14651-42-4|1-(Bromomethyl)adamantane| Ambeed

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Quality Control of [ 14651-42-4 ] Purity: 98% SDS Specification

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Product Details of [ 14651-42-4 ]

CAS No. :	14651-42-4
Formula :	C₁₁H₁₇Br
M.W :	229.16
SMILES Code :	BrCC12CC3CC(C2)CC(C3)C1
MDL No. :	MFCD00185303
InChI Key :	RLRBYCAVZBQANU-UHFFFAOYSA-N
Pubchem ID :	1416304

Safety of [ 14651-42-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Application In Synthesis of [ 14651-42-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 14651-42-4 ]

[ 14651-42-4 ] Synthesis Path-Downstream 1~35

1
[ 770-71-8 ]
[ 14651-42-4 ]

Yield	Reaction Conditions	Operation in experiment
84%	With hydrogen bromide; zinc dibromide; In water;	2. Preparation of 1-adamantyl methyl bromide To 39 g (0.17 moles) of zinc bromide, 29.8 g (0.17 mole) of hydrobromic acid were added. To the solution thus obtained, 11.5 g (0.069 mole) of 1-adamantyl methylalcohol which was prepared by the method shown in (1) was added and the mixture was refluxed for 11 hours. After the reaction mixture was brought to room temperature, 200 ml of water were added to this and extracted with two 300 ml portions of ether. After washing with 100 ml of water saturated with sodium bicarbonate and 100 ml of water, the resulting ether layer was dehydrated with anhydrous magnesium sulfate and was filtered. Ether was then distilled away. Residual solids were recrystallized from methanol or sublimed (1 mmHg, 75 C) to purify it, and 13 g of 1-adamantyl methyl bromide were obtained. Melting point of the product was 37-39 C and the yield was 84%.
	With bromine; triphenylphosphine; In N-methyl-acetamide; water; Petroleum ether;	Preparation of 1-Bromomethyladamantane, IV To 1-Hydroxymethyladamantane (366 gm.) and triphenylphosphine (598 gm.) in 1600 ml. dimethylformamide was added a solution of 366 gm. bromine in 800 ml. dimethylformamide over a 5 hour period. The mixture was left overnight at room temperature and then distilled (under aspirator) to remove solvent and product. The distillate was poured into 8 liters of water and filtered. The solid was dissolved in petroleum ether (30-60), washed with K2 CO3 solution, then with water, dried, and concentrated to dryness. The residue recrystallized from 2.5 liters methanol gave 426.6 gm., m.p. 43-4. (1st crop plus additional crops obtained on concentration of the mother liquors.)
	With bromine; triphenylphosphine; In N-methyl-acetamide; water; Petroleum ether;	Preparation of 1-Bromomethyladamantane, IV To 1-Hydroxymethyladamantane (366 gm.) and triphenylphosphine (598 gm.) in 1600 ml. dimethylformamide was added a solution of 366 gm. bromine in 800 ml. dimethylformamide over a 5 hour period. The mixtue was left overnight at room temperature and then distilled (under aspirator) to remove solvent and product. The distillate was poured into 8 liters of water and filtered. The solid was dissolved in petroleum ether (30-60), washed with K2 CO3 solution, then with water, dried, and concentrated to dryness. The residue recrystallized from 2.5 liters methanol gave 426.6 gm., m.p. 43-4. (1st crop plus additional crops obtained on concentration of the mother liquors.)

References: [1]Journal of the Chemical Society, Dalton Transactions,1980,p. 1879 - 1887.
[2]Journal of the American Chemical Society,2020,vol. 142,p. 10173 - 10183.
[3]Patent: US4001223,1977,A .
[4]Journal of the Chemical Society. Perkin transactions II,1991,p. 2021 - 2024.
[5]Chemical Communications,1998,p. 571 - 572.
[6]Russian Journal of Organic Chemistry,1993,vol. 29,p. 454 - 456.
Zhurnal Organicheskoi Khimii,1993,vol. 29,p. 542 - 545.
[7]Journal of the American Chemical Society,1966,vol. 88,p. 4475 - 4484.
[8]Journal of general chemistry of the USSR,1964,vol. 34,p. 580 - 584.
Zhurnal Obshchei Khimii,1964,vol. 34,p. 579 - 584.
[9]Supramolecular Chemistry,2015,vol. 27,p. 364 - 371.
[10]Patent: US4100170,1978,A .
[11]Patent: US4100170,1978,A .

2
[ 770-71-8 ]
[ 14651-42-4 ]
[ 14504-84-8 ]

References: [1]Journal of the American Chemical Society,1982,vol. 104,p. 3481 - 3487.

3
[ 14651-42-4 ]
[ 120014-28-0 ]
[ 126849-26-1 ]

References: [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 1880 - 1887.

4
[ 14651-42-4 ]
[ 1822-25-9 ]

References: [1]Bulletin de la Societe Chimique de France,1985,p. 905 - 910.
[2]Journal of Organic Chemistry USSR (English Translation),1965,vol. 1,p. 270 - 272.
Zhurnal Organicheskoi Khimii,1965,vol. 1,p. 280 - 283.

5
[ 14651-42-4 ]
[ 114310-71-3 ]

References: [1]Journal of the Chemical Society, Dalton Transactions,1980,p. 1879 - 1887.
[2]Journal of Organic Chemistry USSR (English Translation),1987,vol. 23,p. 875 - 880.
Zhurnal Organicheskoi Khimii,1987,vol. 23,p. 970 - 976.

6
[ 14651-42-4 ]
[ 76270-42-3 ]

References: [1]Journal of the Chemical Society, Dalton Transactions,1980,p. 1879 - 1887.

7
[ 14651-42-4 ]
[ 110517-50-5 ]

References: [1]Journal of the Chemical Society. Perkin transactions II,1991,p. 2021 - 2024.

8
[ 14651-42-4 ]
[ 71-43-2 ]
[ 7131-11-5 ]

References: [1]European Journal of Organic Chemistry,2021,vol. 2021,p. 5227 - 5237.
[2]Journal of Organic Chemistry USSR (English Translation),1966,vol. 2,p. 640 - 643.
Zhurnal Organicheskoi Khimii,1966,vol. 2,p. 640 - 643.

9
[ 14651-42-4 ]
[ 603-35-0 ]
1-(adamantylmethyl)triphenylphosphonium bromide [ No CAS ]

References: [1]Journal of Organic Chemistry,1996,vol. 61,p. 722 - 726.

10
[ 14651-42-4 ]
[ 5587-42-8 ]
1-adamantan-1-ylmethyl-1H-imidazole [ No CAS ]

References: [1]Chemical Communications,1998,p. 571 - 572.

11
[ 2637-34-5 ]
[ 14651-42-4 ]
2-(adamantan-1-ylmethylsulfanyl)-pyridine [ No CAS ]

References: [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,2005,vol. 60,p. 471 - 475.

12
[ 18368-57-5 ]
[ 14651-42-4 ]
2-(adamantan-1-ylmethylsulfanyl)-6-methylpyridine [ No CAS ]

References: [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,2005,vol. 60,p. 471 - 475.

13
[ 14651-42-4 ]
[ 96-53-7 ]
2-(adamantan-1-ylmethylsulfanyl)-4,5-dihydrothiazole [ No CAS ]

References: [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,2005,vol. 60,p. 471 - 475.

14
[ 14651-42-4 ]
[ 131242-36-9 ]
2-(adamantan-1-ylmethylsulfanyl)-pyrimidine [ No CAS ]

References: [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,2005,vol. 60,p. 471 - 475.

15
[ 14651-42-4 ]
[ 774119-15-2 ]
2-(adamantan-1-ylmethylsulfanyl)-4-methylpyrimidine [ No CAS ]

References: [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,2005,vol. 60,p. 471 - 475.

16
[ 14651-42-4 ]
[ 22325-27-5 ]
2-(adamantan-1-ylmethylsulfanyl)-4,6-dimethylpyrimidine [ No CAS ]

References: [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,2005,vol. 60,p. 471 - 475.

17
[ 14651-42-4 ]
[ 60-56-0 ]
2-(adamantan-1-ylmethylsulfanyl)-1-methyl-1H-imidazole [ No CAS ]

References: [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,2005,vol. 60,p. 471 - 475.

18
[ 14651-42-4 ]
[ 39917-51-6 ]

References: [1]Journal of Organic Chemistry USSR (English Translation),1987,vol. 23,p. 875 - 880.
Zhurnal Organicheskoi Khimii,1987,vol. 23,p. 970 - 976.

19
[ 14651-42-4 ]
[ 39917-55-0 ]

References: [1]Journal of Organic Chemistry USSR (English Translation),1987,vol. 23,p. 875 - 880.
Zhurnal Organicheskoi Khimii,1987,vol. 23,p. 970 - 976.

20
[ 14651-42-4 ]
[ 19835-39-3 ]

References: [1]Journal of Organic Chemistry USSR (English Translation),1987,vol. 23,p. 875 - 880.
Zhurnal Organicheskoi Khimii,1987,vol. 23,p. 970 - 976.
[2]Journal of Organic Chemistry USSR (English Translation),1987,vol. 23,p. 875 - 880.
Zhurnal Organicheskoi Khimii,1987,vol. 23,p. 970 - 976.

21
[ 14651-42-4 ]
[ 61417-21-8 ]

References: [1]Journal of Organic Chemistry USSR (English Translation),1987,vol. 23,p. 875 - 880.
Zhurnal Organicheskoi Khimii,1987,vol. 23,p. 970 - 976.

22
[ 14651-42-4 ]
[ 114310-73-5 ]

References: [1]Journal of Organic Chemistry USSR (English Translation),1987,vol. 23,p. 875 - 880.
Zhurnal Organicheskoi Khimii,1987,vol. 23,p. 970 - 976.

23
[ 14651-42-4 ]
[ 114310-74-6 ]

References: [1]Journal of Organic Chemistry USSR (English Translation),1987,vol. 23,p. 875 - 880.
Zhurnal Organicheskoi Khimii,1987,vol. 23,p. 970 - 976.

24
[ 14651-42-4 ]
[ 114310-75-7 ]

References: [1]Journal of Organic Chemistry USSR (English Translation),1987,vol. 23,p. 875 - 880.
Zhurnal Organicheskoi Khimii,1987,vol. 23,p. 970 - 976.

25
[ 14651-42-4 ]
[ 244240-68-4 ]

References: [1]Journal of Organic Chemistry,1996,vol. 61,p. 722 - 726.

26
[ 14651-42-4 ]
[ 70624-80-5 ]

References: [1]Journal of Organic Chemistry,1996,vol. 61,p. 722 - 726.

27
[ 14651-42-4 ]
[ 51849-03-7 ]

References: [1]Journal of Organic Chemistry,1996,vol. 61,p. 722 - 726.

28
[ 14651-42-4 ]
1-((Z)-2-m-Tolyl-vinyl)-adamantane [ No CAS ]

References: [1]Journal of Organic Chemistry,1996,vol. 61,p. 722 - 726.

29
[ 14651-42-4 ]
1-((E)-2-m-Tolyl-vinyl)-adamantane [ No CAS ]

References: [1]Journal of Organic Chemistry,1996,vol. 61,p. 722 - 726.

30
[ 14651-42-4 ]
1-((Z)-2-p-Tolyl-vinyl)-adamantane [ No CAS ]

References: [1]Journal of Organic Chemistry,1996,vol. 61,p. 722 - 726.

31
[ 14651-42-4 ]
1-((E)-4-methylstyryl)adamantane [ No CAS ]

References: [1]Journal of Organic Chemistry,1996,vol. 61,p. 722 - 726.

32
[ 14651-42-4 ]
1-((Z)-2-o-Tolyl-vinyl)-adamantane [ No CAS ]

References: [1]Journal of Organic Chemistry,1996,vol. 61,p. 722 - 726.

33
[ 14651-42-4 ]
(E)-1-(1-adamantyl)-2-(2-methylphenyl)ethene [ No CAS ]

References: [1]Journal of Organic Chemistry,1996,vol. 61,p. 722 - 726.

34
[ 14651-42-4 ]
1-[(Z)-2-(3-Chloro-phenyl)-vinyl]-adamantane [ No CAS ]

References: [1]Journal of Organic Chemistry,1996,vol. 61,p. 722 - 726.

35
[ 14651-42-4 ]
1-[(E)-2-(3-Chloro-phenyl)-vinyl]-adamantane [ No CAS ]

References: [1]Journal of Organic Chemistry,1996,vol. 61,p. 722 - 726.

Historical Records

Technical Information

• Alkyl Halide Occurrence • General Reactivity • Grignard Reaction • Halogenation • Heat of Combustion • Hiyama Cross-Coupling Reaction • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Dihalides • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling

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[ 14651-42-4 ]

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H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 14651-42-4

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