1-Bromo-3,5-dimethyladamantane CAS 941-37-7
1-Bromo-3,5-dimethyladamantane Basic information
| 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 | n |
| 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) |
Safety Information
| 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 |
| 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 | 702-79-4 941-37-7 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
| Raw materials | 1,3-Dimethyladamantane-->Aluminum chloride-->1,2-Dichloroethane |
| Preparation Products | 1,3-Dimethyladamantane-->3-AMINO-5,7-DIMETHYLADAMANTAN-1-OL Hydrochloride-->1,3,5-TRIMETHYLADAMANTANE-->4-(3,5-dimethyl-1-adamantyl)phenol |
