Conditions | Yield |
---|---|
Stage #1: 1-bromo-3-chlorobenzene With n-butyllithium In tetrahydrofuran; hexane at -30℃; Inert atmosphere; Flow reactor; Stage #2: Trimethyl borate In tetrahydrofuran; hexane at -30℃; Inert atmosphere; Flow reactor; | 97% |
Stage #1: 1-bromo-3-chlorobenzene With isopropylmagnesium chloride; lithium chloride; 3-butyl-1-methylimidazolium acetate In tetrahydrofuran at 5 - 10℃; for 3h; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran at 0℃; for 4h; Inert atmosphere; Stage #3: With hydrogenchloride In water at 5℃; for 0.5h; Inert atmosphere; | 66.43 g |
borane
(3-chlorophenyl)magnesium bromide
3-chlorophenylboronic acid
Conditions | Yield |
---|---|
With water In tetrahydrofuran slow addn. of 10 mmol of the Grignard reagent to a stirred soln. of borane in THF (40 mmol); the mixt. was poured into ice-water and acidified with 10% HCl;; extn. into ether three-times; the combined extracts were dried over NaSO4; removal of solvent under reduced pressure; trituration with petroleum ether; recrystn. from H2O;; | 82% |
1-bromo-3-chlorobenzene
3-chlorophenylboronic acid
Conditions | Yield |
---|---|
Stage #1: 1-bromo-3-chlorobenzene With n-butyllithium In tetrahydrofuran; hexane Inert atmosphere; Stage #2: With Trimethyl borate In tetrahydrofuran; hexane Inert atmosphere; | 57% |
With Trimethyl borate | |
With Trimethyl borate |
3-chlorophenylboronic acid
Conditions | Yield |
---|---|
With sulfuric acid In ethanol; toluene at 0 - 40℃; Solvent; Reagent/catalyst; | 57% |
With water at 98℃; for 2h; | 14.37 g |
(3-chlorophenyl)magnesium bromide
3-chlorophenylboronic acid
Conditions | Yield |
---|---|
With boron trifluoride |
3-iodochlorobenzene
3-chlorophenylboronic acid
Conditions | Yield |
---|---|
(i) (UV-irradiation), BBr3, (ii) aq. NaOH; Multistep reaction; |
Conditions | Yield |
---|---|
With water; magnesium In tetrahydrofuran a 2.0 M soln. of borane (40 mmol) in THF was added to flame dried Mg turnings (12 mmol) at 0°C; slow addn. of the aryl bromide (10 mmol)in THF; stirring at room temp. for 12-16 h; the mixt. was poured into ice-water and acidified with 10% HCl;; extn. into ether three-times; the combined extracts were dried over NaSO4; removal of solvent under reduced pressure; trituration with petroleum ether; recrystn. from H2O;; |
1-bromo-3-chlorobenzene
Trimethyl borate
A
3-chlorophenylboronic acid
B
(3-bromophenyl)boronic acid
Conditions | Yield |
---|---|
Stage #1: 1-bromo-3-chlorobenzene With n-butyllithium In tetrahydrofuran; hexane at -78 - -70℃; for 0.5h; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran at -70℃; for 4h; Stage #3: With hydrogenchloride In water Overall yield = 24.6 g; |
1-bromo-3-chlorobenzene
Triisopropyl borate
3-chlorophenylboronic acid
Conditions | Yield |
---|---|
Stage #1: 1-bromo-3-chlorobenzene With iodine; magnesium In tetrahydrofuran for 5h; Inert atmosphere; Reflux; Stage #2: Triisopropyl borate In tetrahydrofuran at -40 - 0℃; Inert atmosphere; Stage #3: With water at 98℃; for 2h; Inert atmosphere; |
1-bromo-3-chlorobenzene
boric acid tributyl ester
3-chlorophenylboronic acid
Conditions | Yield |
---|---|
Stage #1: 1-bromo-3-chlorobenzene With iodine; magnesium In tetrahydrofuran for 5h; Inert atmosphere; Reflux; Stage #2: boric acid tributyl ester In tetrahydrofuran at -40 - 0℃; Inert atmosphere; Stage #3: With water at 98℃; for 2h; Inert atmosphere; |
3-chlorophenylboronic acid
ethylene glycol
3-chlorophenylboronic acid ethylene glycol ester
Conditions | Yield |
---|---|
In tetrahydrofuran for 18h; Heating / reflux; | 100% |
In tetrahydrofuran for 18h; Heating / reflux; | 100% |
In toluene for 3h; Heating; | |
In tetrahydrofuran for 18h; Heating; | |
In tetrahydrofuran at 20℃; for 8h; |
3-chlorophenylboronic acid
Conditions | Yield |
---|---|
With sodium carbonate; tris-(o-tolyl)phosphine; palladium diacetate In 1,2-dimethoxyethane; water Suzuki coupling; Heating; | 100% |
9,10-Dibromoanthracene
3-chlorophenylboronic acid
9,10-di(3-chlorophenyl)anthracene
Conditions | Yield |
---|---|
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetra(n-butyl)ammonium hydroxide In 1,4-dioxane; water at 90℃; for 20h; Suzuki coupling; Inert atmosphere; | 100% |
C17H20BrN3O2
3-chlorophenylboronic acid
2-amino-7''-(3-chlorophenyl)-1-methyl-2',3',5',6'-tetrahydro-3'',4''-dihydro-2''H-dispiro[imidazol-4,1''-naphthalen-3'',4'-pyran]-5(1H)-one
Conditions | Yield |
---|---|
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 95℃; | 100% |
ethyl 5-bromo-4-(3-cyano-4-fluorophenyl)-1,3-thiazole-2-carboxylate
3-chlorophenylboronic acid
5-(3-chlorophenyl)-4-(3-cyano-4-fluorophenyl)-1,3-thiazole-2-carboxylic acid
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate In 1,2-dimethoxyethane; water at 20℃; for 1h; Reflux; | 100% |
3-chlorophenylboronic acid
Conditions | Yield |
---|---|
With potassium phosphate; bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) In 1,4-dioxane; water at 100℃; for 1h; Suzuki Coupling; | 100% |
3-chlorophenylboronic acid
para-nitrophenyl bromide
3‐chloro‐4′‐nitrobiphenyl
Conditions | Yield |
---|---|
With 1,1',1'',1'''-benzene-1,2,4,5-tetrayltetrakis(methylene)tetrakis-(piperidin-4-ol); palladium diacetate; potassium carbonate In ethanol; water at 20℃; Suzuki-Miyaura Coupling; | 100% |
With Pd/C; potassium carbonate In ethanol; water at 100℃; for 3h; Suzuki-Miyaura Coupling; | 98% |
With dichloro bis(acetonitrile) palladium(II); C10H11N3S; potassium carbonate In water; N,N-dimethyl-formamide at 20℃; for 1h; Suzuki Coupling; Schlenk technique; Inert atmosphere; | 96% |
With carbon supported Pd nanoparticles; potassium carbonate at 95℃; for 6h; Suzuki-Miyaura Coupling; Sealed tube; |
1-bromo-3-fluoro-5-methoxybenzene
3-chlorophenylboronic acid
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 90℃; for 0.75h; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
With bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II); sodium carbonate In water; toluene at 75℃; for 16h; Inert atmosphere; | 100% |
3-chlorophenylboronic acid
1-(bromomethyl)-3-fluoro-5-(trifluoromethyl)benzene
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In Dimethyl ether; water; N,N-dimethyl-formamide at 100℃; for 3.05h; Inert atmosphere; Microwave irradiation; | 100% |
cyclopent-2-enone
3-chlorophenylboronic acid
Conditions | Yield |
---|---|
With triethylamine; bis(norbornadiene)rhodium(l)tetrafluoroborate; C46H38N2O5P2 In 1,4-dioxane; water at 25℃; for 2h; Product distribution / selectivity; | 99% |
With potassium hydroxide; C46H38N2O5P2; chlorobis(cyclooctene)rhodium(I) dimer In 1,4-dioxane; water at 50℃; for 16h; Product distribution / selectivity; | 53% |
With potassium hydroxide; (R)-(-)-(3,5-dioxa-4-phosphacyclohepta[2,1-a:3,4-a']dinaphthalen-4-yl)diethylamine; bis(ethylene)rhodium acetylacetonate In 1,4-dioxane at 50℃; for 6h; Title compound not separated from byproducts; |
Conditions | Yield |
---|---|
With Pd/C; potassium carbonate In water; N,N-dimethyl-formamide at 40℃; for 5h; Suzuki Coupling; | 99% |
With C24H20Cl2NPPdS; potassium carbonate; palladium In toluene at 100℃; for 1.5h; | 96% |
With sodium carbonate In ethanol; water at 20℃; for 8h; Suzuki-Miyaura Coupling; Inert atmosphere; | 96% |
cyclopent-2-enone
3-chlorophenylboronic acid
(3R)-3-(3-chlorophenyl)cyclopentanone
Conditions | Yield |
---|---|
With di(norbornadiene)rhodium(I) tetrafluoroborate; chiral modified linked BINOL derivative; triethylamine In 1,4-dioxane; water at 25℃; for 2h; | 99% |
3-chlorophenylboronic acid
PCB 11
Conditions | Yield |
---|---|
With potassium acetate; silver(l) oxide In methanol at 40℃; for 15h; | 99% |
With dipotassium peroxodisulfate; potassium carbonate In water; acetone for 2h; | 99% |
With p-benzoquinone; (SIPr)Pd(OAc)2(H2O) In methanol at 20℃; for 24h; | 95% |
Conditions | Yield |
---|---|
With triethylamine; [Rh(ndb)2]BF4; (R)-BINOL-based bidentate phosphoramidite In 1,4-dioxane; water at 25℃; for 2h; | 99% |
3-chlorophenylboronic acid
4,4-ethylenedioxy-1-oxo-1,4-dihydronaphthalene
Conditions | Yield |
---|---|
With chlorobis(ethylene)rhodium(I) dimer; C41H24F12O2P2; potassium hydroxide In water; toluene at 20℃; for 3h; Inert atmosphere; Schlenk technique; enantioselective reaction; | 99% |
With potassium hydroxide; bis(ethylene)rhodium(I) chloride dimer In 1,4-dioxane at 20℃; for 20h; | 95% |
3-chlorophenylboronic acid
o-chloro-N-tosylbenzaldimine
(S)-N-[(2-chlorophenyl)(3-chlorophenyl)methyl]-4-methylbenzenesulfonamide
Conditions | Yield |
---|---|
With potassium phosphate tribasic trihydrate; (Pd((C10H6N2C7H4CH2C6H5)2)(H2O)2)(2+)*2CF3SO3(1-)=(Pd((C10H6N2C7H4CH2C6H5)2)(H2O)2)(CF3SO3)2 In tetrahydrofuran at 4 - 20℃; Molecular sieve; optical yield given as %ee; enantioselective reaction; | 99% |
methyl o-formylbenzoate
3-chlorophenylboronic acid
3-(3-chlorophenyl)-3H-isobenzofuran-1-one
Conditions | Yield |
---|---|
With bis(η3-allyl-μ-chloropalladium(II)); C27H30N2S(1+)*Cl(1-); cesium fluoride In toluene at 80℃; for 1h; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With [Pd(dppp)(H2O)2](2+)(BF4(1-))2 In 1,4-dioxane at 20℃; for 0.166667h; Inert atmosphere; chemoselective reaction; | 99% |
Conditions | Yield |
---|---|
With [Pd(S,S)-bdpp(H2O)2](2+)(BF4(1-))2 In 1,4-dioxane at 20℃; for 0.666667h; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 99% |
Conditions | Yield |
---|---|
With chlorobis(ethylene)rhodium(I) dimer; potassium hydrogen bifluoride; C28H22 In water; toluene at 100℃; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 99% |
3-chlorophenylboronic acid
3-monochlorophenol
Conditions | Yield |
---|---|
With water In tetrahydrofuran at 100℃; for 12h; | 99% |
With copper(I) oxide; potassium hydroxide In water at 20℃; for 24h; Green chemistry; | 98% |
With copper(II) ferrite; water; sodium hydroxide at 40℃; for 24h; Green chemistry; | 96% |
Conditions | Yield |
---|---|
With 1,1'-bis-(diphenylphosphino)ferrocene; potassium fluoride; palladium diacetate In tetrahydrofuran at 50℃; for 22h; Suzuki-Miyaura coupling; Inert atmosphere; chemoselective reaction; | 99% |
cyclopent-2-enone
3-chlorophenylboronic acid
Conditions | Yield |
---|---|
With C42H46O6Rh2S2; cesium fluoride In 1,4-dioxane at 20℃; Hayashi-Miyaura reaction; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 99% |
Stage #1: 3-chlorophenylboronic acid With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); bis(norbornadiene)rhodium(l)tetrafluoroborate In 1,4-dioxane; water for 2h; Inert atmosphere; Stage #2: cyclopent-2-enone With triethylamine In 1,4-dioxane; water | 89.2% |
With chlorobis(ethylene)rhodium(I) dimer; potassium phosphate tribasic trihydrate; C19H23NOS In 1,4-dioxane; water at 20℃; for 3h; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 62% |
Non-3-en-2-on
3-chlorophenylboronic acid
(S)-4-(3-chlorophenyl)nonan-2-one
Conditions | Yield |
---|---|
With chlorobis(ethylene)rhodium(I) dimer; (S,S)-1,1'-(1,7,7-trimethylbicyclo[2.2.1]hepta-2,5-diene-2,5-diyl)dinaphthalene; triethylamine In ethanol at 20℃; for 16h; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 99% |
Conditions | Yield |
---|---|
With bis(ethylene)rhodium(I) chloride dimer; C19H23NOS; potassium hydroxide In 1,4-dioxane; water at 20 - 50℃; for 4h; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 99% |
di-tert-butyl fumarate
3-chlorophenylboronic acid
(S)-di-tert-butyl-2-(3-chlorophenyl)succinate
Conditions | Yield |
---|---|
Stage #1: 3-chlorophenylboronic acid With chlorobis(ethylene)rhodium(I) dimer; (S,S)-1,7,7-trimethyl-2,5-diphenylbicyclo[2.2.1]hepta-2,5-diene; potassium tert-butylate In methanol; dichloromethane at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: di-tert-butyl fumarate In methanol; dichloromethane; isopropyl alcohol at 60℃; for 1h; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 99% |
3-chlorophenylboronic acid
para-bromoacetophenone
1-(3'-chlorobiphenyl-4-yl)ethanone
Conditions | Yield |
---|---|
With Pd/C; potassium carbonate In ethanol; water at 100℃; for 3h; Suzuki-Miyaura Coupling; | 99% |
With C20H38Cl2N4P2Pd; caesium carbonate In N,N-dimethyl-formamide at 110℃; for 24h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique; | 72.3% |
With potassium carbonate In ethanol at 70℃; for 4h; Catalytic behavior; Suzuki-Miyaura Coupling; Schlenk technique; Sealed tube; | 95 %Spectr. |
With carbon supported Pd nanoparticles; potassium carbonate at 95℃; for 6h; Suzuki-Miyaura Coupling; Sealed tube; |
tetramethylazacalix[1]-arene[3]pyridine
3-chlorophenylboronic acid
Conditions | Yield |
---|---|
With copper(II) perchlorate hexahydrate; triethylamine In dimethyl sulfoxide at 80℃; for 3.5h; | 99% |
3-chlorophenylboronic acid
benzo[e][1,2,3]oxathiazine 2,2-dioxide
Conditions | Yield |
---|---|
With silver tetrafluoroborate; C30H38Cl2NPPd In 1,2-dichloro-ethane at 65℃; for 1h; enantioselective reaction; | 99% |
With nickel(II) perchlorate hexahydrate; (S)-2′-(tert-butyl)-7-(diphenylphosphino)-2,3-dihydro-5′H-spiro[indene-1,4′-oxazole] In 2,2,2-trifluoroethanol at 60℃; for 24h; Inert atmosphere; Schlenk technique; enantioselective reaction; | 97% |
The Boronicacid, B-(3-chlorophenyl)-, with the CAS registry number 63503-60-6, is also known as m-Chlorobenzeneboronic acid. It belongs to the product categories of Blocks; Boronic Acids; Boronic Acid series; Substituted Boronic Acids; Boronic Acid; Aryl; Halogenated; Organoborons; B (Classes of Boron Compounds); Boronic Acids and Derivatives. This chemical's molecular formula is C6H6BClO2 and molecular weight is 156.37. What's more, its systematic name is (3-chlorophenyl)boronic acid. It should be sealed and stored in a cool and dry place. Moreover, it should be protected from oxides.
Physical properties of Boronicacid, B-(3-chlorophenyl)- are: (1)ACD/LogP: 2.18; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.18; (4)ACD/LogD (pH 7.4): 1.95; (5)ACD/BCF (pH 5.5): 26.69; (6)ACD/BCF (pH 7.4): 15.81; (7)ACD/KOC (pH 5.5): 364.3; (8)ACD/KOC (pH 7.4): 215.88; (9)#H bond acceptors: 2; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 18.46 Å2; (13)Index of Refraction: 1.557; (14)Molar Refractivity: 38.11 cm3; (15)Molar Volume: 118.3 cm3; (16)Polarizability: 15.11×10-24cm3; (17)Surface Tension: 46.4 dyne/cm; (18)Density: 1.32 g/cm3; (19)Flash Point: 142.1 °C; (20)Enthalpy of Vaporization: 58.32 kJ/mol; (21)Boiling Point: 311.4 °C at 760 mmHg; (22)Vapour Pressure: 0.000242 mmHg at 25°C.
Uses of Boronicacid, B-(3-chlorophenyl)-: it can be used to produce 1-bromo-3-chloro-benzene at the temperature of 81 °C. It will need reagent NBS and solvent acetonitrile with the reaction time of 8 hours. The yield is about 59%.
When you are using this chemical, please be cautious about it as the following:
This chemical is harmful by inhalation, in contact with skin and if swallowed. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need wear suitable protective clothing, gloves and eye/face protection.
You can still convert the following datas into molecular structure:
(1)SMILES: Clc1cccc(B(O)O)c1
(2)Std. InChI: InChI=1S/C6H6BClO2/c8-6-3-1-2-5(4-6)7(9)10/h1-4,9-10H
(3)Std. InChIKey: SDEAGACSNFSZCU-UHFFFAOYSA-N
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