2,6-Bis(bromomethyl)pyridine supplier

Name
2,6-Bis(bromomethyl)pyridine
EINECS
CAS No. 7703-74-4
Article Data68
CAS DataBase
Density 1.87 g/cm³
Solubility
Melting Point 85-87 °C(lit.)
Formula C₇H₇Br₂N
Boiling Point 275.6 °C at 760 mmHg
Molecular Weight 264.947
Flash Point 120.5 °C
Transport Information
Appearance
Safety 26-36/37/39
Risk Codes 22-36/37/38
Molecular Structure
Hazard Symbols Xn
Synonyms 2,6-BIS(BROMOMETHYL)PYRIDINE
PSA 12.89000
LogP 2.87140

Synthetic route

: 1195-59-1
2.6-bis(hydroxymethyl)pyridine

: 7703-74-4
2,6-bis-(bromomethyl)pyridine

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With diethyl ether anschliessend Behandeln mit Brom;

...Expand

: 108-48-5
2,6-dimethylpyridine

A: 68470-59-7
2-(bromomethyl)-6-methylpyridine

B: 7703-74-4
2,6-bis-(bromomethyl)pyridine

Conditions

Conditions	Yield
With tetrachloromethane; N-Bromosuccinimide; dibenzoyl peroxide

: 5453-67-8
2,6-bis(methoxycarbonyl)pyridine

: 7703-74-4
2,6-bis-(bromomethyl)pyridine

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

: 1195-59-1
2.6-bis(hydroxymethyl)pyridine

concentrated H2 SO4: concentrated H2 SO4

: 7703-74-4
2,6-bis-(bromomethyl)pyridine

Conditions

Conditions	Yield
In hydrogen bromide

: 122637-39-2
6-acetyl-2-pyridinecarboxylic acid

: 7703-74-4
2,6-bis-(bromomethyl)pyridine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: thionyl chloride 2: sodium tetrahydroborate / ethanol / 13 h / 0 - 20 °C / Reflux 3: hydrogen bromide / 15 h / Reflux View Scheme

: 7703-74-4
2,6-bis-(bromomethyl)pyridine

: 122-52-1
triethyl phosphite

: 61973-87-3
tetraethyl 2,6-bis(methanephosphonate)pyridine

Conditions

Conditions	Yield
at 135℃; for 2.5h; Arbuzov Reaction;	100%
at 110℃; for 4h;	85%
for 15h; Condensation; Arbuzov reaction; Heating;	61%
at 135℃; for 2.5h; Arbuzov reaction;

: 7703-74-4
2,6-bis-(bromomethyl)pyridine

: 74199-09-0, 79236-92-3
cyclen-glyoxal

: C27H43N9(2+)*2Br(1-)

Conditions

Conditions	Yield
In acetonitrile at 20℃; for 168000h;	100%

: 7703-74-4
2,6-bis-(bromomethyl)pyridine

: C27H43N9(2+)*2Br(1-)

: C34H50N10(4+)*4Br(1-)

Conditions

Conditions	Yield
In acetonitrile at 20℃; for 168000h;	100%

: 1-(2,2'-dimethylpropyl)-1H-imidazole

: 7703-74-4
2,6-bis-(bromomethyl)pyridine

: 2,6-bis(N-neopentyl-N'-methyleneimidazole)pyridine bromide

Conditions

Conditions	Yield
In 1,4-dioxane Reflux;	100%
In tetrahydrofuran for 144h; Reflux; Inert atmosphere;

: 7703-74-4
2,6-bis-(bromomethyl)pyridine

: 666836-17-5
C7H13N3

: 2Br(1-)*C21H33N7(2+)

Conditions

Conditions	Yield
In 1,4-dioxane Reflux;	100%

: 7703-74-4
2,6-bis-(bromomethyl)pyridine

: 6086-22-2
1-butyl-1H-[1,2,4]triazole

: 2Br(1-)*C19H29N7(2+)

Conditions

Conditions	Yield
In 1,4-dioxane Reflux;	100%

: 7703-74-4
2,6-bis-(bromomethyl)pyridine

: 873-55-2
sodium benzenesulfonate

: 2,6-bis[(phenylsulfonyl)methyl]pyridine

Conditions

Conditions	Yield
With tetra-n-propylammonium bromide In acetonitrile for 24h;	100%
With tetra-n-propylammonium bromide In acetonitrile for 24h;	87%

: 7703-74-4
2,6-bis-(bromomethyl)pyridine

: 200489-04-9
2,6-bis(azidomethyl)pyridine

Conditions

Conditions	Yield
With sodium azide In dimethyl sulfoxide at 20℃; Inert atmosphere;	99%
With sodium azide In dimethyl sulfoxide at 20℃; for 2h;	98%
With sodium azide In N,N-dimethyl-formamide at 60℃; for 10h;	96%

: 7703-74-4
2,6-bis-(bromomethyl)pyridine

: 717110-52-6
1-(2,4,6-trimethylphenyl)-4,5-dihydro-1H-imidazole

: 2,6-bis((1-mesityl-dihydroimidazolium)methyl)pyridine dibromide

Conditions

Conditions	Yield
In N,N-dimethyl-formamide for 18h;	99%

: 7703-74-4
2,6-bis-(bromomethyl)pyridine

: 3425-46-5
potassium selenocyanate

: 85539-82-8
2,6-bis(selenocyanatomethyl)pyridine

Conditions

Conditions	Yield
In acetone Ambient temperature;	98%
In acetone for 4h; Ambient temperature;	98%

: 7703-74-4
2,6-bis-(bromomethyl)pyridine

: 85916-13-8
tert-butyl iminodiacetate

: 144367-62-4
tetra(tert-butyl) 2,2',2'',2'''-<(pyridine-2,6-diyl)bis(methylenenitrilo)>tetrakis(acetate)

Conditions

Conditions	Yield
With sodium carbonate In acetonitrile Heating;	98%

: 7703-74-4
2,6-bis-(bromomethyl)pyridine

: 196301-00-5
N-[6-(2-hydroxymethyl)pyridylmethyl]piperazine

: 196300-94-4
2,6-bis[N'-[N'-(2-hydroxymethyl-6-pyridylmethyl)]piperazidylmethyl]pyridine

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile for 4h; Heating;	98%

: 7703-74-4
2,6-bis-(bromomethyl)pyridine

: 223704-14-1
(R,R)-N,N'-(cyclohexane-1,2-diyl)-N,N',N'',N'''-tetrakis(p-toluenesulphonyl)bis(propane-1,3-diamine)

: (7R,8R)-7,8-(butane-1,4-diyl)-N,N',N'',N'''-tetrakis(p-toluenesulfonyl)-2,6,9,13-tetraaza[14]-(2,6)-pyridinophane

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile for 48h; Heating;	98%

: 7703-74-4
2,6-bis-(bromomethyl)pyridine

: 107-15-3
ethylenediamine

: 117013-61-3
2,6-bis(1,4-diazapentyl)pyridine

Conditions

Conditions	Yield
Stage #1: 2,6-bis-(bromomethyl)pyridine; ethylenediamine In tetrahydrofuran at 25℃; for 12h; Stage #2: With potassium hydroxide In methanol	98%

: 7703-74-4
2,6-bis-(bromomethyl)pyridine

: 109-76-2
Trimethylenediamine

: 118230-14-1
2,6-bis[N-(3-aminopropyl)aminomethyl]pyridine

Conditions

Conditions	Yield
Stage #1: 2,6-bis-(bromomethyl)pyridine; Trimethylenediamine In tetrahydrofuran at 25℃; for 12h; Stage #2: With potassium hydroxide In methanol	98%

: 7703-74-4
2,6-bis-(bromomethyl)pyridine

: 110-60-1
1,4-diaminobutane

: 1104610-19-6
C15H29N5

Conditions

Conditions	Yield
Stage #1: 2,6-bis-(bromomethyl)pyridine; 1,4-diaminobutane In tetrahydrofuran at 25℃; for 12h; Stage #2: With potassium hydroxide In methanol	98%

: 7703-74-4
2,6-bis-(bromomethyl)pyridine

: 1258781-81-5
2,6-bis{[4-(1-(1S)-benzyloxycarbonylamino-2-phenylethyl)-1H-imidazol-1-yl]methyl}pyridine

: 2Br(1-)*C52H50N8O4(2+)

Conditions

Conditions	Yield
In acetone for 144h; Reflux; Inert atmosphere;	98%

: 7703-74-4
2,6-bis-(bromomethyl)pyridine

: 1350538-34-9
(S)-2-(2-nitrophenylsulfonamido)-N-((1R,2R)-2-(2-nitrophenylsulfonamido)cyclohexyl)-3-phenylpropanamide

: 1350538-37-2
(4R,9R,12S)-12-benzyl-3,13-bis(2-nitrobenzenesulfonyl)-3,10,13,19-tetraazatricyclo[13.3.1.0(4,9)]nonadeca-1(19),15,17-trien-11-one

Conditions

Conditions	Yield
Stage #1: (S)-2-(2-nitrophenylsulfonamido)-N-((1R,2R)-2-(2-nitrophenylsulfonamido)cyclohexyl)-3-phenylpropanamide With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 0.5h; Stage #2: 2,6-bis-(bromomethyl)pyridine In N,N-dimethyl-formamide for 3h; Richman-Atkins cyclization; Reflux;	98%

: 7703-74-4
2,6-bis-(bromomethyl)pyridine

: 87265-96-1
N,N',4,8,12,16-hexa(p-toluenesulfonyl)-4,8,12,16-tetraazaundecane-1,19-diamine

: 1448855-81-9
1,5,9,13,17,21-hexakis(p-tolylsulfonyl)-3,7,11,15,19,23-hexaaza-1(2,6)-pyridina cyclotetracosaphane

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile for 20h; Reflux;	98%

: 7703-74-4
2,6-bis-(bromomethyl)pyridine

: 5813-64-9
2,2-dimethylpropylamine

: 2,6-bis[(neo-pentylamino)methyl]pyridine

Conditions

Conditions	Yield
at 20℃; for 17h; Inert atmosphere; Schlenk technique; Glovebox;	98%

: 7703-74-4
2,6-bis-(bromomethyl)pyridine

: 269-07-8
naphtho[2,3-d]imidazole

: 1-((6-((1H-naphtho[2,3-d]imidazol-1-yl)methyl)pyridin-2-yl)methyl)-1H-naphtho[2,3-d]imidazole

Conditions

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 20℃;	98%
With tetrabutylammomium bromide; potassium carbonate In water; toluene at 20℃; for 8h; Solvent; Temperature; Reagent/catalyst;	90%
Stage #1: naphtho[2,3-d]imidazole With tetrabutylammomium bromide; potassium hydroxide In water; toluene Stage #2: 2,6-bis-(bromomethyl)pyridine In water; toluene at 20℃;	71%

: 7703-74-4
2,6-bis-(bromomethyl)pyridine

: 75-64-9
tert-butylamine

: N,N′-(pyridine-2,6-diylbis(methylene))bis(2-methylpropan-2-amine)

Conditions

Conditions	Yield
In chloroform at 50℃; for 5h;	97%

: 7703-74-4
2,6-bis-(bromomethyl)pyridine

: 1220532-30-8
(R)-5-phenyl-6,7-dihydro-5H-pyrrolo-[1,2-c]imidazole

: (R, R)-2,6-bis(5-phenyl-6,7-dihydro-5H-pyrrolo [1,2-c]imidazolium-2-yl)lutidine dibromide

Conditions

Conditions	Yield
In methanol at 75℃; for 48h; Inert atmosphere;	97%
In methanol at 75℃; for 48h; Inert atmosphere;	97%
In methanol at 75℃; for 48h; Inert atmosphere;	97%

: 7703-74-4
2,6-bis-(bromomethyl)pyridine

: C28H24N2P(1+)*F6P(1-)

: C63H55N5P2(4+)*2Br(1-)*2F6P(1-)

Conditions

Conditions	Yield
In acetonitrile for 12h; Schlenk technique; Reflux; Inert atmosphere;	97%

: 7703-74-4
2,6-bis-(bromomethyl)pyridine

: 85539-82-8
2,6-bis(selenocyanatomethyl)pyridine

: 118336-03-1
2,11-diselena<3.3>(2,6)pyridinophane

Conditions

Conditions	Yield
With sodium tetrahydroborate In tetrahydrofuran; ethanol Ambient temperature;	96%
With sodium tetrahydroborate In tetrahydrofuran; ethanol for 20h; Ambient temperature;	96%

: 7703-74-4
2,6-bis-(bromomethyl)pyridine

: 108-95-2
phenol

: 66433-94-1
2,6-bis(phenoxymethyl)pyridine

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile Inert atmosphere; Reflux;	96%
With potassium carbonate In acetone Heating;	65%

: 7703-74-4
2,6-bis-(bromomethyl)pyridine

: 124913-29-7
(o-methylbenzylalcohol)chromiumtricarbonyl sodium salt

: 124913-25-3, 124990-34-7
pyridine-2,6-{o-CH2OCH2C6H4(CH3)(Cr(CO)3)}2

Conditions

Conditions	Yield
In tetrahydrofuran	96%

: 7703-74-4
2,6-bis-(bromomethyl)pyridine

: N,N'-(2S,2'S)-1,1'-(2,2'-oxybis(ethane-2,1-diyl)bis(sulfanediyl))bis(propane-2,1-diyl)bis(4-methylbenzenesulfonamide)

: (4S,14S)-4,14-dimethyl-3,15-bis-(toluene-4-sulfonyl)-9-oxa-6,12-dithia-3,15,21-triazabicyclo[15.3.1]henicosa-1(20),17(21),18-triene

Conditions

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	96%

: 7703-74-4
2,6-bis-(bromomethyl)pyridine

: 603-35-0
triphenylphosphine

: C43H37Br2NP2

Conditions

Conditions	Yield
In acetonitrile at 70℃; for 8h;	96%

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

Product Name

2,6-Bis(bromomethyl)pyridine

Synthetic route

2,6-Bis(bromomethyl)pyridine Specification

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