Production Method 1

702-79-4

941-37-7

Reaction Conditions

1.1 Reagents: Aluminum chloride ,  Bromine ;  0.5 h, 20 - 25 °C; 2 h, 20 - 25 °C

Reference

Process for the preparation of memantine hydrochloride from 1,3-dimethyladamantane

, China, , ,

Production Method 2

702-79-4

941-37-7

Reaction Conditions

1.1 Reagents: Aluminum chloride ,  Bromine Solvents: 1,2-Dichloroethane ;  15 °C

Reference

Method for synthesis of 1,3-diaminophenyl-5,7-dimethyladamantane

, China, , ,

Production Method 3

702-79-4

941-37-7

Reaction Conditions

1.1 Reagents: Bromine ;  rt; 12 h, reflux

Reference

Synthesis and IR/MS study of 3,5-dimethyladamantanamine hydrochloride salt

Ren, Huixue; Ying, Hanjie; Ouyang, Pingkai; Lin, Jimao; Jing, Liu, Asian Journal of Chemistry, 2012, 24(11), 5107-5110

Production Method 4

702-79-4

941-37-7

Reaction Conditions

1.1 Reagents: Bromine Solvents: Dichloromethane ;  0 °C; 4.5 h, < 20 °C; 20 °C → reflux; 19 h, reflux

Reference

Catalyst and application thereof in the synthesis of 1-bromo-3,5-dimethyladamantane from perhydroacenaphthene

, China, , ,

Production Method 5

702-79-4

941-37-7

Reaction Conditions

1.1 Reagents: Bromine ;  6 h, reflux

Reference

A concise two-step method for preparation of memantine hydrochloride from 1, 3-dimethyladamantane

Nguyen, Thi Hong Tham; Nguyen, Trong Diep; Phan, Dinh Chau; Vu, Binh Duong, International Journal of Pharmaceutical Sciences and Research, 2021, 12(12), 6370-6383

Production Method 6

702-79-4

941-37-7

Reaction Conditions

1.1 Reagents: Bromine ;  4 h, reflux; reflux → rt; overnight, rt
1.2 Reagents: Sodium sulfite Solvents: Carbon tetrachloride ,  Water ;  cooled

Reference

Probe to bifunctional memantine derivatives for treatment of Alzheimer's disease

Liu, Zheng; Chen, Haiyun; Luo, Fangcheng; Guo, Baojian; Jing, Xiaoyong; et al, Journal of Pharmaceutical and Biomedical Sciences, 2015, 5(4), 276-290

Production Method 7

702-79-4

941-37-7

Reaction Conditions

1.1 Reagents: Bromine

Reference

The octant rule. XX. Synthesis and circular dichroism of (1S,5S)-dimethyladamantan-2-one, predicted to have zero Cotton effect

Lightner, David A.; Van Toan Vien, Tetrahedron, 1987, 43(21), 4905-16

Production Method 8

702-79-4

941-37-7

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Solvents: Dichloromethane ;  24 h, rt

Reference

Rimantadine analog for treating influenza A virus and synthesis method thereof

, China, , ,

Production Method 9

702-79-4

941-37-7

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Solvents: Dichloromethane ;  24 h, rt

Reference

Memantine analogue for treating Alzheimer's disease and its synthesis method

, China, , ,

Production Method 10

702-79-4

941-37-7

Reaction Conditions

1.1 Reagents: Bromine ;  10 h, 40 °C; 24 h, 40 °C

Reference

Synthesis of memantine hydrochloride intermediate

Wang, Fei-long; Duan, Yi-jie; Fan, Xing-shan, Shandong Huagong, 2013, 42(8), 3-4

Production Method 11

702-79-4

941-37-7

Reaction Conditions

1.1 Reagents: Bromine ;  70 °C; 8 h, 70 °C; 70 °C → 35 °C

Reference

Synthesis method of 1-bromo-3,5-dimethyladamantane from 1,3-dimethyladamantane

, China, , ,

Production Method 12

702-79-4

941-37-7

Reaction Conditions

1.1 Reagents: Bromine ;  75 °C; 26 h, 75 °C; 75 °C → rt
1.2 Reagents: Sodium bisulfite Solvents: Dichloromethane ,  Water ;  cooled

Reference

Process for preparation of memantine hydrochloride

, China, , ,

Production Method 13

702-79-4

941-37-7

Reaction Conditions

1.1 Reagents: Bromine ;  rt; 10 h, reflux

Reference

Process for the preparation of memantine hydrochloride

, China, , ,

Production Method 14

702-79-4

941-37-7

Reaction Conditions

1.1 Reagents: Carbon tetrabromide Catalysts: Iron(III) acetylacetonate Solvents: Dibromomethane ;  3 h, 150 °C

Reference

Bromination of adamantane and its derivatives with tetrabromomethane catalyzed by iron compounds

Khusnutdinov, R. I.; Shchadneva, N. A.; Khisamova, L. F., Russian Journal of Organic Chemistry, 2015, 51(2), 184-187

Production Method 15

702-79-4

941-37-7

Reaction Conditions

1.1 Reagents: Bromine ;  6 h, 70 °C
1.2 Reagents: Sodium bisulfite Solvents: Water ;  45 °C

Reference

Synthesis of memantine hydrochloride

Zou, Yong; Xiong, Xiaoyun; Mei, Qibing, Zhongguo Yiyao Gongye Zazhi, 2003, 34(5), 213-214

Production Method 16

702-79-4

941-37-7

Reaction Conditions

1.1 Reagents: Bromine

Reference

Use of adamantane derivatives in the prevention and treatment of cerebral ischemia

, European Patent Organization, , ,

Production Method 17

702-79-4

941-37-7

Reaction Conditions

1.1 Reagents: Bromine Solvents: Acetic acid ,  Water ;  56 °C; 3 h, reflux; reflux → rt
1.2 Reagents: Sodium bisulfite Solvents: Dichloromethane ,  Water

Reference

Method for synthesizing diadamantanediol and its derivative

, China, , ,

Production Method 18

702-79-4

941-37-7

Reaction Conditions

Reference

Preparation and adamantan-1-ol and its homologs

Burkhard, Jiri; Janku, Josef; Vodicka, Ludek, Sbornik Vysoke Skoly Chemicko-Technologicke v Praze, 1978, , 57-75

Production Method 19

702-79-4

941-37-7

Reaction Conditions

1.1 Reagents: tert-Butyl bromide Catalysts: Aluminum chloride ;  1 h, 18 °C

Reference

Process for preparation of 1-bromo-3,5-dimethyladamantane by reaction of 1,3-dimethyladamantane with tert-butyl bromide in the presence of aluminum chloride and its use as intermediate for memantine and its hydrochloride

, India, , ,

1-Bromo-3,5-dimethyladamantane Raw materials

• 1,3-Dimethyladamantane

1-Bromo-3,5-dimethyladamantane Preparation Products

• 1-Bromo-3,5-dimethyladamantane (941-37-7)

• 1. Dissociation of large gaseous serine clusters produces abundant protonated serine octamer
  Jacob S. Jordan,Evan R. Williams Analyst, 2021,146, 2617-2625
• 2. Evidence of CO2 molecule acting as an electron acceptor on a nanoporous metal–organic-framework MIL-53 or Cr3+(OH)(O2C–C6H4–CO2)?
  Alexandre Vimont,Arnaud Travert,Philippe Bazin,Jean-Claude Lavalley,Marco Daturi,Christian Serre,Gérard Férey,Sandrine Bourrelly,Philip L. Llewellyn Chem. Commun., 2007, 3291-3293
• 3. Exceptionally high temperature spin crossover in amide-functionalised 2,6-bis(pyrazol-1-yl)pyridine iron(ii) complex revealed by variable temperature Raman spectroscopy and single crystal X-ray diffraction?
  Max Attwood,Hiroki Akutsu,Lee Martin,Toby J. Blundell,Pierre Le Maguere,Scott S. Turner Dalton Trans., 2021,50, 11843-11851
• 4. Fe/Fe3C@C nanoparticles encapsulated in N-doped graphene–CNTs framework as an efficient bifunctional oxygen electrocatalyst for robust rechargeable Zn–air batteries?
  Zhiyan Chen,Nan Wu,Yaobing Wang,Bing Wang,Yingde Wang J. Mater. Chem. A, 2018,6, 516-526
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• Solvents and Organic Chemicals Organic Compounds Organohalogen compounds Organobromides Organobromides
• Solvents and Organic Chemicals Organic Compounds Organohalogen compounds Organobromides
• Solvents and Organic Chemicals Organic Compounds Organic Halides

Professional Introduction to 1-Bromo-3,5-dimethyladamantane (CAS No. 941-37-7)

The compound 1-Bromo-3,5-dimethyladamantane (CAS No. 941-37-7) is a significant molecule in the field of organic chemistry and pharmaceutical research. Its unique structural properties make it a valuable intermediate in the synthesis of various bioactive compounds. This introduction provides an in-depth exploration of the compound's chemical characteristics, potential applications, and recent advancements in its utilization within the pharmaceutical industry.

The molecular structure of 1-Bromo-3,5-dimethyladamantane consists of an adamantane core substituted with bromine atoms at the 1-position and methyl groups at the 3- and 5-positions. This arrangement imparts a high degree of steric hindrance, which is crucial for its role in constructing complex molecular architectures. The presence of bromine atoms also makes it a versatile precursor for further functionalization, enabling chemists to explore a wide range of derivatives.

In recent years, 1-Bromo-3,5-dimethyladamantane has garnered attention for its applications in drug discovery and development. Its rigid adamantane framework provides stability and specificity, which are essential qualities for designing molecules that interact with biological targets. Researchers have leveraged this compound to develop novel pharmacophores that exhibit promising activities against various diseases.

One of the most notable areas where 1-Bromo-3,5-dimethyladamantane has been applied is in the synthesis of small-molecule inhibitors targeting protein-protein interactions. These interactions are critical in many biological processes and are often implicated in diseases such as cancer and inflammation. By incorporating the adamantane moiety into these inhibitors, scientists have been able to enhance their binding affinity and selectivity.

The compound's utility extends to the development of radiolabeled probes used in positron emission tomography (PET) imaging. PET scans are invaluable tools for diagnosing and monitoring diseases non-invasively. The incorporation of bromine into the adamantane structure allows for easy radiolabeling with positron-emitting isotopes such as fluorine-18 or carbon-11, enabling researchers to visualize biological processes with high precision.

Recent studies have also explored the use of 1-Bromo-3,5-dimethyladamantane in materials science. Its unique structural features make it a suitable candidate for designing supramolecular assemblies and polymers with specific functionalities. These materials have potential applications in nanotechnology, electronics, and biomedicine.

The synthesis of 1-Bromo-3,5-dimethyladamantane typically involves a multi-step process that begins with the bromination of adamantane derivatives. Advances in synthetic methodologies have improved the efficiency and yield of these reactions, making the compound more accessible for research purposes. Techniques such as transition metal-catalyzed cross-coupling reactions have been particularly useful in introducing additional functional groups onto the adamantane core.

The pharmaceutical industry continues to invest in research aimed at uncovering new applications for 1-Bromo-3,5-dimethyladamantane. Collaborative efforts between academic institutions and pharmaceutical companies have led to innovative approaches in drug design. These efforts are driven by the need for more effective and targeted therapies to address unmet medical needs.

The safety profile of 1-Bromo-3,5-dimethyladamantane is another important consideration in its application. While it is not classified as a hazardous material under standard regulations, proper handling procedures must be followed to ensure safe laboratory practices. Researchers must adhere to guidelines established by organizations such as the National Institute for Occupational Safety and Health (NIOSH) to minimize potential risks.

In conclusion, 1-Bromo-3,5-dimethyladamantane (CAS No. 941-37-7) is a multifaceted compound with significant potential in pharmaceutical research and development. Its unique structural features make it a valuable building block for synthesizing bioactive molecules and materials with diverse applications. As research continues to evolve, it is likely that new uses for this compound will be discovered, further solidifying its importance in the scientific community.

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• 697-40-5(Bicyclo[2.2.2]octane,1-bromo-4-methyl-)
• 105253-36-9(Bicyclo[2.2.2]octane, 1-bromo-4-(1,1-dimethylethyl)-)
• 73152-68-8(1-Bromo-4-pentylbicyclo[2.2.2]octane)
• 1189429-92-2(1-Bromo-3,5-dimethyladamantane-d6)
• 53398-55-3(1-Bromo-3,5,7-trimethyladamantane)
• 25276-12-4(Cyclohexane, 1-bromo-4-(1,1-dimethylethyl)-1-methyl-, trans-)
• 25276-11-3(Cyclohexane, 1-bromo-4-(1,1-dimethylethyl)-1-methyl-, cis-)
• 878-61-5(1-Ethyl-3-bromoadamantane)
• 702-77-2(1-Bromo-3-methyladamantane)