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| | 1,1-DIBROMO-2,2-BIS(CHLOROMETHYL)CYCLOPROPANE Basic information |
| Product Name: | 1,1-DIBROMO-2,2-BIS(CHLOROMETHYL)CYCLOPROPANE | | Synonyms: | Cyclopropane,1,1-dibroMo-2,2-bis(chloroMethyl)-;1,1-DibroMo-2,2-bis(chloroMethyl)cyclopropane 90%, technical grade;1,1-DIBROMO-2,2-BIS(CHLOROMETHYL)CYCLOPROPANE;1,1-BIS(CHLOROMETHYL)-2,2-DIBROMOCYCLOPROPANE;AKOS BBS-00001998;1,1-DIBROMO-2,2-BIS(CHLOROMETHYL)-CYCLOP ROPANE, TECH., 90%;2,2-Bis-(chloromethyl)-1,1-dibromocyclopropane;EOS-60772 | | CAS: | 98577-44-7 | | MF: | C5H6Br2Cl2 | | MW: | 296.82 | | EINECS: | 627-508-0 | | Product Categories: | Halogenated Hydrocarbons;Organic Building Blocks;Alkyl | | Mol File: | 98577-44-7.mol |  |
| | 1,1-DIBROMO-2,2-BIS(CHLOROMETHYL)CYCLOPROPANE Chemical Properties |
| Melting point | 48-50 °C (lit.) | | Boiling point | 277.1±10.0 °C(Predicted) | | density | 2.065±0.06 g/cm3 (20 ºC 760 Torr) | | storage temp. | Inert atmosphere,Room Temperature | | form | powder to crystal | | color | White to Orange to Green | | InChI | InChI=1S/C5H6Br2Cl2/c6-5(7)1-4(5,2-8)3-9/h1-3H2 | | InChIKey | RCRVZCIUKQNOIS-UHFFFAOYSA-N | | SMILES | C1(Br)(Br)CC1(CCl)CCl |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36 | | WGK Germany | 3 | | HS Code | 2902190000 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | 1,1-DIBROMO-2,2-BIS(CHLOROMETHYL)CYCLOPROPANE Usage And Synthesis |
| Uses | 1,1-Dibromo-2,2-bis(chloromethyl)cyclopropane may be used as a starting material in the synthesis of [1.1.1]-propellane and ((3-ethynylbicyclo[1.1.1]pentan-1-yl)ethynyl)trimethylsilane. | | Preparation | 1000 ml 1,1-bis(chloromethyl)-2,2-dibromocyclopropane was added to a vigorously stirred mixture within 10-15 min, which contains bromoform (370 ml, 4.24 mol), 3-chloro-2-chloromethyl-1-propane (250 g, 2.0 mol), 10 g benzyltriethylammonium chloride, 8 ml ethanol and 200 ml methylene chloride . The temperature was maintained between 25°-35° C. After overnight stirring, 500 ml methylene chloride was added and the thick black mixture was allowed to separate into layers. The top aqueous layer was removed and the bottom layer was gently washed with water (500 ml). 500 ml water was then added and well shaken. Separated the organic phase, treated the residual emulsion with solid sodium chloride and filtered through Celite. All aqueous layers were washed with methylene chloride. The organic extracts were combined, dried over magnesium sulfate, and filtered through Celite. Concentration and vacuum distillation gave the mixture of starting material and black-brown residue which was distilled on a Kugel-Rohr giving semicrystalline fraction containing the product. Crystallization from 400 ml of pentane from a dry ice-acetone bath gave the white wet crystals. The crude product was dissolved in 400 ml of penfane, then 7.5 g silica gel was added. Filtered and low temperature recrystallized again. Finally, obtain the product (1,1-DIBROMO-2,2-BIS(CHLOROMETHYL)CYCLOPROPANE ) | | General Description | 1,1-Dibromo-2,2-bis(chloromethyl)cyclopropane is a halogenated cyclopropane derivative. It has been reported to be synthesized from 3-chloro-2-(chloromethyl)-1-propene. It is formed as an intermediate during the synthesis of [1.1.1]propellane by Szeimies method. | | Synthesis | 3-Chloro-2-chloromethylpropene (100 g, 0.8 mol), 18-crown-6 ether (5 g) and pinacol (8 g) were dissolved in tribromomethane (400 g). A 30% aqueous sodium hydroxide solution (1.0 L) was slowly added dropwise over a temperature range of 10°C to 25°C. After the dropwise addition, the reaction mixture was stirred continuously at room temperature for 24 hours. The progress of the reaction was monitored by thin layer chromatography (TLC) with the unfolding agent ratio of petroleum ether/ethyl acetate = 10/1 (v/v). After confirming the completion of the reaction, the reaction system was concentrated and purified by column chromatography with an eluent ratio of petroleum ether/ethyl acetate = 5/1 to 1/1 (v/v). Finally, 1,1-dibromo-2,2-bis(chloromethyl)cyclopropane (168 g) was obtained in 70.7% yield. | | References | [1] Journal of Organic Chemistry, 1995, vol. 60, # 14, p. 4666 - 4668
[2] Organic Syntheses, 1998, vol. 75, p. 98 - 98
[3] Journal of Organic Chemistry, 1994, vol. 59, # 11, p. 2986 - 2996
[4] Patent: CN105294442, 2016, A. Location in patent: Paragraph 0006; 0007
[5] Patent: WO2014/159559, 2014, A1. Location in patent: Page/Page column 66-67 |
| | 1,1-DIBROMO-2,2-BIS(CHLOROMETHYL)CYCLOPROPANE Preparation Products And Raw materials |
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