3, H2O, H2; at room temp.; EtOH added; elem. anal.;98%
tetrapotassium octacyanomolybdate(IV) dihydrate

tetrapotassium octacyanomolybdate(IV) dihydrate

water
7732-18-5

water

tetraphenyl phosphonium chloride
2001-45-8

tetraphenyl phosphonium chloride

hydrazine hydrate
7803-57-8

hydrazine hydrate

tetraphenylphosphonium amminetetracyanooxomolybdate(IV) dihydrate

tetraphenylphosphonium amminetetracyanooxomolybdate(IV) dihydrate

Conditions
ConditionsYield
In water byproducts: N2; Irradiation (UV/VIS); K4Mo(CN)8*2H2O (1.0 mmol) and PPh4Cl (0.67 mmol) dissolved in mixt. of N2H4*H2O (98%, 10 ml) and H2O (1 ml); exposed to sunlight; ppt. filtered off; dried in air; elem. anal.;98%
ethyl acetoacetate
141-97-9

ethyl acetoacetate

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

hydrazine hydrate
7803-57-8

hydrazine hydrate

malononitrile
109-77-3

malononitrile

6-amino-2,4-dihydro-4-(4-nitrophenyl)-3-methylpyrano[2,3-c]pyrazole-5-carbonitrile
89607-34-1, 879451-69-1

6-amino-2,4-dihydro-4-(4-nitrophenyl)-3-methylpyrano[2,3-c]pyrazole-5-carbonitrile

Conditions
ConditionsYield
With silica-supported tetramethylguanidine In neat (no solvent) at 100℃; for 0.333333h;98%
at 20℃; for 0.166667h; Ionic liquid; Inert atmosphere;92%
With trityl chloride In neat (no solvent) at 60℃; for 0.833333h;84%
With sodium sulfate; 4-[(R)-((2S,4S,5R)-5-ethenyl-1-azabicyclo-[2.2.2]octan-2-yl)(hydroxy)methyl]quinolin-6-ol In dichloromethane at 20℃; for 17h; optical yield given as %ee;80%
dibenzoyl(ferrocenylmethyl)methane
83267-90-7

dibenzoyl(ferrocenylmethyl)methane

hydrazine hydrate
7803-57-8

hydrazine hydrate

[1-H-3,5-Ph2-(C3N2)-CH2-(η5-C5H5)Fe(η5-C5H4)]
1194509-63-1

[1-H-3,5-Ph2-(C3N2)-CH2-(η5-C5H5)Fe(η5-C5H4)]

Conditions
ConditionsYield
In ethanol EtOH soln. of Fe compd. treated with excess N2H4*H2O (1:10 molar ratio),mixt. refluxed for 3 h; cooled to room temp., evapd., dissolved (CH2Cl2), chromd. (SiO2, CH2Cl2), evapd., dried (vac., 2 d), elem. anal.;98%
guanidine hydrochloride
50-01-1

guanidine hydrochloride

hydrazine hydrate
7803-57-8

hydrazine hydrate

triaminoguanidine hydrochloride
5329-29-3

triaminoguanidine hydrochloride

Conditions
ConditionsYield
In 1,4-dioxane for 2h; Reflux;98%
perfluorobenzaldehyde
653-37-2

perfluorobenzaldehyde

ethyl acetoacetate
141-97-9

ethyl acetoacetate

hydrazine hydrate
7803-57-8

hydrazine hydrate

malononitrile
109-77-3

malononitrile

6-amino-3-methyl-4-(2,3,4,5,6-pentafluorophenyl)-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
354538-52-6, 879454-49-6

6-amino-3-methyl-4-(2,3,4,5,6-pentafluorophenyl)-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile

Conditions
ConditionsYield
With silica-supported tetramethylguanidine In neat (no solvent) at 100℃; for 0.25h;98%
ethyl acetoacetate
141-97-9

ethyl acetoacetate

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

hydrazine hydrate
7803-57-8

hydrazine hydrate

malononitrile
109-77-3

malononitrile

6‐amino‐4‐(4‐chlorophenyl)‐3‐methyl‐2,4-dihydropyrano[2.3‐c]pyrazol‐5‐carbonitrile
89607-39-6, 298217-11-5

6‐amino‐4‐(4‐chlorophenyl)‐3‐methyl‐2,4-dihydropyrano[2.3‐c]pyrazol‐5‐carbonitrile

Conditions
ConditionsYield
With silica-supported tetramethylguanidine In neat (no solvent) at 100℃; for 0.333333h;98%
With trityl chloride In neat (no solvent) at 60℃; for 0.833333h;82%

Raw Materials

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