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134457-14-0

Basic Information
CAS No.: 134457-14-0
Name: 4,4'-Bis(bromomethyl)-2,2'-bipyridine
Article Data: 46
Molecular Structure:
Molecular Structure of 134457-14-0 (4,4'-Bis(bromomethyl)-2,2'-bipyridine)
Formula: C12H10Br2N2
Molecular Weight: 342.033
Synonyms: 4,4'-Bis(bromomethyl)-2,2'-bipyridine;
Density: 1.708 g/cm3
Melting Point: 135-137 °C(Solv: hexane (110-54-3); dichloromethane (75-09-2))
Boiling Point: 425.2 °C at 760 mmHg
Flash Point: 210.9 °C
PSA: 25.78000
LogP: 3.93340
Synthetic route
199282-52-5

4,4’-bis[(trimethylsilyl)methyl]-2,2’-bipyridine

134457-14-0

4,4'-bis(bromomethyl)-2,2'-bipyridine

Conditions
ConditionsYield
With 1,2-dibromo-1,1,2,2-tetrafluoroethane; cesium fluoride In N,N-dimethyl-formamide at 25℃; for 2h;97%
With hexabromoethane; cesium fluoride97%
With 1,2-dibromo-1,1,2,2-tetrafluoroethane; cesium fluoride In N,N-dimethyl-formamide at 20℃; for 3h;94.8%
With 1,2-dibromo-1,1,2,2-tetrafluoroethane; tetrabutyl ammonium fluoride; silica gel In tetrahydrofuran at -78℃;
With 1,2-dibromo-1,1,2,2-tetrafluoroethane; cesium fluoride In N,N-dimethyl-formamide at 25℃; for 2h; Bromination;
109073-77-0

4,4'-bis(hydroxymethyl)-2,2'-bipyridine

134457-14-0

4,4'-bis(bromomethyl)-2,2'-bipyridine

Conditions
ConditionsYield
With sulfuric acid; hydrogen bromide for 6h; Substitution; Heating;88%
With sulfuric acid; hydrogen bromide at 110℃; for 6h;88%
With sulfuric acid; hydrogen bromide at 110℃; for 6h;88%
1134-35-6

4,4'-dimethyl-2,2'-bipyridines

134457-14-0

4,4'-bis(bromomethyl)-2,2'-bipyridine

Conditions
ConditionsYield
With sulfuric acid; hydrogen bromide for 6h; Reflux;85%
With N-Bromosuccinimide30%
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 3h; Heating;10.1%
109073-77-0

4,4'-bis(hydroxymethyl)-2,2'-bipyridine

A

134457-14-0

4,4'-bis(bromomethyl)-2,2'-bipyridine

B

(4'-Bromomethyl-[2,2']bipyridinyl-4-yl)-methanol

Conditions
ConditionsYield
With hydrogen bromide In water for 3h; Heating;A 75%
B 18%
6813-38-3

2,2'-Bipyridine-4,4'-dicarboxylic acid

134457-14-0

4,4'-bis(bromomethyl)-2,2'-bipyridine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 99 percent / conc. H2SO4 / 60 h / Heating
2: 30 percent / NaBH4 / methanol / 60 h / Heating
3: 30 percent / aq. HBr / 3.5 h / Heating
View Scheme
Multi-step reaction with 3 steps
1: sulfuric acid / 4 h / Reflux
2: sodium tetrahydroborate / ethanol / 3 h / Reflux
3: sulfuric acid; hydrogen bromide / 6 h / Reflux
View Scheme
Multi-step reaction with 3 steps
1: sulfuric acid
2: sodium tetrahydroborate / ethanol
3: hydrogen bromide / sulfuric acid
View Scheme
71071-46-0

4,4'-bis(carbomethoxy)-2,2'-bipyridine

134457-14-0

4,4'-bis(bromomethyl)-2,2'-bipyridine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 30 percent / NaBH4 / methanol / 60 h / Heating
2: 30 percent / aq. HBr / 3.5 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: NaBH4 / ethanol
2: 48percent HBr, drops of conc. H2SO4
View Scheme
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / ethanol
2: hydrogen bromide / sulfuric acid
View Scheme
87855-83-2

4,4’-dimethyl-2,2’-bipyridine N,N’-dioxide

134457-14-0

4,4'-bis(bromomethyl)-2,2'-bipyridine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 43.5 percent / acetic acid / 4 h / Heating
2: 44 percent / NaOH; water / methanol / 3 h / Heating
3: 72.3 percent / hydrobromic acid / 5 h / Heating
View Scheme
279681-06-0

4,4'-bis(acetoxymethyl)-2,2'-bipyridine

134457-14-0

4,4'-bis(bromomethyl)-2,2'-bipyridine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 44 percent / NaOH; water / methanol / 3 h / Heating
2: 72.3 percent / hydrobromic acid / 5 h / Heating
View Scheme
99970-84-0

[2,2']bipyridinyl-4,4'-dicarbaldehyde

134457-14-0

4,4'-bis(bromomethyl)-2,2'-bipyridine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NaBH4; aq. NaOH / methanol / 1 h / 20 °C
2: aq. HBr; H2SO4 / Heating
View Scheme
Multi-step reaction with 4 steps
1: nitric acid / 2 h / Reflux
2: thionyl chloride / 20 h / Reflux
3: sodium tetrahydroborate / ethanol / 3 h / Reflux
4: hydrogen bromide / water / 3 h / Reflux
View Scheme
1762-42-1

4,4'-bis(ethoxycarbonyl)-2,2'-bipyridine

134457-14-0

4,4'-bis(bromomethyl)-2,2'-bipyridine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 89 percent / NaBH4 / ethanol / 3 h / 20 °C
2: 88 percent / HBr; H2SO4 / 6 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / ethanol / 3 h / Reflux
2: sulfuric acid; hydrogen bromide / 6 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / ethanol / 12 h / 80 °C
2: hydrogen bromide; sulfuric acid / 12 h / Reflux
View Scheme
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Specification

The Bis-4,4'-bromomethyl-2,2'-bipyridine, with the CAS registry number 134457-14-0, has the systematic name 4,4'-bis(bromomethyl)-2,2'-bipyridine. Its molecular formula is C12H10Br2N2 and its molecular weight is 342.0292.

Other characteristics of the Bis-4,4'-bromomethyl-2,2'-bipyridine can be summarised as followings: (1)ACD/LogP: 2.69; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.68; (4)ACD/LogD (pH 7.4): 2.69; (5)ACD/BCF (pH 5.5): 63.46; (6)ACD/BCF (pH 7.4): 64.73; (7)ACD/KOC (pH 5.5): 675.15; (8)ACD/KOC (pH 7.4): 688.59; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 25.78 Å2; (13)Index of Refraction: 1.642; (14)Molar Refractivity: 72.32 cm3; (15)Molar Volume: 200.1 cm3; (16)Polarizability: 28.67×10-24cm3; (17)Surface Tension: 55.7 dyne/cm; (18)Density: 1.708 g/cm3; (19)Flash Point: 210.9 °C; (20)Enthalpy of Vaporization: 65.34 kJ/mol; (21)Boiling Point: 425.2 °C at 760 mmHg; (22)Vapour Pressure: 4.84E-07 mmHg at 25°C.

You can still convert the following datas into molecular structure:
1.SMILES: BrCc1cc(ncc1)c2nccc(c2)CBr
2.InChI: InChI=1/C12H10Br2N2/c13-7-9-1-3-15-11(5-9)12-6-10(8-14)2-4-16-12/h1-6H,7-8H2
3.InChIKey: XCMRHOMYGPXALN-UHFFFAOYAI