phenyl-hydrazin
phenyl hydrazine
CAS: 100-63-0
Molecular Formula: C6H8N2
phenyl-hydrazin - Names and Identifiers
| Name | phenyl hydrazine |
| Synonyms | hydrazine Phenylhydrazine phenyl-hydrazin PHENYLHYDRAZINE phenyl hydrazine Phenyl hydrazide hydrazine, phenyl- 1-Hydrazinobenzene Monophenylhydrazine phenylhydrazine sulfate Phenylhydrazine, extra pure |
| CAS | 100-63-0 |
| EINECS | 202-873-5 |
| InChI | InChI=1/C6H5.H3N2/c1-2-4-6-5-3-1;1-2/h1-6H;1-2H2 |
phenyl-hydrazin - Physico-chemical Properties
| Molecular Formula | C6H8N2 |
| Molar Mass | 108.14 |
| Density | 1.098 g/mL at 25 °C (lit.) |
| Melting Point | 18-21 °C (lit.) |
| Boling Point | 238-241 °C (lit.) |
| Flash Point | 192°F |
| Water Solubility | 145 g/L (20 ºC) |
| Solubility | Soluble in dilute acids. |
| Vapor Presure | <0.1 mm Hg ( 20 °C) |
| Vapor Density | 4.3 (vs air) |
| Appearance | Powder |
| Color | White to slightly blue or light beige |
| Exposure Limit | TLV-TWA skin 0.1 ppm (0.44 mg/m3)(ACGIH), 5 ppm (22 mg/m3) (OSHA);STEL 10 ppm (44 mg/m3) (OSHA); carcinogenicity: A2-Suspected Human Carcinogen(ACGIH), Carcinogen (NIOSH).. |
| Merck | 14,7293 |
| BRN | 606080 |
| pKa | 8.79(at 15℃) |
| Storage Condition | Store below +30°C. |
| Stability | Stable, but may decompose in sunlight. May be air or light sensitive. Incompatible with strong oxidizing agents, metal oxides. |
| Sensitive | Air & Light Sensitive |
| Explosive Limit | 1.1%(V) |
| Refractive Index | n20/D 1.607(lit.) |
| Physical and Chemical Properties | Pale yellow crystals or oily liquid (solidifies into crystals when cooled). Red-Brown in the air. Toxic! Density 1.099, boiling point 243.5 degrees C (decomposition). Melting point 19.5 °c. The hydrate containing 1/2 molecule of crystal water had a melting point of 24 °c. Can cause hemolysis of red blood cells. Slightly soluble in water and alkali solution, soluble in dilute acid. Miscible with ethanol, ether, chloroform and benzene. Can volatilize with steam. |
| Use | For the preparation of dyes, drugs, developers, etc |
phenyl-hydrazin - Risk and Safety
| Risk Codes | R45 - May cause cancer R23/24/25 - Toxic by inhalation, in contact with skin and if swallowed. R36/38 - Irritating to eyes and skin. R43 - May cause sensitization by skin contact R48/23/24/25 - R50 - Very Toxic to aquatic organisms R68 - Possible risk of irreversible effects |
| Safety Description | S53 - Avoid exposure - obtain special instructions before use. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. |
| UN IDs | UN 2572 6.1/PG 2 |
| WGK Germany | 3 |
| RTECS | MV8925000 |
| FLUKA BRAND F CODES | 8-10-23 |
| TSCA | Yes |
| HS Code | 2928 00 90 |
| Hazard Class | 6.1 |
| Packing Group | II |
| Toxicity | LD50 orally in Rabbit: 188 mg/kg |
phenyl-hydrazin - Upstream Downstream Industry
phenyl-hydrazin - Reference Information
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| Hydrazine derivative | Phenylhydrazine (Phenylhydrazine), also known as biaminobenzene, was first synthesized by German organic chemist Hermann Emil Fischer in 1875 and was the first synthesized hydrazine derivative. It is a light yellow crystal or oily liquid at room temperature, and a monoclinic prismatic crystal at low temperature. It is easily oxidized in the air and is dark brown or dark red. is one of the derivatives of hydrazine, often abbreviated as PhNHNH2. Slightly soluble in water and alkali solution, soluble in dilute acid. Miscible with ethanol, ether, chloroform and benzene. The commonly used preparation method is to form diazonium salt by aniline and sodium nitrite under the action of hydrochloric acid, and then reduce it with sodium sulfite/sodium hydroxide. Acid precipitation produces phenylhydrazine hydrochloride, which is neutralized to obtain phenylhydrazine. It is used to make dyes, drugs, developers, etc., and is also an important reagent for identifying carbonyl groups. It is used to identify aldehydes, ketones and sugars. Reacts with benzaldehyde to form phenylhydrazone, uses hydrazone generated by phenylhydrazine or 2, 4-dinitrophenylhydrazine to identify aldehydes and ketones, and produces Fischer indole synthesis with aldehydes and ketones (by Herman Emil · Fischer discovered in 1883. The reaction is to use phenylhydrazine, aldehydes and ketones to heat and rearrange under acid catalysis to eliminate one molecule of ammonia to obtain 2-or 3-substituted indole.) Indole ring compound is obtained. |
| Hermann Emile Fischer | Fischer is a German organic chemist. He reacts with phenylhydrazine and sugars to form hydrazone and hydrazone to form crystalline compounds, which are convenient for purification and then decompose them into purer sugars. As a powerful means to study the structure of sugars, and synthesized a variety of sugars, theoretically clarified the structure of glucose, summarized and expounded the common three-dimensional isomerism of sugars, described by Fischer projection. He determined that caffeine, theophylline, uric acid and other substances are all purine derivatives and synthesized purines. He pioneered the research on proteins, determined that amino acids form peptides through peptide bonds, and successfully synthesized peptides. In 1902, Fischer was awarded the Nobel Prize in Chemistry for his research on the synthesis of purines and sugars. |
| Use and preparation method of phenylhydrazine | Phenylhydrazine is the first synthetic hydrazine derivative, commonly used as an intermediate for organic, dye, medicine, and pesticide. Organic intermediates, preparation of pyrazoline, triazole, indole, etc.; dye intermediates, preparation of diazepine dye intermediates, such as 1-phenyl-3-methyl-5-pyrazolone, etc.; pharmaceutical intermediates, Preparation of antipyretic, analgesic, and anti-inflammatory drugs, such as antipyrine and aminopyrine; photographic drugs (photosensitive pigments) and phenylhydrazine are also raw materials for the production of pesticides and insecticides "killing phosphorus; phenylhydrazine is also an important carbonyl identification reagent, used to identify aldehydes, ketones and sugars. Phenylhydrazine is toxic. After inhalation, due to hemolysis, it causes anemia and headache. In severe cases, it causes yellow bile. It also has a stimulating effect on the eyes and can cause corneal disorders. Rat oral LD50188mg/kg. The maximum allowable concentration in the workplace is 0.44mg/m3. The laboratory uses aniline as a raw material, reacts with sodium nitrite in hydrochloric acid to form diazonium salt, and then reacts with sulfurous acid and sulfur dioxide to reduce to form sodium phenyl diazesulfonate, and then salting out with hydrochloric acid to form Phenylhydrazine hydrochloride, neutralization and deacidification can produce phenylhydrazine. |
| Uses | Phenylhydrazine is used in the production of pesticides to synthesize the intermediates of organophosphorus insecticide triazophos 1-phenylsemicarbazide and pyridine thiophos 1-phenyl -3, 6-dihydroxypyridazine is also an intermediate of new fungicides oxazolidone (famoxadone) and imidazolidone (fenamidone). In addition, phenylhydrazine, as an organic synthetic raw material, is also used as an intermediate in dyes, pharmaceuticals and other industries, and is also used as an analytical reagent. used as analytical reagent and chromatographic analysis reagent used in the preparation of dyes, drugs, developers, etc. this product is an intermediate of dyes, medicines and pesticides, and is used in the production of chromophenol AS-G, drugs antipyrine, etc. Dissolve phenylhydrazine in 95% ethanol, then add benzaldehyde, reflux for 1h to obtain phenylhydrazone. Phenylhydrazone is also an intermediate in organic synthesis. Phenylhydrazine is also used as an analytical reagent. As a weak base, it is used to precipitate lead, chromium and other trivalent and tetravalent elements in the form of hydroxides. Photometric determination of aluminum, chromium, copper, molybdenum, titanium, and zirconium. Verification of gold, iridium, molybdenum, palladium, platinum, silver. Colorimetric determination of reducing agent of phosphoric acid. It can form phenylhydrazone with different melting points with aldehydes, ketones, and sugars to identify these substances. |
| Production method | Phenylhydrazine hydrochloride is obtained from aniline by diazotization, reduction, and acid precipitation, and then phenylhydrazine is obtained by neutralization. the preparation method is based on aniline as raw material, through diazotization, reduction, acid analysis, neutralization and obtained. Diazotization: add a certain amount of water, 30% hydrochloric acid and aniline to the reaction pot, cool to 2 ℃, control to add sodium nitrite solution dropwise at 0~5 ℃ until the starch potassium iodide test solution turns blue, stir for 30min, and complete the reaction to obtain diazonium solution. Reduction: add water, sodium disulfite and 30% lye to the reduction kettle, heat to 80 ℃, control at 80~85 ℃, pH = 6.2~6.7, add the above diazo liquid trickle within 20min, continue stirring for 1.5h, then add zinc powder and diatomite, stir and filter, and the filtrate is sucked into the acid separation kettle. Acid precipitation: in the above filtrate, add 30% hydrochloric acid at 70 ℃ for acid precipitation, control the temperature at 85~90 ℃, stir for 10min, cool to below 20 ℃, suck and filter to obtain phenylhydrazine hydrochloride. Neutralization: add lye to the reaction pot, add the above phenylhydrazine hydrochloride and an appropriate amount of water under stirring, raise the temperature to 50 ℃, stir for 1 h at 50~60 ℃, let stand for more than 8h, and separate the lower aqueous solution to obtain the upper oil substance, namely phenylhydrazine, with a content of about 80% and a total yield of 83.5%. |
| category | toxic substances |
| toxicity classification | highly toxic |
| acute toxicity | oral-rat LD50: 188 mg/kg; Oral-mouse LD50: 175 mg/kg |
| flammability hazard characteristics | open flame is combustible; heating emits toxic nitrogen compound gas |
| storage and transportation characteristics | warehouse ventilation and low temperature drying; Store separately from oxidants, acids and food additives |
| fire extinguishing agent | mist water, foam, carbon dioxide, sand. |
| occupational standard | TLV-TWA 0.1 PPM; TWA 5 PPM (22 mg/m3); STEL 2 mg/m3 |
| auto-ignition temperature | 345 °F |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
| immediate life-threatening and health concentration | 15 ppm |
Last Update：2024-04-09 19:55:45
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View History
Raw Materials for phenyl-hydrazin
Downstream Products for phenyl-hydrazin
1,3,3-trimethyl-2-methyleneindoline
2-Phenylindole
Triazophos
Clofentezine
1-Phenyl-3-pyrazolidinone
2,3,5-Triphenyl-2H-tetrazolium chloride
2-Phenylindole
Triazophos
Clofentezine
1-Phenyl-3-pyrazolidinone
2,3,5-Triphenyl-2H-tetrazolium chloride