75806-85-8|2,3,5-Tribromopyridine| Ambeed

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Quality Control of [ 75806-85-8 ] Purity: 98% SDS Specification

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Product Details of [ 75806-85-8 ]

CAS No. :	75806-85-8
Formula :	C₅H₂Br₃N
M.W :	315.79
SMILES Code :	BrC1=CN=C(Br)C(Br)=C1
MDL No. :	MFCD00233999
InChI Key :	BBHYMJRPJFVNPI-UHFFFAOYSA-N
Pubchem ID :	628798

Safety of [ 75806-85-8 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 75806-85-8 ]

* 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 [ 75806-85-8 ]

[ 75806-85-8 ] Synthesis Path-Downstream 1~35

1
[ 109-04-6 ]
[ 624-28-2 ]
[ 75806-85-8 ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1932,vol. 51,p. 940,949.

2
[ 625-92-3 ]
[ 75806-85-8 ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1932,vol. 51,p. 940,949.

3
[ 625-92-3 ]
[ 75806-85-8 ]
[ 2766-64-5 ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1932,vol. 51,p. 940,949.

4
[ 75806-85-8 ]
[ 35486-42-1 ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1916,vol. <2> 93,p. 371.

5
[ 75806-85-8 ]
2-ethoxy-3,5-dibromo-pyridine [ No CAS ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1949,vol. 68,p. 275,282.

6
[ 35486-42-1 ]
[ 75806-85-8 ]

References: [1]Synthesis,2010,p. 2804 - 2810.
[2]European Journal of Medicinal Chemistry,1989,vol. 24,p. 249 - 258.
[3]Journal of Organic Chemistry,2016,vol. 81,p. 4576 - 4587.

7
[ 75806-85-8 ]
[ 109-76-2 ]
[ 92993-50-5 ]
N,N'-Bis-(3,5-dibromo-pyridin-2-yl)-propane-1,3-diamine [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,1989,vol. 24,p. 249 - 258.

8
[ 75806-85-8 ]
ammonium hydroxide [ No CAS ]
[ 35486-42-1 ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1916,vol. <2> 93,p. 371.

10
1-methyl-3.5-dibromo-pyridone-⁽²⁾ [ No CAS ]
[ 75806-85-8 ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1916,vol. <2> 93,p. 371.

11
[ 14529-54-5 ]
[ 7789-60-8 ]
[ 7789-69-7 ]
[ 75806-85-8 ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1916,vol. <2> 93,p. 371.

12
[ 109-04-6 ]
[ 7726-95-6 ]
iron (II)-bromide [ No CAS ]
[ 624-28-2 ]
[ 75806-85-8 ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1932,vol. 51,p. 940,949.

13
[ 625-92-3 ]
[ 7726-95-6 ]
[ 75806-85-8 ]
[ 2766-64-5 ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1932,vol. 51,p. 386,949.

14
[ 75806-85-8 ]
ethanolic NaOH-solution [ No CAS ]
2-ethoxy-3,5-dibromo-pyridine [ No CAS ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1949,vol. 68,p. 275,282.

15
[ 75806-85-8 ]
[ 436799-34-7 ]

Yield	Reaction Conditions	Operation in experiment
83%		3-(5-Bromo-2-methoxypyridin-3-vO-NJV-dirnethylpropan-l -amine 1 ,2-dιmethoxyethane; Step 1 : 2-Iodo-3,5-dibromopyridine; To a sealed tube was added <strong>[75806-85-8]2,3,5-tribromopyridine</strong> (5.63 g, 17.83 mol), sodium iodide (8.02 g, 53.50 mol), propanenitrile (45 mL), and chlorotrimethylsilane (2.26 mL, 17.83 mol). The resulting mixture was allowed to stir for 50 min at 105 0C. The mixture was allowed to cool to rt and 2M NaOH(50 mL) was added. The mixture was extracted with EtOAc (2 x 80 mL). The organic solutions were combined, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give 2-iodo-3,5-dibromopyridine (5.4 g, 83%) as a solid.

References: [1]Patent: WO2010/65134,2010,A1 .Location in patent: Page/Page column 107-108.
[2]European Journal of Organic Chemistry,2002,p. 327 - 330.

16
[ 75806-85-8 ]
bis(2,5-dibromo-3-pyridyl) ditelluride [ No CAS ]

References: [1]European Journal of Inorganic Chemistry,2004,p. 4781 - 4788.

17
[ 75806-85-8 ]
3,5-dibromo-2-(trifluoromethyl)pyridine [ No CAS ]

References: [1]European Journal of Organic Chemistry,2002,p. 327 - 330.

18
[ 75806-85-8 ]
5-bromo-2-trifluoromethyl-3-pyridinecarboxylic acid [ No CAS ]

References: [1]European Journal of Organic Chemistry,2002,p. 327 - 330.

19
[ 75806-85-8 ]
[ 92993-51-6 ]

References: [1]European Journal of Medicinal Chemistry,1989,vol. 24,p. 249 - 258.

20
[ 75806-85-8 ]
[ 76175-77-4 ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1916,vol. <2> 93,p. 371.

21
[ 75806-85-8 ]
[ 99978-99-1 ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1916,vol. <2> 93,p. 371.

22
[ 75806-85-8 ]
[ 76175-78-5 ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1916,vol. <2> 93,p. 371.

23
[ 75806-85-8 ]
[ 584-08-7 ]
5-bromo-2,3-difluoropyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	In sulfolane;	EXAMPLE 5 To a 1 liter 3-necked flask equipped with a simple distillation head, thermometer, stirrer and heater was charged 72 g (0.47 mole) of dried CsF, 2.5 g of K2 CO3 and 400 ml of sulfolane. Ca. 20 ml of the solvent was distilled in vacuo to dry the ystem, and 50 (0.16 mole) of <strong>[75806-85-8]2,3,5-tribromopyridine</strong> was added. The mixture was heated to 180-190 C. for 7 hr. Vacuum distillation yielded a mixture which, by glpc analysis, showed the presence of a 45% of yield of 2,3-difluoro-5-bromopyridine, and small amounts of 2-fluoro-5-bromopyridine and 2,3,5-trifluoropyridine. Analysis of the residual material in the sulfolane showed the presence of 3,5-dibromo-2-fluoropyridine.

References: [1]Patent: US4822887,1989,A .

24
[ 75806-85-8 ]
[ 92993-50-5 ]

Yield	Reaction Conditions	Operation in experiment
		(i) Substituting <strong>[75806-85-8]2,3,5-tribromopyridine</strong> (8.0 g) for 2-bromo-5-methylpyridine and using the corresponding molar proportions of the other reagents in the method of Example 2(i) gave, after stripping the final chloroform extract, an oil which was taken back up in ether, washed with dilute sodium hydroxide, dried and stripped to give 2-(3-aminopropylamino)-3,5-dibromopyridine (3.88 g) which was used without further purification.

References: [1]Patent: US4548940,1985,A .

25
[ 75806-85-8 ]
[ 13472-60-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium methylate;	Referential Example 11. 3,5-Dibromo-2-methoxypyridine 80ml of a 28% sodium methoxide solution was incorporated with 30.0g of <strong>[75806-85-8]2,3,5-tribromopyridine</strong> under ice-cooling, followed by stirring at 50C for 2 hours. The reaction solution was diluted with water and extracted with diethyl ether. The organic layer was washed with brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel chromatography (ethyl acetate/hexane=1:20), to give 18.5g of the title compound. 1H-NMR (400MHz, CDCl3); δ(ppm) 3.99(s,3H), 7.93(d,1H), 8.14(d,1H).

References: [1]Patent: EP1300396,2003,A1 .

26
[ 75806-85-8 ]
[ 1220388-60-2 ]

References: [1]Journal of Organometallic Chemistry,2010,vol. 695,p. 648 - 652.

27
[ 75806-85-8 ]
[ 33513-42-7 ]
[ 852181-11-4 ]

References: [1]Synthesis,2010,p. 2804 - 2810.

28
[ 123-75-1 ]
[ 75806-85-8 ]
[ 1259313-59-1 ]

References: [1]Tetrahedron,2010,vol. 66,p. 9552 - 9559.

29
[ 110-91-8 ]
[ 75806-85-8 ]
[ 1259313-58-0 ]

References: [1]Tetrahedron,2010,vol. 66,p. 9552 - 9559.

30
[ 75806-85-8 ]
[ 31166-44-6 ]
[ 1259313-57-9 ]

References: [1]Tetrahedron,2010,vol. 66,p. 9552 - 9559.

31
[ 75806-85-8 ]
[ 57260-71-6 ]
[ 1223432-03-8 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In butanone; for 8h;Reflux;	To a mixture of <strong>[75806-85-8]2,3,5-tribromopyridine</strong> (10 g), 1-Boc-piperazine (6 g) and potassium carbonate (20 g) was added 2-butanone (80 mL), and the mixture was refluxed for 8 hr. After cooling, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solvent was evaporated to give 4-(3,5-dibromopyridin-2-yl)piperazine-1-carboxylic acid tert-butyl ester (13 g). To a mixture of 4-(3,5-dibromopyridin-2-yl)piperazine-1-carboxylic acid tert-butyl ester (13 g), bis(tricyclohexylphosphine)palladium (II) dichloride (1.3 g), tripotassium phosphate (38 g) and cyclopropylboronic acid (8.4 g) were added toluene (100 mL) and water (5 mL), and the mixture was refluxed for 8 hr. After cooling, the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solvent was evaporated. The residue was purified by column chromatography (hexane:ethyl acetate) to give 4-(3,5-dicyclopropylpyridin-2-yl)piperazine-1-carboxylic acid tert-butyl ester (7 g). 4-(3,5-Dicyclopropylpyridin-2-yl)piperazine-1-carboxylic acid tert-butyl ester (7 g) was dissolved in chloroform (25 mL), 4N hydrogen chloride/ethyl acetate (25 mL) was added, and the mixture was stirred at room temperature overnight. To the reaction mixture was added 1N aqueous sodium hydroxide solution (100 mL), and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, and the solvent was evaporated. The residue was dissolved in ethyl acetate (50 mL), 4N hydrogen chloride/ethyl acetate (8 mL) was added, and the mixture was filtered to give the title compound (3.2 g).
13 g	With potassium carbonate; In butanone; for 8h;Reflux;	[0399] Preparation Example 87: Preparation of 1-(3,5-dicyclopropylpyridin-2-yl)piperazine hydrochloride[0400][0401] To a mixture of <strong>[75806-85-8]2,3,5-tribromopyridine</strong> (10 g), 1-Boc-piperazine (6 g) and potassium carbonate (20 g) was added2-butanone (80 mL), and the mixture was stirred with heating under reflux for 8 hr. The reaction mixture was cooled,water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine,and the solvent was evaporated to give 4-(3,5-dibromopyridin-2-yl)piperazine-1-carboxylic acid tert-butyl ester (13 g).To a mixture of the obtained 4-(3,5-dibromopyridin-2-yl)piperazine-1-carboxylic acid tert-butyl ester (13 g), bis(tricyclohexylphosphine)palladium(II)dichloride (1.3 g), tripotassium phosphate (38 g) and cyclopropylboronic acid (8.4 g)were added toluene (100 mL) and water (5 mL), and the mixture was stirred with heating under reflux for 8 hr. Thereaction mixture was cooled, water was added, and the mixture was extracted with ethyl acetate. The organic layer waswashed with saturated brine, and the solvent was evaporated. The obtained residue was purified by column chromatography(hexane:ethyl acetate) to give 4-(3,5-dicyclopropylpyridin-2-yl)piperazine-1-carboxylic acid tert-butyl ester (7g). The obtained 4-(3,5-dicyclopropylpyridin-2-yl)piperazine-1-carboxylic acid tert-butyl ester (7 g) was dissolved in chloroform(25 mL), 4N hydrogen chloride/ethyl acetate (25 mL) was added, and the mixture was stirred at room temperatureovernight. To the reaction mixture was added 1N aqueous sodium hydroxide solution (100 mL), and the mixture wasextracted with chloroform. The organic layer was washed with saturated brine, and the solvent was evaporated. Theobtained residue was dissolved in ethyl acetate (50 mL), 4N hydrogen chloride/ethyl acetate (8 mL) was added, and theprecipitate was collected by filtration to give the title compound (3.2 g).

References: [1]Tetrahedron,2010,vol. 66,p. 9552 - 9559.
[2]Patent: EP2364975,2011,A1 .Location in patent: Page/Page column 32.
[3]Patent: EP2565182,2013,A1 .Location in patent: Paragraph 0399; 0400; 0401.

32
[ 75806-85-8 ]
[ 57260-71-6 ]
[ 1223432-04-9 ]

References: [1]Patent: EP2364975,2011,A1 .

33
[ 67-56-1 ]
[ 75806-85-8 ]
[ 13472-60-1 ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 10584 - 10600.

34
[ 75806-85-8 ]
[ 1415212-78-0 ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 10584 - 10600.

35
[ 75806-85-8 ]
[ 49667-34-7 ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 10584 - 10600.

Historical Records

Technical Information

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

Related Functional Groups of
[ 75806-85-8 ]

Bromides

A736097 [2402-91-7]

2,3,4-Tribromopyridine

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A411085 [2402-92-8]

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A156193 [13534-89-9]

2,3-Dibromopyridine

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A513026 [624-28-2]

2,5-Dibromopyridine

Similarity: 0.89

A164423 [36963-44-7]

3,4-Dibromoisoquinoline

Similarity: 0.87

Related Parent Nucleus of
[ 75806-85-8 ]

Pyridines

A736097 [2402-91-7]

2,3,4-Tribromopyridine

Similarity: 0.97

A411085 [2402-92-8]

2,3,6-Tribromopyridine

Similarity: 0.97

A156193 [13534-89-9]

2,3-Dibromopyridine

Similarity: 0.97

A513026 [624-28-2]

2,5-Dibromopyridine

Similarity: 0.89

A117225 [2408-70-0]

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Similarity: 0.81

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H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 75806-85-8

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