Product Name

  • Name

    2-Amino-5-bromo-3-methylpyridine

  • EINECS -0
  • CAS No. 3430-21-5
  • Article Data17
  • CAS DataBase
  • Density 1.593 g/cm3
  • Solubility
  • Melting Point 88-95 °C(lit.)
  • Formula C6H7BrN2
  • Boiling Point 250 °C at 760 mmHg
  • Molecular Weight 187.039
  • Flash Point 105 °C
  • Transport Information
  • Appearance Yellow Solid
  • Safety 26-36
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 3430-21-5 (2-Amino-5-bromo-3-methylpyridine)
  • Hazard Symbols IrritantXi
  • Synonyms 5-bromo-3-methyl-pyridin-2-amine;5-bromo-3-methyl-1H-pyridin-2-amine;2-Amino-5-Bromo-3-picoline;2-Amina-5-bromo-3-picoline;5-bromo-3-methylpyridin-2-amine;2-amino-3-methyl-5-bromopyridine;5-Bromo-3-methyl-pyridin-2-ylamine;
  • PSA 38.91000
  • LogP 2.31590

Synthetic route

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

3-methylpyridin-2-ylamine

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

5-bromo-3-methyl-pyridin-2-ylamine

Conditions
ConditionsYield
Stage #1: 3-methylpyridin-2-ylamine With bromine In dichloromethane at 0 - 20℃; for 4.66667h;
Stage #2: With sodium hydroxide In dichloromethane; water pH=9;		100%
With 1-butyl-3-methylpyridinium tribromide at 20℃;97%
With bromine; iodine; acetic acid at 0 - 10℃; Reagent/catalyst; Temperature;95.2%
N-(2-pyridyl-3-methyl)acetamide
7463-30-1

N-(2-pyridyl-3-methyl)acetamide

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

5-bromo-3-methyl-pyridin-2-ylamine

Conditions
ConditionsYield
Stage #1: N-(2-pyridyl-3-methyl)acetamide With bromine at 55℃; for 2.5h;
Stage #2: With sodium hydroxide In water for 0.5h; Temperature;
Stage #1: N-(2-pyridyl-3-methyl)acetamide With bromine at 55℃; for 2.5h;
Stage #2: With water; sodium hydroxide for 0.5h; Temperature;
5-bromo-3-methyl-pyridin-2-ylamine
3430-21-5

5-bromo-3-methyl-pyridin-2-ylamine

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

ethyl N-(5-bromo-3-methylpyridin-2-yl)carboximidate

ethyl N-(5-bromo-3-methylpyridin-2-yl)carboximidate

Conditions
ConditionsYield
With toluene-4-sulfonic acid at 85℃; for 1h; Temperature;99%
5-bromo-3-methyl-pyridin-2-ylamine
3430-21-5

5-bromo-3-methyl-pyridin-2-ylamine

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

2,5-dibromo-3-methylpyridine

Conditions
ConditionsYield
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%
benzyl bromide
100-39-0

benzyl bromide

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

5-bromo-3-methyl-pyridin-2-ylamine

2-dibenzylamino-5-bromo-3-methylpyridine

2-dibenzylamino-5-bromo-3-methylpyridine

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran; N,N-dimethyl acetamide at 0℃; for 16h;94%
5-bromo-3-methyl-pyridin-2-ylamine
3430-21-5

5-bromo-3-methyl-pyridin-2-ylamine

2-amino-3-methyl-5-iodopyridine
166266-19-9

2-amino-3-methyl-5-iodopyridine

Conditions
ConditionsYield
With copper(l) iodide; 2,3-dimethyl-2,3-diaminobutane; sodium iodide In 1,4-dioxane at 110℃;93%
ethyl O-(2-mesitylenesulfonyl)acetohydroxamate
38202-27-6

ethyl O-(2-mesitylenesulfonyl)acetohydroxamate

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

5-bromo-3-methyl-pyridin-2-ylamine

5-bromo-3-methyl-1λ4-pyridine-1,2-diamine 2,4,6-trimethylbenzenesulfonate

5-bromo-3-methyl-1λ4-pyridine-1,2-diamine 2,4,6-trimethylbenzenesulfonate

Conditions
ConditionsYield
Stage #1: ethyl O-(2-mesitylenesulfonyl)acetohydroxamate With perchloric acid In 1,4-dioxane at 0 - 20℃; for 0.5h;
Stage #2: 5-bromo-3-methyl-pyridin-2-ylamine In dichloromethane at 0 - 20℃; for 1h;		93%
ethyl 4,4,4-trifluoro-2-butynate
79424-03-6

ethyl 4,4,4-trifluoro-2-butynate

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

5-bromo-3-methyl-pyridin-2-ylamine

7-bromo-9-methyl-4-trifluoromethylpyrido[1,2-a]pyrimidin-2-one

7-bromo-9-methyl-4-trifluoromethylpyrido[1,2-a]pyrimidin-2-one

Conditions
ConditionsYield
In ethanol at 20℃; for 7h; Inert atmosphere;85%
5-bromo-3-methyl-pyridin-2-ylamine
3430-21-5

5-bromo-3-methyl-pyridin-2-ylamine

trimethyl orthoformate
149-73-5

trimethyl orthoformate

(E)-(ethyl N-(5-bromo-3-methylpyridin-2-yl)carboximidate)

(E)-(ethyl N-(5-bromo-3-methylpyridin-2-yl)carboximidate)

Conditions
ConditionsYield
With toluene-4-sulfonic acid In dichloromethane for 16h; Reflux; Industrial scale;84.4%
5-bromo-3-methyl-pyridin-2-ylamine
3430-21-5

5-bromo-3-methyl-pyridin-2-ylamine

5-bromo-2-hydroxy-3-methyl pyridine
89488-30-2

5-bromo-2-hydroxy-3-methyl pyridine

Conditions
ConditionsYield
With sodium nitrite In dichloromethane; sulfuric acid; water84%
With sulfuric acid; sodium nitrite In water at 0 - 20℃; for 1.5h;84%
With sulfuric acid; water; sodium nitrite at 0 - 20℃; for 0.5h;
zinc(II) cyanide
557-21-1

zinc(II) cyanide

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

5-bromo-3-methyl-pyridin-2-ylamine

6-amino-5-methyl-pyridine-3-carbonitrile
183428-91-3

6-amino-5-methyl-pyridine-3-carbonitrile

Conditions
ConditionsYield
With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) In water; N,N-dimethyl-formamide at 120℃; for 16h;81%
With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) In water; N,N-dimethyl-formamide at 120℃; for 16h; Inert atmosphere;81%
With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) In water; N,N-dimethyl-formamide at 120℃; for 24h;79%
5-bromo-3-methyl-pyridin-2-ylamine
3430-21-5

5-bromo-3-methyl-pyridin-2-ylamine

chloroacetone
78-95-5

chloroacetone

6-bromo-8-methyl-2-methylimidazo[1,2-a]pyridine

6-bromo-8-methyl-2-methylimidazo[1,2-a]pyridine

Conditions
ConditionsYield
In acetonitrile at 100 - 110℃; Inert atmosphere;81%
In neat (no solvent) at 90℃; for 0.5h;30%
5-bromo-3-methyl-pyridin-2-ylamine
3430-21-5

5-bromo-3-methyl-pyridin-2-ylamine

bromoacetaldehyde
17157-48-1

bromoacetaldehyde

6-bromo-8-methylimidazo[1,2-a]pyridine
217435-65-9

6-bromo-8-methylimidazo[1,2-a]pyridine

Conditions
ConditionsYield
In ethanol for 4h; Heating;78%
5-bromo-3-methyl-pyridin-2-ylamine
3430-21-5

5-bromo-3-methyl-pyridin-2-ylamine

ethyl 2-bromo-3-oxopentanoate
87943-99-5

ethyl 2-bromo-3-oxopentanoate

6-bromo-2-ethyl-8-methylimidazo[1,2-a]pyridine-3-carboxylic acid ethyl ester

6-bromo-2-ethyl-8-methylimidazo[1,2-a]pyridine-3-carboxylic acid ethyl ester

Conditions
ConditionsYield
In ethanol for 3h; Reflux;77.5%
In butan-1-ol at 100℃; for 3h; Reagent/catalyst; Large scale;77.6%
In ethanol for 3h; Reflux;71.5%
aconic acid
585-68-2

aconic acid

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

5-bromo-3-methyl-pyridin-2-ylamine

2-[7-bromo-9-methyl-2-oxo-2H-pyrido[1,2-a]pyrimidin-3(4H)-ylidene]acetic acid

2-[7-bromo-9-methyl-2-oxo-2H-pyrido[1,2-a]pyrimidin-3(4H)-ylidene]acetic acid

Conditions
ConditionsYield
In ethanol at 20℃;76%
acetic anhydride
108-24-7

acetic anhydride

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

5-bromo-3-methyl-pyridin-2-ylamine

5-bromo-2-diacetylamino-3-methylpyridine

5-bromo-2-diacetylamino-3-methylpyridine

Conditions
ConditionsYield
With acetic acid for 4h; Heating;75%
With pyridine at 100℃;70%
5-bromo-3-methyl-pyridin-2-ylamine
3430-21-5

5-bromo-3-methyl-pyridin-2-ylamine

tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-1(2H)-pyridinecarboxylate
375853-82-0, 286961-14-6

tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-1(2H)-pyridinecarboxylate

tert-butyl 4-(6-amino-5-methyl-3-pyridyl)-3,6-dihydro-2H-pyridine-1-carboxylate

tert-butyl 4-(6-amino-5-methyl-3-pyridyl)-3,6-dihydro-2H-pyridine-1-carboxylate

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In water; acetonitrile at 70℃; for 1h; Large scale;74%
ethyl Bromopyruvate
70-23-5

ethyl Bromopyruvate

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

5-bromo-3-methyl-pyridin-2-ylamine

ethyl 6-bromo-8-methylimidazo[1,2-a]pyridine-2-carboxylate
907945-82-8

ethyl 6-bromo-8-methylimidazo[1,2-a]pyridine-2-carboxylate

Conditions
ConditionsYield
In ethanol at 90℃; for 16h;73.5%
In 1,2-dimethoxyethane; ethanol at 20℃; for 4.5h; Heating / reflux;
5-bromo-3-methyl-pyridin-2-ylamine
3430-21-5

5-bromo-3-methyl-pyridin-2-ylamine

phenylacetylene
536-74-3

phenylacetylene

3-methyl-5-(phenylethynyl)pyridin-2-amine

3-methyl-5-(phenylethynyl)pyridin-2-amine

Conditions
ConditionsYield
With tetrabutylammomium bromide; sodium acetate In dimethyl sulfoxide at 120℃; for 45h; Sonogashira Cross-Coupling; Inert atmosphere;73%
methyl 3-hydroxy-2-methylidene-3-phenylpropionate
18020-59-2

methyl 3-hydroxy-2-methylidene-3-phenylpropionate

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

5-bromo-3-methyl-pyridin-2-ylamine

3-benzyl-7-bromo-9-methyl-2H-pyrido[1,2-a]pyrimidin-2-one

3-benzyl-7-bromo-9-methyl-2H-pyrido[1,2-a]pyrimidin-2-one

Conditions
ConditionsYield
With 1,1,1,3',3',3'-hexafluoro-propanol Reflux;72%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

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

5-bromo-3-methyl-pyridin-2-ylamine

2-[N,N-bis(tert-butoxycarbonyl)amino]-5-bromo-3-methylpyridine
497159-91-8

2-[N,N-bis(tert-butoxycarbonyl)amino]-5-bromo-3-methylpyridine

Conditions
ConditionsYield
With dmap In tert-butyl alcohol71%
With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1.83333h; Inert atmosphere;
4-Cyanophenacyl bromide
20099-89-2

4-Cyanophenacyl bromide

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

5-bromo-3-methyl-pyridin-2-ylamine

2-(4-cyanophenyl)-6-bromo-8-methylimidazo[1,2-a]pyridine
864941-97-9

2-(4-cyanophenyl)-6-bromo-8-methylimidazo[1,2-a]pyridine

Conditions
ConditionsYield
In ethanol for 24h; Heating;71%

2-Amino-5-bromo-3-methylpyridine Chemical Properties

Molecular Structure of 2-Amino-5-bromo-3-methylpyridine (CAS NO.3430-21-5):

IUPAC Name: 5-bromo-3-methylpyridin-2-amine 
Empirical Formula: C6H7BrN2
Molecular Weight: 187.0372
H bond acceptors: 2
H bond donors: 2
Freely Rotating Bonds: 0
Polar Surface Area: 16.13 Å2
Index of Refraction: 1.617
Molar Refractivity: 41.09 cm3
Molar Volume: 117.3 cm3
Surface Tension: 52 dyne/cm
Density: 1.593 g/cm3
Flash Point: 105 °C
Enthalpy of Vaporization: 48.72 kJ/mol
Boiling Point: 250 °C at 760 mmHg
Vapour Pressure: 0.0222 mmHg at 25°C
Melting point: 88-95 °C(lit.)
Sensitive: Hygroscopic
BRN: 386426
InChI
InChI=1/C6H7BrN2/c1-4-2-5(7)3-9-6(4)8/h2-3H,1H3,(H2,8,9)
Smiles
n1c(c(C)cc(c1)Br)N
Product Categories: Pyridine; Amines and Anilines; Heterocycles; Pyridines, Pyrimidines, Purines and Pteredines; Amines; Pyridines; Heterocyclic Compounds; Chemical Amines; Anilines, Amides & Amines; Bromine Compounds; Miscellaneous Compounds; Bromopyridines; Halopyridines; Bases & Related Reagents; Heterocyclic; Nucleotides; Boronic Acid; C6Heterocyclic Building Blocks; Halogenated Heterocycles; Heterocyclic Building Blocks

2-Amino-5-bromo-3-methylpyridine Safety Profile

Hazard Codes oF 2-Amino-5-bromo-3-methylpyridine (CAS NO.3430-21-5): XiIrritant
Risk Statements: 36/37/38
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36:Wear suitable protective clothing.
WGK Germany: 3
Hazard Note: Irritant
HazardClass: Irritant

2-Amino-5-bromo-3-methylpyridine Specification

  2-Amino-5-bromo-3-methylpyridine , with CAS number of 3430-21-5, can be called 2-pyridinamine, 5-bromo-3-methyl- ; 5-Bromo-3-methylpyridin-2-amine . It is a yellow solid.

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