1-aminonaphthalene
1-naphthylamine
CAS: 134-32-7
Molecular Formula: C10H9N
1-aminonaphthalene - Names and Identifiers
1-aminonaphthalene - Physico-chemical Properties
| Molecular Formula | C10H9N |
| Molar Mass | 143.19 |
| Density | 1.114 g/mL at 25 °C (lit.) |
| Melting Point | 47-50 °C (lit.) |
| Boling Point | 301 °C (lit.) |
| Flash Point | >230°F |
| Water Solubility | Insoluble. 0.1698 g/100 mL |
| Solubility | 1.7g/l |
| Vapor Presure | 0.003 hPa (20 °C) |
| Appearance | flakes |
| Color | light tan to purple |
| Odor | Ammonia odor |
| Exposure Limit | TLV-TWA not assigned; carcinogenicity:Human Carcinogen (skin) (MSHA andOSHA). |
| Merck | 14,6398 |
| BRN | 386133 |
| pKa | 3.92(at 25℃) |
| PH | 7.1 (1g/l, H2O, 20℃) |
| Storage Condition | Store below +30°C. |
| Refractive Index | 1.6703 |
| Physical and Chemical Properties | White needle crystal. Has an unpleasant odor. Slightly soluble in water, soluble in ethanol, ether. |
| Use | Used as analytical reagents, fluorescent indicators and gas chromatography stationary liquid, also used in organic synthesis |
1-aminonaphthalene - Risk and Safety
| Risk Codes | R34 - Causes burns R51/53 - Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. R22 - Harmful if swallowed R45 - May cause cancer |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. 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. S24 - Avoid contact with skin. S53 - Avoid exposure - obtain special instructions before use. |
| UN IDs | UN 2790 8/PG 3 |
| WGK Germany | 2 |
| RTECS | QM1400000 |
| FLUKA BRAND F CODES | 8-23 |
| HS Code | 2921 45 00 |
| Hazard Class | 6.1(b) |
| Packing Group | III |
| Toxicity | LD50 orally in Rabbit: 680 mg/kg |
1-aminonaphthalene - Nature
Open Data Verified Data
White needle crystal. The relative density was 1. 129. Melting point 50 °c. Boiling point 300.8 °c. Flash point 69.4 °c. Refractive index 6703. Exposure to air gradually turned red, flammable. Has an unpleasant odor. Sublimation. Slightly soluble in water, soluble in ethanol, ether. Powder and vapour are toxic.
Last Update：2024-01-02 23:10:35
1-aminonaphthalene - Preparation Method
Open Data Verified Data
a nitronaphthalene was nitrated with mixed acid, and the latter was reduced with sodium disulfide. The product is then obtained by distillation.
Last Update：2022-01-01 10:54:42
1-aminonaphthalene - Use
Open Data Verified Data
intermediates for direct dyes (e. G., Direct Fast Blue B2RL, direct fast tan 3B), acid dyes, ice dyes, and disperse dyes. Or rubber antioxidant, pesticide raw materials.
Last Update：2022-01-01 10:54:42
1-aminonaphthalene - Safety
Open Data Verified Data
- toxic. Inhalation of its vapor, feel Head Pain, through the skin into the blood can destroy red blood cells, can cause urinary system diseases. The maximum allowable concentration in air is 1mg/m3. Dogs were injected subcutaneously with LD 400mg/kg. Long-term chronic poisoning can cause bladder cancer. Production equipment should be sealed and leak-proof. Operation and handling personnel should wear protective equipment, regular medical examination.
- sealed in iron drum, 200kg net weight per barrel. Store in a ventilated and dry place, away from flammable materials and oxidants, and avoid sun exposure.
Last Update：2022-01-01 10:54:43
1-aminonaphthalene - Reference Information
| pH range of acid-base indicator discoloration | Non & uoresce (3.4) to blue & uoresce (4.8) |
| Henry's Law Constant | 6.13 x 10-10 atm?m3/mol at 25 °C (thermodynamic method-GC/UV spectrophotometry, Altschuh et al., 1999) |
| Main application | color filter, photoresists, recording media, light-emitting device, disk, display device, oil products, |
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| (IARC) carcinogen classification | 3 (Vol. 4, Sup 7) 1987 |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Overview | aromatic amines are an important class of nitrogen-containing compounds, which are widely used in explosives, dyes and pharmaceutical industry. The method of synthesis is generally by using well-known reactions. Simple aromatic amines can be prepared by reduction of nitro compounds or by amino substitution of halogenated aromatic hydrocarbons. In addition, there are some other specific preparation methods. in recent years, α-naphthylamine (also known as 1-Naphthylamine) has been widely used in dye chemistry and organic synthesis, especially in the synthesis of chiral catalysts. |
| Application | α-naphthylamine is an intermediate for a variety of dye products such as direct dyes, acid dyes, ice dyes and disperse dyes, it is also the main raw material of a variety of rubber antioxidant, and the α-naphthol produced by α-naphthylamine is an important intermediate of the pesticide carbaryl. |
| toxicity | α-naphthylamine can be absorbed through the skin to produce methemoglobin, causing blood poisoning and urinary system diseases, chronic poisoning can cause bladder cancer. The wastewater discharged in the production process is high in organic matter content, toxic to microorganisms, teratogenic and carcinogenic to human body, and difficult to degrade in the environment. Sufficient treatment must be carried out to meet the discharge standard. |
| preparation | specific methods: 1. Intermediate 1-naphthyl ethyl ketone oxime (α-naphthyl ethyl ketone oxime) 1-naphthalenetone (200g,1.18mol), hydroxylamine hydrochloride (83G, 1.2mol) and sodium acetate (98G, 1.2mol) were dissolved in mL of ethanol and 90ml of water, the reaction was heated at 50 ° C. For 20 minutes, cooled to room temperature, filtered, washed with water and dried to give a white solid (215g, yield 99%). Melting Point: 150-152 °c. 2. Preparation of intermediate 1-acetylnaphthylamine (α-acetylnaphthylamine) 500ml of Polyphosphoric acid was poured into a 2000mL beaker, and 1-naphthalenetone oxime (185g,1mol) was added with mechanical stirring. Added to the reaction solution in batches, The reaction temperature was raised to 70 °c after the completion of the addition of 1-naphthoethanone oxime. After 2 hours of reaction at this temperature, the mixture was poured into 100% ml of water to obtain a white precipitate, which was filtered and washed with ml of water. After drying, 185g of white solid was obtained, yield. 3. Preparation of target product α-naphthylamine (1-Naphthylamine) 1-acetylnaphthylamine (185g,1mol) was dissolved in 200ml of ethanol and 80ml of concentrated hydrochloric acid, and heated under reflux for 1 hour, cool to room temperature. The solution was adjusted to basic (pH>7) with 6M NaOH to give a white precipitate, which was filtered and washed with 100% ml of water to give a pink solid 143g after drying in yield. The pink solid was recrystallized from 95% of a toluene-petroleum ether mixed solvent (1: 1) to give α-naphthylamine as a white solid, 136G, yield. |
| Application | is an intermediate of direct dyes, acid dyes, ice dyes and disperse dyes, and is also an antioxidant for rubber, pesticide raw materials used as analytical reagents, fluorescent indicators and gas chromatography stationary liquid, also used in organic synthesis 1-naphthol produced from 1-Naphthylamine is an important intermediate of pesticide carbaryl, 1-Naphthylamine is also an intermediate of the rodenticide, or an important dye intermediate, and many dyes can be produced. This product is an intermediate of a variety of dye products such as direct dyes, acid dyes, ice dyes and disperse dyes, and is also the main raw material of a variety of rubber antioxidant, 1-naphthol produced from 1-naphthylamine is an important intermediate of the pesticide carbaryl. 1-naphthylamine can be absorbed through the skin to generate methemoglobin, resulting in liquid poisoning, causing urinary system diseases; Chronic poisoning can cause bladder cancer. The maximum soluble concentration in air is 0.001mg/L. staining with nitrous acid. fluorescent indicator. Tests for osmium, rubidium, vanadium, chromium, copper, mercury, thallium, and ozone. Nitrous acid reagent. Catalytic determination of ruthenium, osmium and palladium. Gas chromatography stationary liquid (the highest temperature is 85 ℃, the solvent is acetone), selective retention of aromatic compounds, can separate cycloalkanes and alkanes, para and ortho xylene, but can not separate p-xylene and ethylbenzene. Organic Synthesis. |
| production method | is derived from the reduction of 1-nitronaphthalene (see C10H7NO2,[86-57-7]). Raw material consumption (kg/t) refined naphthalene 1116 nitric acid (96%) 561 sulfuric acid (92.5%) 312 alkali sulfide (60%) 703 sulfur (99%) 211 1-Naphthylamine is derived from the reduction of 1-nitronaphthalene. Equimolar amounts of sodium sulfide and sulfur are added to water at 90 ° C. To prepare a sodium disulfide solution having a concentration of 370 to 380g/L. Nitronaphthalene was first added to the reaction pan, and the temperature was raised to 100 ° C. The sodium disulfide solution was added uniformly within 6h, and the boiling was maintained for 4.5h. Stand still, separate the sodium thiosulfate (lower layer), wash the upper layer with hot water at 55~65 ℃ twice, and reduce the pressure to 8.0kPa or so for distillation, fractions with a collection freezing point above 45.4 ° C. Are 1-Naphthylamine. |
| category | toxic substances |
| toxicity grade | high toxicity |
| Acute toxicity | intraperitoneal-mouse LD50: 96 mg/kg |
| flammability hazard characteristics | open flame, high temperature combustible, combustion release of toxic nitrogen oxide smoke |
| storage and transportation characteristics | The warehouse is ventilated and dried at low temperature; Stored separately from oxidant and strong acid |
| extinguishing agent | water, foam, sand mist. |
| spontaneous combustion temperature | 460°C |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-26 11:30:56
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View History
1-aminonaphthalene
4(3H)-Quinazolinone, 2-[3,5-dimethyl-4-[2-[(1-methylethyl)amino]ethoxy]phenyl]-5,7-dimethoxy-
(Z)-2-(TERT-BUTOXYCARBOUYLMETHOXYIMINO)-2-(2-AMINOTHIAZOL-4-YL)ACETIC ACID
曲唑酮杂质QZT-IM-3-Z5
2-bromo-1-(4-methoxyphenyl)ethanone
METHYL FURFURYL DISULPHIDE
辛二酸二乙酯
乙酸-N-琥珀酰亚胺酯(AC-OSU)
britesilh20
4-methylacethophenone oxime
4(3H)-Quinazolinone, 2-[3,5-dimethyl-4-[2-[(1-methylethyl)amino]ethoxy]phenyl]-5,7-dimethoxy-
(Z)-2-(TERT-BUTOXYCARBOUYLMETHOXYIMINO)-2-(2-AMINOTHIAZOL-4-YL)ACETIC ACID
曲唑酮杂质QZT-IM-3-Z5
2-bromo-1-(4-methoxyphenyl)ethanone
METHYL FURFURYL DISULPHIDE
辛二酸二乙酯
乙酸-N-琥珀酰亚胺酯(AC-OSU)
britesilh20
4-methylacethophenone oxime