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2-Bromo-4-methylpyridine is an organic compound with the molecular formula C6H6BrN. It is a colorless to orange oily liquid and is a derivative of pyridine, featuring a bromine atom at the 2nd position and a methyl group at the 4th position.

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  • 4926-28-7 Structure
  • Basic information

    1. Product Name: 2-Bromo-4-methylpyridine
    2. Synonyms: 2-BROMO-4-METHYLPYRIDINE;2-BROMO-4-PICOLINE;RARECHEM AH CK 0041;2-BROMO-4-METHYLPYRIDINE 99%;2-Bromo-4-MythylPyridine;2-BROMO-4-MEFHYL PYRIDINE;-Bromo-4-methylpyridine;2-BROMO-4-METHYLPYRIDINE (2-BROMO-4-PICOLINE)
    3. CAS NO:4926-28-7
    4. Molecular Formula: C6H6BrN
    5. Molecular Weight: 172.02
    6. EINECS: -0
    7. Product Categories: compounds of pyridine;Pyridine;pyridine derivative;Pyridine Series;Pyridines, Pyrimidines, Purines and Pteredines;Pyridines;Bromopyridines;Halopyridines;Boronic Acid;C6Heterocyclic Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Brominated heterocyclic series;Aromatics;Heterocycles;alkyl bromide
    8. Mol File: 4926-28-7.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 87 °C10 mm Hg(lit.)
    3. Flash Point: >230 °F
    4. Appearance: Clear yellow/Liquid
    5. Density: 1.545 g/mL at 25 °C(lit.)
    6. Vapor Pressure: 0.173mmHg at 25°C
    7. Refractive Index: n20/D 1.561(lit.)
    8. Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
    9. Solubility: Chloroform, Methanol (Slightly)
    10. PKA: 1.46±0.10(Predicted)
    11. BRN: 107331
    12. CAS DataBase Reference: 2-Bromo-4-methylpyridine(CAS DataBase Reference)
    13. NIST Chemistry Reference: 2-Bromo-4-methylpyridine(4926-28-7)
    14. EPA Substance Registry System: 2-Bromo-4-methylpyridine(4926-28-7)
  • Safety Data

    1. Hazard Codes: Xi,Xn
    2. Statements: 36/37/38-20/21/22
    3. Safety Statements: 26-36-36/37/39
    4. WGK Germany: 3
    5. RTECS:
    6. HazardClass: IRRITANT
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 4926-28-7(Hazardous Substances Data)

4926-28-7 Usage

Uses

Used in Pharmaceutical Synthesis:
2-Bromo-4-methylpyridine is used as an intermediate in the total synthesis of ocular age pigment A2-E, which is crucial for understanding the chemical processes involved in age-related eye conditions.
Used in Chemical Research:
In the preparation of methoxy-2-(2-pyridyl)indoles, 2-bromo-4-methylpyridine serves as a key building block. These indole derivatives have potential applications in various fields, including pharmaceuticals and materials science.
Used in Organic Synthesis:
2-Bromo-4-methylpyridine is utilized in the preparation of 2-(2′,4′-difluorophenyl)-4-methylpyridine through a Suzuki coupling reaction with 2,4-difluorophenylboronic acid. 2-Bromo-4-methylpyridine may have applications in the development of new pharmaceuticals or other specialty chemicals.
Used in the Chemical Industry:
2-Bromo-4-methylpyridine can be employed as a versatile intermediate for the synthesis of various other pyridine-based compounds, which are widely used in the chemical industry for the production of dyes, agrochemicals, and other specialty chemicals.

Check Digit Verification of cas no

The CAS Registry Mumber 4926-28-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,9,2 and 6 respectively; the second part has 2 digits, 2 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 4926-28:
(6*4)+(5*9)+(4*2)+(3*6)+(2*2)+(1*8)=107
107 % 10 = 7
So 4926-28-7 is a valid CAS Registry Number.
InChI:InChI=1/C6H6BrN/c1-5-2-3-8-6(7)4-5/h2-4H,1H3

4926-28-7 Well-known Company Product Price

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  • Alfa Aesar

  • (B25253)  2-Bromo-4-methylpyridine, 96%   

  • 4926-28-7

  • 1g

  • 260.0CNY

  • Detail
  • Alfa Aesar

  • (B25253)  2-Bromo-4-methylpyridine, 96%   

  • 4926-28-7

  • 5g

  • 720.0CNY

  • Detail
  • Alfa Aesar

  • (B25253)  2-Bromo-4-methylpyridine, 96%   

  • 4926-28-7

  • 25g

  • 3058.0CNY

  • Detail
  • Aldrich

  • (349984)  2-Bromo-4-methylpyridine  97%

  • 4926-28-7

  • 349984-1G

  • 341.64CNY

  • Detail
  • Aldrich

  • (349984)  2-Bromo-4-methylpyridine  97%

  • 4926-28-7

  • 349984-10G

  • 2,418.39CNY

  • Detail

4926-28-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Bromo-4-methylpyridine

1.2 Other means of identification

Product number -
Other names 2-Br-4-Me-pyridine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:4926-28-7 SDS

4926-28-7Synthetic route

2-Amino-4-methylpyridine
695-34-1

2-Amino-4-methylpyridine

2-Bromo-4-picoline
4926-28-7

2-Bromo-4-picoline

Conditions
ConditionsYield
With hydrogen bromide; bromine; sodium nitrite In water at 0℃; for 3h;94%
With sodium hydroxide; hydrogen bromide; bromine; sodium nitrite In water90%
With hydrogen bromide; bromine; sodium nitrite at 5℃;87%
picoline
108-89-4

picoline

2-Bromo-4-picoline
4926-28-7

2-Bromo-4-picoline

Conditions
ConditionsYield
Stage #1: picoline With n-butyllithium; 2-(N,N-dimethylamino)ethanol In hexane at 0℃; for 1h;
Stage #2: With carbon tetrabromide In tetrahydrofuran; hexane at -78℃; for 1h; Further stages.;
70%
picoline
108-89-4

picoline

acetyl hypofluorite
78948-09-1

acetyl hypofluorite

A

2-Bromo-4-picoline
4926-28-7

2-Bromo-4-picoline

B

4-methylpyridin-2-yl acetate
108168-80-5

4-methylpyridin-2-yl acetate

Conditions
ConditionsYield
With 1,2-dibromomethane Ambient temperature;A 55%
B n/a
2-hydroksy-4-methyl-pyridine
13466-41-6

2-hydroksy-4-methyl-pyridine

ethyl acetate-water

ethyl acetate-water

Bromoform
75-25-2

Bromoform

2-Bromo-4-picoline
4926-28-7

2-Bromo-4-picoline

Conditions
ConditionsYield
With phosphorus tribromide In water
2-Amino-4-methylpyridine
695-34-1

2-Amino-4-methylpyridine

A

2-Bromo-4-picoline
4926-28-7

2-Bromo-4-picoline

B

2-bromo-4-bromomethyl pyridine
83004-14-2

2-bromo-4-bromomethyl pyridine

4-methylpicolinic acid
4021-08-3

4-methylpicolinic acid

2-Bromo-4-picoline
4926-28-7

2-Bromo-4-picoline

Conditions
ConditionsYield
With tert-butylhypochlorite; dichloromethane; oxygen; sodium hydrogencarbonate at 70℃; for 20h; Green chemistry;55 %Spectr.
2-Bromo-4-picoline
4926-28-7

2-Bromo-4-picoline

4'-((2-butyl-4-oxo-8-oxa-1,3-diazaspiro[4.5]dec-1-en-3-yl)methyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-2-carbonitrile

4'-((2-butyl-4-oxo-8-oxa-1,3-diazaspiro[4.5]dec-1-en-3-yl)methyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-2-carbonitrile

4'-((2-butyl-4-oxo-8-oxa-1,3-diazaspiro[4.5]dec-1-en-3-yl)methyl)-5-(4-methylpyridin-2-yl)-[1,1'-biphenyl]-2-carbonitrile

4'-((2-butyl-4-oxo-8-oxa-1,3-diazaspiro[4.5]dec-1-en-3-yl)methyl)-5-(4-methylpyridin-2-yl)-[1,1'-biphenyl]-2-carbonitrile

Conditions
ConditionsYield
With potassium phosphate; methanesulfonic acid(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II) In tetrahydrofuran at 120℃; for 0.75h; Inert atmosphere; Sealed tube; Microwave irradiation;100%
2-Bromo-4-picoline
4926-28-7

2-Bromo-4-picoline

benzyl bromide
100-39-0

benzyl bromide

2-benzyl-4-methyl pyridine
5191-54-8

2-benzyl-4-methyl pyridine

Conditions
ConditionsYield
With zinc; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran Alkylation;99%
2-Bromo-4-picoline
4926-28-7

2-Bromo-4-picoline

2-(3-(quinolin-2-yl)phenoxy)-9H-carbazole

2-(3-(quinolin-2-yl)phenoxy)-9H-carbazole

9-(4-methylpyridin-2-yl)-2-(3-(quinolin-2-yl)phenoxy)-9H-carbazole

9-(4-methylpyridin-2-yl)-2-(3-(quinolin-2-yl)phenoxy)-9H-carbazole

Conditions
ConditionsYield
With 1H-imidazole; copper(l) iodide; potassium carbonate In toluene at 120℃; for 72.41h; Inert atmosphere;99%
2-Bromo-4-picoline
4926-28-7

2-Bromo-4-picoline

2-methyl-1-propenylbromide
3017-69-4

2-methyl-1-propenylbromide

4-methyl-2-(2-methylprop-1-en-1-yl)pyridine

4-methyl-2-(2-methylprop-1-en-1-yl)pyridine

Conditions
ConditionsYield
With potassium fluoride; bis(1,5-cyclooctadiene)nickel (0); N,N-dimethyl acetamide; 4,4'-di-tert-butyl-2,2'-bipyridine; magnesium chloride; zinc at 0 - 20℃; for 15h; Schlenk technique; Sealed tube; Inert atmosphere; chemoselective reaction;99%
2-Bromo-4-picoline
4926-28-7

2-Bromo-4-picoline

3-Bromophenol
591-20-8

3-Bromophenol

2-(3-bromophenoxy)-4-methylpyridine

2-(3-bromophenoxy)-4-methylpyridine

Conditions
ConditionsYield
With 2-Picolinic acid; potassium phosphate; copper(l) iodide In dimethyl sulfoxide at 105℃; for 48h; Inert atmosphere;99%
With 2-Picolinic acid; copper(l) iodide In dimethyl sulfoxide at 120℃; for 48h; Inert atmosphere;55%
With 2-Picolinic acid; potassium phosphate; copper(l) iodide In dimethyl sulfoxide at 120℃; for 48h; Inert atmosphere;55%
2-Bromo-4-picoline
4926-28-7

2-Bromo-4-picoline

9-phenanthrenylboronic acid
68572-87-2

9-phenanthrenylboronic acid

4-methyl-2-(phenanthren-9-yl)pyridine

4-methyl-2-(phenanthren-9-yl)pyridine

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 24h; Suzuki Coupling; Inert atmosphere;98.9%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran at 80℃; for 24h; Inert atmosphere;98.9%
2-Bromo-4-picoline
4926-28-7

2-Bromo-4-picoline

1-bromo-1-propene
590-14-7

1-bromo-1-propene

(E)-4-methyl-2-(prop-1-en-1-yl)pyridine

(E)-4-methyl-2-(prop-1-en-1-yl)pyridine

Conditions
ConditionsYield
With potassium fluoride; bis(1,5-cyclooctadiene)nickel (0); N,N-dimethyl acetamide; 4,4'-di-tert-butyl-2,2'-bipyridine; magnesium chloride; zinc at 0 - 20℃; for 15h; Schlenk technique; Sealed tube; Inert atmosphere; chemoselective reaction;98%
2-Bromo-4-picoline
4926-28-7

2-Bromo-4-picoline

2-methoxy-9H-carbazole
6933-49-9

2-methoxy-9H-carbazole

2-methoxy-9-(4-methylpyridin-2-yl)-9H-carbazole

2-methoxy-9-(4-methylpyridin-2-yl)-9H-carbazole

Conditions
ConditionsYield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate In toluene at 125℃; for 18h; Inert atmosphere;98%
2-Bromo-4-picoline
4926-28-7

2-Bromo-4-picoline

1-bromo-1-propene
590-14-7

1-bromo-1-propene

2-propenyl-4-methylpyridine

2-propenyl-4-methylpyridine

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel (0); 4,4'-di-tert-butyl-2,2'-bipyridine; magnesium chloride; zinc In N,N-dimethyl acetamide at 20℃; Schlenk technique; Cooling with ice;98%
2-Bromo-4-picoline
4926-28-7

2-Bromo-4-picoline

2-iodo-4-methylpyridine
22282-60-6

2-iodo-4-methylpyridine

Conditions
ConditionsYield
With copper(l) iodide; sodium iodide; N,N`-dimethylethylenediamine In 1,4-dioxane at 110℃; for 18h; Finkelstein Reaction; Inert atmosphere; Schlenk technique;97%
Stage #1: 2-Bromo-4-picoline With nBu4ZnLi2*TMEDA In toluene at 20℃; for 1h; Inert atmosphere;
Stage #2: With iodine In tetrahydrofuran; toluene at 20℃; for 1h; Inert atmosphere; chemoselective reaction;
88%
2-Bromo-4-picoline
4926-28-7

2-Bromo-4-picoline

1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

4-methyl-2-(naphthalen-1-yl)pyridine
100004-76-0

4-methyl-2-(naphthalen-1-yl)pyridine

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In toluene Suzuki-Miyaura Coupling; Inert atmosphere; Reflux;97%
With tetrakis(triphenylphosphine) palladium(0); 1-chloroisoquinoline; sodium carbonate In ethanol; water; toluene at 120℃; for 12h; Inert atmosphere; Glovebox; Schlenk technique;
2-Bromo-4-picoline
4926-28-7

2-Bromo-4-picoline

4-methyl-1-naphthylboronic acid
103986-53-4

4-methyl-1-naphthylboronic acid

C17H15N

C17H15N

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In toluene Suzuki-Miyaura Coupling; Inert atmosphere; Reflux;97%
2-Bromo-4-picoline
4926-28-7

2-Bromo-4-picoline

4-(diphenylamino)phenyl boronic acid
201802-67-7

4-(diphenylamino)phenyl boronic acid

N,N-diphenyl-4-(4-methylpyridinyl-2-yl)aniline
1422183-04-7

N,N-diphenyl-4-(4-methylpyridinyl-2-yl)aniline

Conditions
ConditionsYield
With palladium diacetate; potassium carbonate In ethanol; water at 80℃; for 0.133333h; Suzuki Coupling;96%
With palladium diacetate; potassium carbonate In ethanol; water at 80℃; Suzuki Coupling;
With palladium diacetate; potassium carbonate In ethanol; water at 80℃; for 1h; Suzuki Coupling;
2-Bromo-4-picoline
4926-28-7

2-Bromo-4-picoline

2-methoxyphenylmagnesium bromide
16750-63-3

2-methoxyphenylmagnesium bromide

2-(2-methoxyphenyl)-4-methylpyridine
100004-77-1

2-(2-methoxyphenyl)-4-methylpyridine

Conditions
ConditionsYield
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In tetrahydrofuran96%
2-Bromo-4-picoline
4926-28-7

2-Bromo-4-picoline

methyl 2-[(tert-butoxycarbonyl)amino]acrylate
55477-80-0

methyl 2-[(tert-butoxycarbonyl)amino]acrylate

C15H22N2O4

C15H22N2O4

Conditions
ConditionsYield
With (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate In water; dimethyl sulfoxide at 23℃; for 16h; Irradiation;96%
2-Bromo-4-picoline
4926-28-7

2-Bromo-4-picoline

C10H11BrClMgNSi*LiCl

C10H11BrClMgNSi*LiCl

3-bromo-4'-methyl-6-((trimethylsilyl)ethynyl)-2,2'-bipyridine

3-bromo-4'-methyl-6-((trimethylsilyl)ethynyl)-2,2'-bipyridine

Conditions
ConditionsYield
Stage #1: 2-Bromo-4-picoline With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere;
Stage #2: With magnesium chloride In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere;
Stage #3: C10H11BrClMgNSi*LiCl Further stages;
96%
2-Bromo-4-picoline
4926-28-7

2-Bromo-4-picoline

aniline
62-53-3

aniline

4-methyl-N-phenyl-2-aminopyridine
19933-06-3

4-methyl-N-phenyl-2-aminopyridine

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); potassium tert-butylate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In 1,4-dioxane at 100℃; Inert atmosphere;95%
With tris-(dibenzylideneacetone)dipalladium(0); potassium tert-butylate; bis[2-(diphenylphosphino)phenyl] ether In toluene at 100℃; Inert atmosphere;90%
With copper at 140 - 150℃; under 40 Torr; Badtemperatur;
2-Bromo-4-picoline
4926-28-7

2-Bromo-4-picoline

phenylmagnesium chloride
100-59-4

phenylmagnesium chloride

4-methyl-2-phenylpyridine
3475-21-6

4-methyl-2-phenylpyridine

Conditions
ConditionsYield
1,1'-bis-(diphenylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at -25℃; for 18h;95%
2-Bromo-4-picoline
4926-28-7

2-Bromo-4-picoline

phenylboronic acid
98-80-6

phenylboronic acid

4-methyl-2-phenylpyridine
3475-21-6

4-methyl-2-phenylpyridine

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In tetrahydrofuran at 60℃; for 12h; Schlenk technique; Inert atmosphere;95%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol at 100℃; for 15h; Inert atmosphere;94%
With palladium diacetate; potassium carbonate; triphenylphosphine In methanol; acetonitrile at 65℃; for 24h; Inert atmosphere;85%
2-Bromo-4-picoline
4926-28-7

2-Bromo-4-picoline

3,4-ethylenedioxythiophene-2-carboxaldehyde
204905-77-1

3,4-ethylenedioxythiophene-2-carboxaldehyde

2-(2-bromopyrid-4-yl)-1-(3,4-ethylenedioxythien-2-yl)ethanol
1281847-13-9

2-(2-bromopyrid-4-yl)-1-(3,4-ethylenedioxythien-2-yl)ethanol

Conditions
ConditionsYield
Stage #1: 2-Bromo-4-picoline With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h;
Stage #2: 3,4-ethylenedioxythiophene-2-carboxaldehyde In tetrahydrofuran at 20℃; for 0.5h;
Stage #3: With water In tetrahydrofuran; ethyl acetate
95%
Stage #1: 2-Bromo-4-picoline With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h;
Stage #2: 3,4-ethylenedioxythiophene-2-carboxaldehyde In tetrahydrofuran at 20℃; for 0.5h;
Stage #3: With water In tetrahydrofuran; ethyl acetate
95%
Stage #1: 2-Bromo-4-picoline With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h;
Stage #2: 3,4-ethylenedioxythiophene-2-carboxaldehyde In tetrahydrofuran at 20℃; for 0.5h;
94%
2-Bromo-4-picoline
4926-28-7

2-Bromo-4-picoline

2-bromo-9H-carbazole
3652-90-2

2-bromo-9H-carbazole

2-bromo-9-(4-methylpyridine-2-yl)-9H-carbazole
1404169-08-9

2-bromo-9-(4-methylpyridine-2-yl)-9H-carbazole

Conditions
ConditionsYield
With 1-methyl-1H-imidazole; copper(l) chloride; lithium tert-butoxide In toluene at 130℃; for 2.5h; Inert atmosphere;95%
With 1-methyl-1H-imidazole; copper(l) chloride; lithium tert-butoxide In toluene at 130℃; for 2.5h; Ullmann Condensation; chemoselective reaction;95%
With 1-methyl-1H-imidazole; copper(l) iodide; lithium tert-butoxide In toluene at 20 - 130℃; for 48h; Inert atmosphere;95%
2-Bromo-4-picoline
4926-28-7

2-Bromo-4-picoline

1-butyn-4-ol
927-74-2

1-butyn-4-ol

4-(4-methylpyridin-2-yl)but-3-yn-1-ol

4-(4-methylpyridin-2-yl)but-3-yn-1-ol

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; for 24h; Sonogashira Cross-Coupling; Inert atmosphere;95%
2-Bromo-4-picoline
4926-28-7

2-Bromo-4-picoline

C14H13NO

C14H13NO

C20H18N2O

C20H18N2O

Conditions
ConditionsYield
With 1-methyl-1H-imidazole; copper(l) iodide; lithium tert-butoxide In toluene Inert atmosphere; Heating; Sealed tube;95%
2-Bromo-4-picoline
4926-28-7

2-Bromo-4-picoline

(4S)-4-isopropyl-1,3-oxazolidin-2-one
17016-83-0

(4S)-4-isopropyl-1,3-oxazolidin-2-one

(S)-4-isopropyl-3-(4-methylpyridin-2-yl)oxazolidin-2-one
737760-93-9

(S)-4-isopropyl-3-(4-methylpyridin-2-yl)oxazolidin-2-one

Conditions
ConditionsYield
With copper(l) iodide; 1,10-Phenanthroline; potassium carbonate In toluene at 140℃; for 16h; Inert atmosphere; Schlenk technique;95%
2-Bromo-4-picoline
4926-28-7

2-Bromo-4-picoline

4-fluoro-N-methoxy-N-methylbenzamide
116332-54-8

4-fluoro-N-methoxy-N-methylbenzamide

2-(2-bromopyridin-4-yl)-1-(4-fluorophenyl)ethan-1-one
158876-70-1

2-(2-bromopyridin-4-yl)-1-(4-fluorophenyl)ethan-1-one

Conditions
ConditionsYield
Stage #1: 2-Bromo-4-picoline With lithium diisopropyl amide In tetrahydrofuran; hexane at -85℃;
Stage #2: 4-fluoro-N-methoxy-N-methylbenzamide In tetrahydrofuran; hexane at -85 - 0℃;
94%
2-Bromo-4-picoline
4926-28-7

2-Bromo-4-picoline

2-(3-(3,5-dimethyl-1H-pyrazol-1-yl)phenoxy)-9H-carbazole
1393812-51-5

2-(3-(3,5-dimethyl-1H-pyrazol-1-yl)phenoxy)-9H-carbazole

2-(3-(3,5-dimethyl-1H-pyrazol-1-yl)phenoxy)-9-(4-methylpyridin-2-yl)-9H-carbazole

2-(3-(3,5-dimethyl-1H-pyrazol-1-yl)phenoxy)-9-(4-methylpyridin-2-yl)-9H-carbazole

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); johnphos; sodium t-butanolate In 1,4-dioxane; toluene at 95 - 105℃; for 48h; Inert atmosphere; Sealed tube;94%
With tris-(dibenzylideneacetone)dipalladium(0); johnphos; sodium t-butanolate In 1,4-dioxane; toluene at 95 - 105℃; for 48h; Schlenk technique; Inert atmosphere; Sealed tube;94%
2-Bromo-4-picoline
4926-28-7

2-Bromo-4-picoline

4-dibenzofurylboronic acid
100124-06-9

4-dibenzofurylboronic acid

2-(dibenzo[b,d]furan-4-yl)-4-methylpyridine

2-(dibenzo[b,d]furan-4-yl)-4-methylpyridine

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; ethanol; water for 24h; Suzuki-Miyaura Coupling; Reflux; Inert atmosphere;94%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 100℃; for 2h;67%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 100℃; for 2h;67%
2-Bromo-4-picoline
4926-28-7

2-Bromo-4-picoline

3-(trimethylsilyl)phenylboronic acid
177171-16-3

3-(trimethylsilyl)phenylboronic acid

4-methyl-2-(3-trimethylsilylphenyl)pyridine

4-methyl-2-(3-trimethylsilylphenyl)pyridine

Conditions
ConditionsYield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; water for 18h; Heating;93%
2-Bromo-4-picoline
4926-28-7

2-Bromo-4-picoline

2,4-difluorophenylboronic acid
144025-03-6

2,4-difluorophenylboronic acid

2-(2',4'-difluorophenyl)-4-methylpyridine
391250-41-2

2-(2',4'-difluorophenyl)-4-methylpyridine

Conditions
ConditionsYield
Stage #1: 2-Bromo-4-picoline; 2,4-difluorophenylboronic acid With potassium carbonate In 1,2-dimethoxyethane for 0.5h;
Stage #2: tetrakis(triphenylphosphine) palladium(0) In water-d2 at 90℃; for 18h; Heating / reflux;
93%
Stage #1: 2-Bromo-4-picoline; 2,4-difluorophenylboronic acid With potassium carbonate In 1,2-dimethoxyethane for 0.5h;
Stage #2: tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane at 90℃; for 18h; Heating / reflux;
93%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; ethanol for 24h; Reflux; Inert atmosphere;89%

4926-28-7Relevant articles and documents

2-Carbaldoximes of pyridine-4- and 5-carboxylic acids

Reyes-Rivera,Hutchins,Dalton

, p. 665 - 669 (1995)

A series of pyridine-2-carbaldoximes, all of which are substituted at the 4- or 5-position with derivatives of the corresponding carboxylic acids, have been prepared via the corresponding pyridine-2-carbaldehydes.

Transition-metal-free decarboxylative halogenation of 2-picolinic acids with dihalomethane under oxygen conditions

Zhang, Xitao,Feng, Xiujuan,Zhang, Haixia,Yamamoto, Yoshinori,Bao, Ming

supporting information, p. 5565 - 5570 (2019/10/22)

A convenient and efficient method for the synthesis of 2-halogen-substituted pyridines is described. The decarboxylative halogenation of 2-picolinic acids with dihalomethane proceeded smoothly via N-chlorocarbene intermediates to afford 2-halogen-substituted pyridines in satisfactory to excellent yields under transition-metal-free conditions. This new type of decarboxylative halogenation is operationally simple and exhibits high functional-group tolerance.

Benzothiazole Formulations and Use Thereof

-

Page/Page column 9; 24, (2010/11/30)

The present invention is related to macrogol glyceride pharmaceutical formulations containing benzothiazole derivatives. In particular, the invention is related to benzothiazole stearoyl macrogol pharmaceutical formulations, method of preparation and use thereof.

Inhibitors of P2X3

-

Page/Page column 23, (2008/06/13)

Compounds of formula 1 are modulators of P2X3 useful for the treatment of pain and genito-urinary, gastrointestinal, and respiratory disorders: wherein R1 is —C(═S)CH3, pyridyl, pyrimidinyl, pyrazinyl, thiazolyl, furyl, furylcarbonyl, acetyl, or carbamoyl; R2a and R2b are independently H, methyl, or ethyl; R3 is H or methyl; Y is a bond, —(CR4R5)n— or —CR4═CR5—; wherein R4 and R5 are each independently H or methyl and n is 1 or 2; X is N or CH; A is phenyl, 5-membered heterocyclyl, or 6-membered heterocyclyl; R6, R7 and R8 are each independently H, halo, lower alkyl, cycloalkyl, alkylthio, alkylthio-lower alkyl, alkylsulfonyl-lower alkyl, di(lower alkyl)amino-lower alkyl, morpholinyl-lower alkyl, 4-methyl-piperazinyl-methyl, trifluoromethyl, pyridyl, tetrazolyl, thiophenyl, phenyl, biphenyl, or benzyl (where thiophenyl, phenyl and benzyl are substituted with 0-3 lower alkyl, halo, sulfonamido, trifluoromethyl, lower alkoxy or lower alkylthio) or R6 and R7 together form a 5-membered or 6-membered carbocyclic or heterocyclic ring substituted with 0-3 substituents selected from the group consisting of lower alkyl, lower alkoxy, oxo, halo, thiophenyl-lower alkyl, phenyl, benzyl (where phenyl and benzyl are substituted with 0-3 lower alkyl, halo, sulfonamido, trifluoro-methyl, lower alkoxy, lower alkylthio, amino-lower alkyl, lower alkylamino-lower alkyl, or di(lower alkyl)amino-lower alkyl); and pharmaceutically acceptable salts thereof; wherein when R1 is pyrimidin-2-yl, X is N, Y is a bond and A is oxazol-5-yl the carbon atom at position 4 in said oxazol-5-yl is not substituted by propyl when the carbon atom at position 2 in said oxazol-5-yl is substituted by substituted phenyl and the carbon atom at position 4 in said oxazol-5-yl is not substituted by phenyl when the carbon atom at position 2 is substituted by unsubstituted or substituted phenyl.

Cyclometalated transition metal complex and organic electroluminescent device using the same

-

, (2008/06/13)

A cyclometalated transition metal complex emitting phosphorescence of high efficiency and an organic electroluminescent display device employing the same are provided. The cyclometalated transition metal complex has a transition metal atom and a phosphorus ligand having at least one alkylene oxide and a phosphorus atom. The phosphorus atom is bound to the transition metal atom. The cyclometalated transition metal complex can be employed when forming an organic film of an organic electroluminescent display device, can emit light at a wavelength range of 400 nm to 650 nm, and can emit white light as well when used with a green light emitting material and a red light emitting material.

The expedient access to bromo-pyridine carbaldehyde scaffolds using gem-dibromomethyl intermediates

Mandal, Ashis Baran,Augustine, John Kallikat,Quattropani, Anna,Bombrun, Agnes

, p. 6033 - 6036 (2007/10/03)

A simple, efficient, and general two-step synthesis to bromo-pyridine carbaldehyde scaffolds is described. This direct route involves sequential reactions employing the dibromination of bromo-picolines followed by hydrolysis using an aqueous solution of calcium carbonate. Bromo-pyridine carbaldehyde scaffolds 1-7 were obtained in good overall yield. Bromo-dibromomethyl-pyridine intermediates have been isolated and characterized.

Side-chain retention during lithiation of 4-picoline and 3,4-lutidine: Easy access to molecular diversity in pyridine series

Kaminski, Thomas,Gros, Philippe,Fort, Yves

, p. 3855 - 3860 (2007/10/03)

The first direct ring-selective lithiation of 4-picoline and 3,4-lutidine has been achieved through the use of BuLi/LiDMAE aggregates to prevent the usual side-chain metallation. Several functionalities have been introduced at the C-2, C-6 and C-5 positions by ring-selective sequential lithiation, opening a simple and fast route to polysubstituted pyridine building blocks. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

Syntheses of substituted pyridines, quinolines and diazines via palladium-catalyzed cross-coupling of aryl Grignard reagents

Bonnet, Véronique,Mongin, Florence,Trécourt, Fran?ois,Quéguiner, Guy,Knochel, Paul

, p. 4429 - 4438 (2007/10/03)

The palladium-catalyzed cross-coupling reactions between arylmagnesium halides (phenylmagnesium chloride, mesitylmagnesium bromide, 4-(methoxycarbonyl)phenylmagnesium chloride and 4-cyanophenylmagnesium chloride) and halopyridines allowed the synthesis of substituted pyridines. Owing to the remarkably mild conditions used (often below 0°C), the reaction could be extended to the use of functionalized halopyridines, haloquinolines and halodiazines.

Preparation and characterization of methyl substituted 2,2′-dipyridyl diselenides and -ditellurides: X-ray structure of 6,6′-dimethyl-2,2′-dipyridyl diselenide

Bhasin,Venugopalan,Singh

, p. 2579 - 2587 (2007/10/03)

A convenient method for the preparation of various methyl substituted 2,2′-dipyridyl diselenides and -ditellurides by the aerial oxidation of lithium 2-pyridylselenolate/tellurolate, prepared from the lithium-halogen exchange between n-butyllithium and 2-bromo methyl substituted pyridines is reported. All the compounds prepared are new and have been characterized by elemental analysis, IR, 1H, 13C, 11Se NMR, and mass spectral studies. Crystal structure of 6,6′-dimethyl-2,2′-dipyridyl diselenide has been determined.

Inhibitors of prenyl-protein transferase

-

, (2008/06/13)

The present invention is directed to compounds which inhibit prenyl-protein transferase (FTase) and the prenylation of the oncogene protein Ras. The invention is further directed to chemotherapeutic compositions containing the compounds of this invention and methods for inhibiting prenyl-protein transferase and the prenylation of the oncogene protein Ras.

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