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143418-49-9

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143418-49-9 Usage

Uses

Different sources of media describe the Uses of 143418-49-9 differently. You can refer to the following data:
1. Reactant involved in: ??Preparation of phenylboronic catechol esters and determination of Lewis acidity ??Synthesis of benzopyranone derivatives as GABAA receptor modulators ??Synthesis of multisubstituted olefins and conjugate dienes ??Suzuki cross-coupling reactions ??Preparation of fluorinated aromatic poly(ether-amide)s
2. suzuki reaction
3. Reactant involved in:Preparation of phenylboronic catechol esters and determination of Lewis aciditySynthesis of benzopyranone derivatives as GABAA receptor modulatorsSynthesis of multisubstituted olefins and conjugate dienesSuzuki cross-coupling reactionsPreparation of fluorinated aromatic poly(ether-amide)s
4. Intermediates of Liquid Crystals

Chemical Properties

Tan powder

Check Digit Verification of cas no

The CAS Registry Mumber 143418-49-9 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,4,3,4,1 and 8 respectively; the second part has 2 digits, 4 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 143418-49:
(8*1)+(7*4)+(6*3)+(5*4)+(4*1)+(3*8)+(2*4)+(1*9)=119
119 % 10 = 9
So 143418-49-9 is a valid CAS Registry Number.
InChI:InChI=1/C6H4BF3O2/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1-2,11-12H

143418-49-9 Well-known Company Product Price

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  • Alfa Aesar

  • (L18519)  3,4,5-Trifluorobenzeneboronic acid, 97%   

  • 143418-49-9

  • 250mg

  • 923.0CNY

  • Detail
  • Alfa Aesar

  • (L18519)  3,4,5-Trifluorobenzeneboronic acid, 97%   

  • 143418-49-9

  • 1g

  • 1684.0CNY

  • Detail

143418-49-9SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 3,4,5-Trifluorophenylboronic acid

1.2 Other means of identification

Product number -
Other names (3,4,5-trifluorophenyl)boronic acid

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:143418-49-9 SDS

143418-49-9Synthetic route

Trimethyl borate
121-43-7

Trimethyl borate

3,4,5-trifluoro-1-bromobenzene
138526-69-9

3,4,5-trifluoro-1-bromobenzene

3,4,5-trifluorophenylboronic acid
143418-49-9

3,4,5-trifluorophenylboronic acid

Conditions
ConditionsYield
Stage #1: 3,4,5-trifluoro-1-bromobenzene With magnesium; ethylene dibromide In tetrahydrofuran at 5 - 20℃; for 2h; Inert atmosphere;
Stage #2: Trimethyl borate In tetrahydrofuran at -30 - -27℃;
Stage #3: With hydrogenchloride In tetrahydrofuran; water at 20℃; for 4h; Temperature;
82%
Stage #1: 3,4,5-trifluoro-1-bromobenzene With magnesium In tetrahydrofuran; ethylene dibromide at 5 - 25℃; for 2h; Inert atmosphere;
Stage #2: Trimethyl borate In tetrahydrofuran; ethylene dibromide at -30 - -27℃; for 2h; Inert atmosphere;
Stage #3: With hydrogenchloride In tetrahydrofuran; water; ethylene dibromide at 20℃; for 4h; Temperature; Inert atmosphere;
81%
With magnesium In diethyl ether Grignard-comp. prepd. from Br-compd. and Mg in ether at 0 °C was added dropwise to 1.5 equiv. of pre-cooled (0 °C) soln. of B(OMe)3 in ether, mixt. was maintained at 0-10 °C for 1 h and allowed to warm up to 20 °C; pouring into 10 % HCl, org. layer was sepd., aq. layer was twice extd. with ether, extracts were combined, dried with MgSO4, evapd. under vac., end-product was contaminated with dehydration product;
Stage #1: 3,4,5-trifluoro-1-bromobenzene With magnesium In tetrahydrofuran at 25 - 35℃; for 7h; Grignard Reaction; Inert atmosphere;
Stage #2: Trimethyl borate In tetrahydrofuran at -5 - 25℃; for 4.5h;
Stage #3: With hydrogenchloride In tetrahydrofuran; water at 25 - 50℃; for 1h;
Stage #1: 3,4,5-trifluoro-1-bromobenzene With magnesium In 2-methyltetrahydrofuran at 20 - 80℃; for 4h; Inert atmosphere;
Stage #2: Trimethyl borate In 2-methyltetrahydrofuran at -5 - 20℃; for 2.5h;
Stage #3: With hydrogenchloride In 2-methyltetrahydrofuran; water at 20 - 50℃; for 1h;
Trimethyl borate
121-43-7

Trimethyl borate

3,4,5-trifluorophenylmagnesium bromide
156006-28-9

3,4,5-trifluorophenylmagnesium bromide

3,4,5-trifluoro-1-bromobenzene
138526-69-9

3,4,5-trifluoro-1-bromobenzene

3,4,5-trifluorophenylboronic acid
143418-49-9

3,4,5-trifluorophenylboronic acid

Conditions
ConditionsYield
Stage #1: 3,4,5-trifluorophenylmagnesium bromide; 3,4,5-trifluoro-1-bromobenzene With magnesium In tetrahydrofuran at 5 - 15℃; for 3h; Inert atmosphere;
Stage #2: Trimethyl borate In tetrahydrofuran at -20℃; for 3h; Inert atmosphere;
Stage #3: With hydrogenchloride In tetrahydrofuran at -20 - 25℃; for 15h; Temperature; Inert atmosphere;
82%
Trimethyl borate
121-43-7

Trimethyl borate

water
7732-18-5

water

3,4,5-trifluoro-1-bromobenzene
138526-69-9

3,4,5-trifluoro-1-bromobenzene

3,4,5-trifluorophenylboronic acid
143418-49-9

3,4,5-trifluorophenylboronic acid

Conditions
ConditionsYield
Stage #1: 3,4,5-trifluoro-1-bromobenzene With iodine; magnesium In 2-methyltetrahydrofuran at 40 - 50℃;
Stage #2: Trimethyl borate In 2-methyltetrahydrofuran at 10 - 20℃; for 8h;
Stage #3: water With hydrogenchloride In 2-methyltetrahydrofuran Temperature;
78%
Triisopropyl borate
5419-55-6

Triisopropyl borate

3,4,5-trifluoro-1-bromobenzene
138526-69-9

3,4,5-trifluoro-1-bromobenzene

A

3,4,5-trifluorophenylboronic acid
143418-49-9

3,4,5-trifluorophenylboronic acid

B

3,4,5-C6H2F3B(O-i-Pr)2

3,4,5-C6H2F3B(O-i-Pr)2

Conditions
ConditionsYield
Stage #1: 3,4,5-trifluoro-1-bromobenzene With magnesium In diethyl ether Grignard reaction;
Stage #2: Triisopropyl borate In diethyl ether at -30 - 10℃; for 0.5h; boronation;
Stage #3: With hydrogenchloride In diethyl ether at 20℃; for 1h; Hydrolysis; Title compound not separated from byproducts;
3,4,5-trifluoro-1-bromobenzene
138526-69-9

3,4,5-trifluoro-1-bromobenzene

3,4,5-trifluorophenylboronic acid
143418-49-9

3,4,5-trifluorophenylboronic acid

Conditions
ConditionsYield
Stage #1: 3,4,5-trifluoro-1-bromobenzene With magnesium
Stage #2: With Trimethyl borate
Stage #3: With hydrogenchloride In water
tris(3,4,5-trifluorophenyl)boroxine
223440-94-6

tris(3,4,5-trifluorophenyl)boroxine

water
7732-18-5

water

3,4,5-trifluorophenylboronic acid
143418-49-9

3,4,5-trifluorophenylboronic acid

Conditions
ConditionsYield
In acetonitrile
In diethyl ether
Trimethyl borate
121-43-7

Trimethyl borate

3,4,5-trifluorophenylmagnesium bromide
156006-28-9

3,4,5-trifluorophenylmagnesium bromide

3,4,5-trifluorophenylboronic acid
143418-49-9

3,4,5-trifluorophenylboronic acid

Conditions
ConditionsYield
In tetrahydrofuran at 0 - 20℃; for 1h; Inert atmosphere;
C34H20B2F12O3

C34H20B2F12O3

A

tris(3,4,5-trifluorophenyl)boroxine
223440-94-6

tris(3,4,5-trifluorophenyl)boroxine

B

3,4,5-trifluorophenylboronic acid
143418-49-9

3,4,5-trifluorophenylboronic acid

Conditions
ConditionsYield
at 20℃; for 144h;
C31H14B2F12O3

C31H14B2F12O3

A

tris(3,4,5-trifluorophenyl)boroxine
223440-94-6

tris(3,4,5-trifluorophenyl)boroxine

B

3,4,5-trifluorophenylboronic acid
143418-49-9

3,4,5-trifluorophenylboronic acid

Conditions
ConditionsYield
at 20℃; for 144h;
(S)-3,3'-dibromo-6,6'-dimethoxy-2,2'-dimethyl-1,1'-biphenyl

(S)-3,3'-dibromo-6,6'-dimethoxy-2,2'-dimethyl-1,1'-biphenyl

3,4,5-trifluorophenylboronic acid
143418-49-9

3,4,5-trifluorophenylboronic acid

(S)-2,2'-dimethoxy-6,6'-dimethyl-5,5'-bis(3,4,5-trifluorophenyl)biphenyl

(S)-2,2'-dimethoxy-6,6'-dimethyl-5,5'-bis(3,4,5-trifluorophenyl)biphenyl

Conditions
ConditionsYield
With potassium phosphate; tris-(o-tolyl)phosphine; palladium diacetate In N,N-dimethyl-formamide Suzuki-Miyaura coupling; Heating;100%
With tripotassium phosphate "n" hydrate; palladium diacetate; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide Suzuki-Miyaura coupling; Reflux; Inert atmosphere;100%
With tripotassium phosphate "n" hydrate; palladium diacetate; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide Suzuki-Miyaura Coupling; Reflux; Inert atmosphere;100%
para-bromoacetophenone
99-90-1

para-bromoacetophenone

3,4,5-trifluorophenylboronic acid
143418-49-9

3,4,5-trifluorophenylboronic acid

1-(3',4',5'-trifluoro-[1,1'-biphenyl]-4-yl)ethan-1-one

1-(3',4',5'-trifluoro-[1,1'-biphenyl]-4-yl)ethan-1-one

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In tetrahydrofuran for 2h; Suzuki Coupling; Inert atmosphere; Reflux;100%
With 4-methoxy-6-(((methyl-2-pyridinylmethyl)imino)methyl)phenol; palladium diacetate; potassium hydroxide In ethanol; water for 1h; Suzuki-Miyaura Coupling; Reflux;99%
With C34H54N2O2; palladium diacetate; potassium carbonate In water; acetone for 1h; Suzuki Coupling; Reflux; Green chemistry;98%
para-iodoanisole
696-62-8

para-iodoanisole

3,4,5-trifluorophenylboronic acid
143418-49-9

3,4,5-trifluorophenylboronic acid

4-methoxy-3',4',5'-trifluorobiphenyl

4-methoxy-3',4',5'-trifluorobiphenyl

Conditions
ConditionsYield
With sodium carbonate In ethanol; water at 80℃; for 0.25h; Catalytic behavior; Suzuki-Miyaura Coupling;100%
2-bromo-9H-fluorene
1133-80-8

2-bromo-9H-fluorene

3,4,5-trifluorophenylboronic acid
143418-49-9

3,4,5-trifluorophenylboronic acid

2-(3,4,5-trifluorophenyl)-9H-fluorene

2-(3,4,5-trifluorophenyl)-9H-fluorene

Conditions
ConditionsYield
With C35H40N4O9(2+)*2Cl(1-); palladium diacetate; potassium hydroxide In ethanol at 100℃; for 1.5h; Suzuki Coupling; Green chemistry;99%
With potassium tert-butylate In ethanol; water Reflux;98%
With palladium diacetate; potassium carbonate In ethanol; water at 110℃; for 1h; Suzuki Coupling; Inert atmosphere; Schlenk technique; Sealed tube;97%
With 1-[2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)ethyl]-3-[2-hydroxy-(2,4-dichlorophenyl)ethyl]imidazolium bromide; potassium tert-butylate; potassium carbonate; palladium dichloride In tetrahydrofuran; water at 60 - 90℃; for 0.5h; Suzuki-Miyaura Coupling; Inert atmosphere;97%
1,2,4,5-tetrafluoro-3-iodobenzene
5243-24-3

1,2,4,5-tetrafluoro-3-iodobenzene

3,4,5-trifluorophenylboronic acid
143418-49-9

3,4,5-trifluorophenylboronic acid

2,3,3′,4′,5,5′,6-heptafluoro-1,1′-biphenyl

2,3,3′,4′,5,5′,6-heptafluoro-1,1′-biphenyl

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate; XPhos In tetrahydrofuran; water; toluene at 95℃; for 60h; Reagent/catalyst; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique;99%
1,3,5-trifluoro-2-iodobenzene
41860-63-3

1,3,5-trifluoro-2-iodobenzene

3,4,5-trifluorophenylboronic acid
143418-49-9

3,4,5-trifluorophenylboronic acid

2,3′,4,4′,5′,6-hexafluoro-1,1′-biphenyl

2,3′,4,4′,5′,6-hexafluoro-1,1′-biphenyl

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate; CyJohnPhos In tetrahydrofuran; water; toluene at 95℃; for 60h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique;99%
2-Chloroaniline
95-51-2

2-Chloroaniline

3,4,5-trifluorophenylboronic acid
143418-49-9

3,4,5-trifluorophenylboronic acid

3’,4’,5’-trifluoro-[1,1’-biphenyl]-2-amine
915416-45-4

3’,4’,5’-trifluoro-[1,1’-biphenyl]-2-amine

Conditions
ConditionsYield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium carbonate; palladium dichloride In water; isopropyl alcohol at 25 - 85℃; for 5.25h; Reagent/catalyst; Temperature; Inert atmosphere;99%
2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

3,4,5-trifluorophenylboronic acid
143418-49-9

3,4,5-trifluorophenylboronic acid

2-nitro-3',4',5'-trifluoro-1,1'-biphenyl
1056196-56-5

2-nitro-3',4',5'-trifluoro-1,1'-biphenyl

Conditions
ConditionsYield
With potassium tert-butylate; C33H46Cl2N4Pd In 2-methyltetrahydrofuran at 100℃; for 3h; Solvent; Reagent/catalyst; Temperature;98%
With potassium phosphate tribasic trihydrate; (2-(anthracen-9-yl)-1H-inden-3-yl)dicyclohexylphosphine; palladium diacetate In water; isopropyl alcohol; toluene at 90℃; for 16h; Catalytic behavior; Suzuki-Miyaura Coupling; Schlenk technique; Inert atmosphere;96%
With diamminedichloropalladium(II); triphenylphosphine; sodium hydroxide In tetrahydrofuran; water for 10h; Reagent/catalyst; Suzuki Coupling; Reflux; Inert atmosphere;95%
4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

3,4,5-trifluorophenylboronic acid
143418-49-9

3,4,5-trifluorophenylboronic acid

4-(3,4,5-trifluorophenyl)benzaldehyde
954369-65-4

4-(3,4,5-trifluorophenyl)benzaldehyde

Conditions
ConditionsYield
With potassium carbonate In ethanol at 75℃; for 3h; Suzuki-Miyaura Coupling;98%
With sodium hydrogencarbonate In water at 90℃; for 0.166667h; Suzuki Coupling; Green chemistry;93%
With sodium hydrogencarbonate In ethanol; water at 70℃; for 4h; Catalytic behavior; Suzuki Coupling;93%
2,7-dibromo-9H-fluorene
16433-88-8

2,7-dibromo-9H-fluorene

3,4,5-trifluorophenylboronic acid
143418-49-9

3,4,5-trifluorophenylboronic acid

2,7-bis(3,4,5-trifluorophenyl)-9H-fluorene

2,7-bis(3,4,5-trifluorophenyl)-9H-fluorene

Conditions
ConditionsYield
With palladium diacetate; potassium carbonate In ethanol; water at 110℃; for 1h; Suzuki Coupling; Inert atmosphere; Schlenk technique; Sealed tube;98%
With potassium tert-butylate In ethanol; water Reflux;96%
With 1-[2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)ethyl]-3-[2-hydroxy-(2,4-dichlorophenyl)ethyl]imidazolium bromide; potassium tert-butylate; potassium carbonate; palladium dichloride In tetrahydrofuran; water at 60 - 90℃; for 0.5h; Suzuki-Miyaura Coupling; Inert atmosphere;96%
2,3,5,6-tetrafluoropyridin-4-yliodine
16297-19-1

2,3,5,6-tetrafluoropyridin-4-yliodine

3,4,5-trifluorophenylboronic acid
143418-49-9

3,4,5-trifluorophenylboronic acid

2,3,5,6-tetrafluoro-4-(3,4,5-trifluorophenyl)pyridine

2,3,5,6-tetrafluoro-4-(3,4,5-trifluorophenyl)pyridine

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate; CyJohnPhos In tetrahydrofuran; water; toluene at 95℃; for 60h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique;98%
9,9-bis-(n-butyl)-2,7-dibromofluorene
188200-91-1

9,9-bis-(n-butyl)-2,7-dibromofluorene

3,4,5-trifluorophenylboronic acid
143418-49-9

3,4,5-trifluorophenylboronic acid

9,9-dibutyl-2,7-bis(3,4,5-trifluorophenyl)-9H-fluorene

9,9-dibutyl-2,7-bis(3,4,5-trifluorophenyl)-9H-fluorene

Conditions
ConditionsYield
With C35H40N4O9(2+)*2Cl(1-); palladium diacetate; potassium hydroxide In ethanol at 100℃; for 1.5h; Suzuki Coupling; Green chemistry;98%
With 1-[2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)ethyl]-3-[2-hydroxy-(2,4-dichlorophenyl)ethyl]imidazolium bromide; potassium tert-butylate; potassium carbonate; palladium dichloride In tetrahydrofuran; water at 60 - 90℃; for 0.5h; Suzuki-Miyaura Coupling; Inert atmosphere;98%
With potassium tert-butylate In ethanol; water Reflux;97%
2-Chlorobenzonitrile
873-32-5

2-Chlorobenzonitrile

3,4,5-trifluorophenylboronic acid
143418-49-9

3,4,5-trifluorophenylboronic acid

3’,4’,5’-trifluoro-[1,1’-biphenyl]-2-carbonitrile

3’,4’,5’-trifluoro-[1,1’-biphenyl]-2-carbonitrile

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; tricyclohexylphosphine tetrafluoroborate; sodium hydroxide In water; toluene at 85℃; for 12h; Catalytic behavior; Reagent/catalyst; Suzuki-Miyaura Coupling; Inert atmosphere;98%
With potassium dihydrogenphosphate; tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; tricyclohexylphosphine tetrafluoroborate In water; isopropyl alcohol; toluene at 100℃; for 12h; Temperature; Inert atmosphere;92%
o-nitroiodobenzene
609-73-4

o-nitroiodobenzene

3,4,5-trifluorophenylboronic acid
143418-49-9

3,4,5-trifluorophenylboronic acid

2-nitro-3',4',5'-trifluoro-1,1'-biphenyl
1056196-56-5

2-nitro-3',4',5'-trifluoro-1,1'-biphenyl

Conditions
ConditionsYield
With sodium hydrogencarbonate; palladium dichloride In methanol at 40℃;98%
(R)-3,3’-dibromo-5,5’,6,6’,7,7’,8,8’-octahydro-[1,1’-binaphthalene]-2,2’-diol
765278-73-7

(R)-3,3’-dibromo-5,5’,6,6’,7,7’,8,8’-octahydro-[1,1’-binaphthalene]-2,2’-diol

3,4,5-trifluorophenylboronic acid
143418-49-9

3,4,5-trifluorophenylboronic acid

(R)-3,3'-bis-(3,4,5-trifluorophenyl)-5,5',6,6',7,7',8,8'-octahydro-[1,1'-binaphthalene]-2,2'-diol

(R)-3,3'-bis-(3,4,5-trifluorophenyl)-5,5',6,6',7,7',8,8'-octahydro-[1,1'-binaphthalene]-2,2'-diol

Conditions
ConditionsYield
With palladium diacetate; potassium carbonate; catacxium A In 1,2-dimethoxyethane; water at 100℃; for 18h; Inert atmosphere; Sealed tube;98%
iodobenzene
591-50-4

iodobenzene

3,4,5-trifluorophenylboronic acid
143418-49-9

3,4,5-trifluorophenylboronic acid

3,4,5-trifluoro-1-1’-biphenyl
178820-23-0

3,4,5-trifluoro-1-1’-biphenyl

Conditions
ConditionsYield
With sodium t-butanolate In water at 28℃; for 4h; Catalytic behavior; Suzuki-Miyaura Coupling; Irradiation;97%
3,4,5-trifluorophenylboronic acid
143418-49-9

3,4,5-trifluorophenylboronic acid

3,3'-Dibromo-5,5'-di-tert-butyl-4,4'-dimethoxy-2,2'-dimethyl-1,1'-biphenyl
600172-56-3

3,3'-Dibromo-5,5'-di-tert-butyl-4,4'-dimethoxy-2,2'-dimethyl-1,1'-biphenyl

5,5’-di-tert-butyl-4,4’-dimethoxy-2,2’-dimethyl-3,3’-(3,4,5-trifluorophenyl)biphenyl

5,5’-di-tert-butyl-4,4’-dimethoxy-2,2’-dimethyl-3,3’-(3,4,5-trifluorophenyl)biphenyl

Conditions
ConditionsYield
With potassium fluoride; tris-(dibenzylideneacetone)dipalladium(0); water; tri tert-butylphosphoniumtetrafluoroborate In 1,4-dioxane at 110℃; for 24h; Inert atmosphere; Sealed tube;97%
tert-butyl (5R,8S)-2-methyl-3-(((trifluoromethyl)sulfonyl)oxy)-2,4,5,6,7,8-hexahydro-5,8-epiminocyclohepta[c]pyrazole-9-carboxylate

tert-butyl (5R,8S)-2-methyl-3-(((trifluoromethyl)sulfonyl)oxy)-2,4,5,6,7,8-hexahydro-5,8-epiminocyclohepta[c]pyrazole-9-carboxylate

3,4,5-trifluorophenylboronic acid
143418-49-9

3,4,5-trifluorophenylboronic acid

tert-butyl (5R,8S)-2-methyl-3-(3,4,5-trifluorophenyl)-2,4,5,6,7,8-hexahydro-5,8-epiminocyclohepta[c]pyrazole-9-carboxylate

tert-butyl (5R,8S)-2-methyl-3-(3,4,5-trifluorophenyl)-2,4,5,6,7,8-hexahydro-5,8-epiminocyclohepta[c]pyrazole-9-carboxylate

Conditions
ConditionsYield
With (chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II)); sodium carbonate In 1,4-dioxane; water at 110℃; for 0.583333h; Inert atmosphere; Microwave irradiation;97%
para-bromotoluene
106-38-7

para-bromotoluene

3,4,5-trifluorophenylboronic acid
143418-49-9

3,4,5-trifluorophenylboronic acid

3',4',5'-trifluoro-4-methyl-1,1'-biphenyl
524018-97-1

3',4',5'-trifluoro-4-methyl-1,1'-biphenyl

Conditions
ConditionsYield
With potassium carbonate In ethanol; water at 80℃; for 0.75h; Suzuki Coupling;96%
With Ph2P(CH2CH2O)22CH3; triethylamine; palladium dichloride In water at 80℃; for 4h; Suzuki coupling; Inert atmosphere;68%
ethyl benzo[h]quinoline-10-carboxylate
1015758-32-3

ethyl benzo[h]quinoline-10-carboxylate

3,4,5-trifluorophenylboronic acid
143418-49-9

3,4,5-trifluorophenylboronic acid

10-(3,4,5-trifluorophenyl)benzo[h]quinoline
1415320-69-2

10-(3,4,5-trifluorophenyl)benzo[h]quinoline

Conditions
ConditionsYield
With tris(triphenylphosphine)rhodium(I) chloride; copper(l) chloride In toluene at 130℃; for 30h; Inert atmosphere;96%
2,2',7,7'-tetrabromo-9,9'-spirobifluorene
128055-74-3

2,2',7,7'-tetrabromo-9,9'-spirobifluorene

3,4,5-trifluorophenylboronic acid
143418-49-9

3,4,5-trifluorophenylboronic acid

2,2',7,7'-tetrakis(3,4,5-trifluorophenyl)spiro-9,9'-bifuorene
1425942-31-9

2,2',7,7'-tetrakis(3,4,5-trifluorophenyl)spiro-9,9'-bifuorene

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 24h; Inert atmosphere; Reflux;96%
10,10'-dibromo-9,9'-bianthryl
121848-75-7

10,10'-dibromo-9,9'-bianthryl

3,4,5-trifluorophenylboronic acid
143418-49-9

3,4,5-trifluorophenylboronic acid

10,10'-bis(3,4,5-trifluorophenyl)-9,9'-bianthracene
1505455-99-1

10,10'-bis(3,4,5-trifluorophenyl)-9,9'-bianthracene

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); water; potassium carbonate In tetrahydrofuran for 24h; Suzuki Coupling; Inert atmosphere; Reflux;96%
4-methoxycarbonylphenyl bromide
619-42-1

4-methoxycarbonylphenyl bromide

3,4,5-trifluorophenylboronic acid
143418-49-9

3,4,5-trifluorophenylboronic acid

C14H9F3O2

C14H9F3O2

Conditions
ConditionsYield
With potassium phosphate; C18H9F5NOP(2-)*Pd(2+)*C3H7NO In ethanol at 20℃; for 2h; Suzuki-Miyaura Coupling; Schlenk technique;96%
p-nitrobenzene iodide
636-98-6

p-nitrobenzene iodide

3,4,5-trifluorophenylboronic acid
143418-49-9

3,4,5-trifluorophenylboronic acid

C12H6F3NO2

C12H6F3NO2

Conditions
ConditionsYield
With potassium carbonate In ethanol; water at 100℃; for 1h; Suzuki-Miyaura Coupling;96%
C15H21Cl

C15H21Cl

3,4,5-trifluorophenylboronic acid
143418-49-9

3,4,5-trifluorophenylboronic acid

4'-(trans-4-propylcyclohexyl)-3,4,5-trifluorobiphenyl

4'-(trans-4-propylcyclohexyl)-3,4,5-trifluorobiphenyl

Conditions
ConditionsYield
With dichloro(cycloocta-1,5-diene)palladium (II); 2,2-[μ-(N,N'-piperazindiyl)dimethyl]-bis(4,6-di-tert-butyl-phenol); potassium carbonate In methanol Suzuki cross-coupling reaction; Microwave irradiation; Inert atmosphere;95%
1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

3,4,5-trifluorophenylboronic acid
143418-49-9

3,4,5-trifluorophenylboronic acid

4-methoxy-3',4',5'-trifluorobiphenyl

4-methoxy-3',4',5'-trifluorobiphenyl

Conditions
ConditionsYield
With potassium phosphate; C18H9F5NOP(2-)*Pd(2+)*C3H7NO In ethanol at 20℃; for 5h; Suzuki-Miyaura Coupling; Schlenk technique;95%
C19H15FeIN2

C19H15FeIN2

3,4,5-trifluorophenylboronic acid
143418-49-9

3,4,5-trifluorophenylboronic acid

5-ferrocenyl-1-phenyl-4-(3,4,5-trifluorophenyl)-1H-pyrazole

5-ferrocenyl-1-phenyl-4-(3,4,5-trifluorophenyl)-1H-pyrazole

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; potassium hydrogencarbonate In water; N,N-dimethyl-formamide at 110℃; for 4h; Suzuki-Miyaura Coupling; Inert atmosphere;95%
9-(5'-bromo-[2,2'-bipyridine]-5-yl)-9H-carbazole
1206209-16-6

9-(5'-bromo-[2,2'-bipyridine]-5-yl)-9H-carbazole

3,4,5-trifluorophenylboronic acid
143418-49-9

3,4,5-trifluorophenylboronic acid

C28H16F3N3

C28H16F3N3

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 85℃; for 24h; Inert atmosphere; Reflux;95%
C48H52BrIN2O4

C48H52BrIN2O4

3,4,5-trifluorophenylboronic acid
143418-49-9

3,4,5-trifluorophenylboronic acid

C60H56F6N2O4

C60H56F6N2O4

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran for 16h; Inert atmosphere; Reflux;95%
3,4,5-trifluorophenylboronic acid
143418-49-9

3,4,5-trifluorophenylboronic acid

1-bromo-2,3,4-trifluorobenzene
176317-02-5

1-bromo-2,3,4-trifluorobenzene

2,3,3′,4,4′,5′-hexafluoro-1,1′-biphenyl

2,3,3′,4,4′,5′-hexafluoro-1,1′-biphenyl

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate; CyJohnPhos In tetrahydrofuran; water; toluene at 95℃; for 60h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique;95%

143418-49-9Relevant articles and documents

Mechanistic insights into boron-catalysed direct amidation reactions

Arkhipenko, Sergey,Sabatini, Marco T.,Batsanov, Andrei S.,Karaluka, Valerija,Sheppard, Tom D.,Rzepa, Henry S.,Whiting, Andrew

, p. 1058 - 1072 (2018)

The generally accepted monoacyloxyboron mechanism of boron-catalysed direct amidation is brought into question in this study, and new alternatives are proposed. We have carried out a detailed investigation of boron-catalysed amidation reactions, through study of the interaction between amines/carboxylic acids and borinic acids, boronic acids and boric acid, and have isolated and characterised by NMR/X-ray crystallography many of the likely intermediates present in catalytic amidation reactions. Rapid reaction between amines and boron compounds was observed in all cases, and it is proposed that such boron-nitrogen interactions are highly likely to take place in catalytic amidation reactions. These studies also clearly show that borinic acids are not competent catalysts for amidation, as they either form unreactive amino-carboxylate complexes, or undergo protodeboronation to give boronic acids. It therefore seems that at least three free coordination sites on the boron atom are necessary for amidation catalysis to occur. However, these observations are not consistent with the currently accepted 'mechanism' for boron-mediated amidation reactions involving nucleophilic attack of an amine onto a monomeric acyloxyboron intermediate, and as a result of our observations and theoretical modelling, alternative proposed mechanisms are presented for boron-mediated amidation reactions. These are likely to proceed via the formation of a dimeric B-X-B motif (X = O, NR), which is uniquely able to provide activation of the carboxylic acid, whilst orchestrating the delivery of the amine nucleophile to the carbonyl group. Quantum mechanical calculations of catalytic cycles at the B3LYP+D3/Def2-TZVPP level (solvent = CH2Cl2) support the proposal of several closely related potential pathways for amidation, all of which are likely to be lower in energy than the currently accepted mechanism.

PROCESS FOR THE PREPARATION OF BIPHENYLAMINES

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Page/Page column 23-24, (2021/01/29)

The invention relates to a method for the preparation of 2-aminobiphenyls, key intermediates in the preparation of compounds of interest in the agrochemical industry. The process comprises reacting an ortho-substituted aniline and a phenylboro derivative in the presence of a base and a palladium catalyst, said palladium catalyst comprising a palladium source and a biphenyl phosphine ligand of formula (III) or a salt thereof

A 3 ', 4', 5' - trifluoro -2 - amino biphenyl chemical synthesis method

-

Paragraph 0061-0069, (2019/07/11)

The invention discloses a 3 ', 4', 5 '- trifluoro - 2 - amino biphenyl chemical synthesis method, it to 3, 4, 5 - trifluoro bromobenzene as the starting material, passes through formatting reaction, reaction and coupling reaction to obtain a sediment 3', 4 ', 5' - trifluoro - 2 - nitro-biphenyl, 3 ', 4', 5 '- trifluoro - 2 - nitro-biphenyl through catalytic reduction reaction to obtain the target product 3', 4 ', 5' - trifluoro - 2 - phenylaniline. The present invention provides compound 3 ', 4', 5' - trifluoro - 2 - amino biphenyl synthesis of new routes, the advantages of the simple process operation, mild reaction conditions, high yield, is simple in separation purification. Wherein the 3 ', 4', 5' - trifluoro - 2 - nitro-biphenyl synthesis in the process, the catalyst consumption is low, and the production cost is reduced, more suitable for large-scale industrial application.

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