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| | 1-Bromo-3,5-dimethyladamantane Basic information | | Uses |
| Product Name: | 1-Bromo-3,5-dimethyladamantane | | Synonyms: | 1-Bromo-3,5-dimethyltricyclo[3.3.1.13,7]decane;1-BROMO-3,5-DIMETHYLADAMANTANE;3,5-dimethyl-1-bromo- adamantane;1-Bromo-3,5-Dimethyl;1,3-Dimethyl-5-bromoadamantane;tricyclo[3.3.1.1~3,7~]decane, 1-bromo-3,5-dimethyl-;NSC 102293;1-BROMO-3,5- DIMETHYL DAMANTANE | | CAS: | 941-37-7 | | MF: | C12H19Br | | MW: | 243.18 | | EINECS: | 213-378-9 | | Product Categories: | Adamantane derivatives;Adamantanes;Alkyl;Halogenated Hydrocarbons;Organic Building Blocks;Intermediates & Fine Chemicals;Pharmaceuticals;Chemical intermediate for Memantine HCl;bc0001;941-37-7 | | Mol File: | 941-37-7.mol |  |
| | 1-Bromo-3,5-dimethyladamantane Chemical Properties |
| Boiling point | 201 °C (lit.) | | density | 1.224 g/mL at 25 °C (lit.) | | refractive index | n20/D 1.52(lit.) | | Fp | 228 °F | | storage temp. | 2-8°C | | solubility | Chloroform (Sparingly), Dichloromethane (Slightly), Methanol (Slightly) | | form | Oil | | color | Colourless to Pale Yellow | | Specific Gravity | 1.224 | | BRN | 1927514 | | Major Application | pharmaceutical small molecule | | InChI | InChI=1S/C12H19Br/c1-10-3-9-4-11(2,6-10)8-12(13,5-9)7-10/h9H,3-8H2,1-2H3 | | InChIKey | QUCXLVDIVQWYJR-UHFFFAOYSA-N | | SMILES | C12(Br)CC3(C)CC(CC(C)(C3)C1)C2 | | CAS DataBase Reference | 941-37-7(CAS DataBase Reference) |
| Hazard Codes | C | | Risk Statements | 34-36 | | Safety Statements | 26-27-36/37/39-45 | | WGK Germany | 3 | | HazardClass | IRRITANT | | HS Code | 2903890002 | | Storage Class | 10 - Combustible liquids |
| | 1-Bromo-3,5-dimethyladamantane Usage And Synthesis |
| Uses | 1-Bromo-3,5-dimethyladamantane (cas# 941-37-7) is a compound useful in organic synthesis. | | Description | 1-Bromo-3,5-dimethyladamantane is a precursor substance of memantine and memantine hydrochloride (MH), which can be synthesised by direct amination with thiourea. MH is an FDA-approved first-line treatment for moderate to severe Alzheimer's disease. | | Chemical Properties | Clear Colorless Oil | | Uses | 1-Bromo-3,5-dimethyladamantane was used in the one pot synthesis of 1,3-dicarbonyl adamantanes. It was also used in the synthesis of 3,5-dimethyladamantan-1-ol. | | Synthesis | A) Add 59.9 g (0.345 mol) of bromine, 10 g (0.075 mol) of anhydrous aluminum trichloride, and 37.8 g of 1,2-dichloroethane to the reactor with thorough stirring; B) Heat the reaction mixture A to 15°C; C) Add 50 g (0.3 mol) of 1,3-dimethyladamantane to the mixture obtained in step B, and absorb the resulting gas using a 5% sodium hydroxide solution; D) Add 400 g of saturated sodium bisulfite solution to reaction mixture B until the red color of the reaction solution completely disappears, and separate the organic phase C and the aqueous phase D; and D) Add 400 g of saturated sodium bisulfite solution to the reaction mixture B until the red color of the reaction solution completely disappears, and separate the organic phase C and the aqueous phase D; E) Wash the organic phase C with 400 g of water, and then dry it with 20 g of anhydrous sodium sulfate; F) Perform distillation on the organic phase C obtained in step E to obtain the crude product E; G) Perform decompression distillation on the crude product E to obtain the 1-(3-methyladamantyl)-1,3-dimethyladamantane. G) the crude product E was distilled under reduced pressure to obtain 1-bromo-3,5-dimethyladamantane in 92% yield and ≥99% purity by gas chromatography. | | References | [1] Patent: CN104592034, 2016, B. Location in patent: Paragraph 0092-0099
[2] Asian Journal of Chemistry, 2012, vol. 24, # 11, p. 5107 - 5110
[3] Russian Journal of Organic Chemistry, 2015, vol. 51, # 2, p. 184 - 187
[4] Zh. Org. Khim., 2015, vol. 51, # 2, p. 196 - 199
[5] Patent: US5061703, 1991, A |
| | 1-Bromo-3,5-dimethyladamantane Preparation Products And Raw materials |
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