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1-Acetyl-2-phenylhydrazine

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Name

1-Acetyl-2-phenylhydrazine

EINECS 204-055-3
CAS No. 114-83-0 Density 1.143 g/cm3
PSA 41.13000 LogP 1.61350
Solubility insoluble in water Melting Point 128-131 °C(lit.)
Formula C8H10N2O Boiling Point 214.1 °C at 760 mmHg
Molecular Weight 150.18 Flash Point 87.8 °C
Transport Information UN 2811 Appearance colorless prisms or white solid
Safety 22-26-36-24/25 Risk Codes 22-36/37/38-43-20/21/22
Molecular Structure Molecular Structure of 114-83-0 (1-Acetyl-2-phenylhydrazine) Hazard Symbols HarmfulXn
Synonyms

N(1)-Acetylphenylhydrazine;1-Phenyl-2-acetylhydrazine;AI3-01560;APH;Acetic acid phenylhydrazone;Acetylphenylhydrazine;BRN 0742880;CCRIS 4569;Fenylhydrazid kyseliny octove;

Article Data 113

1-Acetyl-2-phenylhydrazine Synthetic route

108-24-7

acetic anhydride

100-63-0

phenylhydrazine

114-83-0

1-acetyl-2-phenylhydrazine

Conditions
ConditionsYield
In diethyl ether at 0℃; for 10h;100%
Stage #1: phenylhydrazine With triethylamine In dichloromethane at 0℃; Inert atmosphere;
Stage #2: acetic anhydride In dichloromethane at 0 - 20℃; Inert atmosphere;
97%
With pyridine; aluminum oxide at 90 - 92℃; for 1h; microwave irradiation;65%
918-00-3

1,1,1-trichloroacetone

100-63-0

phenylhydrazine

114-83-0

1-acetyl-2-phenylhydrazine

Conditions
ConditionsYield
With triethylamine In acetonitrile for 8h; Heating;98%
64-19-7

acetic acid

100-63-0

phenylhydrazine

114-83-0

1-acetyl-2-phenylhydrazine

Conditions
ConditionsYield
at 80℃; for 3.5h; Inert atmosphere;96%
at 80℃; for 1.5h;85%
at 20 - 80℃; for 1.5h; Inert atmosphere;81%
622-50-4

4-Acetamido-1-iodobenzene

100-63-0

phenylhydrazine

114-83-0

1-acetyl-2-phenylhydrazine

Conditions
ConditionsYield
at 95℃; for 2.5h; Temperature;93%
100-63-0

phenylhydrazine

507-09-5

thioacetic acid

114-83-0

1-acetyl-2-phenylhydrazine

Conditions
ConditionsYield
With copper(II)-grafted guanidine acetic acid-modified magnetite nanoparticles In water at 20℃; for 0.0833333h; Green chemistry; chemoselective reaction;90%
With Fe3O4(at)Chit-TCT-Salen-Cu(II) In water at 20℃; for 0.0833333h; regioselective reaction;89%
59-88-1

phenylhydrazine hydrochloride

64-19-7

acetic acid

114-83-0

1-acetyl-2-phenylhydrazine

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; Inert atmosphere;89%
59-88-1

phenylhydrazine hydrochloride

108-24-7

acetic anhydride

114-83-0

1-acetyl-2-phenylhydrazine

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 24h;87%
With potassium carbonate In ethyl acetate at 20℃; for 7h; Inert atmosphere; regioselective reaction;82%
With sodium hydroxide In tetrahydrofuran for 0.5h; Inert atmosphere;
With sodium hydroxide In tetrahydrofuran for 0.5h;
100-63-0

phenylhydrazine

67-64-1

acetone

114-83-0

1-acetyl-2-phenylhydrazine

Conditions
ConditionsYield
With chloroform; dimethyl sulfoxide at 120℃; for 24h; Green chemistry;84%
60-35-5

acetamide

100-63-0

phenylhydrazine

114-83-0

1-acetyl-2-phenylhydrazine

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene In neat (no solvent) at 120℃; for 0.333333h; Microwave irradiation; Green chemistry;83%
In 1,4-dioxane at 20℃; for 0.5h; Microwave irradiation; Sealed tube;78%
With [Mn((N'1E,N'2E)-N'1,N'2-bis(phenyl(pyridin-2-yl)methylene)oxalohydrazide(-H))(OAc)(H2O)]2*6H2O In neat (no solvent) at 120℃; for 24h;70%
at 160℃; under 12929 Torr; for 0.166667h; Microwave irradiation; Sealed tube;54%
at 150℃;
2684-02-8

benzenediazonium

431-03-8

dimethylglyoxal

A

13732-32-6

biacetyl phenylhydrazone

B

114-83-0

1-acetyl-2-phenylhydrazine

Conditions
ConditionsYield
With titanium(III) chloride In acetic acid for 0.666667h; Ambient temperature;A 16%
B 65%

1-Acetyl-2-phenylhydrazine Consensus Reports

Reported in EPA TSCA Inventory.

1-Acetyl-2-phenylhydrazine Specification

The Acetic acid, 2-phenylhydrazide, with the CAS registry number 114-83-0, is also known as 1-Acetyl-2-phenylhydrazine. Its molecular formula is C8H10N2O and its classification codes are Agricultural Chemical; Drug / Therapeutic Agent; Fungicide, bactericide, wood preservative; Mutation data; Tumor data. Additionally, it has the IUPAC name N'-phenylacetohydrazide. The product categories of this chemical are Aromatic Hydrazides, Hydrazines, Hydrazones and Oximes; Phenylhydrazine; Cancer Research; Carcinogens. Besides, it used as organic intermediates and stabilizer. Dry powder, foam, sand, carbon dioxide and water spray are made from this chemical which is soluble in water, ethanol and benzene. However, keep this chemical in the cool and dry place where there is no heat and oxides.

Other characteristics of the Acetic acid, 2-phenylhydrazide can be summarised as followings: (1)ACD/LogP: 0.84; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.84; (4)ACD/LogD (pH 7.4): 0.84; (5)ACD/BCF (pH 5.5): 2.58; (6)ACD/BCF (pH 7.4): 2.58; (7)ACD/KOC (pH 5.5): 68.51; (8)ACD/KOC (pH 7.4): 68.54; (9)#H bond acceptors: 3; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 23.55 Å2; (13)Index of Refraction: 1.586; (14)Molar Refractivity: 44.11 cm3; (15)Molar Volume: 131.3 cm3; (16)Polarizability: 17.49×10-24cm3; (17)Surface Tension: 44.3 dyne/cm; (18)Density: 1.143 g/cm3; (19)Flash Point: 87.8 °C; (20)Enthalpy of Vaporization: 45.05 kJ/mol; (21)Boiling Point: 214.1 °C at 760 mmHg; (22)Vapour Pressure: 0.158 mmHg at 25°C.

Production method of this chemical: It could be obtained by the reactants of phenylhydrazine and acetic acid. This reaction shoudl be heated for 6h. Then cool the product below 0 °C and crude is filtered. Crystallization with water,  drying at 80 °C, the Acetic acid, 2-phenylhydrazide is derived.

Uses of the Acetic acid, 2-phenylhydrazide: It could react with propenal to obtain the 1-acetyl-5-hydroxy-2-phenylpyrazolidine. This reaction needs the solvent of diethyl ether. The yield is 74 %. In addition, this reaction should be taken for 20 minutes at the temperature of 20 °C. The type of this reaction is cyclization / condensation.

 the Acetic acid, 2-phenylhydrazide could react with propenal to obtain the 1-acetyl-5-hydroxy-2-phenylpyrazolidine

When you are using this chemical, please be cautious about it as the following: This chemical is irritating to eyes, respiratory system and skin. You should wear suitable protective clothing to avoid contacting with skin and eyes. In case of contacting 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(NNc1ccccc1)C
2.InChI: InChI=1/C8H10N2O/c1-7(11)9-10-8-5-3-2-4-6-8/h2-6,10H,1H3,(H,9,11)
3.InChIKey: UICBCXONCUFSOI-UHFFFAOYAT

The toxicity data is as follows: 
 

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 oral 270mg/kg (270mg/kg)   Pharmaceutical Chemistry Journal Vol. 14, Pg. 162, 1980.
mouse LDLo intraperitoneal 150mg/kg (150mg/kg)   National Technical Information Service. Vol. AD691-490,

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