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| CAS No.: | 80-05-7 |
|---|---|
| Name: | Bisphenol A |
| Molecular Structure: | |
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| Formula: | C15H16O2 |
| Molecular Weight: | 228.291 |
| Synonyms: | 4,4'-(propane-2,2-diyl)diphenol;p,p'-isopropylidenebisphenol;BPA;4,4'-(1-Methylethylidene)bisphenol;2,2-(4,4'-Dihydroxydiphenyl)propane;2,2-Bis(4-hydroxyphenyl)propane;4,4'-Bisphenol A;4,4'-Isopropylidenediphenol;2,2-Di(4-phenylol)propane; |
| EINECS: | 201-245-8 |
| Density: | 1.195 g/cm3 |
| Melting Point: | 158 to 159 °C (430 K) |
| Boiling Point: | 220 °C (493 K) / 4 mmHg |
| Flash Point: | 227 °C |
| Solubility: | 120–300 ppm (at 21.5 °C) in water |
| Appearance: | White to light brown flakes or powder |
| Hazard Symbols: |
 Xn
|
| Risk Codes: | 37-41-43-62 |
| Safety: | 26-36/37/39-45-46 |
| PSA: | 40.46000 |
| LogP: | 3.42370 |
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| Conditions | Yield |
|---|---|
| With hydrogen; triethylamine In methanol; water at 120℃; under 22502.3 Torr; for 116h; Autoclave; | 95% |
| With hydrogen; triethylamine In ethanol; water at 120℃; under 22502.3 Torr; for 116h; Autoclave; | 95% |
| With cadmium selenide; triethylamine In N,N-dimethyl-formamide at 20℃; for 24h; Irradiation; Sealed tube; | 87% |
| With sodium sulfite In water at 130℃; for 12h; Sealed tube; Microwave irradiation; Green chemistry; | 80% |
| Conditions | Yield |
|---|---|
| With silica supported perchloric acid In neat (no solvent) for 3.75h; Heating; Green chemistry; | 88% |
| With magnetic mesoporous silica supported azacrown ether hexafluorophosphate ionic liquid In water at 50℃; for 5h; Temperature; Green chemistry; | 86% |
| sulfonic-acid-form cation-exchange resin (DIAION "SK104H") modified with hydrolyzed 2-pyridylethyl thioacetate at 70℃; for 2h; Product distribution / selectivity; Inert atmosphere; Cooling; | 58% |
| Conditions | Yield |
|---|---|
| In chlorobenzene; acetone | 83% |
| Conditions | Yield |
|---|---|
| In ethanol; water at 80℃; for 12h; Green chemistry; | A n/a B 81% |
| Conditions | Yield |
|---|---|
| In ethanol; water at 80℃; for 12h; Green chemistry; | A n/a B 81% |
| Conditions | Yield |
|---|---|
| With hydrogenchloride at 40℃; for 48h; | 80% |
| Conditions | Yield |
|---|---|
| In ethanol; water at 80℃; for 12h; Green chemistry; | A n/a B 78% |
- 80-05-7
BPA
| Conditions | Yield |
|---|---|
| With iron(III) chloride; potassium phosphate; tetrabutylammomium bromide; N,N`-dimethylethylenediamine In water at 180℃; under 5250.53 Torr; for 20h; | 76% |
| Conditions | Yield |
|---|---|
| Stage #1: 2,2'-[isopropylidenebis(1,4-phenyleneoxy)]diacetic acid With triethylamine In N,N-dimethyl-formamide; toluene for 3h; Curtius rearrangement; Heating; Stage #2: With potassium hydroxide; glycerol In ethanol; N,N-dimethyl-formamide; toluene for 2h; Heating; Further stages.; | 72% |
| Conditions | Yield |
|---|---|
| In ethanol; water at 80℃; for 12h; Green chemistry; | A n/a B 68% |
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Specification
Bisphenol A, with the CAS register number 80-05-7, is commonly abbreviated as BPA. Its EINECS register number is 201-245-8. Bisphenol A has IUPAC name which is called 4,4'-(propane-2,2-diyl)diphenol. The substance is an organic compound with the formula C15H16O2. It is a white to light brown flakes or powder with a weak medicine odor. Bisphenol A should be sealed and stored in cool and dry place. What's more, it should be protected from water and explosions.Bisphenol A, incompatible with strong oxidizers, strong bases, acid chlorides and acid anhydrides, will sink in water. Bisphenol A is combustible which may form explosive dust clouds. Bisphenol A is an endocrine disruptor, which can mimic the body's own hormones and may lead to negative health effects. September 2010, Canada became the first country to declare BPA as a toxic substance. In the European Union and Canada, BPA use is banned in baby bottles.
Physical properties about Bisphenol A are: (1)ACD/LogP: 3.641; (2)ACD/LogD (pH 5.5): 3.64; (3)ACD/LogD (pH 7.4): 3.64; (4)ACD/BCF (pH 5.5): 344.43; (5)ACD/BCF (pH 7.4): 343.99; (6)ACD/KOC (pH 5.5): 2278.55; (7)ACD/KOC (pH 7.4): 2275.67; (8)#H bond acceptors: 2; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 4; (11)Index of Refraction: 1.599; (12)Molar Refractivity: 68.168 cm3; (13)Molar Volume: 199.565 cm3; (14)Polarizability: 27.024 10-24cm3; (15)Surface Tension: 46.023998260498 dyne/cm; (16)Density: 1.144 g/cm3; (17)Flash Point: 192.423 °C; (18)Enthalpy of Vaporization: 67.716 kJ/mol; (19)Boiling Point: 400.837 °C at 760 mmHg;
Production of Bisphenol A: Bisphenol A can be prepared by the condensation of acetone with two equivalents of phenol. The reaction is catalyzed by a strong acid, such as hydrochloric acid (HCl) or a sulfonated polystyrene resin. It is commonly that a large excess of phenol is used to ensure full condensation in industry. The product mixture of the cumene process may also be used as starting material.
Uses of Bisphenol A: Bisphenol A is used to make polycarbonate plastic and epoxy resins. Bisphenol A is primarily used to make plastics. It is a key monomer in production of epoxy resins and in the most common form of polycarbonate plastic which is clear and nearly shatter-proof and is used to make a variety of common products including baby and water bottles, sports equipment, medical and dental devices, dental fillings and sealants, eyeglass lenses, CDs and DVDs, and household electronics. As an antioxidant in some plasticizers, and as a polymerization inhibitor in PVC, Bisphenol A is also used in the synthesis of polysulfones and polyether ketones. Bisphenol A is also a precursor to the flame retardant tetrabromobisphenol A, and was formerly used as a fungicide. BPA-based products are also used in foundry castings and for lining water pipes.
When you are using Bisphenol A, you should be very cautious about it for its harmful. It is irritating to respiratory system. There will be a risk of serious damage to eyes and possible risk of impaired fertility. In addition, it may cause sensitisation by skin contact. In case of contact with eyes, you must rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell seek medical advice immediately. If swallowed, you can seek medical advice immediately and show this container or label.
You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CC(C)(C1=CC=C(C=C1)O)C2=CC=C(C=C2)O
(2)InChI: InChI=1S/C15H16O2/c1-15(2,11-3-7-13(16)8-4-11)12-5-9-14(17)10-6-12/h3-10,16-17H,1-2H3
(3)InChIKey: IISBACLAFKSPIT-UHFFFAOYSA-N
The toxicity data is as follows:
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| guinea pig | LD50 | oral | 4gm/kg (4000mg/kg) | AUTONOMIC NERVOUS SYSTEM: OTHER (DIRECT) PARASYMPATHOMIMETIC BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: ATAXIA | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 33(7), Pg. 25, 1968. |
| mammal (species unspecified) | LD50 | oral | 6500mg/kg (6500mg/kg) | "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 135, 1969. | |
| mouse | LC | inhalation | > 1700mg/m3/2H (1700mg/m3) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: ATAXIA LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Toksikologiya Novykh Promyshlennykh Khimicheskikh Veshchestv. Toxicology of New Industrial Chemical Substances. For English translation, see TNICS*. Vol. 2, Pg. 50, 1961. |
| mouse | LD50 | intraperitoneal | 150mg/kg (150mg/kg) | National Technical Information Service. Vol. AD691-490, | |
| mouse | LD50 | oral | 2400mg/kg (2400mg/kg) | AUTONOMIC NERVOUS SYSTEM: OTHER (DIRECT) PARASYMPATHOMIMETIC BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: ATAXIA | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 33(7), Pg. 25, 1968. |
| mouse | LDLo | subcutaneous | 2500mg/kg (2500mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LIVER: FATTY LIVER DEGERATION | Toksikologiya Novykh Promyshlennykh Khimicheskikh Veshchestv. Toxicology of New Industrial Chemical Substances. For English translation, see TNICS*. Vol. 2, Pg. 50, 1961. |
| rabbit | LD50 | oral | 2230mg/kg (2230mg/kg) | American Industrial Hygiene Association Journal. Vol. 28, Pg. 301, 1967. | |
| rabbit | LD50 | skin | 3mL/kg (3mL/kg) | AMA Archives of Industrial Hygiene and Occupational Medicine. Vol. 4, Pg. 119, 1951. | |
| rat | LD50 | oral | 3250mg/kg (3250mg/kg) | American Industrial Hygiene Association Journal. Vol. 28, Pg. 301, 1967. |