1-Bromoadamantane

Base Information

• Chemical Name: 1-Bromoadamantane
• CAS No.: 768-90-1
• Molecular Formula: C10H15Br
• Molecular Weight: 215.133
• Hs Code.: 29035990
• European Community (EC) Number: 212-200-7
• NSC Number: 527914
• UNII: GKV2KDH3R5
• DSSTox Substance ID: DTXSID50880632
• Nikkaji Number: J147.982B
• Wikipedia: 1-Bromoadamantane
• Wikidata: Q2806575
• Mol file: 768-90-1.mol

Synonyms:1-Adamantyl bromide;1-Bromotricyclo(3.3.1.13,7)decane;Tricyclo[3.3.1.13, 7]decane, 1-bromo-;Adamantane, 1-bromo-;Adamantyl bromide;1-Bromo adamantane;1-Bromotricyclo[3.3.1.13,7]decane;

Chemical Property of 1-Bromoadamantane

Chemical Property:

• Appearance/Colour: white to almost white crystals or cryst. powder
• Vapor Pressure: 0.0587mmHg at 25°C
• Melting Point: 116-118 °C
• Refractive Index: 1.586
• Boiling Point: 240.5 °C at 760 mmHg
• Flash Point: 96.4 °C
• PSA: 0.00000
• Density: 1.448 g/cm³
• LogP: 3.35010
• Storage Temp.: Store below +30°C.
• Sensitive.: Moisture Sensitive
• Solubility.: Chloroform (Sparingly), Ethyl Acetate (Slightly), Methanol (Slightly)
• Water Solubility.: It is soluble in organic solvents and insoluble in water.
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 214.03571
• Heavy Atom Count: 11
• Complexity: 144

Purity/Quality:

>95% ^*data from raw suppliers

1-AdamantylBromide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 22-24/25-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Other Organic Compounds
• Canonical SMILES: C1C2CC3CC1CC(C2)(C3)Br
• Uses: 1-Bromoadamantane shows some anti-viral activity due to the adamantane structure. In addition it shows anti-microbial activity and cytotoxic application. use: Amantadine, Rimantadine, Somantadine, Tromantadine 1-Bromoadamantane is an important intermediate, used in synthesizing medicines and new materials etc.

Technology Process of 1-Bromoadamantane

There total 68 articles about 1-Bromoadamantane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

adamantane (281-23-2) → 1-Adamantyl bromide (768-90-1) + 1,3-dibromoadamantane (876-53-9)

Guidance literature:

With iron(III)-acetylacetonate; carbon tetrabromide; Reagent/catalyst; Sealed tube; Inert atmosphere;

DOI:10.1134/S1070428015020074

Reference yield: 91.5%

4-(1-adamantyl)benzene-1,3-diol (74131-25-2) → 1-Adamantyl bromide (768-90-1) + 2,4,6-tribromoresorcinol (2437-49-2) + 2,6-Dibromo-4-(1-adamantyl)resorcinol (74131-27-4)

Guidance literature:

With bromine; In methanol; acetic acid; for 1h; Ambient temperature;

DOI:10.1007/BF00765913

Reference yield: 90.0%

Bromotrichloromethane (75-62-7) + adamantane (281-23-2) + acetonitrile (75-05-8,26809-02-9) → 1-Adamantyl bromide (768-90-1) + chloroform (67-66-3,8013-54-5) + N-(1-adamantyl)acetamide (880-52-4)

Guidance literature:

With water; molybdenum hexacarbonyl; at 140 ℃; for 2h;

DOI:10.1134/S1070428011120220

upstream raw materials:

adamantane

Acetyl bromide

1-chloroadamantane

t-butyl bromide

Downstream raw materials:

N-cyclohexyl-1-aminoadamantane

2-(1-adamantyloxy)ethan-1-ol

1-(4-methoxyphenyl)adamantane

N-(adamantan-1-yl)benzamide

Refernces

• 1、 Grob, Cyril A.,Sawlewicz, Pawel. "164. The Mild Bromination of Adamantane and (Trimethylsilyl)adamantanes". . p. 1508 - 1510. Retrieved 1988.
• 2、 Cheprakov, A. V.,Makhon'kov, D. I.,Beletskaya, I. P.. "OXIDATIVE BROMINATION OF ADAMANTANE UNDER MILD CONDITIONS". . p. 637. Retrieved 1987.
• 3、 Barfield, Michael,Marshall, J. L.,Canada, E. D.. "Nuclear Spin-Spin Coupling via Nonbonded Interactions. 2. γ-Substituent Effects for Vicinal Coupling Constant Involving 13C". . p. 7 - 12. Retrieved 1980.
• 4、 Baughman. "". . p. 238. Retrieved 1964.
• 5、 -. "Method for synthesizing and preparing amantadine dry product". Paragraph 0057-0063; 0068. . Retrieved 2021/03/13.
• 6、 Sneh, Kumar,Torigoe, Takeru,Kuninobu, Yoichiro. "Manganese/bipyridine-catalyzed non-directed C(sp3)–H bromination using NBS and TMSN3". supporting information. p. 885 - 890. Retrieved 2021/05/05.