2,5-Dibromo-3-picoline supplier

Name
2,5-Dibromo-3-methylpyridine
EINECS -0
CAS No. 3430-18-0
Article Data13
CAS DataBase
Density 1.911 g/cm³
Solubility
Melting Point 43-47 °C(lit.)
Formula C₆H₅Br₂N
Boiling Point 260 °C at 760 mmHg
Molecular Weight 250.92
Flash Point 111.1 °C
Transport Information UN 2811 6.1/PG 3
Appearance Off-white to beige crystalline powder
Safety 26-36/37/39-36
Risk Codes 22-36/38-36/37/38-20/21/22
Molecular Structure
Hazard Symbols Xn， Xi
Synonyms pyridine, 2,5-dibromo-3-methyl-;2,5-Dibromo-3-methylpyridine;
PSA 12.89000
LogP 2.91500

Synthetic route

: 3430-21-5
5-bromo-3-methyl-pyridin-2-ylamine

: 3430-18-0
2,5-dibromo-3-methylpyridine

Conditions

Conditions	Yield
With hydrogen bromide; bromine; sodium nitrite In water at -15℃; for 3h;	94%
With hydrogen bromide; bromine; sodium nitrite In water at -15 - 23℃; for 3h;	94%
Stage #1: 5-bromo-3-methyl-pyridin-2-ylamine With hydrogen bromide; bromine at -15 - -10℃; Stage #2: With sodium nitrite at 15 - 20℃; Temperature;	91.8%

: 1603-40-3
3-methylpyridin-2-ylamine

: 3430-18-0
2,5-dibromo-3-methylpyridine

Conditions

Conditions	Yield
With hydrogen bromide; bromine; sodium nitrite 1.) bromination; 2.) water, -10 deg C, 1.5 h, 0 deg C, 0.5 h; Multistep reaction;
Multi-step reaction with 2 steps 1: N-Bromosuccinimide; ammonium acetate / acetonitrile / 0.42 h / 20 °C / Cooling with ice 2: hydrogen bromide; bromine; sodium nitrite / water / 3 h / -15 °C View Scheme
Multi-step reaction with 2 steps 1: N-Bromosuccinimide; ammonium acetate / acetonitrile / 0.42 h / 0 - 23 °C 2: hydrogen bromide; bromine; sodium nitrite / water / 3 h / -15 - 23 °C View Scheme

: 3430-18-0
2,5-dibromo-3-methylpyridine

: (R)-(+)-3-(dimethylamino)pyrrolidine

: [(R)-1-(5-bromo-3-methyl-pyridin-2-yl)-pyrrolidin-3-yl]-dimethyl-amine

Conditions

Conditions	Yield
With toluene-4-sulfonic acid at 100℃;	99%

: 3430-18-0
2,5-dibromo-3-methylpyridine

: 124-40-3
dimethyl amine

: N-(5-bromo-3-methyl-2-pyridyl)-N,N-dimethylamine

Conditions

Conditions	Yield
In water at 150℃; for 1h; Microwave irradiation;	98%
In water at 150℃; for 1h; Microwave irradiation;	98%

: 3430-18-0
2,5-dibromo-3-methylpyridine

: 376587-52-9
5-bromo-2-iodo-3-methylpyridine

Conditions

Conditions	Yield
With sodium iodide In acetyl chloride; acetonitrile for 24h; Reflux;	97%
With acetyl chloride; sodium iodide In acetonitrile for 24h; Reflux;	97%
With acetyl chloride; sodium iodide In acetonitrile for 16h; Reflux;	94.78%

: 110-91-8
morpholine

: 3430-18-0
2,5-dibromo-3-methylpyridine

: 566158-47-2
4-(5-bromo-3-methylpyridin-2-yl)morpholine

Conditions

Conditions	Yield
at 210℃; for 0.166667h; Sealed tube; Microwave irradiation;	97%
at 140℃; for 6h;

: 3430-18-0
2,5-dibromo-3-methylpyridine

: 75-05-8
acetonitrile

: 5-bromo-3-methyl-2-pyridineacetonitrile

Conditions

Conditions	Yield
Stage #1: acetonitrile With n-butyllithium In tetrahydrofuran at -78℃; for 0.916667h; Stage #2: 2,5-dibromo-3-methylpyridine In tetrahydrofuran at -78 - 20℃; for 2h;	97%
Stage #1: acetonitrile With n-butyllithium In tetrahydrofuran at -78℃; for 1.5h; Inert atmosphere; Stage #2: 2,5-dibromo-3-methylpyridine In tetrahydrofuran at 33℃; for 3h; Temperature;	86%

: 3430-18-0
2,5-dibromo-3-methylpyridine

: 100-51-6
benzyl alcohol

: 2-benzyloxy-5-bromo-3-methylpyridine

Conditions

Conditions	Yield
Stage #1: benzyl alcohol With sodium hydride In tetrahydrofuran for 1.5h; Reflux; Stage #2: 2,5-dibromo-3-methylpyridine In tetrahydrofuran at 20℃; for 12h; Reflux;	95%

: 3430-18-0
2,5-dibromo-3-methylpyridine

: 124-41-4
sodium methylate

: 2,5-dibromo-3-(methoxymethyl)pyridine

Conditions

Conditions	Yield
In methanol at 20℃; for 18h;	93%

: 3430-18-0
2,5-dibromo-3-methylpyridine

: 109-86-4
2-methoxy-ethanol

: 1288996-83-7
5-bromo-2-(2-methoxy-ethoxy)-3-methyl-pyridine

Conditions

Conditions	Yield
Stage #1: 2-methoxy-ethanol With sodium hydride In dimethyl sulfoxide; mineral oil at 20℃; for 0.5h; Stage #2: 2,5-dibromo-3-methylpyridine In dimethyl sulfoxide; mineral oil at 60℃; for 1h;	91%
Stage #1: 2-methoxy-ethanol With sodium hydride In dimethyl sulfoxide; mineral oils at 20℃; for 0.5h; Stage #2: 2,5-dibromo-3-methylpyridine In dimethyl sulfoxide; mineral oils at 60℃; for 1h;	91%

: 3430-18-0
2,5-dibromo-3-methylpyridine

: 2-{9H-pyrido[2,3-b]indol-9-yl}-9H-carbazole

: 9-(5-bromo-3-methylpyridin-2-yl)-2-{9H-pyrido[2,3-b]indol-9-yl}-9H-carbazole

Conditions

Conditions	Yield
With 1-methyl-1H-imidazole; copper(l) iodide; potassium carbonate In toluene at 120℃; for 16h; Sealed tube; Inert atmosphere;	90%

: 3430-18-0
2,5-dibromo-3-methylpyridine

: 124-41-4
sodium methylate

: 760207-87-2
5-bromo-2-methoxy-3-methylpyridine

Conditions

Conditions	Yield
In methanol at 120℃; for 0.666667h;	89%
Stage #1: 2,5-dibromo-3-methylpyridine; sodium methylate In methanol at 120℃; for 0.666667h; Stage #2: With hydrogenchloride In methanol; water at 0℃;	89%
In methanol at 100℃; for 2h; Inert atmosphere;	77.8%

: 3430-18-0
2,5-dibromo-3-methylpyridine

: 2516-33-8
Cyclopropylmethanol

: 1566224-20-1
5-bromo-2-(cyclopropylmethoxy)-3-methylpyridine

Conditions

Conditions	Yield
Stage #1: Cyclopropylmethanol With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.333333h; Stage #2: 2,5-dibromo-3-methylpyridine In N,N-dimethyl-formamide at 60℃;	89%

: 3430-18-0
2,5-dibromo-3-methylpyridine

: 75336-86-6
(2R)-methylpiperazine

: 878809-59-7
(R)-1-(5-bromo-3-methylpyridin-2-yl)-3-methylpiperazine

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl acetamide at 130℃; for 24h; Large scale;	88%
In N,N-dimethyl acetamide at 130℃; for 16h;
In N,N-dimethyl acetamide at 130℃; for 16h; Product distribution / selectivity;

: 3430-18-0
2,5-dibromo-3-methylpyridine

: 98-80-6
phenylboronic acid

: 1469759-14-5
5-bromo-3-methyl-2-phenylpyridine

Conditions

Conditions	Yield
With palladium diacetate; potassium carbonate; triphenylphosphine In methanol; acetonitrile at 50℃; for 24h; Suzuki Coupling; Inert atmosphere; regioselective reaction;	88%

: 3430-18-0
2,5-dibromo-3-methylpyridine

: 100-53-8
phenylmethanethiol

: 2-(benzylthio)-5-bromo-3-methylpyridine

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran at 0 - 20℃; for 4h;	86.9%

: 3430-18-0
2,5-dibromo-3-methylpyridine

: potassium 6-bromo-5-methylpyridin-3-yltrifluoroborate

Conditions

Conditions	Yield
Stage #1: 2,5-dibromo-3-methylpyridine With n-butyllithium; Triisopropyl borate In tetrahydrofuran; hexane at -78 - 20℃; for 2h; Inert atmosphere; Stage #2: With potassium hydrogen difluoride In tetrahydrofuran; hexane at 20℃;	85%

: 123-39-7
N-Methylformamide

: 3430-18-0
2,5-dibromo-3-methylpyridine

: 245765-66-6
(5-bromo-3-methylpyridin-2-yl)methylamine

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 100℃; for 3h; Temperature; Reagent/catalyst;	84.2%
Stage #1: N-Methylformamide With potassium tert-butylate In N,N-dimethyl-formamide at 20 - 80℃; for 1.5h; Stage #2: 2,5-dibromo-3-methylpyridine In N,N-dimethyl-formamide for 2h;	70.4%

: 3430-18-0
2,5-dibromo-3-methylpyridine

: 536-74-3
phenylacetylene

: 5-bromo-3-methyl-2-(phenylethynyl)pyridine

Conditions

Conditions	Yield
With copper(l) iodide; palladium(II) trifluoroacetate; palladium diacetate; diisopropylamine In methanol; acetonitrile for 24h; Reflux; Inert atmosphere; regioselective reaction;	84%

: 3430-18-0
2,5-dibromo-3-methylpyridine

: 151169-74-3
2,3-dichlorobenzeneboronic acid

: 5-bromo-2-(2,3-dichlorophenyl)-3-methylpyridine

Conditions

Conditions	Yield
With palladium diacetate; potassium carbonate; triphenylphosphine In methanol; acetonitrile at 50℃; for 24h; Inert atmosphere;	81%

: 3430-18-0
2,5-dibromo-3-methylpyridine

: 201230-82-2
carbon monoxide

: 62-53-3
aniline

: 213771-38-1
3-methyl-5-bromopyridine-2-N-phenylamide

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium diacetate In toluene; acetonitrile at 65℃; under 4137.29 Torr; for 48h; Product distribution / selectivity;	76%
With triethylamine; bis-triphenylphosphine-palladium(II) chloride In acetonitrile at 60℃; under 4137.29 Torr; for 72h; Product distribution / selectivity;	59%

...Expand

: 4394-85-8
4-morpholinecarboxaldehyde

: 3430-18-0
2,5-dibromo-3-methylpyridine

: 885167-81-7
6-bromo-5-methylpyridine-3-carbaldehyde

Conditions

Conditions	Yield
Stage #1: 2,5-dibromo-3-methylpyridine With isopropylmagnesium chloride In tetrahydrofuran at 0 - 25℃; for 3h; Stage #2: 4-morpholinecarboxaldehyde In tetrahydrofuran at 17 - 25℃; for 1h;	74%
Stage #1: 2,5-dibromo-3-methylpyridine With isopropylmagnesium chloride In tetrahydrofuran at 0 - 20℃; for 3h; Stage #2: 4-morpholinecarboxaldehyde In tetrahydrofuran at 20℃; for 1h;	74%
Stage #1: 2,5-dibromo-3-methylpyridine With isopropylmagnesium chloride In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; Stage #2: 4-morpholinecarboxaldehyde In tetrahydrofuran at 0℃; for 2.5h;

: 3430-18-0
2,5-dibromo-3-methylpyridine

: copper(l) cyanide

: 156072-86-5
5-bromo-3-methylpyridine-2-carbonitrile

Conditions

Conditions	Yield
In N,N-dimethyl-formamide for 2h; Reflux;	74%
In N,N-dimethyl-formamide for 2h; Reflux;	74%
In water; N,N-dimethyl-formamide	61.3%

: 3430-18-0
2,5-dibromo-3-methylpyridine

: 1415306-66-9
ethyl 3-[6-cyano-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-yl]-propanoate

: 1415306-74-9
Ethyl 3-(5-bromo-2’-cyano-3-methyl-2,3’-bipyridine-5’-yl)-propanoate

Conditions

Conditions	Yield
With potassium phosphate; palladium diacetate; triphenylphosphine In 1,4-dioxane; water at 80℃; for 4h; Inert atmosphere;	74%
Stage #1: 2,5-dibromo-3-methylpyridine With potassium phosphate; palladium diacetate; triphenylphosphine In 1,4-dioxane; water at 20℃; for 0.166667h; Suzuki Coupling; Inert atmosphere; Stage #2: ethyl 3-[6-cyano-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-yl]-propanoate In 1,4-dioxane; water at 80℃; for 2.5h; Suzuki Coupling; Inert atmosphere; regioselective reaction;	74%
With potassium phosphate; triphenylphosphine; palladium diacetate In 1,4-dioxane; water at 20 - 80℃; Inert atmosphere;

: 3430-18-0
2,5-dibromo-3-methylpyridine

: 201230-82-2
carbon monoxide

: 142-25-6
N,N',N'-trimethylenediamine

A: 5-bromo-3-methyl-pyridine-2-carboxylic acid (2-dimethylamino-ethyl)-methyl-amide

B: C18H31N5O2

Conditions

Conditions	Yield
With triethylamine; bis-triphenylphosphine-palladium(II) chloride In toluene; acetonitrile at 55℃; under 517.162 - 5171.62 Torr; for 6h;	A 72% B n/a

...Expand

: 3430-18-0
2,5-dibromo-3-methylpyridine

: 1169698-48-9
9-cyclopentyl-9H-pyrido[4′,3′:4,5]pyrrolo[2,3-d]pyrimidin-2-amine

: 1169698-68-3
N-(5-bromo-3-methyl-2-pyridinyl)-9-cyclopentyl-9H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-2-amine

Conditions

Conditions	Yield
With sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 140℃; for 1h; Microwave irradiation;	71%

: 92-54-6
4-phenyl-1-piperazine

: 3430-18-0
2,5-dibromo-3-methylpyridine

: 201230-82-2
carbon monoxide

A: C17H18BrN3O

B: C28H31N5O2

Conditions

Conditions	Yield
With triethylamine; bis-triphenylphosphine-palladium(II) chloride In toluene; acetonitrile at 55℃; under 517.162 - 5171.62 Torr; for 6h;	A 70% B n/a

...Expand

: 109-01-3
1-methyl-piperazine

: 3430-18-0
2,5-dibromo-3-methylpyridine

: 201230-82-2
carbon monoxide

A: C12H16BrN3O

B: C18H27N5O2

Conditions

Conditions	Yield
With triethylamine; bis-triphenylphosphine-palladium(II) chloride In toluene; acetonitrile at 55℃; under 517.162 - 5171.62 Torr; for 6h;	A 69% B n/a

...Expand

: 3430-18-0
2,5-dibromo-3-methylpyridine

: 3430-16-8
5-bromo-3-picoline

Conditions

Conditions	Yield
With sodium tetrahydroborate; N,N,N,N,-tetramethylethylenediamine; palladium diacetate; triphenylphosphine In tetrahydrofuran at 25℃; for 0.5h; Inert atmosphere; regioselective reaction;	68%

: 3430-18-0
2,5-dibromo-3-methylpyridine

: 201230-82-2
carbon monoxide

: 75-64-9
tert-butylamine

A: C16H25N3O2

B: 156072-91-2
5-bromo-N-(tert-butyl)-3-methylpicolinamide

Conditions

Conditions	Yield
With triethylamine; bis-triphenylphosphine-palladium(II) chloride In toluene; acetonitrile at 55℃; under 517.162 - 5171.62 Torr; for 6h;	A n/a B 67%

...Expand

: 3430-18-0
2,5-dibromo-3-methylpyridine

: 17231-95-7
2,3-dichlorobenzenethiol

: 5-bromo-2-(2,3-dichlorophenyl)sulfanyl-3-methyl-pyridine

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 25℃; Heating;	67%

2,5-Dibromo-3-picoline Chemical Properties

Molecular Structure of 2,5-Dibromo-3-picoline (CAS NO.3430-18-0):

IUPAC Name: 2,5-dibromo-3-methylpyridine
Empirical Formula: C₆H₅Br₂N
Molecular Weight: 250.9186
H bond acceptors: 1
H bond donors: 0
Freely Rotating Bonds: 0
Polar Surface Area: 12.89 Å²
Index of Refraction: 1.593
Molar Refractivity: 44.54 cm³
Molar Volume: 131.3 cm³
Surface Tension: 44.9 dyne/cm
Density: 1.911 g/cm³
Flash Point: 111.1 °C
Enthalpy of Vaporization: 47.76 kJ/mol
Boiling Point: 260 °C at 760 mmHg
Vapour Pressure: 0.0203 mmHg at 25°C
Melting point: 42-47 ^oC
SMILES: Cc1cc(cnc1Br)Br
InChI: InChI=1/C6H5Br2N/c1-4-2-5(7)3-9-6(4)8/h2-3H,1H3
Product Categories: Pyridine; Pyridines, Pyrimidines, Purines and Pteredines; Halides; Pyridines; Bromopyridines; Halopyridines; Boronic Acid; C6Heterocyclic Building Blocks; Halogenated Heterocycles; Heterocyclic Building Blocks

2,5-Dibromo-3-picoline Safety Profile

Hazard Codes: Harmful Xn, Irritant Xi
Risk Statements: 22-36/38-36/37/38-20/21/22
R22:Harmful if swallowed.
R36/38:Irritating to eyes and skin.
R36/37/38:Irritating to eyes, respiratory system and skin.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 26-36/37/39-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S36:Wear suitable protective clothing.
RIDADR: UN 2811 6.1/PG 3
WGK Germany: 3
HazardClass: 6.1
PackingGroup: III

2,5-Dibromo-3-picoline Specification

2,5-Dibromo-3-picoline , with CAS number of 3430-18-0, can be called 2,5-Dibromo-3-methylpyridine ; 2,5-Dibromo-3-methylpyridine ; pyridine, 2,5-dibromo-3-methyl- . It is an off-white to beige crystalline powder.

Product Name

2,5-Dibromo-3-methylpyridine

Synthetic route

2,5-Dibromo-3-picoline Chemical Properties

2,5-Dibromo-3-picoline Safety Profile

2,5-Dibromo-3-picoline Specification

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