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2,6-Bis(bromomethyl)pyridine
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  • Name 2,6-Bis(bromomethyl)pyridine
  • EINECSN/A
  • CAS No. 7703-74-4
  • Density1.87 g/cm3
  • PSA12.89000
  • LogP2.87140
  • SolubilityN/A
  • Melting Point85-87 °C(lit.)
  • FormulaC7H7Br2N
  • Boiling Point275.6 °C at 760 mmHg
  • Molecular Weight264.947
  • Flash Point120.5 °C
  • Transport InformationN/A
  • AppearanceN/A
  • Safety26-36/37/39
  • Risk Codes22-36/37/38
  • Molecular Structure
    Molecular Structure of 7703-74-4 (2,6-Bis(bromomethyl)pyridine)
  • Hazard SymbolsHarmfulXn
  • SynonymsHarmfulXn
  • Article Data68

2,6-Bis(bromomethyl)pyridine Synthetic route

1195-59-1

2.6-bis(hydroxymethyl)pyridine

7703-74-4

2,6-bis-(bromomethyl)pyridine

Conditions
ConditionsYield
Stage #1: 2.6-bis(hydroxymethyl)pyridine With hydrogen bromide In water at 125℃;
Stage #2: With sodium hydrogencarbonate In water pH=8;		96%
With hydrogen bromide In water at 125℃; for 6h; Inert atmosphere;96%
With phosphorus tribromide In N,N-dimethyl-formamide at 0 - 20℃; for 4h;95%
108-48-5

2,6-dimethylpyridine

96-21-9

1,3-dibromo-2-hydroxypropane

7703-74-4

2,6-bis-(bromomethyl)pyridine

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 80℃; for 24h; Reagent/catalyst;95%
1195-59-1

2.6-bis(hydroxymethyl)pyridine

7789-60-8

phosphorus tribromide

7703-74-4

2,6-bis-(bromomethyl)pyridine

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere;91%
108-48-5

2,6-dimethylpyridine

7703-74-4

2,6-bis-(bromomethyl)pyridine

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); bromine; nitric acid In dichloromethane for 5h; Reflux;86.5%
With 2,2'-azobis(isobutyronitrile); bromine In dichloromethane for 5h; Reflux;84.8%
Stage #1: 2,6-dimethylpyridine With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane Heating;
Stage #2: With Diethyl phosphonate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 25℃; for 5h;		76%
1195-59-1

2.6-bis(hydroxymethyl)pyridine

A

7703-74-4

2,6-bis-(bromomethyl)pyridine

B

40054-01-1

(6-(bromomethyl)pyridin-2-yl)methanol

Conditions
ConditionsYield
With hydrogen bromide for 15h; Heating;A 51%
B 24%
With hydrogen bromide for 17h; Heating;A 41%
B 44%
With hydrogen bromide Heating;A 27%
B 41%
With hydrogen bromide for 1h; Heating;A 11%
B 39%
108-48-5

2,6-dimethylpyridine

591-51-5

phenyllithium

A

68470-59-7

2-(bromomethyl)-6-methylpyridine

B

7703-74-4

2,6-bis-(bromomethyl)pyridine

Conditions
ConditionsYield
With diethyl ether anschliessend Behandeln mit Brom;
108-48-5

2,6-dimethylpyridine

A

68470-59-7

2-(bromomethyl)-6-methylpyridine

B

7703-74-4

2,6-bis-(bromomethyl)pyridine

Conditions
ConditionsYield
With tetrachloromethane; N-Bromosuccinimide; dibenzoyl peroxide
5453-67-8

2,6-bis(methoxycarbonyl)pyridine

7703-74-4

2,6-bis-(bromomethyl)pyridine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / ethanol / 13 h / 0 - 20 °C / Reflux
2: hydrogen bromide / 15 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere
2: hydrogen bromide; acetic acid / 1.5 h / 100 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: methanol; sodium tetrahydroborate / Inert atmosphere; Reflux
2: hydrogen bromide; acetic acid / 1.5 h / 100 °C / Inert atmosphere
View Scheme
499-83-2

Pyridine-2,6-dicarboxylic acid

7703-74-4

2,6-bis-(bromomethyl)pyridine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: ethanolic HCl
2: lithium alanate; diethyl ether
3: sulfuric acid; aqueous hydrobromic acid
View Scheme
Multi-step reaction with 3 steps
1: thionyl chloride / 5 h / 0 °C / Reflux; Inert atmosphere
2: sodium tetrahydroborate / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere
3: hydrogen bromide; acetic acid / 1.5 h / 100 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1.1: thionyl chloride / 6 h / -20 - 20 °C
2.1: sodium tetrahydroborate / tetrahydrofuran / 10 h / 20 °C / Inert atmosphere
2.2: pH Ca. 3
2.3: pH Ca. 9
3.1: hydrogen bromide / water / 10 h / Reflux
3.2: pH Ca. 9
View Scheme
Multi-step reaction with 3 steps
1: thionyl chloride / 18 h / Inert atmosphere; Reflux
2: methanol; sodium tetrahydroborate / Inert atmosphere; Reflux
3: hydrogen bromide; acetic acid / 1.5 h / 100 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1: sulfuric acid / 8 h / Reflux
2: sodium tetrahydroborate / tetrahydrofuran / 12 h / 20 °C / Cooling with ice
3: phosphorus tribromide / diethyl ether / 4.5 h / 0 °C / Reflux
View Scheme
diethyl-2,6-pyridinedicarbonyl ester

diethyl-2,6-pyridinedicarbonyl ester

7703-74-4

2,6-bis-(bromomethyl)pyridine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: lithium alanate; diethyl ether
2: sulfuric acid; aqueous hydrobromic acid
View Scheme
Multi-step reaction with 2 steps
1.1: sodium tetrahydroborate / tetrahydrofuran / 10 h / 20 °C / Inert atmosphere
1.2: pH Ca. 3
1.3: pH Ca. 9
2.1: hydrogen bromide / water / 10 h / Reflux
2.2: pH Ca. 9
View Scheme
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / tetrahydrofuran / 12 h / 20 °C / Cooling with ice
2: phosphorus tribromide / diethyl ether / 4.5 h / 0 °C / Reflux
View Scheme

2,6-Bis(bromomethyl)pyridine Specification

The 2,6-Bis(bromomethyl)pyridine, with the CAS registry number 7703-74-4, is also known as Pyridine, 2,6-bis(bromomethyl)-. It belongs to the product categories of C7 and C8 Heterocyclic Building Blocks; Halogenated Heterocycles; Heterocyclic Building Blocks; Pyridines. This chemical's molecular formula is C7H7Br2N and molecular weight is 264.95. Its systematic name is called 2,6-bis(bromomethyl)pyridine.

Physical properties of 2,6-Bis(bromomethyl)pyridine: (1)ACD/LogP: 2.13; (2)ACD/LogD (pH 5.5): 2.13; (3)ACD/LogD (pH 7.4): 2.13; (4)ACD/BCF (pH 5.5): 24.37; (5)ACD/BCF (pH 7.4): 24.38; (6)ACD/KOC (pH 5.5): 342.25; (7)ACD/KOC (pH 7.4): 342.29; (8)#H bond acceptors: 1; (9)#Freely Rotating Bonds: 2; (10)Index of Refraction: 1.618; (11)Molar Refractivity: 49.64 cm3; (12)Molar Volume: 141.6 cm3; (13)Surface Tension: 51.4 dyne/cm; (14)Density: 1.87 g/cm3; (15)Flash Point: 120.5 °C; (16)Enthalpy of Vaporization: 49.34 kJ/mol; (17)Boiling Point: 275.6 °C at 760 mmHg; (18)Vapour Pressure: 0.00848 mmHg at 25°C.

Preparation of 2,6-Bis(bromomethyl)pyridine: this chemical can be prepared by 2,6-bis-hydroxymethyl-pyridine. This reaction will need reagents aq. HBr and PBr3. The reaction time is 24 hours with reaction temperature of 140 °C. The yield is about 84%.

2,6-Bis(bromomethyl)pyridine can be prepared by 2,6-bis-hydroxymethyl-pyridine

Uses of 2,6-Bis(bromomethyl)pyridine: it can be used to produce 2,6-bis-methoxymethyl-pyridine hy heating. This reaction will need reagent NaH and solvent tetrahydrofuran with reaction time of 15 min. The yield is about 87%.

2,6-Bis(bromomethyl)pyridine can be used to produce 2,6-bis-methoxymethyl-pyridine with methanol

When you are using this chemical, please be cautious about it as the following:
This chemical may cause damage to health. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing, gloves and eye/face protection.

You can still convert the following datas into molecular structure:
(1)SMILES: BrCc1nc(ccc1)CBr
(2)InChI: InChI=1/C7H7Br2N/c8-4-6-2-1-3-7(5-9)10-6/h1-3H,4-5H2
(3)InChIKey: QUTSYCOAZVHGGT-UHFFFAOYAW

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