134457-14-0

Basic information

• Product Name: 4,4'-Bis(bromomethyl)-2,2'-bipyridine
• Synonyms: 4,4'-Bis(bromomethyl)-2,2'-bipyridine;bis-4,4'-broMoMethyl-2,2'-bipyridine
• CAS NO: 134457-14-0
• Molecular Formula: C₁₂H₁₀Br₂N₂
• Molecular Weight: 342.0292
• Mol File: 134457-14-0.mol
• Article Data: 46

Chemical Properties

• 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
• Appearance: /
• Density: 1.708
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 3.81±0.30(Predicted)
• CAS DataBase Reference: 4,4'-Bis(bromomethyl)-2,2'-bipyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-Bis(bromomethyl)-2,2'-bipyridine(134457-14-0)
• EPA Substance Registry System: 4,4'-Bis(bromomethyl)-2,2'-bipyridine(134457-14-0)

Safety Data

• Hazardous Substances Data: 134457-14-0(Hazardous Substances Data)

Usage

General Description

4,4'-Bis(bromomethyl)-2,2'-bipyridine is a chemical compound with the molecular formula C14H10Br2N2. It is a yellow solid that is commonly used as a building block for the synthesis of various organic compounds. 4,4'-Bis(bromomethyl)-2,2'-bipyridine is known for its reactivity and ability to undergo substitution reactions with nucleophiles, making it a useful intermediate in organic synthesis. It is also used as a ligand in coordination chemistry and catalysis. Additionally, 4,4'-Bis(bromomethyl)-2,2'-bipyridine has been studied for its potential applications in materials science and as a pharmaceutical intermediate. However, it is important to handle this compound with caution as it is toxic and can be harmful if ingested or inhaled.

Synthetic route

4,4’-bis[(trimethylsilyl)methyl]-2,2’-bipyridine (199282-52-5) → 4,4'-bis(bromomethyl)-2,2'-bipyridine (134457-14-0)

Conditions	Yield
With 1,2-dibromo-1,1,2,2-tetrafluoroethane; cesium fluoride In N,N-dimethyl-formamide at 25℃; for 2h;	97%
With hexabromoethane; cesium fluoride	97%
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;

4,4'-bis(hydroxymethyl)-2,2'-bipyridine (109073-77-0) → 4,4'-bis(bromomethyl)-2,2'-bipyridine (134457-14-0)

Conditions	Yield
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%

4,4'-dimethyl-2,2'-bipyridines (1134-35-6) → 4,4'-bis(bromomethyl)-2,2'-bipyridine (134457-14-0)

Conditions	Yield
With sulfuric acid; hydrogen bromide for 6h; Reflux;	85%
With N-Bromosuccinimide	30%
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 3h; Heating;	10.1%

4,4'-bis(hydroxymethyl)-2,2'-bipyridine (109073-77-0) → 4,4'-bis(bromomethyl)-2,2'-bipyridine (134457-14-0) + (4'-Bromomethyl-[2,2']bipyridinyl-4-yl)-methanol

Conditions	Yield
With hydrogen bromide In water for 3h; Heating;	A 75% B 18%

2,2'-Bipyridine-4,4'-dicarboxylic acid (6813-38-3) → 4,4'-bis(bromomethyl)-2,2'-bipyridine (134457-14-0)

Conditions	Yield
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

4,4'-bis(carbomethoxy)-2,2'-bipyridine (71071-46-0) → 4,4'-bis(bromomethyl)-2,2'-bipyridine (134457-14-0)

Conditions	Yield
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

4,4’-dimethyl-2,2’-bipyridine N,N’-dioxide (87855-83-2) → 4,4'-bis(bromomethyl)-2,2'-bipyridine (134457-14-0)

Conditions	Yield
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

4,4'-bis(acetoxymethyl)-2,2'-bipyridine (279681-06-0) → 4,4'-bis(bromomethyl)-2,2'-bipyridine (134457-14-0)

Conditions	Yield
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

[2,2']bipyridinyl-4,4'-dicarbaldehyde (99970-84-0) → 4,4'-bis(bromomethyl)-2,2'-bipyridine (134457-14-0)

Conditions	Yield
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

4,4'-bis(ethoxycarbonyl)-2,2'-bipyridine (1762-42-1) → 4,4'-bis(bromomethyl)-2,2'-bipyridine (134457-14-0)

Conditions	Yield
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

2,2'-bipyridyl-4,4'-dicarboxylic acid chloride (72460-28-7) → 4,4'-bis(bromomethyl)-2,2'-bipyridine (134457-14-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: 12 h / Reflux 2: sodium tetrahydroborate / ethanol / 3 h / Reflux 3: hydrogen bromide; sulfuric acid; sodium hydroxide / 6 h / pH 7.0 / Reflux View Scheme

4,4'-bis(bromomethyl)-2,2'-bipyridine (134457-14-0) + trimethylamine (75-50-3) → 4,4’‐bis(trimethylammoniummethyl)‐2,2’‐bipyridine

Conditions	Yield
In dichloromethane; water at 20℃; for 24h;	100%
In ethanol; water at 20℃; for 1h; Inert atmosphere;	100%
In ethanol; water at 20℃; for 1h;
In dichloromethane; water at 20℃; for 24h;
In dichloromethane at 20℃; for 24h;

4,4'-bis(bromomethyl)-2,2'-bipyridine (134457-14-0) → 4,4'-bis(azidomethylene)-2,2-bipyridine

Conditions	Yield
With sodium azide In dimethyl sulfoxide at 20℃; Inert atmosphere;	99%
With sodium azide In dimethyl sulfoxide; acetonitrile at 20℃; for 120h;	94%

4,4'-bis(bromomethyl)-2,2'-bipyridine (134457-14-0) + triethyl phosphite (122-52-1) → 4,4'-bis(diethylphosphonomethyl)-2,2'-bipyridine (176220-38-5)

Conditions	Yield
at 80℃; for 12h; Inert atmosphere;	98%
at 80℃; for 6h; Inert atmosphere;	95%
In chloroform	95%

4,4'-bis(bromomethyl)-2,2'-bipyridine (134457-14-0) → 4,4'-bis(aminomethyl)-2,2'-bipyridine (727380-18-9)

Conditions	Yield
Stage #1: 4,4'-bis(bromomethyl)-2,2'-bipyridine With potassium phtalimide In N,N-dimethyl-formamide Stage #2: With hydrazine hydrate In ethanol	98%
Stage #1: 4,4'-bis(bromomethyl)-2,2'-bipyridine With potassium phtalimide In N,N-dimethyl-formamide at 50℃; for 15h; Inert atmosphere; Stage #2: With hydrazine In ethanol; water at 100℃; for 18h;	71%
Multi-step reaction with 2 steps 1: sodium azide / dimethyl sulfoxide / 20 °C / Inert atmosphere 2: triethylamine; palladium 10% on activated carbon; hydrogen / tetrahydrofuran / 48 h / Inert atmosphere View Scheme

3-aminopropyltriethoxysilane (919-30-2) + 4,4'-bis(bromomethyl)-2,2'-bipyridine (134457-14-0) → 4,4'-bis[3-(triethoxysilyl)propylaminomethyl]-2,2'-bipyridine

Conditions	Yield
With triethylamine In tetrahydrofuran at 50℃; for 6h;	96%
With triethylamine In tetrahydrofuran at 50℃; for 6h; Inert atmosphere;	92%
With triethylamine In tetrahydrofuran at 50℃; for 6h; Inert atmosphere;	92%
With triethylamine In tetrahydrofuran at 50℃; for 6h;

bis[dimethyl(μ-dimethylsulfide)platinum(II)] + 4,4'-bis(bromomethyl)-2,2'-bipyridine (134457-14-0) → (CH2C5H3NC5H3N(CH2Br))Pt(Br)(CH3)2((CH2C5H3N)2)[Pt(Br)(CH3)2((BrCH2C5H3N)2)]Pt(Br)(CH3)2(CH2C5H3NC5H3NCH2Br)Pt(Br)(CH3)2

Conditions	Yield
In acetone washing (ether); elem. anal.;	95%

[iridium(III)(μ-chloro)(2-phenylpyridine)2]2 + 4,4'-bis(bromomethyl)-2,2'-bipyridine (134457-14-0) → C34H26Br2IrN4(1+)*Cl(1-)

Conditions	Yield
In methanol; dichloromethane for 12h; Reflux; Inert atmosphere;	95%
In methanol; dichloromethane Reflux;

dimethyl amine (124-40-3) + 4,4'-bis(bromomethyl)-2,2'-bipyridine (134457-14-0) → C16H22N4 (1036649-23-6)

Conditions	Yield
With potassium hydroxide In ethanol at 50℃; for 20h;	95%

triethylamine (121-44-8) + 4,4'-bis(bromomethyl)-2,2'-bipyridine (134457-14-0) → C24H40N4(2+)*F6P(1-)

Conditions	Yield
Stage #1: triethylamine; 4,4'-bis(bromomethyl)-2,2'-bipyridine In dichloromethane; water at 20℃; for 24h; Stage #2: With ammonium hexafluorophosphate In dichloromethane; water	92.1%

1-hexylimidazole (33529-01-0) + 4,4'-bis(bromomethyl)-2,2'-bipyridine (134457-14-0) → C30H42N6(2+)*2Br(1-)

Conditions	Yield
In chloroform	92%

1-methyl-1H-imidazole (616-47-7) + 4,4'-bis(bromomethyl)-2,2'-bipyridine (134457-14-0) → C20H22N6(2+)*2Br(1-)

Conditions	Yield
In toluene for 12h; Reflux; Inert atmosphere;	92%

1‐(naphthalen‐2‐ylmethyl)imidazole (98318-77-5) + 4,4'-bis(bromomethyl)-2,2'-bipyridine (134457-14-0) → C40H34N6(2+)*2Br(1-)

Conditions	Yield
In acetonitrile Reflux;	92%

4,4'-bis(bromomethyl)-2,2'-bipyridine (134457-14-0) + salicylic acid (69-72-7) → [2,2'-bipyridine]-4,4'-diylbis(methylene) bis(2-hydroxybenzoate)

Conditions	Yield
Stage #1: salicylic acid With potassium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; Stage #2: 4,4'-bis(bromomethyl)-2,2'-bipyridine In N,N-dimethyl-formamide at 20℃; for 6h;	91%

ammonium hexafluorophosphate + Ammonium iron sulfate + 4,4'-bis(bromomethyl)-2,2'-bipyridine (134457-14-0) → {Fe(4,4`-bis(bromomethyl)-2,2`-bipyridine)3}(PF6)2

Conditions	Yield
In methanol Ar; stirred for 1 h;; pptd. from NH4PF6 in H2O; elem. anal.;;	90%

(4,4'-di-tert-butyl-2,2'-bipyridine)dimethylplatinum(II) + 4,4'-bis(bromomethyl)-2,2'-bipyridine (134457-14-0) → [Pt(Br)(CH3)2(((CH3)3CC5H3N)2)]2((CH2C5H3N)2)

Conditions	Yield
In acetone filtering, washing (ether); elem. anal.;	90%
In not given

4,4'-bis(bromomethyl)-2,2'-bipyridine (134457-14-0) + 4-(4-[4-(1,1-diallyl-but-3-enyl)-phenoxy]-1,1-bis-{3-[4-(1,1-diallyl-but-3-enyl)-phenoxy]-propyl}-butyl)-phenol (224191-95-1) → (C5H3NCH2OC6H4C((CH2)3OC6H4C(CH2CHCH2)3)3)2 (1144500-85-5)

Conditions	Yield
With potassium carbonate In acetonitrile at 80℃; for 24h;	90%

potassium hexafluorophosphate (17084-13-8) + tetrakis(2-phenylquinoline-C2,N')(μ-dichloro)diiridium(III) + 4,4'-bis(bromomethyl)-2,2'-bipyridine (134457-14-0) → C42H30Br2IrN4(1+)*F6P(1-)

Conditions	Yield
Stage #1: tetrakis(2-phenylquinoline-C2,N')(μ-dichloro)diiridium(III); 4,4'-bis(bromomethyl)-2,2'-bipyridine In methanol; dichloromethane at 40℃; for 4h; Stage #2: potassium hexafluorophosphate In methanol; dichloromethane at 20℃;	90%

sodium methylate (124-41-4) + 4,4'-bis(bromomethyl)-2,2'-bipyridine (134457-14-0) → 4,4'-Bis(methoxymethyl)-2,2'-bipyridin

Conditions	Yield
In toluene for 12h; Heating;	89%

HOC6H4(C((CH2)3OC6H4C((CH2)3Si(CH3)2(C5H4))3)3)(9-)*9Fe(2+)*9C5H5(1-)=HOC6H4C(C3H6OC6H4C(C3H6Si(CH3)2C5H4FeC5H5)3)3 + 4,4'-bis(bromomethyl)-2,2'-bipyridine (134457-14-0) → (C5H3NCH2OC6H4C((CH2)3OC6H4C((CH2)3Si(CH3)2(C5H4)Fe(C5H5))3)3)2

Conditions

Yield

With potassium carbonate In tetrahydrofuran; acetonitrile treatment of 1 equiv. of 4,4'-bis(bromomethyl)-2,2'-bipy with 2 equiv. of nonaferrocenyl dendrone in the presence of K2CO3 in mixt. of MeCN and THF (v/v 1:1); heating at 80°C for 24 h with stirring; removal of solvent under vac.; extn. with Et2O; drying over Na2SO4; evapn. of solvent; chromy. (silica gel, pentane/diethyl ether 8:2; then diethyl ether); elem. anal.;

89%

[Pt(Br)(CH3)2(((CH3)3CC5H3N)2)]2((CH2C5H3N)2)Pt(CH3)2 (155761-57-2) + 4,4'-bis(bromomethyl)-2,2'-bipyridine (134457-14-0) → [[Pt(Br)(CH3)2(((CH3)3CC5H3N)2)]2((CH2C5H3N)2)Pt(Br)(CH3)2]2((CH2C5H3N)2)

Conditions	Yield
In acetone; benzene evapn., washing (ether), drying (vac.); elem. anal.;	88%
In not given

2,2,3,3,4,4,4-heptafluorobutanol (375-01-9) + 4,4'-bis(bromomethyl)-2,2'-bipyridine (134457-14-0) → 4,4'-bis(n-C3F7CH2OH2)-2,2'-bpy (949116-85-2)

Conditions	Yield
Stage #1: 2,2,3,3,4,4,4-heptafluorobutanol With methanol; sodium methylate at 80℃; for 4h; Inert atmosphere; Stage #2: 4,4'-bis(bromomethyl)-2,2'-bipyridine In tetrahydrofuran Reflux;	86.2%
Stage #1: 2,2,3,3,4,4,4-heptafluorobutanol With sodium methylate In methanol Stage #2: 4,4'-bis(bromomethyl)-2,2'-bipyridine

2,2,2-trifluoroethanol (75-89-8) + 4,4'-bis(bromomethyl)-2,2'-bipyridine (134457-14-0) → 4,4'-bis(2,2,2-trifluoroethoxymethyl)-2,2'-bipyridine (1289642-74-5)

Conditions	Yield
Stage #1: 2,2,2-trifluoroethanol With methanol; sodium methylate at 80℃; for 4h; Inert atmosphere; Stage #2: 4,4'-bis(bromomethyl)-2,2'-bipyridine In tetrahydrofuran Reflux;	86%

potassium hexafluorophosphate (17084-13-8) + [iridium(III)(μ-chloro)(2-phenylpyridine)2]2 + 4,4'-bis(bromomethyl)-2,2'-bipyridine (134457-14-0) → [Ir(ppy)2-bpy-Br]+PF6-

Conditions	Yield
In methanol; dichloromethane for 24h; Inert atmosphere; Reflux;	86%

potassium hexafluorophosphate (17084-13-8) + pq2Ir(μ-Cl)2Irpq2 (632327-37-8, 337526-84-8) + 4,4'-bis(bromomethyl)-2,2'-bipyridine (134457-14-0) → C42H32Br2IrN4(1+)*F6P(1-)

Conditions	Yield
In methanol; dichloromethane at 45℃; for 24h; Inert atmosphere;	86%

1H,1H,9H-hexadecafluoro-1-nonanol (376-18-1) + 4,4'-bis(bromomethyl)-2,2'-bipyridine (134457-14-0) → 4,4'-bis(HCF2(CF2)7CH2OCH2)-2,2'-bipyridine

Conditions	Yield
With sodium methylate In acetonitrile at 65℃; for 4h;	85%

4,4'-bis(bromomethyl)-2,2'-bipyridine (134457-14-0) + 4-triallylmethylphenol (224191-80-4) → (C5H3NCH2OC6H4C(CH2CHCH2)3)2 (1144500-84-4)

Conditions	Yield
With potassium carbonate In acetonitrile at 80℃; for 24h;	85%

tert-butyl (R)-(+)-(1-(4-hydroxyphenyl)ethyl)carbamate (931093-11-7) + 4,4'-bis(bromomethyl)-2,2'-bipyridine (134457-14-0) → di-tert-butyl ((1R,1'R)-((([2,2'-bipyridine]-4,4'-diylbis(methylene))bis(oxy))bis(4,1-phenylene))bis(ethane-1,1-diyl))dicarbamate

Conditions	Yield
With potassium carbonate In acetonitrile at 65℃; for 20h; Inert atmosphere;	85%

Upstream product

• 279681-06-0 2,2'-bipyridine-4,4'-diyldimethanediyl diacetate 
• 72460-28-7 2,2'-bipyridyl-4,4'-dicarboxylic acid chloride 
• 99970-84-0 [2,2']bipyridinyl-4,4'-dicarbaldehyde 
• 87855-83-2 4,4’-dimethyl-2,2’-bipyridine N,N’-dioxide 
• 6813-38-3 2,2'-Bipyridine-4,4'-dicarboxylic acid 
• 109073-77-0 4,4'-bis(hydroxymethyl)-2,2'-bipyridine 
• 1134-35-6 4,4'-dimethyl-2,2'-bipyridines 
• 199282-52-5 4,4’-bis[(trimethylsilyl)methyl]-2,2’-bipyridine 
• 71071-46-0 4,4'-bis(carbomethoxy)-2,2'-bipyridine 
• 1762-42-1 4,4'-bis(ethoxycarbonyl)-2,2'-bipyridine 

Downstream Products

• 176220-38-5 4,4'-bis(diethylphosphonomethyl)-2,2'-bipyridine 
• 109073-77-0 4,4'-bis(hydroxymethyl)-2,2'-bipyridine 
• 825621-06-5 (E,E′)-4,4′-bisstyryl-2,2′-bipyridine 
• 1323999-45-6 C₃₀H₂₈N₂O₂ 
• 1346558-31-3 4,4'-((4-iodophenoxy)methyl)-2,2'-bipyridine 
• 727380-18-9 4,4'-bis(aminomethyl)-2,2'-bipyridine 
• 1144500-85-5 (C₅H₃NCH₂OC₆H₄C((CH₂)3OC₆H₄C(CH₂CHCH₂)3)3)2 
• 1144500-84-4 (C₅H₃NCH₂OC₆H₄C(CH₂CHCH₂)3)2 
• 915225-35-3 C₅₈H₅₆N₂O₆ 

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Abstract: Four heteroleptic ruthenium(II) complexes, [Ru(L1)(L2)(NCS)2] (where L1 = 4,4′-bis[2-(1,1′-biphenyl)-4-ylethenyl]-2,2′-bipyridine (bpbpy) or 4,4′-bis[2-(3,4-dimethoxyphenyl)ethenyl]-2,2′-bipyridine (dmpbpy); L2 = 4,4′-dicarboxy-2,2′-bipyridine (dcbpy) or 4,4′-bis(E-carboxyvinyl)-2,2′-bipyridine (dcvbpy)), were synthesized from a one-pot reaction of [RuCl2(p-cymene)]2 and L1 followed by the addition of the anchoring ligand, L2. From these new heteroleptic ruthenium(II) complexes containing carboxylic acid-functionalized ligands, the tetrabutylammonium salt forms of the ruthenium(II) complexes, [Ru(L1)(L2)(NCS)2][TBA], were obtained in reasonable yields and applied as dyes in dye-sensitized solar cell (DSSC) devices. Among the DSSCs fabricated with the [Ru(L1)(L2)(NCS)2][TBA] dyes, a DSSC fabricated with the [Ru(bpbpy)(dcbpy)(NCS)2][TBA] dye exhibited the best power conversion efficiency (η) of 4.27%, while the cells fabricated with other dyes had η between 1.94 and 2.68%. Graphic abstract: [Figure not available: see fulltext.].

XYLOSE DERIVATIVES AND PROCESS FOR PREPARATION THEREOF

Disclosure of the present invention relates to a method for synthesis of a xylose derivative, which comprises protecting a xylose with a protective group, followed by incorporating to a halogen atom as a leaving group removing the protective groups and using water-soluble ligands to carry out a Suzuki cross-couplings reaction with a palladium catalyst in a water solution. Ten new xylose derivatives as obtained by the method are also provided.