Conditions | Yield |
---|---|
With pyridine; aluminum oxide; hydrazine at 131 - 133℃; for 5h; microwave irradiation; | 100% |
With hydrazine hydrate | |
With hydrazine hydrate |
Conditions | Yield |
---|---|
In ethanol; water; ethyl acetate at 40 - 45℃; for 4h; | 98% |
Conditions | Yield |
---|---|
Amano PS Lipase at 25℃; for 48h; | 78% |
acetic anhydride
N-(2-acetylamino)phenylglyoxylyl-N'-acetylhydrazine
A
1-acetyl-1H-indole-2,3-dione
B
Diacetylhydrazin
Conditions | Yield |
---|---|
In benzene for 5h; Heating; | A 63% B 36% |
Conditions | Yield |
---|---|
With pyridine; hydrazine hydrate In tetrahydrofuran at 0℃; | 34% |
Conditions | Yield |
---|---|
With hydrazinium sulfate at 100℃; Behandeln des Produktes mit Essigsaeureanhydrid; |
Conditions | Yield |
---|---|
at 200℃; |
Conditions | Yield |
---|---|
With hydrazine hydrate |
Conditions | Yield |
---|---|
With pyridine; chloroform |
Conditions | Yield |
---|---|
With benzene |
Conditions | Yield |
---|---|
With diethyl ether |
1,3-diphenyl-propen-3-one
A
Diacetylhydrazin
B
1-acetyl-3,5-diphenyl-4,5-dihydro-1H-pyrazole
Conditions | Yield |
---|---|
With hydrazine hydrate; acetic acid |
Conditions | Yield |
---|---|
With trifluoroacetic acid In dimethylsulfoxide-d6 | |
With peracetic acid |
bromobenzene
1,6-bis-(4-chlorophenyl)-3,4-diacetyl-1,5-hexazadiene
A
Diacetylhydrazin
B
4'-chloro-4-bromo-biphenyl
C
2-bromo-4,4’-dichloro-1,1’-biphenyl
D
3-bromo-4'-chloro-1,1'-biphenyl
E
1-acetyl-1-p-chlorophenylhydrazine
Conditions | Yield |
---|---|
at 131℃; Product distribution; Mechanism; thermolysis, var.: atmosphere : N2, O2, catalyst : m-dinitrobenzene; |
triethyl 1,3,5-triazine-2,4,6-tricarboxylate
acetic acid hydrazide
A
Diacetylhydrazin
B
1-acetylethoxycarbonylformamidrazone
C
2-acetyl-5-ethoxycarbonyltetrazole
D
3,5-diethoxycarbonyl-1,2,4-triazole
Conditions | Yield |
---|---|
In ethanol for 2h; Heating; Further byproducts given; | A 0.14 g B 0.57 g C 0.09 g D 0.57 g |
triethyl 1,3,5-triazine-2,4,6-tricarboxylate
A
Diacetylhydrazin
B
1-acetylethoxycarbonylformamidrazone
C
2-acetyl-5-ethoxycarbonyltetrazole
D
3,5-diethoxycarbonyl-1,2,4-triazole
Conditions | Yield |
---|---|
With acetic acid hydrazide In ethanol for 2h; Heating; Further byproducts given; | A 0.14 g B 0.57 g C 0.09 g D 0.57 g |
1,6-bis-(4-chlorophenyl)-3,4-diacetyl-1,5-hexazadiene
A
Diacetylhydrazin
B
1,6-di-p-bromophenyl-3,4-diacetyl-1,5-hexazadiene
C
1-acetyl-1-p-chlorophenylhydrazine
D
4'-biphenyl chloride
Conditions | Yield |
---|---|
In benzene at 10℃; for 6h; Product distribution; Mechanism; Irradiation; var.: concn., time; |
acetic anhydride
A
Diacetylhydrazin
B
trisacetylhydrazine
C
tetraacetylhydrazine
Conditions | Yield |
---|---|
With hydrazine hydrate at 150℃; for 3h; | A 4 g B 25.6 g C 4.3 g |
1-p-chlorophenyl-3,4-diacetyl-1-tetrazene
A
Diacetylhydrazin
B
4,4'-dichlorobiphenyl
C
1-acetyl-1-p-chlorophenylhydrazine
D
4'-biphenyl chloride
Conditions | Yield |
---|---|
In benzene at 10℃; for 2h; Product distribution; Mechanism; Irradiation; |
Conditions | Yield |
---|---|
With hydrazine hydrate In ethanol for 5h; Heating; | 90 % Turnov. |
8-fluoro-5-(4-fluorophenyl)-1,3,4,5-tetrahydro-1-benzazepin-2-thione
acetic acid hydrazide
A
Diacetylhydrazin
B
9-fluoro-6-(4-fluorophenyl)-1-methyl-5,6-dihydro-4H-s-triazolo<4,3-a>-1-benzazepine
Conditions | Yield |
---|---|
In butan-1-ol for 34h; Heating; |
acetic acid hydrazide
A
Diacetylhydrazin
B
1-acetylethoxycarbonylformamidrazone
C
2-acetyl-5-ethoxycarbonyltetrazole
D
3,5-diethoxycarbonyl-1,2,4-triazole
Conditions | Yield |
---|---|
With triethyl 1,3,5-triazine-2,4,6-tricarboxylate In ethanol for 2h; Heating; Further byproducts given; | A 0.14 g B 0.57 g C 0.09 g D 0.57 g |
1,6-bis-(4-chlorophenyl)-3,4-diacetyl-1,5-hexazadiene
chlorobenzene
A
Diacetylhydrazin
B
2,4'-dichlorobiphenyl
C
3,4'-dichlorobiphenyl
D
4,4'-dichlorobiphenyl
E
1-acetyl-1-p-chlorophenylhydrazine
Conditions | Yield |
---|---|
at 131℃; Product distribution; Mechanism; thermolysis, var.: photolysis; | |
at 10℃; for 6h; Product distribution; Mechanism; Irradiation; |
1-p-chlorophenyl-3,4-diacetyl-1-tetrazene
chlorobenzene
A
Diacetylhydrazin
B
2,4'-dichlorobiphenyl
C
3,4'-dichlorobiphenyl
D
4,4'-dichlorobiphenyl
E
1-acetyl-1-p-chlorophenylhydrazine
Conditions | Yield |
---|---|
Product distribution; Mechanism; thermolysis, var.: photolysis, 10 degC; | |
at 10℃; for 2h; Product distribution; Mechanism; Irradiation; |
1,6-bis-(4-chlorophenyl)-3,4-diacetyl-1,5-hexazadiene
chlorobenzene
isopropyl alcohol
A
Dimethyl ether
B
diacetyl diazene
C
Diacetylhydrazin
D
2,4'-dichlorobiphenyl
E
3,4'-dichlorobiphenyl
F
4,4'-dichlorobiphenyl
Conditions | Yield |
---|---|
at 83℃; Product distribution; Mechanism; |
1,6-bis-(4-chlorophenyl)-3,4-diacetyl-1,5-hexazadiene
isopropyl alcohol
A
Dimethyl ether
B
Diacetylhydrazin
C
chlorobenzene
Conditions | Yield |
---|---|
at 83℃; Product distribution; Mechanism; thermolysis; |
Conditions | Yield |
---|---|
With fluorine; sodium fluoride In [D3]acetonitrile at -40℃; for 0.166667h; |
Diacetylhydrazin
2,5-dimethyl-1,3,4-thiadiazole
Conditions | Yield |
---|---|
With Lawessons reagent In xylene at 140℃; for 3.5h; | 100% |
With tetraphosphorus decasulfide In xylene for 1h; Heating; | |
With tetraphosphorus decasulfide |
Diacetylhydrazin
N,N-bis[chloro(phenyl)phosphino]methylamine
Conditions | Yield |
---|---|
With triethylamine In N,N-dimethyl-formamide at 75℃; | 97% |
Diacetylhydrazin
Conditions | Yield |
---|---|
With hydrogenchloride; dihydrogen peroxide; acetic acid; titanium(III) chloride; hydrogen bromide In methanol at 20℃; | 91% |
With lead(IV) acetate In dichloromethane at 25℃; for 2h; | 36% |
Diacetylhydrazin
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol; water heating cis-Ru(bpy)2Cl2*2H2O with 1,2-diacetylhydrazine and NaOH in H2O/EtOH (reflux, 24 h), adding NH4PF6 in H2O, pptn.; drying (vac.), dissolving (acetone), adding Et2O (pptn.), drying (vac.); elem. anal.; | 91% |
With NaOH In ethanol; water Ar atmosphere; refluxing Ru-complex, hydrazine derivative and NaOH in H2O/EtOH=5:1 (24 h), cooling to room temp., addn. of aq. NH4PF6, (pptn.); drying (vac.), dissolving (acetone), pptn. (Et2O), drying (vac.); | 91% |
Diacetylhydrazin
2-chloro-ethanol
1,2-bis(2'-hydroxyethyl)-1,2-diacetylhydrazine
Conditions | Yield |
---|---|
With sodium hydroxide for 24h; Ambient temperature; | 85% |
Conditions | Yield |
---|---|
In acetone at 20℃; for 24h; | 85% |
Diacetylhydrazin
tert-butylisonitrile
dimethyl acetylenedicarboxylate
Conditions | Yield |
---|---|
In acetone at 20℃; for 24h; | 84% |
1,3-bis-(2,6-diisopropyl-phenyl)-6-methyl-4-methylene-1,2,3,4-tetrahydro-[1,3,2]diazasiline
Diacetylhydrazin
C33H48N4O2Si
Conditions | Yield |
---|---|
In hexane at 20℃; for 12h; Inert atmosphere; | 84% |
Diacetylhydrazin
Di-tert-butyl acetylenedicarboxylate
Tri(p-tolyl)phosphine
Conditions | Yield |
---|---|
In acetone at -10℃; | 83% |
Conditions | Yield |
---|---|
In acetone at -10℃; | 80% |
Diacetylhydrazin
2,5-dimethyl-1,3,4-oxadiazole
Conditions | Yield |
---|---|
With methanesulfonic acid; pyrophosphoric acid at 70℃; for 4h; | 78% |
With thionyl chloride In 1,4-dioxane Heating; | |
With acetic anhydride Heating; |
chloro-trimethyl-silane
Diacetylhydrazin
bis trimethylsilyl diacetylhydrazine
Conditions | Yield |
---|---|
With triethylamine for 10h; Heating; | 78% |
Conditions | Yield |
---|---|
In acetone at -10℃; | 77% |
cis-[bis(2,2'-bipyridine)dichloridoosmium(II)]
Diacetylhydrazin
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol; water heating mixt. of cis-Os(bpy)2Cl2, 1,2-diacetylhydrazine and NaOH in EtOH/H2O (reflux, 48 h), cooling, adding NH4PF6 in H2O, pptn.; drying, recrystn. (acetone/Et2O 1:4), chromy. (alumina, acetone); elem. anal.; | 77% |
Diacetylhydrazin
tert-butylisonitrile
acetylenedicarboxylic acid diethyl ester
Conditions | Yield |
---|---|
In acetone at 20℃; for 24h; | 75% |
Cyclohexyl isocyanide
Diacetylhydrazin
acetylenedicarboxylic acid diethyl ester
Conditions | Yield |
---|---|
In acetone at 20℃; for 24h; | 72% |
Diacetylhydrazin
Di-tert-butyl acetylenedicarboxylate
triphenylphosphine
Conditions | Yield |
---|---|
In acetone at -10℃; | 67% |
Diacetylhydrazin
p-chlorobenzenediazonium chloride
1-p-chlorophenyl-3,4-diacetyl-1-tetrazene
Conditions | Yield |
---|---|
With sodium carbonate In diethyl ether at 0℃; | 65% |
cis-dichlorobis(trimethylphosphine)platinum(II)
Diacetylhydrazin
Conditions | Yield |
---|---|
With NaHCO3 In ethanol (Ar); refluxing (4 h); solvent removal (vac.), dissolving (benzene), pptn. on hexane addn.; elem. anal.; | 65% |
Conditions | Yield |
---|---|
With triethylamine for 10h; Heating; | 60% |
Diacetylhydrazin
3-oxa-1,5-dichloropentane
N,N'-diacetyl[1,4,5]-oxadiazepane
Conditions | Yield |
---|---|
With potassium hydroxide; potassium carbonate; tetramethlyammonium chloride In dimethyl sulfoxide at 80 - 85℃; under 15.0015 - 30.003 Torr; for 5h; | 52.3% |
Diacetylhydrazin
di-tert-butyl dicarbonate
Conditions | Yield |
---|---|
With dmap In acetonitrile at 20℃; for 17h; | 51% |
NH-pyrazole
bis(acetylacetonate)oxovanadium
Diacetylhydrazin
oxygen
Conditions | Yield |
---|---|
In water; acetonitrile aq. soln. of H2diah added to MeCN soln. of Himdz and V compd. (1:2:2 molaer ratio), mixt. refluxed for 6 h; filtered, crystd. on storage at 5°c for 7 d, ppt. filtered off, washed (MeCN), dried in air, elem. anal.; | 48% |
3,5-dimethyl-1H-pyrazole
bis(acetylacetonate)oxovanadium
Diacetylhydrazin
oxygen
Conditions | Yield |
---|---|
In water; acetonitrile aq. soln. of H2diah added to MeCN soln. of Himdz and V compd. (1:2:2 molaer ratio), mixt. refluxed for 6 h; filtered, crystd. on storage at 5°c for 7 d, ppt. filtered off, washed (MeCN), dried in air, elem. anal.; | 47% |
1H-imidazole
bis(acetylacetonate)oxovanadium
Diacetylhydrazin
water
oxygen
Conditions | Yield |
---|---|
In water; acetonitrile aq. soln. of H2diah added to MeCN soln. of Himdz and V compd. (1:2:2 molaer ratio), mixt. refluxed for 6 h; filtered, crystd. on storage at 5°c for 7 d, ppt. filtered off, washed (MeCN), dried in air, elem. anal.; | 41% |
The Diacetyl hydrazine, with CAS registry number 3148-73-0, belongs to the following product categories: (1)Aromatic Hydrazides, Hydrazines, Hydrazones and Oximes; (2)Carbonyl Compounds; (3)Hydrazides; (4)Organic Building Blocks. It has the systematic name of N'-acetylacetohydrazide. This chemical is a kind of white crystalline powder. And the chemical formula of this chemical is C4H8N2O2. What's more, its EINECS is 221-576-1.
Physical properties of Diacetyl hydrazine: (1)ACD/LogP: -1.29; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.29; (4)ACD/LogD (pH 7.4): -1.29; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 4.72; (8)ACD/KOC (pH 7.4): 4.72; (9)#H bond acceptors: 4; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 40.62 Å2; (13)Index of Refraction: 1.436; (14)Molar Refractivity: 27.82 cm3; (15)Molar Volume: 106.4 cm3; (16)Polarizability: 11.03×10-24cm3; (17)Surface Tension: 34.1 dyne/cm; (18)Density: 1.091 g/cm3; (19)Flash Point: 183.3 °C; (20)Enthalpy of Vaporization: 59.44 kJ/mol; (21)Boiling Point: 349.9 °C at 760 mmHg; (22)Vapour Pressure: 4.56E-05 mmHg at 25°C.
Preparation: this chemical can be prepared by acetic acid ethyl ester and acetic acid hydrazide. This reaction will need catalyst Amano PS lipase. The reaction time is 2 day(s) with reaction temperature of 25℃. The yield is about 78%.
Uses of Diacetyl hydrazine: it can be used to produce 2,5-dimethyl-[1,3,4]oxadiazole. This reaction will need reagent Ac2O.
When you are using this chemical, please be cautious about it as the following:
The Diacetyl hydrazine irritates to eyes, respiratory system and skin. And it is harmful by inhalation, in contact with skin and if swallowed. When use it, wear suitable protective clothing, gloves and eye/face protection. If contact with eyes, rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
(1)SMILES: O=C(NNC(=O)C)C
(2)InChI: InChI=1/C4H8N2O2/c1-3(7)5-6-4(2)8/h1-2H3,(H,5,7)(H,6,8)
(3)InChIKey: ZLHNYIHIHQEHJQ-UHFFFAOYAD
(4)Std. InChI: InChI=1S/C4H8N2O2/c1-3(7)5-6-4(2)8/h1-2H3,(H,5,7)(H,6,8)
(5)Std. InChIKey: ZLHNYIHIHQEHJQ-UHFFFAOYSA-N
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