Benzo[def]phenanthrene
Pyrene
CAS: 129-00-0
Molecular Formula: C16H10
Benzo[def]phenanthrene - Names and Identifiers
| Name | Pyrene |
| Synonyms | Pyrene Pyrenepract Pyrene (purity) AKOS BBS-00004612 41164, Pyrene (purity) Benzo[def]phenanthrene PYRENE, FOR FLUORESCENCE |
| CAS | 129-00-0 |
| EINECS | 204-927-3 |
| InChI | InChI=1/C16H10/c1-3-11-7-9-13-5-2-6-14-10-8-12(4-1)15(11)16(13)14/h1-10H |
| InChIKey | BBEAQIROQSPTKN-UHFFFAOYSA-N |
Benzo[def]phenanthrene - Physico-chemical Properties
| Molecular Formula | C16H10 |
| Molar Mass | 202.25 |
| Density | 1.271 |
| Melting Point | 148 °C |
| Boling Point | 393 °C |
| Flash Point | 210 °C |
| Water Solubility | almost insoluble |
| Solubility | ethanol: soluble |
| Vapor Presure | 180 at 25 °C (extrapolated from vapor pressures determined at higher temperatures, Tesconi andYalkowsky, 1998) |
| Appearance | White powder |
| Specific Gravity | 1.271 |
| Color | Pale yellow to yellow-greenish |
| Exposure Limit | OSHA: TWA 0.2 mg/m3 |
| Maximum wavelength(λmax) | ['330nm(EtOH)(lit.)'] |
| Merck | 14,7963 |
| BRN | 1307225 |
| pKa | >15 (Christensen et al., 1975) |
| Storage Condition | room temp |
| Refractive Index | 1.8520 (estimate) |
| MDL | MFCD00004136 |
| Physical and Chemical Properties | Trait: light yellow monoclinic crystal. melting point 150 ℃ boiling point 393 ℃ relative density 1.271 solubility insoluble in water, soluble in ether, carbon disulfide, benzene and toluene. |
| Use | It is used as a raw material for producing 1,4,5, 8-naphthalenetetracarboxylic acid, and also used as a raw material for dyes, synthetic resins and engineering plastics |
Benzo[def]phenanthrene - Risk and Safety
| Risk Codes | R50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. R36/37/38 - Irritating to eyes, respiratory system and skin. R26 - Very Toxic by inhalation R39/23/24/25 - R23/24/25 - Toxic by inhalation, in contact with skin and if swallowed. R11 - Highly Flammable R63 - Possible risk of harm to the unborn child R43 - May cause sensitization by skin contact R45 - May cause cancer R67 - Vapors may cause drowsiness and dizziness R65 - Harmful: May cause lung damage if swallowed R38 - Irritating to the skin R51/53 - Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. R52/53 - Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment. R40 - Limited evidence of a carcinogenic effect |
| Safety Description | S60 - This material and its container must be disposed of as hazardous waste. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S36/37 - Wear suitable protective clothing and gloves. S28A - S22 - Do not breathe dust. S16 - Keep away from sources of ignition. S7 - Keep container tightly closed. S24/25 - Avoid contact with skin and eyes. S23 - Do not breathe vapour. S53 - Avoid exposure - obtain special instructions before use. S62 - If swallowed, do not induce vomitting; seek medical advice immediately and show this container or label. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| UN IDs | UN 3077 9/PG 3 |
| WGK Germany | 2 |
| RTECS | UR2450000 |
| TSCA | Yes |
| HS Code | 29349990 |
| Hazard Class | 6.1(b) |
| Packing Group | III |
| Toxicity | LD50 orally in Rabbit: 2700 mg/kg |
Benzo[def]phenanthrene - Reference
| Reference Show more | 1. [IF=6.057] Qi Li et al."Green choline amino acid ionic liquids aqueous two-phase extraction coupled with synchronous fluorescence spectroscopy for analysis naphthalene and pyrene in water samples."Talanta. 2020 Nov;219:121305 |
Benzo[def]phenanthrene - Nature
Open Data Verified Data
light yellow monoclinic crystal, insoluble in water, soluble in ether, carbon disulfide, benzene and toluene. The relative density was 1. 271. Melting point 150 °c. Boiling point 393 °c.
Last Update：2024-01-02 23:10:35
Benzo[def]phenanthrene - Preparation Method
Open Data Verified Data
in high temperature tar content of about 1.2% ~ 1. 8%.
- with two anthracene oil as raw material, vacuum distillation, extraction, recrystallization, purification.
- with distillation of anthracene oil residue higher than 360 ℃ as raw material, cut pyrene fraction, with benzene as solvent, concentrated sulfuric acid washing, remove base and unsaturated compounds, and then re-crystallized with solvent oil to obtain pure product.
Last Update：2022-01-01 10:40:22
Benzo[def]phenanthrene - Introduction
Insoluble in water, easily soluble in ether, carbon disulfide, benzene and toluene.
Last Update：2022-10-16 17:13:06
Benzo[def]phenanthrene - Use
Open Data Verified Data
organic synthesis raw materials, by oxidation can be prepared 1,4,5,8 A naphthalene four acid, for dyes, synthetic resins and engineering plastics; after acylation, the vat dye Brilliant Orange GR and other dyes can be prepared. Also available in the system of pesticides, plasticizers, etc.
Last Update：2022-01-01 10:40:21
Benzo[def]phenanthrene - Safety
Open Data Verified Data
- This product is toxic. Acute poisoning, the first cause excitement, followed by inhibition, spasm, limb paresis, eye and upper respiratory tract mucosal irritation. LD50 was 0. 17mg/L in rats and 0.8g/kg in mice. The operator should wear protective gear.
- plastic bags, which are dangerous goods, shall be transported according to the provisions of dangerous goods.
Last Update：2022-01-01 10:40:22
Benzo[def]phenanthrene - Reference Information
| Henry's Law Constant | 0.490 at 25 °C (thermodynamic method-GC/UV spectrophotometry, Altschuh et al., 1999) |
| LogP | 5.43 at 30℃ and pH5-8 |
| (IARC) carcinogen classification | 3 (Vol. Sup 7, 92) 2010 |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| synthesis method | 1. pyrene is prepared by separation and purification in high temperature tar with a content of about 1.2% ~ 1.8%. 2. Using anthracene oil as raw material, vacuum distillation, extraction, recrystallization and purification. 3. Distilled anthracene oil residue higher than 360 ℃ as raw material, rectifying and cutting pyrene fraction, using benzene as solvent, washing with concentrated sulfuric acid, removing base and unsaturated compounds, and recrystallization with solvent oil to obtain pure pyrene. |
| coal tar chemical products | pyrene, also known as inlaid naphthalene, is one of the products processed by coal tar. its content in coal tar is about 0.6 ~ 1.2%, mainly concentrated in anthracene oil fraction. Pyrene is a solid aromatic compound whose molecule is composed of four benzene rings connected. The molecular formula of pyrene is C16H10, molecular weight is 202.26, melting point is 150 ℃, boiling point is 393 ℃, density is 1.277g/cm3. Pyrene is a light yellow monoclinic crystal, insoluble in water, soluble in benzene, toluene, carbon disulfide, ether and other organic solvents. Pyrene is a carcinogen, which is converted into mutagenic 1-nitropyrene under the action of nitrogen dioxide. The 1 and 6 positions in the pyrene molecule are easy to react with electrophiles, and oxidation and hydrogenation reactions can also occur. Pyrene can also undergo substitution reactions such as halogenation, nitration, and sulfonation. One substituent is 3-position, and the two substituents are 3,10-and 3,8-positions, with more 3,10-positions. 3,10-pyrene quinone and 3,8-pyrene quinone are obtained during oxidation, which are further oxidized to 1,4,5, 8-naphthalenic acid. pyrene can be used to produce dyes, such as indanthrine dye and anthraquinone vat dye. The extraction method of pyrene is: use the residual oil or asphalt distillate oil produced during the distillation of the anthracene oil fraction as the raw material, perform vacuum distillation, cut the fraction containing about 40% pyrene at 390~400 ℃, and then use the 25% coal tar solvent oil and 75% ethanol mixed solvent (the ratio of solvent amount to pyrene fraction is 1:12), and perform recrystallization several times until the product is qualified. Pyrene is a low-toxic compound. Mild irritation to skin, eyes, upper respiratory tract mucosa. Long-term inhalation can cause red blood cell reduction and mild liver and kidney damage. Long-term exposure to 3mg/m3~5mg/m3 can cause headache, fatigue, loss of appetite, and excitement. |
| Probe for determining membrane lipid fluidity | Pyrene is a commonly used probe for determining membrane lipid fluidity. Its quantum yield is relatively high, but the excitation life is shorter than DPH(1,6-diphenyl-1, 3,5-hexatriene), so it is not sensitive enough to determine slight changes in lipid fluidity, suitable for systems with greater liquidity. The excitation wavelength of pyrene is 342nm and the emission wavelength is 383nm. The excitation spectrum and emission spectrum obviously overlap. Pyrene is mainly bound to the hydrocarbon chain of membrane lipids. After the monomer formed by the combination of a pyrene molecule and a membrane lipid molecule is excited by light, it approaches another unexcited pyrene molecule through lateral diffusion motion to form a collision compound, that is, an excitation dimer. The efficiency of exciting dimer formation depends on the concentration of pyrene binding to membrane lipids and the microviscosity of the medium in which pyrene is located. When the concentration and temperature of pyrene are constant, the ratio of the fluorescence intensity of the dimer to the monomer decreases with the increase of the micro-viscosity of the medium in which the pyrene is located, that is, the ratio of the fluorescence intensity of the dimer to the monomer to reflect The rate of lateral diffusion of lipid molecules. If the medium viscosity is large, the lateral diffusion rate is small and the fluidity is small. Reference materials: Liu Shanhui, Liu Bingxue, Editor-in-Chief Fang Zedai; Xu Shuyun, Chief Reviewer Ma Chuangeng. English-Chinese Dictionary of Pharmacology. |
| uses | organic synthetic raw materials, 1,4,5,8-naphthalenedic acid can be prepared after oxidation, and used in dyes, synthetic resins and engineering plastics; After acylation, vat dye brilliant orange GR and other dyes can be produced. It can also make pesticides, plasticizers, etc. Used to make synthetic resins, vat dyes and dispersible dyes. Direct oxidation to pyrene quinone, used to make vat dyes Pyrene can be prepared by oxidation 1,4,5, 8-naphthalenic acid, used in the production of dyes, synthetic resins, pesticides and other products Used as a raw material for the production of 1,4,5, 8-naphthalenic acid, and also used as a raw material for dyes, synthetic resins and engineering plastics |
| production method | pyrene mainly exists in the distillate of coal tar pitch. Distill the medium-temperature asphalt under reduced pressure, and at the same time pass a small amount of direct superheated steam into the distillation kettle, cut the narrow fraction of pyrene, and then recrystallize with a mixed solution of solvent oil and ethanol, or a mixed solution of benzene and solvent oil to obtain industrial pyrene with 95% purity. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-10 22:29:15
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