1-Bromoadamantane

Last updated
1-Bromoadamantane
1-bromoadamantane.png
Names
Preferred IUPAC name
1-Bromoadamantane
Other names
1-Adamantyl bromide, adamantane, 1-bromo-, adamantyl bromide, tricyclo[3.3.1.1(3,7)]decane, 1-bromo-
Identifiers
3D model (JSmol)
1098857
ChemSpider
ECHA InfoCard 100.011.091 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 230-777-3
PubChem CID
UNII
  • InChI=1S/C10H15Br/c11-10-4-7-1-8(5-10)3-9(2-7)6-10/h7-9H,1-6H2
    Key: VQHPRVYDKRESCL-UHFFFAOYSA-N
  • InChI=1/C10H15Br/c11-10-4-7-1-8(5-10)3-9(2-7)6-10/h7-9H,1-6H2
    Key: VQHPRVYDKRESCL-UHFFFAOYAL
  • C1C2CC3CC1CC(C2)(C3)Br
Properties
C10H15Br
Molar mass 215.134 g·mol−1
AppearanceSolid
Melting point 117 °C (243 °F)
Boiling point 226 °C (439 °F)
Insoluble
Hazards
NFPA 704 (fire diamond)
1
0
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

1-Bromoadamantane is the organobromine compound with the formula (CH2)6(CH)3CBr. A colorless solid, the compound is a derivative of adamantane with a bromine atom at one of the four equivalent methine positions.

Reactions

Although of no commercial value, 1-bromoadamantane has often been employed for testing methodology. Hydrolysis of this bromide gives the alcohol 1-hydroxyadamantane. [1]

It reacts with phenol to give para-adamantylphenol. [2]

Classified as a tertiary alkyl bromide, it is reluctant to form organometallic derivatives. With Rieke calcium however it forms the organocalcium derivative, which functions like a Grignard reagent. [3]

Related Research Articles

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Phenol is an aromatic organic compound with the molecular formula C6H5OH. It is a white crystalline solid that is volatile. The molecule consists of a phenyl group bonded to a hydroxy group. Mildly acidic, it requires careful handling because it can cause chemical burns.

<span class="mw-page-title-main">Aldehyde</span> Organic compound containing the functional group R−CH=O

In organic chemistry, an aldehyde is an organic compound containing a functional group with the structure R−CH=O. The functional group itself can be referred to as an aldehyde but can also be classified as a formyl group. Aldehydes are common and are important in technology and biology.

<span class="mw-page-title-main">Phenyl group</span> Cyclic chemical group (–C₆H₅)

In organic chemistry, the phenyl group, or phenyl ring, is a cyclic group of atoms with the formula C6H5, and is often represented by the symbol Ph. Phenyl group is closely related to benzene and can be viewed as a benzene ring, minus a hydrogen, which may be replaced by some other element or compound to serve as a functional group. Phenyl group has six carbon atoms bonded together in a hexagonal planar ring, five of which are bonded to individual hydrogen atoms, with the remaining carbon bonded to a substituent. Phenyl groups are commonplace in organic chemistry. Although often depicted with alternating double and single bonds, phenyl group is chemically aromatic and has equal bond lengths between carbon atoms in the ring.

<span class="mw-page-title-main">Diazomethane</span> Simplest diazo compound and methylating agent

Diazomethane is the chemical compound CH2N2, discovered by German chemist Hans von Pechmann in 1894. It is the simplest diazo compound. In the pure form at room temperature, it is an extremely sensitive explosive yellow gas; thus, it is almost universally used as a solution in diethyl ether. The compound is a popular methylating agent in the laboratory, but it is too hazardous to be employed on an industrial scale without special precautions. Use of diazomethane has been significantly reduced by the introduction of the safer and equivalent reagent trimethylsilyldiazomethane.

<span class="mw-page-title-main">Anisole</span> Organic compound (CH₃OC₆H₅) also named methoxybenzene

Anisole, or methoxybenzene, is an organic compound with the formula CH3OC6H5. It is a colorless liquid with a smell reminiscent of anise seed, and in fact many of its derivatives are found in natural and artificial fragrances. The compound is mainly made synthetically and is a precursor to other synthetic compounds. Structurally, it is an ether with a methyl and phenyl group attached. Anisole is a standard reagent of both practical and pedagogical value.

<span class="mw-page-title-main">1,10-Phenanthroline</span> Heterocyclic organic compound

1,10-Phenanthroline (phen) is a heterocyclic organic compound. It is a white solid that is soluble in organic solvents. The 1,10 refer to the location of the nitrogen atoms that replace CH's in the hydrocarbon called phenanthrene.

<span class="mw-page-title-main">Sulfonic acid</span> Organic compounds with the structure R−S(=O)2−OH

In organic chemistry, sulfonic acid refers to a member of the class of organosulfur compounds with the general formula R−S(=O)2−OH, where R is an organic alkyl or aryl group and the S(=O)2(OH) group a sulfonyl hydroxide. As a substituent, it is known as a sulfo group. A sulfonic acid can be thought of as sulfuric acid with one hydroxyl group replaced by an organic substituent. The parent compound is the parent sulfonic acid, HS(=O)2(OH), a tautomer of sulfurous acid, S(=O)(OH)2. Salts or esters of sulfonic acids are called sulfonates.

<span class="mw-page-title-main">Biphenyl</span> Chemical compound

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<span class="mw-page-title-main">Radical anion</span> Free radical species

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Isoamyl alcohol is a colorless liquid with the formula C
5
H
12
O
, specifically (H3C–)2CH–CH2–CH2–OH. It is one of several isomers of amyl alcohol (pentanol). It is also known as isopentyl alcohol, isopentanol, or (in the IUPAC recommended nomenclature) 3-methyl-butan-1-ol. An obsolete name for it was isobutyl carbinol.

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<span class="mw-page-title-main">Organotitanium chemistry</span>

Organotitanium chemistry is the science of organotitanium compounds describing their physical properties, synthesis, and reactions. Organotitanium compounds in organometallic chemistry contain carbon-titanium chemical bonds. They are reagents in organic chemistry and are involved in major industrial processes.

<span class="mw-page-title-main">Triacetonamine</span> Chemical compound

Triacetonamine is an organic compound with the formula OC(CH2CMe2)2NH (where Me = CH3). It is a colorless or white solid that melts near room temperature. The compound is an intermediate in the preparation of 2,2,6,6-tetramethylpiperidine, a sterically hindered base and precursor to the reagent called TEMPO. Triacetonamine is formed by the poly-aldol condensation of acetone in the presence of ammonia and calcium chloride:

<span class="mw-page-title-main">Group 2 organometallic chemistry</span>

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<span class="mw-page-title-main">Organobismuth chemistry</span>

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References

  1. Ōsawa, Eiji (1974). "Bromination of adamantane and bicyclo(2.2.2)octane with liquid bromine". Tetrahedron Letters. 15: 115–117. doi:10.1016/S0040-4039(01)82150-X.
  2. V. Prakash Reddy. G. K. Surya Prakash (2003). "Electrophilic reactions of phenols". In Zvi Rappoport (ed.). The Chemistry of Phenols. PATAI'S Chemistry of Functional Groups. John Wiley & Sons. pp. 605–660. doi:10.1002/0470857277.ch9. ISBN   0471497371.
  3. Reuben D. Rieke; Tse-Chong Wu; Loretta I. Rieke (1995). "Highly Reactive Calcium for the Preparation of Organocalcium Reagents: 1-Adamantyl Calcium Halides and Their Addition to Ketones: 1-(1-Adamantyl)cyclohexanol". Organic Syntheses. 72: 147. doi:10.15227/orgsyn.072.0147.