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2-Bromo-5-methylpyridine is an organic compound characterized by its light brown solid appearance. It is a derivative of pyridine, a heterocyclic aromatic compound, with a bromine atom at the 2nd position and a methyl group at the 5th position. 2-Bromo-5-methylpyridine is known for its chemical reactivity and is commonly utilized as a building block in the synthesis of various complex organic molecules, particularly those with potential applications in the pharmaceutical and chemical industries.

3510-66-5

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3510-66-5 Usage

Uses

Used in Pharmaceutical Industry:
2-Bromo-5-methylpyridine is used as a key intermediate in the preparation of [[(triazolylmethyl)pyridyl]phenyl]tetrazoles and related compounds. These compounds are of significant interest due to their potential as cardiovascular agents, which can be used in the development of new drugs to treat heart-related conditions.
Used in Chemical Synthesis:

Check Digit Verification of cas no

The CAS Registry Mumber 3510-66-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,5,1 and 0 respectively; the second part has 2 digits, 6 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 3510-66:
(6*3)+(5*5)+(4*1)+(3*0)+(2*6)+(1*6)=65
65 % 10 = 5
So 3510-66-5 is a valid CAS Registry Number.
InChI:InChI=1/C6H6BrN/c1-5-2-3-6(7)8-4-5/h2-4H,1H3

3510-66-5 Well-known Company Product Price

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  • Alfa Aesar

  • (B25083)  2-Bromo-5-methylpyridine, 98+%   

  • 3510-66-5

  • 5g

  • 309.0CNY

  • Detail
  • Alfa Aesar

  • (B25083)  2-Bromo-5-methylpyridine, 98+%   

  • 3510-66-5

  • 25g

  • 1014.0CNY

  • Detail
  • Alfa Aesar

  • (B25083)  2-Bromo-5-methylpyridine, 98+%   

  • 3510-66-5

  • 100g

  • 3655.0CNY

  • Detail
  • Aldrich

  • (263354)  2-Bromo-5-methylpyridine  98%

  • 3510-66-5

  • 263354-5G

  • 479.70CNY

  • Detail
  • Aldrich

  • (263354)  2-Bromo-5-methylpyridine  98%

  • 3510-66-5

  • 263354-25G

  • 1,552.59CNY

  • Detail

3510-66-5SDS

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-5-methylpyridine

1.2 Other means of identification

Product number -
Other names 2-brom-5-methylpyridin

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:3510-66-5 SDS

3510-66-5Synthetic route

(5-methyl-pyridin-2-yl)amine
1603-41-4

(5-methyl-pyridin-2-yl)amine

2-Bromo-5-methylpyridine
3510-66-5

2-Bromo-5-methylpyridine

Conditions
ConditionsYield
With hydrogen bromide; bromine; sodium nitrite 1.) -20 deg C, 90 min; 2.) 15 deg C, 1 h 45 min;93%
With hydrogen bromide; bromine; sodium nitrite at 0℃;91%
Stage #1: (5-methyl-pyridin-2-yl)amine With hydrogen bromide; bromine In water at -20℃; for 3h;
Stage #2: With sodium nitrite at -20℃; for 1h;
90%
(5-methyl-pyridin-2-yl)amine
1603-41-4

(5-methyl-pyridin-2-yl)amine

A

2-Bromo-5-methylpyridine
3510-66-5

2-Bromo-5-methylpyridine

B

3-[4-(5-methylpyrid-2-yl)piperazin-1-yl]methyl-1H-pyrrolo[2,3-b]pyridine

3-[4-(5-methylpyrid-2-yl)piperazin-1-yl]methyl-1H-pyrrolo[2,3-b]pyridine

Conditions
ConditionsYield
With sodium hydroxide; bromine; sodium nitrite In water; hydrogen bromideA n/a
B 75%
3-Methylpyridine
108-99-6

3-Methylpyridine

2-Bromo-5-methylpyridine
3510-66-5

2-Bromo-5-methylpyridine

Conditions
ConditionsYield
Stage #1: 3-Methylpyridine With n-butyllithium; lithium 2-(dimethylamino)ethanolate In hexane at 0℃; for 1h; Metallation;
Stage #2: With carbon tetrabromide In tetrahydrofuran; hexane at -78℃; for 1h; Substitution; Further stages.;
65%
Multi-step reaction with 2 steps
1.1: boron trifluoride diethyl etherate / diethyl ether / 0.17 h / 0 °C / Inert atmosphere
2.1: n-butyllithium; diisopropylamine / diethyl ether / 0.42 h / -78 °C
2.2: -78 - 20 °C
View Scheme
5-methyl-pyridin-2-ol
1003-68-5

5-methyl-pyridin-2-ol

2-Bromo-5-methylpyridine
3510-66-5

2-Bromo-5-methylpyridine

Conditions
ConditionsYield
With phosphorus tribromide at 190℃;
6-hydroxy-3-methylpicolinic acid
115185-81-4

6-hydroxy-3-methylpicolinic acid

2-Bromo-5-methylpyridine
3510-66-5

2-Bromo-5-methylpyridine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: copper-powder / 300 °C
2: phosphorus (III)-bromide / 190 °C
View Scheme
5-methyl-6-carboxy-2-pyrone
3060-42-2

5-methyl-6-carboxy-2-pyrone

2-Bromo-5-methylpyridine
3510-66-5

2-Bromo-5-methylpyridine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: aqueous NH3 / 120 - 140 °C
2: copper-powder / 300 °C
3: phosphorus (III)-bromide / 190 °C
View Scheme
(5-methyl-pyridin-2-yl)amine
1603-41-4

(5-methyl-pyridin-2-yl)amine

ice-ethanol

ice-ethanol

2-Bromo-5-methylpyridine
3510-66-5

2-Bromo-5-methylpyridine

Conditions
ConditionsYield
With sodium hydroxide; bromine; sodium hydrogensulfite; sodium nitrite In hexane; water
2,5-dibromopyridine
624-28-2

2,5-dibromopyridine

methyl iodide
74-88-4

methyl iodide

2-Bromo-5-methylpyridine
3510-66-5

2-Bromo-5-methylpyridine

Conditions
ConditionsYield
Stage #1: 2,5-dibromopyridine With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 1.52778E-05h;
Stage #2: methyl iodide In tetrahydrofuran; hexane at 0℃; for 0.0025h;
84 %Chromat.
Stage #1: 2,5-dibromopyridine With n-butyllithium In hexane at 0℃; for 1.52778E-05h;
Stage #2: methyl iodide In tetrahydrofuran; hexane at 0℃; for 0.0025h;
84 %Chromat.
(3-methylpyridine)BF3
6457-37-0

(3-methylpyridine)BF3

2-Bromo-5-methylpyridine
3510-66-5

2-Bromo-5-methylpyridine

Conditions
ConditionsYield
Stage #1: (3-methylpyridine)BF3 With n-butyllithium; diisopropylamine In diethyl ether at -78℃; for 0.416667h;
Stage #2: With bromine In diethyl ether at -78 - 20℃;
Stage #3: With water In diethyl ether regioselective reaction;
1.05 g
2-chloro-5-methylpyridine
18368-64-4

2-chloro-5-methylpyridine

2-Bromo-5-methylpyridine
3510-66-5

2-Bromo-5-methylpyridine

Conditions
ConditionsYield
With hydrogen bromide; lithium bromide Reflux;
2-carboxy-5-methylpyridine
4434-13-3

2-carboxy-5-methylpyridine

2-Bromo-5-methylpyridine
3510-66-5

2-Bromo-5-methylpyridine

Conditions
ConditionsYield
With tert-butylhypochlorite; dichloromethane; oxygen; sodium hydrogencarbonate at 70℃; for 30h; Green chemistry;40 %Spectr.
2-bromo-pyridine
109-04-6

2-bromo-pyridine

2-Bromo-5-methylpyridine
3510-66-5

2-Bromo-5-methylpyridine

5-methyl-2,2'-bipyridine
56100-20-0

5-methyl-2,2'-bipyridine

Conditions
ConditionsYield
Stage #1: 2-bromo-pyridine With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 0.5h;
Stage #2: With zinc(II) chloride In tetrahydrofuran; pentane at 20℃; for 2.5h;
Stage #3: 2-Bromo-5-methylpyridine; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; pentane at 20℃; for 18h; Negishi cross-coupling reaction; Further stages.;
100%
Stage #1: 2-bromo-pyridine With tert.-butyl lithium In tetrahydrofuran at -78℃;
Stage #2: With zinc(II) chloride In tetrahydrofuran at -78 - 20℃;
Stage #3: 2-Bromo-5-methylpyridine With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 20℃;
73%
2-Bromo-5-methylpyridine
3510-66-5

2-Bromo-5-methylpyridine

phenylboronic acid
98-80-6

phenylboronic acid

5-methyl-2-phenylpyridine
27012-22-2

5-methyl-2-phenylpyridine

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene for 18h; Inert atmosphere; Reflux;100%
With potassium phosphate tribasic heptahydrate; palladium diacetate In ethylene glycol at 80℃; for 0.583333h; Suzuki coupling;99%
With palladium diacetate; potassium carbonate In ethanol; water at 80℃; for 0.333333h; Suzuki Coupling;96%
2-Bromo-5-methylpyridine
3510-66-5

2-Bromo-5-methylpyridine

(5-methyl-pyridin-2-yl)amine
1603-41-4

(5-methyl-pyridin-2-yl)amine

Conditions
ConditionsYield
With [Cu2(2,7-bis(pyridin-2-yl)-l,8-naphthyridine)(OH)(CF3COO)3]; tetrabutylammomium bromide; ammonia; caesium carbonate In water at 110 - 120℃; for 16h; Sealed tube;100%
With ammonium hydroxide; potassium phosphate; 1-(5,6,7,8-tetrahydroquinolin-8-yl)-2-methylpropan-1-one; copper(I) bromide In dimethyl sulfoxide at 110℃; for 24h; Inert atmosphere; Sealed tube;85%
4-(carbazol-9-yl)phenylboronic acid
419536-33-7

4-(carbazol-9-yl)phenylboronic acid

2-Bromo-5-methylpyridine
3510-66-5

2-Bromo-5-methylpyridine

9-(4-(5-methylpyridin-2-yl)phenyl)-9H-carbazole
1380225-65-9

9-(4-(5-methylpyridin-2-yl)phenyl)-9H-carbazole

Conditions
ConditionsYield
With palladium diacetate; potassium carbonate In ethanol; water at 80℃; for 0.333333h; Suzuki Coupling;99%
With palladium diacetate; potassium carbonate In ethanol; water at 80℃;
2-Bromo-5-methylpyridine
3510-66-5

2-Bromo-5-methylpyridine

(5-(tert-butyl)-2-methoxyphenyl)boronic acid
128733-85-7

(5-(tert-butyl)-2-methoxyphenyl)boronic acid

2-(5-(tert-butyl)-2-methoxyphenyl)-5-methylpyridine
1609654-41-2

2-(5-(tert-butyl)-2-methoxyphenyl)-5-methylpyridine

Conditions
ConditionsYield
Stage #1: 2-Bromo-5-methylpyridine; (5-(tert-butyl)-2-methoxyphenyl)boronic acid With potassium carbonate In 1,2-dimethoxyethane; water for 0.333333h; Suzuki Coupling; Inert atmosphere;
Stage #2: With tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water at 80℃; for 22h; Suzuki Coupling; Inert atmosphere; Sealed tube;
99%
2-Bromo-5-methylpyridine
3510-66-5

2-Bromo-5-methylpyridine

2-methoxyphenylmagnesium bromide
16750-63-3

2-methoxyphenylmagnesium bromide

2-(2-methoxyphenyl)-5-methyl-pyridine
884494-43-3

2-(2-methoxyphenyl)-5-methyl-pyridine

Conditions
ConditionsYield
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In tetrahydrofuran99%
2-Bromo-5-methylpyridine
3510-66-5

2-Bromo-5-methylpyridine

1-tert-Butyl 4-methyl piperidine-1,4-dicarboxylate
124443-68-1

1-tert-Butyl 4-methyl piperidine-1,4-dicarboxylate

1-tert-butyl 4-methyl 4-(5-methylpyridin-2-yl)piperidine-1,4-dicarboxylate

1-tert-butyl 4-methyl 4-(5-methylpyridin-2-yl)piperidine-1,4-dicarboxylate

Conditions
ConditionsYield
With lithium hexamethyldisilazane; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine In toluene at 23℃; for 12h;95%
2-Bromo-5-methylpyridine
3510-66-5

2-Bromo-5-methylpyridine

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

2-(4-methoxylphenyl)-5-methylpyridine
25363-55-7

2-(4-methoxylphenyl)-5-methylpyridine

Conditions
ConditionsYield
With [Pd(Cl)κ2-S,N-C6H4CS=N-(4-Py)(PPh3)]; potassium carbonate In toluene at 80℃; for 5h; Suzuki coupling;95%
With C28H23ClN3PPdS2; potassium carbonate In water; isopropyl alcohol at 80℃; for 5h; Suzuki-Miyaura Coupling;89%
With potassium phosphate tribasic heptahydrate; palladium diacetate In isopropyl alcohol at 80℃; for 1h; Suzuki coupling;85%
1H-imidazole
288-32-4

1H-imidazole

2-Bromo-5-methylpyridine
3510-66-5

2-Bromo-5-methylpyridine

2-(imidazol-1-yl)-5-methylpyridine
1343101-24-5

2-(imidazol-1-yl)-5-methylpyridine

Conditions
ConditionsYield
With potassium carbonate In neat (no solvent) at 190℃; for 18h; Schlenk technique; Inert atmosphere;95%
With copper(l) iodide; potassium carbonate; L-proline In dimethyl sulfoxide at 100℃; for 24h; Ullmann Condensation;
2-Bromo-5-methylpyridine
3510-66-5

2-Bromo-5-methylpyridine

9H-carbazole
86-74-8

9H-carbazole

9-(4-methylpyridin-2-yl)-9H-carbazole
1570075-58-9

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

Conditions
ConditionsYield
With 1-methyl-1H-imidazole; copper(l) chloride; lithium tert-butoxide In toluene at 130℃; for 11h; Ullmann Condensation;95%
2-Bromo-5-methylpyridine
3510-66-5

2-Bromo-5-methylpyridine

3-phenyl-2H-thiete 1,1-dioxide
25903-17-7

3-phenyl-2H-thiete 1,1-dioxide

4-(5-Methylpyridin-2-yl)-3-phenyl-2H-thiete 1,1-dioxide

4-(5-Methylpyridin-2-yl)-3-phenyl-2H-thiete 1,1-dioxide

Conditions
ConditionsYield
With palladium diacetate; potassium carbonate; tricyclohexylphosphine; Trimethylacetic acid In toluene at 120℃; for 16h; Inert atmosphere; Sealed tube;95%
2-Bromo-5-methylpyridine
3510-66-5

2-Bromo-5-methylpyridine

copper(II) bromide dihydrate

copper(II) bromide dihydrate

[Cu(2-bromo-5-methylpyridine)2Br2]

[Cu(2-bromo-5-methylpyridine)2Br2]

Conditions
ConditionsYield
In ethanol95%
2-Bromo-5-methylpyridine
3510-66-5

2-Bromo-5-methylpyridine

sodium methylate
124-41-4

sodium methylate

2-methoxy-5-methylpyridine
13472-56-5

2-methoxy-5-methylpyridine

Conditions
ConditionsYield
In methanol at 20 - 80℃; for 12h; Cooling with ice;94.3%
polyethylene glycol dimethyl ether; copper(I) bromide In methanol at 90℃; for 17h;91%
2-Bromo-5-methylpyridine
3510-66-5

2-Bromo-5-methylpyridine

hex-1-yne
693-02-7

hex-1-yne

2-hex-1-ynyl-5-methyl-pyridine

2-hex-1-ynyl-5-methyl-pyridine

Conditions
ConditionsYield
With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride at 60℃; for 1.5h;94%
2-Bromo-5-methylpyridine
3510-66-5

2-Bromo-5-methylpyridine

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

4-(diphenylamino)phenyl boronic acid

N,N-diphenyl-4-(5-methylpyridinyl-2-yl)aniline
1263145-40-9

N,N-diphenyl-4-(5-methylpyridinyl-2-yl)aniline

Conditions
ConditionsYield
With palladium diacetate; potassium carbonate In ethanol; water at 80℃; for 0.333333h; Suzuki Coupling;94%
With potassium phosphate tribasic heptahydrate; palladium diacetate In water; isopropyl alcohol at 80℃; for 0.666667h; Suzuki reaction;93%
With palladium diacetate; potassium carbonate In ethanol; water at 80℃; Suzuki Coupling;
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-5-methylpyridine
3510-66-5

2-Bromo-5-methylpyridine

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-(5-methylpyridin-2-yl)-9H-carbazole

2-(3-(3,5-dimethyl-1H-pyrazol-1-yl)phenoxy)-9-(5-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; Schlenk technique; Inert atmosphere; Sealed tube;94%
2-Bromo-5-methylpyridine
3510-66-5

2-Bromo-5-methylpyridine

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;93%
2-Bromo-5-methylpyridine
3510-66-5

2-Bromo-5-methylpyridine

1,4-di(pyrimidin-2-yl)benzene
174303-49-2

1,4-di(pyrimidin-2-yl)benzene

2,2'-(2,3,5,6-tetrakis(5-methylpyridin-2-yl)-1,4-phenylene)dipyrimidine

2,2'-(2,3,5,6-tetrakis(5-methylpyridin-2-yl)-1,4-phenylene)dipyrimidine

Conditions
ConditionsYield
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; potassium pivalate; sodium carbonate; triphenylphosphine In water at 200℃; for 4h; Inert atmosphere; Microwave irradiation;93%
2-Bromo-5-methylpyridine
3510-66-5

2-Bromo-5-methylpyridine

6-amino-1H-indazole-7-carboxylic acid methyl ester
73907-98-9

6-amino-1H-indazole-7-carboxylic acid methyl ester

9-methylpyrazolo[3,4-f]pyrido[2,1-b]quinazolin-12(1H)-one

9-methylpyrazolo[3,4-f]pyrido[2,1-b]quinazolin-12(1H)-one

Conditions
ConditionsYield
With 1,8-Cineole; palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene at 120℃; Buchwald-Hartwig Coupling;93%
2-Bromo-5-methylpyridine
3510-66-5

2-Bromo-5-methylpyridine

4-formylphenylboronic acid,
87199-17-5

4-formylphenylboronic acid,

2-(4-formylphenyl)-5-methylpyridine
1008744-15-7

2-(4-formylphenyl)-5-methylpyridine

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water at 90℃; for 8h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique;92%
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 110℃; for 6h;

3510-66-5Relevant academic research and scientific papers

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.

PROCESS FOR THE PREPARATION OF ABAMETAPIR AND ITS PHARMACEUTICALLY ACCEPTABLE SALTS

-

Page/Page column 13, (2019/10/04)

The present invention relates to process for the preparation of Abametapir. The present 5 invention further relates to Abametapir salts and their preparation thereof.

Direct Transformation of Arylamines to Aryl Halides via Sodium Nitrite and N-Halosuccinimide

Mukhopadhyay, Sushobhan,Batra, Sanjay

supporting information, p. 14622 - 14626 (2018/09/21)

A one-pot universal approach for transforming arylamines to aryl halides via reaction with sodium nitrite (NaNO2) and N-halosuccinimide (NXS) in DMF at room temperature under metal- and acid-free condition is described. This new protocol that is complementary to the Sandmeyer reaction, is suggested to involve the in situ generation of nitryl halide induce nitrosylation of aryl amine to form the diazo intermediate which is halogenated to furnish the aryl halide.

Thermodynamic Programming of Erbium(III) Coordination Complexes for Dual Visible/Near-Infrared Luminescence

Golesorkhi, Bahman,Guénée, Laure,Nozary, Homayoun,Fürstenberg, Alexandre,Suffren, Yan,Eliseeva, Svetlana V.,Petoud, Stéphane,Hauser, Andreas,Piguet, Claude

supporting information, p. 13158 - 13169 (2018/09/11)

Intrigued by the unexpected room-temperature dual visible/near-infrared (NIR) luminescence observed for fast-relaxing erbium complexes embedded in triple-stranded helicates, in this contribution, we explore a series of six tridentate N-donor receptors L4–L9 with variable aromaticities and alkyl substituents to extricate the stereoelectronic features responsible for such scarce optical signatures. Detailed solid-state (X-ray diffraction, differential scanning calorimetry, optical spectroscopy) and solution (speciations and thermodynamic stabilities, spectrophotometry, NMR and optical spectroscopy) studies of mononuclear unsaturated [Er(Lk)2]3+ and saturated triple-helical [Er(Lk)3]3+ model complexes reveal that the stereoelectronic changes induced by the organic ligands affect inter- and intramolecular interactions to such an extent that 1) melting temperatures in solids, 2) the affinity for trivalent erbium in solution, and 3) optical properties in luminescent complexes can be rationally varied and controlled. With this toolkit in hand, mononuclear erbium complexes with low stabilities displaying only NIR emission can be transformed into molecular-based dual Er-centered visible/NIR emitters operating at room temperature in both solid and solution states.

2,6-DIOXO,-2,3-DIHYDRO-1H-PURINE COMPOUNDS USEFUL FOR TREATING DISORDERS RELATED TO THE ACTIVITY OF THE TRPA1 CHANNEL

-

Paragraph 0624, (2017/07/14)

Compounds of formula (VIII) and compositions for treating disorders related to TRPA1 are described herein.

Generation and reactions of pyridyllithiums via Br/li exchange reactions using continuous flow microreactor systems

Nagaki, Aiichiro,Yamada, Daisuke,Yamada, Shigeyuki,Doi, Masatomo,Ichinari, Daisuke,Tomida, Yutaka,Takabayashi, Naofumi,Yoshida, Jun-Ichi

, p. 199 - 207 (2013/03/28)

A continuous flow microreactor method for generating and carrying out reactions on pyridyllithiums has been developed based on Br/Li exchange reactions of bromopyridines and dibromopyridines. The reactions can be carried out without using cryogenic conditions by virtue of short residence times and efficient heat transfer, while very low temperatures such as-78 or-110°C are required for conventional batch macro methods. Moreover, sequential introduction of two different electrophiles has been successfully achieved using dibromopyridines in an integrated flow microreactor system composed of four micromixers and four microtube reactors.

Complex-induced proximity effect in the regioselective lithiation of pyridine derivatives

Dhau, Jaspreet S.,Singh, Amritpal,Kasetti, Yoganjaneyulu,Bharatam

experimental part, p. 1746 - 1752 (2012/05/04)

The regioselective ring lithiation of BF3-complexed 3-picoline (1a), 3,4-lutidine (1b), and 3,5-lutidine (1c) was studied. The dilithiation of 1a, 1b, and 1c was also investigated to experimentally explore the relative preference of the sites on the substituted pyridine ring for lithiation. The role of the complex-induced proximity effect (CIPE) for inducing lithiation in these moieties was investigated using both experimental and computational studies.

Flow microreactor synthesis of disubstituted pyridines from dibromopyridines via Br/Li exchange without using cryogenic conditions

Nagaki, Aiichiro,Yamada, Shigeyuki,Doi, Masatomo,Tomida, Yutaka,Takabayashi, Naofumi,Yoshida, Jun-Ichi

supporting information; experimental part, p. 1110 - 1113 (2011/06/26)

A flow microreactor method for the synthesis of disubstituted pyridines by generation of pyridyllithiums followed by reactions with electrophiles has been developed. By using a short residence time and efficient temperature control, the cryogenic conditions required for conventional batch macro processes can be avoided. Sequential introduction of two different electrophiles into dibromopyridines has been achieved using an integrated flow microreactor system composed of four micromixers and four microtube reactors, to obtain disubstituted pyridine compounds.

Synthesis of a novel ditopic ligand incorporating directly bonded 1,10-phenanthroline and 2,2′:6′,2″-terpyridine units

Gavi?a, Pablo,Tatay, Sergio

, p. 3471 - 3473 (2007/10/03)

The synthesis of a rigid ditopic ligand incorporating a 1,10-phenanthroline directly connected through its 3-position to the 5-position of a 2,2′:6′,2″-terpyridine is described. The synthesis is based on a series of palladium(0)-catalyzed cross-coupling reactions (Stille and Suzuki couplings) starting from 1,10-phenanthroline and bromo-substituted pyridines.

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.

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