63503-60-6

Basic information

• Product Name: 3-Chlorophenylboronic acid
• Synonyms: RARECHEM AH PB 0179;M-CHLOROPHENYLBORONIC ACID;AKOS BRN-0010;3-CHLOROPHENYLBORNIC ACID;3-CHLOROPHENYLBORONIC ACID;3-CHLOROBENZENEBORONIC ACID;3-Chlorophenylboronic acid, CAS 63503-60-6, C6H6BClO2;3-CHLOROBENZENEBORONIC ACID / 3-CHLOROPHENYLBORONIC ACID
• CAS NO: 63503-60-6
• Molecular Formula: C₆H₆BClO₂
• Molecular Weight: 156.37
• EINECS: 1312995-182-4
• Product Categories: blocks;BoronicAcids;Boronic Acid series;Substituted Boronic Acids;Boronic acids;Boronic Acid;Aryl;Halogenated;Organoborons;B (Classes of Boron Compounds);Boronic Acids;Boronic Acids and Derivatives;Boronate Ester;Potassium Trifluoroborate
• Mol File: 63503-60-6.mol
• Article Data: 9

Chemical Properties

• Melting Point: 185-189 °C(lit.)
• Boiling Point: 311.4 °C at 760 mmHg
• Flash Point: 142.1 °C
• Appearance: White to light yellow-green/Crystalline Powder or Needles
• Density: 1.32 g/cm³
• Vapor Pressure: 0.000242mmHg at 25°C
• Refractive Index: 1.557
• Storage Temp.: 0-6°C
• Solubility: soluble in Methanol
• PKA: 7.55±0.10(Predicted)
• Water Solubility: Slightly soluble in water. soluble in ether, tetrahydrofuran,, dimethyl sulfoxide, dimethyl formamide, methanol.
• BRN: 2936343
• CAS DataBase Reference: 3-Chlorophenylboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Chlorophenylboronic acid(63503-60-6)
• EPA Substance Registry System: 3-Chlorophenylboronic acid(63503-60-6)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 36-37/39-26
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 63503-60-6(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow-green crystalline powder or

Uses

Different sources of media describe the Uses of 63503-60-6 differently. You can refer to the following data:
1. suzuki reaction
2. It is employed as a reactant involved in 1,4-conjugate addition reactions with ethenesulfonamides to form arylethanesulfonamides, Suzuki-Miyaura reactions with dibromotrifluoromethylbenzene, cross-coupling reactions with diazoesters3 or potassium cyanate. It is involved in the synthesis of biarylketones and phthalides and synthesis of inhibitors including PDE4 inhibitors6 among others.
3. Reactant involved in: 1,4-conjugate addition reactions with ethenesulfonamides to form arylethanesulfonamidesSuzuki-Miyaura reactions with dibromotrifluoromethylbenzeneCross-coupling reactions with diazoesters or potassium cyanateSynthesis of biarylketones and phthalidesSynthesis of inhibitors including PDE4 inhibitors among others

InChI:InChI=1/C6H6BClO2/c8-6-3-1-2-5(4-6)7(9)10/h1-4,9-10H

Synthetic route

1-bromo-3-chlorobenzene (108-37-2) + Trimethyl borate (121-43-7) → 3-chlorophenylboronic acid (63503-60-6)

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 (13283-31-3) + (3-chlorophenyl)magnesium bromide (36229-42-2) → 3-chlorophenylboronic acid (63503-60-6)

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 (108-37-2) → 3-chlorophenylboronic acid (63503-60-6)

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

C8H10BClO2 → 3-chlorophenylboronic acid (63503-60-6)

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 (36229-42-2) → 3-chlorophenylboronic acid (63503-60-6)

Conditions	Yield
With boron trifluoride

3-iodochlorobenzene (625-99-0) → 3-chlorophenylboronic acid (63503-60-6)

Conditions	Yield
(i) (UV-irradiation), BBr3, (ii) aq. NaOH; Multistep reaction;

1-bromo-3-chlorobenzene (108-37-2) + borane (13283-31-3) → 3-chlorophenylboronic acid (63503-60-6)

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 (108-37-2) + Trimethyl borate (121-43-7) → 3-chlorophenylboronic acid (63503-60-6) + (3-bromophenyl)boronic acid (89598-96-9)

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 (108-37-2) + Triisopropyl borate (5419-55-6) → 3-chlorophenylboronic acid (63503-60-6)

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 (108-37-2) + boric acid tributyl ester (688-74-4) → 3-chlorophenylboronic acid (63503-60-6)

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 (63503-60-6) + ethylene glycol (107-21-1) → 3-chlorophenylboronic acid ethylene glycol ester (402488-97-5)

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 (63503-60-6) + 7-tert-butoxycarbonyl-2-exo-(3'-bromo-5'-pyridinyl)-7-azabicyclo[2.2.1]heptane → 7-tert-butoxycarbonyl-2-exo-[3-(3-chlorophenyl)-5-pyridinyl]-7-azabicyclo[2.2.1]heptane

Conditions	Yield
With sodium carbonate; tris-(o-tolyl)phosphine; palladium diacetate In 1,2-dimethoxyethane; water Suzuki coupling; Heating;	100%

9,10-Dibromoanthracene (523-27-3) + 3-chlorophenylboronic acid (63503-60-6) → 9,10-di(3-chlorophenyl)anthracene (1261083-80-0)

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 (1338094-20-4) + 3-chlorophenylboronic acid (63503-60-6) → 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 (1338092-32-2)

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 (1266520-43-7) + 3-chlorophenylboronic acid (63503-60-6) → 5-(3-chlorophenyl)-4-(3-cyano-4-fluorophenyl)-1,3-thiazole-2-carboxylic acid (1266520-47-1)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate In 1,2-dimethoxyethane; water at 20℃; for 1h; Reflux;	100%

6-chloropyrido[3,2-d]pyrimidin-4-amine + 3-chlorophenylboronic acid (63503-60-6) → 6-(3-chlorophenyl)pyrido[3,2-d]pyrimidin-4-amine

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 (63503-60-6) + para-nitrophenyl bromide (586-78-7) → 3‐chloro‐4′‐nitrobiphenyl (952-22-7)

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 (29578-39-0) + 3-chlorophenylboronic acid (63503-60-6) → 3'-chloro-3-fluoro-5-methoxy-1,1'-biphenyl

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 90℃; for 0.75h; Inert atmosphere;	100%

2-bromofluoranthene (26885-42-7) + 3-chlorophenylboronic acid (63503-60-6) → C22H13Cl

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 (63503-60-6) + 1-(bromomethyl)-3-fluoro-5-(trifluoromethyl)benzene (239087-09-3) → 1-[(3-chlorophenyl)methyl]-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 (930-30-3) + 3-chlorophenylboronic acid (63503-60-6) → (R)-3-(3-Chloro-phenyl)-cyclopentanone

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;

bromobenzene (108-86-1) + 3-chlorophenylboronic acid (63503-60-6) → m-chlorobiphenyl (2051-61-8)

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 (930-30-3) + 3-chlorophenylboronic acid (63503-60-6) → (3R)-3-(3-chlorophenyl)cyclopentanone (583960-72-9)

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 (63503-60-6) → PCB 11 (2050-67-1)

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%

cyclopent-2-enone (930-30-3) + 3-chlorophenylboronic acid (63503-60-6) → C5H7O(C6H4Cl)

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 (63503-60-6) + 4,4-ethylenedioxy-1-oxo-1,4-dihydronaphthalene (6541-89-5) → (R)-3-(3-chlorophenyl)-4,4-ethylenedioxy-1-oxo-1,2,3,4-tetrahydronaphthalene

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 (63503-60-6) + o-chloro-N-tosylbenzaldimine (135822-90-1) → (S)-N-[(2-chlorophenyl)(3-chlorophenyl)methyl]-4-methylbenzenesulfonamide (1112116-73-0)

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 (4122-56-9) + 3-chlorophenylboronic acid (63503-60-6) → 3-(3-chlorophenyl)-3H-isobenzofuran-1-one (4889-71-8)

Conditions	Yield
With bis(η3-allyl-μ-chloropalladium(II)); C27H30N2S(1+)*Cl(1-); cesium fluoride In toluene at 80℃; for 1h; Inert atmosphere;	99%

C11H8O3 (1202929-10-9) + 3-chlorophenylboronic acid (63503-60-6) → C17H13ClO3

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%

C11H8O3 (1202929-10-9) + 3-chlorophenylboronic acid (63503-60-6) → C17H13ClO3

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%

(2-nitroethenyl)benzene (102-96-5) + 3-chlorophenylboronic acid (63503-60-6) → C14H12ClNO2 (1245819-50-4)

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 (63503-60-6) → 3-monochlorophenol (108-43-0)

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%

C21H15F3O5S (1287702-26-4) + 3-chlorophenylboronic acid (63503-60-6) → C26H19ClO2 (1287702-28-6)

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 (930-30-3) + 3-chlorophenylboronic acid (63503-60-6) → (3S)-3-(3-chlorophenyl)cyclopentanone

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 (14309-57-0) + 3-chlorophenylboronic acid (63503-60-6) → (S)-4-(3-chlorophenyl)nonan-2-one (1346758-83-5)

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%

3-chlorophenylboronic acid (63503-60-6) + benzil (134-81-6) → C20H15ClO2

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 (7633-38-7) + 3-chlorophenylboronic acid (63503-60-6) → (S)-di-tert-butyl-2-(3-chlorophenyl)succinate (1378314-39-6)

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 (63503-60-6) + para-bromoacetophenone (99-90-1) → 1-(3'-chlorobiphenyl-4-yl)ethanone (5002-13-1)

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 (1169706-60-8) + 3-chlorophenylboronic acid (63503-60-6) → C31H28ClN7

Conditions	Yield
With copper(II) perchlorate hexahydrate; triethylamine In dimethyl sulfoxide at 80℃; for 3.5h;	99%

3-chlorophenylboronic acid (63503-60-6) + benzo[e][1,2,3]oxathiazine 2,2-dioxide (71730-46-6) → (S)-4-(3-chlorophenyl)-3,4-dihydrobenzo[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%

Upstream product

• 625-99-0 3-iodochlorobenzene 
• 13283-31-3 borane 
• 36229-42-2 (3-chlorophenyl)magnesium bromide 
• 108-37-2 1-bromo-3-chlorobenzene 
• 121-43-7 Trimethyl borate 
• 688-74-4 boric acid tributyl ester 
• 5419-55-6 Triisopropyl borate 

Downstream Products

• 5728-43-8 3'-chloro-[1,1'-biphenyl]-4-carboxylic acid 
• 38444-87-0 3,5,3'-trichloro-biphenyl 
• 952-22-7 3‐chloro‐4′‐nitrobiphenyl 
• 583960-72-9 (3R)-3-(3-chlorophenyl)cyclopentanone 
• 21469-77-2 (E)-3-(3-chlorophenyl)-N,N-dimethylacrylamide 
• 60233-24-1 2,3',4,6-tetrachlorobiphenyl 
• 833445-95-7 8-(3-chlorophenyl)adenosine 
• 41019-39-0 5-(3-chlorophenyl)furan-2-carboxylic acid methyl ester 
• 89901-01-9 methyl 3'-chloro-[1,1'-biphenyl]-4-carboxylate 
• 1024448-92-7 C₁₂H₉ClO₂S 

Relevant articles and documents

Preparation method of 3-chlorophenylboronic acid

The invention belongs to the technical field of chemical synthesis, and particularly discloses a preparation method of 3-chlorophenylboronic acid. The preparation method comprises the following steps:preparing 3-chlorophenylboronic acid by using m-bromochlorobenzene as a raw material, preparing a Grignard reaction reagent, reacting with borate to generate 3-chlorophenylborate, and carrying out acid hydrolysis on the 3-chlorophenylborate to obtain a crude product; carrying out gradient cooling crystallization, filtering, ether solvent pulping and filter cake washing on the crude product to obtain a product with the purity of 99.5% or above and the single impurity content smaller than 0.1%, meeting the purity requirement of the bulk drug production process for the medical intermediate. Besides, the total yield of the 3-chlorophenylboronic acid synthesized by the method is over 70 percent and is obviously superior to the yield of the 3-chlorophenylboronic acid synthesized by the conventional Grignard reagent method; the intermediate product Grignard reagent can be directly used for the next reaction without separation, so that the process is effectively simplified, the sewage discharge is reduced, and the cost is reduced.

Synthesis method of 3-chlorobenzeneboronic acid

The invention provides a synthesis method of 3-chlorobenzeneboronic acid. The synthesis method comprises the following steps: with m-dichlorobenzene as a starting material and iodine particles or 1,2-dibromoethane as an initiator, reacting with magnesium in the presence of an organic solvent to obtain a 3-chlorophenylmagnesium chloride reaction solution; then, reacting with trimethyl borate in anorganic solvent to obtain dimethyl 3-chlorobenzeneborate; then, hydrolyzing by using an acid aqueous solution, extracting by using an organic solvent and crystallizing by using an organic solvent to obtain the 3-chlorophenylboronic acid with the purity being higher than or equal to 98.5%. By the synthesis method, raw materials are cheap and easy to obtain, reaction steps are few, the production cost is low, a technology is simple, the pollution is small, and achievement of the industrial production is facilitated.

Flow Chemistry on Multigram Scale: Continuous Synthesis of Boronic Acids within 1 s

The benefits and limitations of a simple continuous flow setup for handling and performing of organolithium chemistry on the multigram scale is described. The developed metalation platform embodies a valuable complement to existing methodologies, as it combines the benefits of Flash Chemistry (chemical synthesis on a time scale of 1 s) with remarkable throughput (g/min) while mitigating the risk of blockages.