Product Name

  • Name

    DIETHYL(3-PYRIDYL)BORANE

  • EINECS
  • CAS No. 89878-14-8
  • Article Data5
  • CAS DataBase
  • Density 0.86 g/cm3
  • Solubility Slightly soluble in water.
  • Melting Point 172-175 °C(lit.)
  • Formula C9H14BN
  • Boiling Point 205.9 °C at 760 mmHg
  • Molecular Weight 147.028
  • Flash Point 78.3 °C
  • Transport Information
  • Appearance
  • Safety 26-37/39
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 89878-14-8 (DIETHYL(3-PYRIDYL)BORANE)
  • Hazard Symbols IrritantXi
  • Synonyms 3-(Diethylboryl)pyridine;3-Diethylboropyridine;3-Pyridinyldiethylborane;3-Pyridyldiethylborane;Diethyl-3-pyridylborane;
  • PSA 12.89000
  • LogP 1.82320

Synthetic route

3-Bromopyridine
626-55-1

3-Bromopyridine

diethyl methoxy borane
7397-46-8

diethyl methoxy borane

3-Diethylboranylpyridine
89878-14-8

3-Diethylboranylpyridine

Conditions
ConditionsYield
Stage #1: 3-Bromopyridine With isopropylmagnesium chloride In tetrahydrofuran at 0℃; for 1h;
Stage #2: diethyl methoxy borane In tetrahydrofuran at 0℃; for 1h;		78%
Stage #1: 3-Bromopyridine With n-butyllithium In hexane; tert-butyl methyl ether at -28℃; Inert atmosphere; Large scale;
Stage #2: diethyl methoxy borane In tert-butyl methyl ether at -40 - -32℃; for 8.5h; Inert atmosphere; Large scale;		75%
3-Bromopyridine
626-55-1

3-Bromopyridine

n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

diethylmethoxyborane

diethylmethoxyborane

3-Diethylboranylpyridine
89878-14-8

3-Diethylboranylpyridine

Conditions
ConditionsYield
In tetrahydrofuran
...Expand
4-bromopyridin
1120-87-2

4-bromopyridin

A

3-Diethylboranylpyridine
89878-14-8

3-Diethylboranylpyridine

B

diethyl (pyridin-4-yl)borane
93830-58-1

diethyl (pyridin-4-yl)borane

Conditions
ConditionsYield
With n-butyllithium
3-Bromopyridine
626-55-1

3-Bromopyridine

triethyl borane
97-94-9

triethyl borane

3-Diethylboranylpyridine
89878-14-8

3-Diethylboranylpyridine

Conditions
ConditionsYield
With n-butyllithium In diethyl ether; hexane at -78 - 20℃; Inert atmosphere;
3-Bromopyridine
626-55-1

3-Bromopyridine

diethyl methoxy borane
7397-46-8

diethyl methoxy borane

3-Diethylboranylpyridine
89878-14-8

3-Diethylboranylpyridine

Conditions
ConditionsYield
With n-butyllithium In dibutyl ether
benzyl 7-bromo-3,4-dihydro-1H-isoquinoline-2-carboxylate
625127-09-5

benzyl 7-bromo-3,4-dihydro-1H-isoquinoline-2-carboxylate

3-Diethylboranylpyridine
89878-14-8

3-Diethylboranylpyridine

C22H20N2O2
625127-14-2

C22H20N2O2

Conditions
ConditionsYield
With sodium carbonate; bis-triphenylphosphine-palladium(II) chloride In methanol; water; toluene at 80℃;100%
3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

3-Diethylboranylpyridine
89878-14-8

3-Diethylboranylpyridine

3-(3-methoxyphenyl)pyridine
4373-67-5

3-(3-methoxyphenyl)pyridine

Conditions
ConditionsYield
With sodium carbonate; bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran; water for 4h; Heating / reflux;99%
3-Diethylboranylpyridine
89878-14-8

3-Diethylboranylpyridine

4-iodo-2-methoxy-1-methylbenzene
220728-62-1

4-iodo-2-methoxy-1-methylbenzene

3-(3-methoxy-4-methylphenyl)pyridine
702683-21-4

3-(3-methoxy-4-methylphenyl)pyridine

Conditions
ConditionsYield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; ethanol; water for 24h; Heating / reflux;99%
C22H29F3O5S
1382471-65-9

C22H29F3O5S

3-Diethylboranylpyridine
89878-14-8

3-Diethylboranylpyridine

(5S,8R,9S,10S,13S)-10,13-dimethyl-17-(pyridin-3-yl)-2,3,4,5,6,7,8,9,10,11,12,13-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate
1382471-66-0

(5S,8R,9S,10S,13S)-10,13-dimethyl-17-(pyridin-3-yl)-2,3,4,5,6,7,8,9,10,11,12,13-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate

Conditions
ConditionsYield
With potassium carbonate; bis-triphenylphosphine-palladium(II) chloride In 1,4-dioxane; water at 80℃; Suzuki Coupling; Ultrasonic degassing; Inert atmosphere;98.5%
5-chloro-2-methyl-benzoic acid ethyl ester
56427-54-4

5-chloro-2-methyl-benzoic acid ethyl ester

3-Diethylboranylpyridine
89878-14-8

3-Diethylboranylpyridine

ethyl 5-(3-pyridyl)-2-methylbenzoate
702682-38-0

ethyl 5-(3-pyridyl)-2-methylbenzoate

Conditions
ConditionsYield
With sodium carbonate; DavePhos; palladium diacetate In tetrahydrofuran; water for 6h; Heating / reflux;97%
3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate
115375-60-5

3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate

3-Diethylboranylpyridine
89878-14-8

3-Diethylboranylpyridine

abiraterone acetate
154229-18-2

abiraterone acetate

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In tetrahydrofuran at 65℃; for 4h; Reflux;95%
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In tetrahydrofuran; water for 1h; Reflux;95%
With bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate In tetrahydrofuran; water at 60℃; for 1h;94%
3-Diethylboranylpyridine
89878-14-8

3-Diethylboranylpyridine

3,3-dimethyl-6-(3'-methylbut-3'-enyl)-6-methoxycarbonylcyclohexenyl triflate
157520-44-0

3,3-dimethyl-6-(3'-methylbut-3'-enyl)-6-methoxycarbonylcyclohexenyl triflate

(1R,3aR)-1,6,6-Trimethyl-1-pyridin-3-ylmethyl-1,2,3,4,5,6-hexahydro-indene-3a-carboxylic acid methyl ester

(1R,3aR)-1,6,6-Trimethyl-1-pyridin-3-ylmethyl-1,2,3,4,5,6-hexahydro-indene-3a-carboxylic acid methyl ester

Conditions
ConditionsYield
With palladium diacetate; tetraethylammonium chloride; sodium carbonate; triphenylphosphine In toluene Heating;92%
With tetraethylammonium chloride; sodium carbonate; triphenylphosphine; palladium diacetate In water; toluene for 8h; Cyclization; hetarylation; Heating;92%
6-chloro-3-pyridinecarboxamide
6271-78-9

6-chloro-3-pyridinecarboxamide

3-Diethylboranylpyridine
89878-14-8

3-Diethylboranylpyridine

5-carbamoyl-2,3'-bipyridine
164074-61-7

5-carbamoyl-2,3'-bipyridine

Conditions
ConditionsYield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; water for 6h; Heating;92%
3-Diethylboranylpyridine
89878-14-8

3-Diethylboranylpyridine

6-trifluoromethanesulfonyloxy-3,4-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester
171288-01-0

6-trifluoromethanesulfonyloxy-3,4-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

5,6-dihydro-4H-[2,3']bipyridinyl-1-carboxylic acid tert-butyl ester

5,6-dihydro-4H-[2,3']bipyridinyl-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With sodium carbonate; bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran at 80℃; for 2h; Substitution;91%
3β-acetoxy-5α-androsta-16-ene-17-yl trifluoromethanesulfonate
91934-55-3

3β-acetoxy-5α-androsta-16-ene-17-yl trifluoromethanesulfonate

3-Diethylboranylpyridine
89878-14-8

3-Diethylboranylpyridine

3β-acetyloxy-17-(3-pyridinyl)-5α-androst-16-ene
219843-76-2

3β-acetyloxy-17-(3-pyridinyl)-5α-androst-16-ene

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In tetrahydrofuran at 80℃; for 1h;90%
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In tetrahydrofuran; water for 18h; Suzuki Coupling; Inert atmosphere; Reflux;90%
3α-acetoxy-5β-androsta-16-ene-17-yl trifluoromethanesulfonate

3α-acetoxy-5β-androsta-16-ene-17-yl trifluoromethanesulfonate

3-Diethylboranylpyridine
89878-14-8

3-Diethylboranylpyridine

3α-acetoxy-17-(3-pyridyl)-5β-androsta-16-ene

3α-acetoxy-17-(3-pyridyl)-5β-androsta-16-ene

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In tetrahydrofuran; water for 18h; Suzuki Coupling; Inert atmosphere; Reflux;90%
3-Diethylboranylpyridine
89878-14-8

3-Diethylboranylpyridine

(2R,3R,4S,5R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-[1-iodo-meth-(Z)-ylidene]-tetrahydro-pyran
607715-89-9

(2R,3R,4S,5R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-[1-iodo-meth-(Z)-ylidene]-tetrahydro-pyran

(Z)-2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-1-(3-pyridyl)-D-gluco-hept-1-enitol

(Z)-2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-1-(3-pyridyl)-D-gluco-hept-1-enitol

Conditions
ConditionsYield
With sodium hydroxide; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; water for 3h; B-alkyl Suzuki cross-coupling reaction; Heating;89%
Phenyl triflate
17763-67-6

Phenyl triflate

3-Diethylboranylpyridine
89878-14-8

3-Diethylboranylpyridine

3-phenylpyridine
1008-88-4

3-phenylpyridine

Conditions
ConditionsYield
With potassium hydroxide In tetrahydrofuran; water at 60℃; for 0.0833333h; Suzuki-Miyaura Coupling;89%
C20H27F3O4S

C20H27F3O4S

3-Diethylboranylpyridine
89878-14-8

3-Diethylboranylpyridine

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In tetrahydrofuran; water at 20 - 75℃; for 0.5h;88.8%

3-Diethylboranylpyridine

3-Diethylboranylpyridine

3-(pyridin-3-yl)phenol
93851-31-1

3-(pyridin-3-yl)phenol

Conditions
ConditionsYield
Stage #1: 3-Bromophenol; 3-Diethylboranylpyridine With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; ethanol; water at 20℃; for 2 - 20h; Heating / reflux;
Stage #2: With hydrogenchloride In tetrahydrofuran; ethanol; water for 0.25h;		88%
1-bromo-4-phenylethynylbenzene
13667-12-4

1-bromo-4-phenylethynylbenzene

3-Diethylboranylpyridine
89878-14-8

3-Diethylboranylpyridine

C19H13N
1064194-22-4

C19H13N

Conditions
ConditionsYield
With potassium hydroxide; tetrabutylammomium bromide; triphenylphosphine; bis(dibenzylideneacetone)-palladium(0) In N,N-dimethyl-formamide at 80℃; for 3h; Suzuki coupling; Inert atmosphere; Microwave irradiation;88%
3-Diethylboranylpyridine
89878-14-8

3-Diethylboranylpyridine

para-nitrophenyl bromide
586-78-7

para-nitrophenyl bromide

3-(4'-nitrophenyl)pyridine
4282-46-6

3-(4'-nitrophenyl)pyridine

Conditions
ConditionsYield
With potassium hydroxide; tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide In tetrahydrofuran for 2h; Heating;87%
abiraterone

abiraterone

3-Diethylboranylpyridine
89878-14-8

3-Diethylboranylpyridine

C27H39NOSi

C27H39NOSi

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In tetrahydrofuran; ethanol; water; toluene at 20 - 75℃; for 0.5h;86.2%
bromochlorobenzene
106-39-8

bromochlorobenzene

3-Diethylboranylpyridine
89878-14-8

3-Diethylboranylpyridine

4-(3'-pyridinyl)-1-chlorobenzene
5957-97-1

4-(3'-pyridinyl)-1-chlorobenzene

Conditions
ConditionsYield
With potassium hydroxide; tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide In tetrahydrofuran for 2h; Heating;86%
2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

3-Diethylboranylpyridine
89878-14-8

3-Diethylboranylpyridine

3-(o-carbomethoxyphenyl)pyridine
90395-46-3

3-(o-carbomethoxyphenyl)pyridine

Conditions
ConditionsYield
With potassium hydroxide; tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide In tetrahydrofuran for 18h; Heating;86%
With potassium hydroxide; tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide In tetrahydrofuran for 3h; Heating;59%
C25H35F3O5S

C25H35F3O5S

3-Diethylboranylpyridine
89878-14-8

3-Diethylboranylpyridine

C29H39NO2

C29H39NO2

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In tetrahydrofuran; ethanol; water; toluene at 20 - 75℃; for 2h;85.5%
2-bromo-pyridine
109-04-6

2-bromo-pyridine

3-Diethylboranylpyridine
89878-14-8

3-Diethylboranylpyridine

2,3'-bipyridine
581-50-0

2,3'-bipyridine

Conditions
ConditionsYield
With potassium hydroxide; tetrabutylammomium bromide; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran for 8h; Heating;85%
bromobenzene
108-86-1

bromobenzene

3-Diethylboranylpyridine
89878-14-8

3-Diethylboranylpyridine

3-phenylpyridine
1008-88-4

3-phenylpyridine

Conditions
ConditionsYield
With potassium hydroxide; tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide In tetrahydrofuran for 1h; Heating;85%
1-(2'-Bromo-biphenyl-4-ylmethyl)-1H-[1,2,4]triazole
735333-61-6

1-(2'-Bromo-biphenyl-4-ylmethyl)-1H-[1,2,4]triazole

3-Diethylboranylpyridine
89878-14-8

3-Diethylboranylpyridine

3-(4'-[1,2,4]Triazol-1-ylmethyl-biphenyl-2-yl)-pyridine
735333-63-8

3-(4'-[1,2,4]Triazol-1-ylmethyl-biphenyl-2-yl)-pyridine

Conditions
ConditionsYield
With sodium carbonate; bis(triphenylphosphine)palladium(II)-chloride In tetrahydrofuran; water at 20 - 80℃; for 24h;85%
3-Diethylboranylpyridine
89878-14-8

3-Diethylboranylpyridine

N'-tosyl phenylhydrazine
29110-75-6

N'-tosyl phenylhydrazine

3-phenylpyridine
1008-88-4

3-phenylpyridine

Conditions
ConditionsYield
With palladium diacetate; potassium carbonate In dimethyl sulfoxide at 60℃; Suzuki Coupling; Inert atmosphere;85%
C39H41F3O4S

C39H41F3O4S

3-Diethylboranylpyridine
89878-14-8

3-Diethylboranylpyridine

C43H45NO

C43H45NO

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In tetrahydrofuran; ethanol; water; toluene at 20 - 75℃; for 0.5h;85%
3β-acetoxy-5,6-seco-5-keto-17-O-triflyl-androstan-6-al

3β-acetoxy-5,6-seco-5-keto-17-O-triflyl-androstan-6-al

3-Diethylboranylpyridine
89878-14-8

3-Diethylboranylpyridine

3β-acetoxy-5-keto-5,6-seco-17-(3-pyridyl)-androst-16-en-6-al

3β-acetoxy-5-keto-5,6-seco-17-(3-pyridyl)-androst-16-en-6-al

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate In tetrahydrofuran; water at 50℃; for 1h;85%
1-(2-(4-bromophenyl)ethynyl)-4-methylbenzene
62856-42-2

1-(2-(4-bromophenyl)ethynyl)-4-methylbenzene

3-Diethylboranylpyridine
89878-14-8

3-Diethylboranylpyridine

3-(4-p-tolylethynyl-phenyl)-pyridine

3-(4-p-tolylethynyl-phenyl)-pyridine

Conditions
ConditionsYield
With potassium hydroxide; tetrabutylammomium bromide; triphenylphosphine; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 80℃; for 18h;84.5%
para-bromotoluene
106-38-7

para-bromotoluene

3-Diethylboranylpyridine
89878-14-8

3-Diethylboranylpyridine

4-(3-pyridyl)toluene

4-(3-pyridyl)toluene

Conditions
ConditionsYield
With potassium hydroxide; tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide In tetrahydrofuran for 2h; Heating;84%

3-Diethylboranylpyridine

3-Diethylboranylpyridine

Conditions
ConditionsYield
With potassium hydroxide; tetrakis(triphenylphosphine) palladium(0); tetra-(n-butyl)ammonium iodide In tetrahydrofuran for 12h; Heating;84%
With tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; sodium hydroxide In tetrahydrofuran; water at 4 - 66℃; Suzuki Coupling; Inert atmosphere; Large scale;

Diethyl(3-pyridyl)borane Specification

The Diethyl(3-pyridyl)borane, with the CAS registry number 89878-14-8, has the IUPAC name of diethyl(pyridin-3-yl)borane. And its product categories are including Nitrogen cyclic compounds; B (Classes of Boron Compounds); Boranes.

The characteristics of this chemical are as follows: (1)ACD/LogP: 1.42; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.39; (4)ACD/LogD (pH 7.4): 1.42; (5)ACD/BCF (pH 5.5): 6.53; (6)ACD/BCF (pH 7.4): 7.04; (7)ACD/KOC (pH 5.5): 130.43; (8)ACD/KOC (pH 7.4): 140.62; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 12.89; (13)Index of Refraction: 1.457; (14)Molar Refractivity: 46.53 cm3; (15)Molar Volume: 170.7 cm3; (16)Polarizability: 18.44 ×10-24 cm3; (17)Surface Tension: 28.2 dyne/cm; (18)Density: 0.86 g/cm3; (19)Flash Point: 78.3 °C; (20)Enthalpy of Vaporization: 42.41 kJ/mol; (21)Boiling Point: 205.9 °C at 760 mmHg; (22)Vapour Pressure: 0.35 mmHg at 25°C; (23)Exact Mass: 147.12193; (24)MonoIsotopic Mass: 147.12193; (25)Topological Polar Surface Area: 12.9; (26)Heavy Atom Count: 11; (27)Complexity: 102; (28)Covalently-Bonded Unit Count: 1.

Use of Diethyl(3-pyridyl)borane: Diethyl(3-pyridyl)borane could react with 2-bromo-thiophene to produce 3-thiophen-2-yl-pyridine. The reaction could happen in the reagent of KOH, tetra-n-butylammonium bromide, the solvent of tetrahydrofuran, the catalytic agent of terakispalladium. And it needs the reaction time of 8 hours in the condition of heating. Besides, its yield is 75 %.

When you are dealing with this chemical, you should be very cautious. This is a kind of irritant  chemical, it is irritating to eyes, respiratory system and skin and may cause inflammation to the skin or other mucous membranes. Therefore, you should wear suitable gloves and eye/face protection and then avoid contacting with skin and eyes. And then if in case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

In addition, you could convert the following datas into the molecular structure:
(1)Canonical SMILES: B(CC)(CC)C1=CN=CC=C1
(2)InChI: InChI=1S/C9H14BN/c1-3-10(4-2)9-6-5-7-11-8-9/h5-8H,3-4H2,1-2H3
(3)InChIKey: OJKBCQOJVMAHDX-UHFFFAOYSA-N 

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