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2,5-Dibromopyridine
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Name

2,5-Dibromopyridine

 EINECS 210-839-6
CAS No. 624-28-2 Density 2.059 g/cm3
PSA 12.89000 LogP 2.60660
Solubility insoluble in water Melting Point 92-95 °C(lit.)
Formula C5H3Br2N Boiling Point 235.7 °C at 760 mmHg
Molecular Weight 236.894 Flash Point 96.4 °C
Transport Information N/A Appearance Off-white crystals
Safety 26-37/39-36/37/39-36 Risk Codes 36/37/38-20/21/22
Molecular Structure Molecular Structure of 624-28-2 (2,5-Dibromopyridine) Hazard Symbols HarmfulXn, IrritantXi
Synonyms

Pyridine, 2,5-dibromo-;2,5-Dibromo Pyridine;

Article Data 21

2,5-Dibromopyridine Synthetic route

13466-38-1

5-bromopyridin-2-ol

624-28-2

2,5-dibromopyridine

Conditions
ConditionsYield
With triphenylborane; phosphorus tribromide In 1,2-dichloro-ethane for 10h; Reagent/catalyst; Solvent; Inert atmosphere; Reflux;88.7%
With phosphorus(V) oxybromide In acetonitrile at 80℃; for 21h; Reagent/catalyst; Temperature;470 mg
1072-97-5

5-bromo-2-pyridylamine

624-28-2

2,5-dibromopyridine

Conditions
ConditionsYield
Stage #1: 5-bromo-2-pyridylamine With hydrogen bromide; bromine In water at 0 - 20℃; for 0.166667h;
Stage #2: With sodium nitrite In water at 0 - 5℃; for 0.5h;		87%
With tert.-butylnitrite; trimethylbenzylammonium bromide; 1,2-dibromomethane at 20℃;83%
With tert.-butylnitrite; trimethylbenzylammonium bromide In 1,2-dibromomethane at 20℃;83%
109-04-6

2-bromo-pyridine

A

624-28-2

2,5-dibromopyridine

B

75806-85-8

2,3,5-tribromopyridine

Conditions
ConditionsYield
With bromine at 300℃; Leiten ueber mit Eisen(II)-bromid impraegnierten Bimsstein;
626-55-1

3-Bromopyridine

A

624-28-2

2,5-dibromopyridine

B

2402-92-8

2,3,6-tribromopyridine

Conditions
ConditionsYield
With bromine at 500℃; Leiten ueber Bimsstein;
694-85-9

1-methyl-2-pyridone

7789-69-7

phosphorus pentabromide

624-28-2

2,5-dibromopyridine

Conditions
ConditionsYield
at 140 - 150℃;
diazotized 5-bromo-2-amino-pyridine

diazotized 5-bromo-2-amino-pyridine

624-28-2

2,5-dibromopyridine

Conditions
ConditionsYield
With hydrogen bromide
N-methyl-α-pyridone

N-methyl-α-pyridone

A

109-04-6

2-bromo-pyridine

B

624-28-2

2,5-dibromopyridine

Conditions
ConditionsYield
With phosphorus pentabromide; phosphorus(V) oxybromide at 120 - 130℃;
With phosphorus pentabromide at 140 - 150℃;
626-55-1

3-Bromopyridine

7726-95-6

bromine

pumice stone

pumice stone

A

624-28-2

2,5-dibromopyridine

B

2402-92-8

2,3,6-tribromopyridine

Conditions
ConditionsYield
at 500℃;
109-04-6

2-bromo-pyridine

7726-95-6

bromine

iron (II)-bromide

iron (II)-bromide

A

624-28-2

2,5-dibromopyridine

B

75806-85-8

2,3,5-tribromopyridine

Conditions
ConditionsYield
at 300℃;
504-29-0

2-aminopyridine

624-28-2

2,5-dibromopyridine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: ethanol; bromine / <20
2: bromine; aqueous hydrobromic acid / anschliessend Behandeln mit wss. Natriumnitrit-Loesung unterhalb von 0grad
View Scheme
Multi-step reaction with 2 steps
1: N-Bromosuccinimide; ammonium acetate / acetonitrile / 0.08 h / 20 °C
2: tert.-butylnitrite; trimethylbenzylammonium bromide; 1,2-dibromomethane / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: N-Bromosuccinimide; ammonium acetate / acetonitrile / 0.08 h / 20 °C
2: tert.-butylnitrite; trimethylbenzylammonium bromide / 1,2-dibromomethane / 20 °C
View Scheme

2,5-Dibromopyridine Specification

The 2,5-Dibromopyridine is an organic compound with the formula C5H3Br2N. The IUPAC name of this chemical is 2,5-dibromopyridine. With the CAS registry number 624-28-2, it is also named as Pyridine, 2,5-dibromo-. The product's categories are Nitrogen Cyclic Compounds; Blocks; Bromides; Pyridines; Pyridine Derivative; Pyridines, Pyrimidines, Purines and Pteredines; Halides; Pyridine; Pyridines Derivates; Aromatics Compounds; Bromopyridines; Halopyridines;Pyridine Series; Aromatics; Bases & Related Reagents; Nucleotides; C5Heterocyclic Building Blocks; Halogenated Heterocycles; Heterocyclic Building Blocks; Brominated Heterocyclic Series. Besides, it is a off-white crystals, which should be stored in a closed cool and dry palce. It is used as pharmaceutical intermediates.

Physical properties about 2,5-Dibromopyridine are: (1)ACD/LogP: 2.58; (2)ACD/LogD (pH 5.5): 2.58; (3)ACD/LogD (pH 7.4): 2.58; (4)ACD/BCF (pH 5.5): 54.12; (5)ACD/BCF (pH 7.4): 54.12; (6)ACD/KOC (pH 5.5): 605.84; (7)ACD/KOC (pH 7.4): 605.84; (8)#H bond acceptors: 1; (9)Polar Surface Area: 12.89 Å2; (10)Index of Refraction: 1.607; (11)Molar Refractivity: 39.72 cm3; (12)Molar Volume: 115 cm3; (13)Polarizability: 15.74×10-24cm3; (14)Surface Tension: 47.7 dyne/cm; (15)Density: 2.059 g/cm3; (16)Flash Point: 96.4 °C; (17)Enthalpy of Vaporization: 45.34 kJ/mol; (18)Boiling Point: 235.7 °C at 760 mmHg; (19)Vapour Pressure: 0.0754 mmHg at 25°C.

Uses of 2,5-Dibromopyridine: it can be used to produce 5,5'-dibromo-[2,2']bipyridinyl at temperature of 225 °C. It will need reagent copper-powder.

When you are using this chemical, please be cautious about it as the following:
It is harmful by inhalation, in contact with skin and if swallowed. 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: c1cc(ncc1Br)Br
(2)InChI: InChI=1/C5H3Br2N/c6-4-1-2-5(7)8-3-4/h1-3H
(3)InChIKey: ZHXUWDPHUQHFOV-UHFFFAOYAU
(4)Std. InChI: InChI=1S/C5H3Br2N/c6-4-1-2-5(7)8-3-4/h1-3H
(5)Std. InChIKey: ZHXUWDPHUQHFOV-UHFFFAOYSA-N

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