3-Amino-2-bromopyridine supplier

Name
3-Amino-2-bromopyridine
EINECS -0
CAS No. 39856-58-1
Article Data13
CAS DataBase
Density 1.71 g/cm³
Solubility Slightly soluble in water.
Melting Point 76-80 °C
Formula C₅H₅BrN₂
Boiling Point 292.5 °C at 760 mmHg
Molecular Weight 173.012
Flash Point 130.7 °C
Transport Information UN 2811 6.1/PG 3
Appearance Light yellow Cryst.
Safety 26-36/39-37/39
Risk Codes 22-37/38-41-36/37/38
Molecular Structure
Hazard Symbols Xi, Xn
Synonyms 2-bromopyridin-3-amine;2-bromo-pyridin-3-ylamine;2-Bromo-3-aminopyridine;
PSA 38.91000
LogP 2.00750

Synthetic route

: 19755-53-4
2-bromo-3-nitropyridine

: 39856-58-1
3-amino-2-bromopyridine

Conditions

Conditions	Yield
With iron; ammonium chloride In tetrahydrofuran; water at 60 - 70℃; for 5h;	100%
With aluminum (III) chloride; iron In tetrahydrofuran; water	100%
With iron; acetic acid for 2h; Heating;	66%
With iron; acetic acid at 100℃;
With iron In acetic acid

: 87674-18-8
2-bromonicotinamide

: 39856-58-1
3-amino-2-bromopyridine

Conditions

Conditions	Yield
With sodium hydroxide; bromine In water 1) 0.5 hr, rt; 2) 3hr, 80 deg C;	75%

: 462-08-8
pyridin-3-ylamine

A: 13534-97-9
6-bromopyridine-3-amine

B: 39856-58-1
3-amino-2-bromopyridine

C: 39856-57-0
2,6-dibromo-3-aminopyridine

Conditions

Conditions	Yield
With N-Bromosuccinimide In methanol at 20℃; for 144h;	A 6 % Spectr. B 43% C 20 % Spectr.
With N-Bromosuccinimide In acetonitrile at 20℃; for 24h;	A 32 % Spectr. B 40 % Spectr. C 14 % Spectr.

...Expand

: 462-08-8
pyridin-3-ylamine

: 39856-58-1
3-amino-2-bromopyridine

Conditions

Conditions	Yield
With N-Bromosuccinimide In acetonitrile at 20℃; for 20h;	12%
With D-glucose; Escherichia coli flavin reductase; Bacillus megaterium glucose dehydrogenase; Lechevalieria aerocolonigenes tryptophan-7-halogenase; flavin adenine dinucleotide; NADH In aq. phosphate buffer; isopropyl alcohol pH=7.4; Enzymatic reaction;

: 4214-75-9
2-amino-3-nitropyridine

: 39856-58-1
3-amino-2-bromopyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: HBr 47 percent; NaNO2 1.2: CuBr 2.1: Fe / acetic acid View Scheme

: 6332-56-5
2-hydroxy-3-nitropyridine

: 39856-58-1
3-amino-2-bromopyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: bromine; phosphorus (III)-bromide / 100 °C 2: iron-turnings; acetic acid / 100 °C View Scheme

: 462-08-8
pyridin-3-ylamine

N-bromo-succinimide (NBS): N-bromo-succinimide (NBS)

: 39856-58-1
3-amino-2-bromopyridine

Conditions

Conditions	Yield
In trifluoroacetic acid

: 39856-58-1
3-amino-2-bromopyridine

: 591-50-4
iodobenzene

: 2-bromo-N-phenylpyridin-3-amine

Conditions

Conditions	Yield
With 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene at 110℃; for 6h; Sealed tube;	99%
With tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; sodium t-butanolate In toluene at 110℃; for 6h; Sealed tube;	99%
With 1,1'-bis-(diphenylphosphino)ferrocene; sodium t-butanolate; tris(dibenzylideneacetone)dipalladium (0) In toluene at 100℃; for 17h; Cross-coupling;	64%
With sodium t-butanolate; 1,1'-bis-(diphenylphosphino)ferrocene; tris(dibenzylideneacetone)dipalladium (0) In toluene at 100℃; for 14h;	36.6%
Stage #1: 3-amino-2-bromopyridine With copper(l) iodide; palladium 10% on activated carbon; caesium carbonate; triphenylphosphine at 20℃; for 0.25h; Inert atmosphere; Stage #2: iodobenzene at 95 - 100℃; for 2.5h; Inert atmosphere;

: 39856-58-1
3-amino-2-bromopyridine

: 1374041-14-1
tert-butyl [(2S)-1-{[tert-butyl(diphenyl)silyl]oxy}but-3-yn-2-yl]carbamate

: 1374041-15-2
tert-butyl [(2S)-4-(3-aminopyridin-2-yl)-1-{[tert-butyl(diphenyI)silyl]oxy}but-3-yn-2-yl]carbamate

Conditions

Conditions	Yield
Stage #1: 3-amino-2-bromopyridine; tert-butyl [(2S)-1-{[tert-butyl(diphenyl)silyl]oxy}but-3-yn-2-yl]carbamate With triethylamine; bis-triphenylphosphine-palladium(II) chloride In acetonitrile at 20℃; for 0.0833333h; Stage #2: With copper(l) iodide In acetonitrile at 52℃; for 4.5h; Inert atmosphere;	99%

: 39856-58-1
3-amino-2-bromopyridine

: (S)-(2-(1-((tert-butoxycarbonyl)amino)but-3-en-1-yl)pyridin-4-yl)boronic acid trifluoroacetic acid

: (S)-tert-butyl (1-(3-amino-[2,4‘-bipyridin]-2‘-yl)but-3-en-1yl)carbamate

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane at 120℃; for 0.5h; Inert atmosphere;	99%

: 39856-58-1
3-amino-2-bromopyridine

: 62348-22-5
2-methyl-1,3-oxazole-4-carboxylic acid chloride

: N-(2-bromopyridin-3-yl)-2-methyl-1,3-oxazole-4-carboxamide

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0 - 40℃; for 18h; Inert atmosphere;	98%

: 39856-58-1
3-amino-2-bromopyridine

: 140-89-6
potassium ethyl xanthogenate

: 57135-09-8
2-mercaptothiazolo[5,4-b]pyridine

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 130℃;	97%

: 39856-58-1
3-amino-2-bromopyridine

: 586-75-4
4-chlorobenzoyl chloride

: 4-bromo-N-(2-bromopyridin-3-yl)benzamide

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 0 - 20℃; for 4h; Inert atmosphere;	97%

: 39856-58-1
3-amino-2-bromopyridine

: 540-80-7
tert.-butylnitrite

: 75-89-8
2,2,2-trifluoroethanol

: 2-bromo-3-(2,2,2-trifluoroethoxy)pyridine

Conditions

Conditions	Yield
With methanesulfonic acid	96%

...Expand

: 39856-58-1
3-amino-2-bromopyridine

: 3-amino-2-iodopyridine

Conditions

Conditions	Yield
With copper(l) iodide; trans-N,N'-dimethylcyclohexane-1,2-diamine; sodium iodide In 1,4-dioxane at 110℃; for 24h;	94%

: 39856-58-1
3-amino-2-bromopyridine

: 1204-70-2
2-phenyl-1,3-oxazole-4-carbonyl chloride

: N-(2-bromopyridin-3-yl)-2-phenyl-1,3-oxazole-4-carboxamide

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0 - 40℃; for 18h; Inert atmosphere;	94%

: 39856-58-1
3-amino-2-bromopyridine

: 657425-07-5
4-chloro-2-ethynyl-1-fluorobenzene

: 2-((5-chloro-2-fluorophenyl)ethynyl)pyridin-3-amine

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In N,N-dimethyl-formamide at 110℃; for 1h; Inert atmosphere;	94%

: 39856-58-1
3-amino-2-bromopyridine

: 3282-30-2
pivaloyl chloride

: 835882-02-5
N-(2-bromopyridin-3-yl)trimethylacetamide

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 3h;	93%
With triethylamine In dichloromethane at 0 - 20℃; for 3h;	93%
With triethylamine In dichloromethane at 0 - 20℃; for 1h;	90%

: 39856-58-1
3-amino-2-bromopyridine

: 109-94-4
formic acid ethyl ester

: 1160653-52-0
N-(2-bromopyridin-3-yl)formamide

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 24h;	91%

: 39856-58-1
3-amino-2-bromopyridine

: 93-10-7
quinoline-2-carboxylic acid

: N-(2-bromo-3-pyridyl)quinoline-2-carboxamide

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 15h;	91%

: 39856-58-1
3-amino-2-bromopyridine

: 1692-25-7
3-pyridylboronic acid

: 101002-03-3
2-bromo-3,3'-bipyridine

Conditions

Conditions	Yield
With bis(η3-allyl-μ-chloropalladium(II)); N,N,N′,N′-tetra(diphenylphosphinomethyl)-1,2-ethylenediamine; potassium carbonate In N,N-dimethyl acetamide; butan-1-ol at 110℃; for 20h; Suzuki Coupling; Inert atmosphere;	90%

: 100-48-1
pyridine-4-carbonitrile

: 39856-58-1
3-amino-2-bromopyridine

: 1505566-25-5
C11H9BrN4

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃;	90%

: 39856-58-1
3-amino-2-bromopyridine

: 106-95-6
allyl bromide

: 1013629-47-4
2-bromo-3-(N,N-diallylamino)pyridine

Conditions

Conditions	Yield
Stage #1: 3-amino-2-bromopyridine With sodium hexamethyldisilazane In tetrahydrofuran at -78℃; Inert atmosphere; Stage #2: allyl bromide In tetrahydrofuran at -78℃; Inert atmosphere;	87%

: 39856-58-1
3-amino-2-bromopyridine

: 1809-20-7
diisopropyl hydrogenphosphonate

: diisopropyl 3-aminopyridin-2-ylphosphonate

Conditions

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; N-ethyl-N,N-diisopropylamine In 1,2-dimethoxyethane; N,N-dimethyl-formamide at 115℃; for 24h; Solvent; Inert atmosphere;	87%

: 39856-58-1
3-amino-2-bromopyridine

: 75318-43-3
4,5-dichloro-1,2,3-dithiazolium chloride

: (Z)-2-bromo-N-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)pyridin-3-amine

Conditions

Conditions	Yield
With pyridine In dichloromethane at 20℃; Inert atmosphere;	87%

: 39856-58-1
3-amino-2-bromopyridine

: 98-88-4
benzoyl chloride

: 942220-36-2
N-(2-bromopyridin-3-yl)benzamide

Conditions

Conditions	Yield
With pyridine In dichloromethane at 0 - 25℃; for 16h;	86%
With pyridine at -10 - 20℃;	74%
With dmap; triethylamine In dichloromethane at 20℃; for 0.5h; Inert atmosphere;
for 3h;	161 mg

: 39856-58-1
3-amino-2-bromopyridine

: 74-88-4
methyl iodide

: 872492-60-9
N-(2-bromopyridin-3-yl)-N-methylamine

Conditions

Conditions	Yield
Stage #1: 3-amino-2-bromopyridine With lithium diisopropyl amide In tetrahydrofuran at 0℃; for 1h; Stage #2: methyl iodide In tetrahydrofuran at -78 - 20℃;	85%

: 39856-58-1
3-amino-2-bromopyridine

: 125097-83-8
methyl 1-tert-butoxycarbonyl-1,2,5,6-tetrahydropyridine-3-carboxylate

: 320774-02-5
tert-butyl 3-[(2-bromo-3-pyridyl)carbamoyl]-1,2,5,6-tetrahydropyridine-1-carboxylate

Conditions

Conditions	Yield
With trimethylaluminum In dichloromethane at 0℃; Heating / reflux;	85%

: 39856-58-1
3-amino-2-bromopyridine

: 6783-05-7
trans-2-phenylvinylboronic acid

: (E)-2-styrylpyridin-3-amine

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 100℃; for 16h; Suzuki Coupling; Inert atmosphere;	85%

: 39856-58-1
3-amino-2-bromopyridine

: 3333-24-2
4-bromo-1,2-dihydronaphthalene

: 25726-64-1
6,11-dihydro-5H-benzo[g]pyrido[3,2-b]indole

Conditions

Conditions	Yield
With bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate; XPhos In tert-butyl alcohol at 110℃; for 24h; Sealed tube; Inert atmosphere;	85%

: 39856-58-1
3-amino-2-bromopyridine

: 772-38-3
4-tert-Butylphenylacetylene

: 2-(4-(tert-butyl)phenyl)-1H-pyrrolo[3,2-b]pyridine

Conditions

Conditions	Yield
Stage #1: 3-amino-2-bromopyridine; 4-tert-Butylphenylacetylene With bis-triphenylphosphine-palladium(II) chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; di(1-adamantyl)benzylphosphonium hydrobromide In dimethyl sulfoxide at 100℃; for 1h; Schlenk technique; Inert atmosphere; Stage #2: With potassium tert-butylate In dimethyl sulfoxide at 100℃; for 0.25h; Schlenk technique; Inert atmosphere;	85%

: 39856-58-1
3-amino-2-bromopyridine

: 35037-73-1
1-isocyanato-4-trifluoromethoxy-benzene

: 917966-91-7
1-(2-bromopyridin-3-yl)-3-(4-(trifluoromethoxy)phenyl)urea

Conditions

Conditions	Yield
In tetrahydrofuran at 23℃; for 16h;	84%

: 39856-58-1
3-amino-2-bromopyridine

: 98-80-6
phenylboronic acid

: 101601-80-3
3-amino-2-phenylpyridine

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 95℃; for 16h; Sealed tube;	84%
With potassium phosphate; tetrabutylammomium bromide In water at 85℃; for 1h; Suzuki-Miyaura Coupling; Green chemistry;	82%
Suzuki Coupling;

: 39856-58-1
3-amino-2-bromopyridine

: {3-[(1S)-1-{[(tert-butoxy)carbonyl]amino}but-3-en-1-yl]phenyl}boronic acid

: tert-butyl N-[(1S)-1-[3-(3-aminopyridin-2-yl)phenyl]but-3-en-1yl]carbamate

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane at 120℃; for 0.5h; Inert atmosphere; Microwave irradiation;	84%
With tetrakis(triphenylphosphine) palladium(0); sodium sulfate In 1,4-dioxane at 120℃; for 0.5h; Suzuki Coupling; Inert atmosphere; Microwave irradiation;	84%
With tetrakis(triphenylphosphine) palladium(0)

: 39856-58-1
3-amino-2-bromopyridine

: C16H19NO2

: C21H23N3O2

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In N,N-dimethyl-formamide at 80℃; for 1h; Inert atmosphere;	84%

: 39856-58-1
3-amino-2-bromopyridine

: 24424-99-5
di-tert-butyl dicarbonate

: 149489-04-3
tert-butyl N-(3-bromo-2-pyridyl)-carbamate

Conditions

Conditions	Yield
Stage #1: 3-amino-2-bromopyridine With sodium hexamethyldisilazane In tetrahydrofuran for 0.166667h; Inert atmosphere; Cooling; Large scale; Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran at 15℃; for 1h; Inert atmosphere; Large scale;	84%

3-Amino-2-bromopyridine Specification

The 3-Amino-2-bromopyridine is an organic compound with the formula C₅H₅BrN₂. The IUPAC name of this chemical is 2-bromopyridin-3-amine. With the CAS registry number 39856-58-1, it is also named as 3-Pyridinamine, 2-bromo-. The product's categories are Pyridine Series; Amines; Pyridines; Pyridine; Bromopyridines; Halopyridines; C5Heterocyclic Building Blocks; Halogenated Heterocycles; Heterocyclic Building Blocks; Amino-pyridine Series. Besides, it should be stored in a closed cool and dry place.

Physical properties about 3-Amino-2-bromopyridine are: (1)ACD/LogP: 1.27; (2)ACD/LogD (pH 5.5): 1.27; (3)ACD/LogD (pH 7.4): 1.27; (4)ACD/BCF (pH 5.5): 5.45; (5)ACD/BCF (pH 7.4): 5.46; (6)ACD/KOC (pH 5.5): 117.22; (7)ACD/KOC (pH 7.4): 117.24; (8)#H bond acceptors: 2; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 1; (11)Polar Surface Area: 16.13 Å²; (12)Index of Refraction: 1.636; (13)Molar Refractivity: 36.27 cm³; (14)Molar Volume: 101.1 cm³; (15)Polarizability: 14.37×10^-24cm³; (16)Surface Tension: 56.9 dyne/cm; (17)Density: 1.71 g/cm³; (18)Flash Point: 130.7 °C; (19)Enthalpy of Vaporization: 53.2 kJ/mol; (20)Boiling Point: 292.5 °C at 760 mmHg; (21)Vapour Pressure: 0.00182 mmHg at 25°C.

When you are using this chemical, please be cautious about it as the following:
It is harmful if swallowed and risk of serious damage to eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Besides, this chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable gloves and eye/face protection.

You can still convert the following datas into molecular structure:
(1)SMILES: Brc1ncccc1N
(2)InChI: InChI=1/C5H5BrN2/c6-5-4(7)2-1-3-8-5/h1-3H,7H2
(3)InChIKey: HKDVVTLISGIPFE-UHFFFAOYAH
(4)Std. InChI: InChI=1S/C5H5BrN2/c6-5-4(7)2-1-3-8-5/h1-3H,7H2
(5)Std. InChIKey: HKDVVTLISGIPFE-UHFFFAOYSA-N

Product Name

3-Amino-2-bromopyridine

Synthetic route

3-Amino-2-bromopyridine Specification

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