4612-26-4

Basic information

• Product Name: 1,4-Phenylenebisboronic acid
• Synonyms: BENZENE-1,4-DIBORONIC ACID;1,4-BENZENEDIBORONIC ACID;1,4-PHENYLENEDIBORONIC ACID;1,4-PHENYLENEBIS(BORONIC ACID);4-(DIHYDROXYBORYL)PHENYLBORONIC ACID;AKOS BRN-0002;P-PHENYLENEDIBORONIC ACID;1,4-Phenyldiboronic acid
• CAS NO: 4612-26-4
• Molecular Formula: C₆H₈B₂O₄
• Molecular Weight: 165.75
• EINECS: 1312995-182-4
• Product Categories: blocks;BoronicAcids;Boronic acids;B (Classes of Boron Compounds)
• Mol File: 4612-26-4.mol
• Article Data: 13

Chemical Properties

• Melting Point: >350 °C(lit.)
• Boiling Point: 420.1 °C at 760 mmHg
• Flash Point: 207.9 °C
• Appearance: /liquid
• Density: 1.33 g/cm³
• Vapor Pressure: 8.27E-08mmHg at 25°C
• Refractive Index: 1.555
• Storage Temp.: 0-6°C
• Solubility: soluble in Methanol
• PKA: 8.30±0.17(Predicted)
• Water Solubility: Soluble in water 2.5%.
• BRN: 2836921
• CAS DataBase Reference: 1,4-Phenylenebisboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Phenylenebisboronic acid(4612-26-4)
• EPA Substance Registry System: 1,4-Phenylenebisboronic acid(4612-26-4)

Safety Data

• Hazard Codes: Xn,C,Xi
• Statements: 22-36/37/38-20/21/22
• Safety Statements: 36-26
• WGK Germany: 3
• TSCA: No
• HazardClass: IRRITANT
• Hazardous Substances Data: 4612-26-4(Hazardous Substances Data)

Usage

Chemical Properties

1,4-Phenylenebisboronic acid is off-white powder

Uses

Different sources of media describe the Uses of 4612-26-4 differently. You can refer to the following data:
1. suzuki reaction
2. Reagent used for . Externally initiated Kumada catalyst-transfer polycondensation . Suzuki-Miyaura cross-coupling reactions . Energy transfer processes in optoelectronic devices . Palladium-catalyzed sequential alkenylation and conjugate addition reactions . Scholl cyclizations
3. It is used for palladium-catalyzed sequential alkenylation and conjugate addition reactions, scholl cyclizations, Suzuki-Miyaura cross-coupling reactions. It is also used in the preparation of indolizine derivatives as OLEDs, in organic thin-film transistors, Fluorescence and solution-processable coordination polymers.

InChI:InChI=1/C6H8B2O4/c9-7(10)5-1-2-6(4-3-5)8(11)12/h1-4,9-12H

Synthetic route

1.4-dibromobenzene (106-37-6) → 1,4-Phenyldiboronic acid (4612-26-4)

Conditions	Yield
Stage #1: 1.4-dibromobenzene With magnesium In tetrahydrofuran Reflux; Stage #2: With Trimethyl borate In tetrahydrofuran; diethyl ether at -70℃; Stage #3: With sulfuric acid; water In tetrahydrofuran; diethyl ether at 20℃;	88%
Stage #1: 1.4-dibromobenzene With magnesium In tetrahydrofuran Heating; Stage #2: With Trimethyl borate In tetrahydrofuran at -70℃; for 2h; Stage #3: With hydrogenchloride In tetrahydrofuran pH=3;	35%
Stage #1: 1.4-dibromobenzene With magnesium In tetrahydrofuran Metallation; Stage #2: With Trimethyl borate In tetrahydrofuran at -78℃; Substitution; Stage #3: With hydrogen cation at 0℃; Substitution;

Trimethyl borate (121-43-7) + 1.4-dibromobenzene (106-37-6) → 1,4-Phenyldiboronic acid (4612-26-4)

Conditions	Yield
Stage #1: 1.4-dibromobenzene With iodine; magnesium In tetrahydrofuran at 30℃; for 3h; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran at -70℃; for 1h; Temperature; Concentration;	84.6%
Stage #1: 1.4-dibromobenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: Trimethyl borate In tetrahydrofuran; hexane for 2h;	47%

borane (13283-31-3) + water (7732-18-5) + 1,4-bis(trimethylstannyl)benzene (1012-73-3) → 1,4-Phenyldiboronic acid (4612-26-4) + trimethylstannane (1631-73-8)

Conditions	Yield
In tetrahydrofuran (N2); addn. of a soln. of boron compd. in THF to a soln. of tin compd. in THF, stirring at room temp. for 1 h, refluxing for 3 h, addn. of water;	A 83% B n/a

hydrogenchloride (7647-01-0) + Trimethyl borate (121-43-7) + 1.4-dibromobenzene (106-37-6) → 1,4-Phenyldiboronic acid (4612-26-4)

Conditions	Yield
Stage #1: 1.4-dibromobenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: Trimethyl borate In tetrahydrofuran; hexane for 2h; Stage #3: hydrogenchloride In tetrahydrofuran; hexane; water	47%

phen-1,4-ylenbis(magnesiumbromid) (2425-81-2) → 1,4-Phenyldiboronic acid (4612-26-4)

Conditions	Yield
(i) B(OMe)3, (ii) aq. H2SO4; Multistep reaction;

1,4-bis(dichloroboryl)benzene (71258-12-3) → 1,4-Phenyldiboronic acid (4612-26-4)

Conditions	Yield
hydrolysis;

Trimethyl borate (121-43-7) + (4-ClC6H4)BF2 + 2,4,6-tris(4-bromophenyl)boroxin (7519-94-0) → 1,4-Phenyldiboronic acid (4612-26-4)

Conditions	Yield
With Na In hexane
With Na In hexane

C10H16B2O4 (93687-09-3) → 1,4-Phenyldiboronic acid (4612-26-4)

Conditions	Yield
With sulfuric acid; water at 0℃; Inert atmosphere;	3.44 g
With hydrogenchloride; water at 20℃; for 1h;	1.6 g

1,4-bis(di-n-butoxy)-boryl-phenylene (2449-19-6) → 1,4-Phenyldiboronic acid (4612-26-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrachloromethane View Scheme
Multi-step reaction with 2 steps 1: tetrachloromethane View Scheme

Trimethyl borate (121-43-7) + 1.4-dibromobenzene (106-37-6) + water (7732-18-5) → 1,4-Phenyldiboronic acid (4612-26-4)

Conditions	Yield
With HCl In tetrahydrofuran (inert atm.); addn. of THF soln. of dibromobenzene to Mg in dry THF, refluxing for 24-48 h, addn. of trimethylborate in dry THF, refluxing for 2h, addn. into aq. HCl, stirring at room temp. for 1 h; extn. (diethyl ether), drying over Na2SO4, filtration, evapn., NMR and MS;

C18H32B2O4 → 1,4-Phenyldiboronic acid (4612-26-4)

Conditions	Yield
With water In water Inert atmosphere;

tetrahydroxydiboron (13675-18-8) + 1-Chloro-4-iodobenzene (637-87-6) → 1,4-Phenyldiboronic acid (4612-26-4)

Conditions	Yield
With [{Pd(μ-Cl){κ2-P,C-P(iPr)2(OC6H3-2-Ph)}}2]; sodium acetate In dichloromethane; water at 40℃; for 6h; Inert atmosphere;

1,4-Phenyldiboronic acid (4612-26-4) + 2,2-Dimethyl-1,3-propanediol (126-30-7) → 1,4-bis-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzene (5565-36-6)

Conditions	Yield
With toluene-4-sulfonic acid In benzene for 12h; Inert atmosphere; Reflux;	100%
With toluene-4-sulfonic acid In benzene for 24h; Reflux; Dean-Stark;	90%
In toluene for 24h; Reflux;	80%
With toluene-4-sulfonic acid In benzene at 70℃; for 12h;

5-bromo-3-methoxysalicylaldehyde (5034-74-2) + 1,4-Phenyldiboronic acid (4612-26-4) → 4,4''-dihydroxy-5,5''-dimethoxy-[1,1':4',1''-terphenyl]-3,3''-dicarbaldehyde

Conditions	Yield
With palladium diacetate; potassium carbonate; triphenylphosphine In 1,2-dimethoxyethane; water for 24h; Reflux;	100%

1,4-Phenyldiboronic acid (4612-26-4) + para-nitrophenyl bromide (586-78-7) → p,p-dinitro-p-terphenyl (3282-11-9)

Conditions	Yield
With [PdCl2(2-pyridin-2-yl-benzo[b]thiophen-3-ol)]; potassium carbonate In water; N,N-dimethyl-formamide at 90℃; for 6h; Catalytic behavior; Reagent/catalyst; Temperature; Solvent; Suzuki-Miyaura Coupling;	99%
With palladium; potassium carbonate In methanol; acetonitrile at 20℃; for 2h; Suzuki Coupling;	88%
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran for 18h; Suzuki cross-coupling; Heating;	76%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 65h;	54%

1,4-Phenyldiboronic acid (4612-26-4) + 7,8,13,14-tetrahydro-6-(3'-bromophenyl)chino[8,7-k][1,8]phenanthroline (695150-26-6) → 3,3''-di-(7,8,13,14-tetrahydroquino[8,7-k][1,8]phenanthrolin-6-yl)-[1,1';4',1'']terphenyl

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In methanol; toluene for 24h; Suzuki cross-coupling reaction; Heating;	99%

1,4-Phenyldiboronic acid (4612-26-4) + benzene-1,2-diol (120-80-9) → 2,2'-(1,4-phenylene)bis-1,3,2-benzodioxaborole (98494-81-6)

Conditions	Yield
In toluene for 48h; Heating;	99%
In dichloromethane; ethyl acetate at 20℃;	36%
In water; toluene byproducts: H2O; bisdioxaborole synthesized from mixt. of diboronic acid and excess catechol through azeotropic removal of water with toluene; unreacted catechol sublimited under reduced pressure; (1)H NMR, MS;
Stage #1: 1,4-Phenyldiboronic acid; benzene-1,2-diol With 4,4'-bipyridine In tetrahydrofuran; toluene for 4h; Inert atmosphere; Dean-Stark; Reflux; Stage #2: In chloroform-d1 Heating; Inert atmosphere;

4-bromobenzenecarbonitrile (623-00-7) + 1,4-Phenyldiboronic acid (4612-26-4) → [1,1′:4′,1”‐terphenyl]‐4,4″‐dicarbonitrile (17788-93-1)

Conditions	Yield
With C37H28N8O*2Cl(1-)*Pd(2+); potassium carbonate In ethanol at 70℃; for 2h; Suzuki-Miyaura Coupling;	99%
With [PdCl2(2-pyridin-2-yl-benzo[b]thiophen-3-ol)]; potassium carbonate In water; N,N-dimethyl-formamide at 90℃; for 6h; Catalytic behavior; Reagent/catalyst; Temperature; Solvent; Suzuki-Miyaura Coupling;	95%
With palladium; potassium carbonate In methanol; acetonitrile at 20℃; for 2h; Suzuki Coupling;	86%
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In methanol; toluene at 80℃; for 12h; Suzuki coupling;	73%

di-isopropyl azodicarboxylate (2446-83-5) + 1,4-Phenyldiboronic acid (4612-26-4) → 1,2-bis(isopropoxycarbonyl)-1-(4-(1,2-bis(isopropoxycarbonyl)hydrazinyl)phenyl)hydrazine

Conditions	Yield
2,9-dimethyl-1,10-phenanthroline-based palladium(II) complex In N,N-dimethyl-formamide at 60℃; for 12h;	99%

bromobenzene (108-86-1) + 1,4-Phenyldiboronic acid (4612-26-4) → [1,1';4',1'']terphenyl (92-94-4)

Conditions	Yield
With C37H28N8O*2Cl(1-)*Pd(2+); potassium carbonate In ethanol at 70℃; for 2h; Suzuki-Miyaura Coupling;	99%
With 1,3-bis[3-(3-phenylpropyl)-1-ylbenzimidazolium]propane dibromide; palladium diacetate; potassium carbonate In water; N,N-dimethyl-formamide at 100℃; for 0.0833333h; Reagent/catalyst; Suzuki-Miyaura Coupling; Microwave irradiation;	94%
With palladium diacetate; 3,3'-(propane-1,3-diyl)bis(1-pentyl-1,3-dihydro-2H-benzo[d]imidazole-2-tellurone); potassium carbonate In water; N,N-dimethyl-formamide at 100℃; for 0.166667h; Reagent/catalyst; Suzuki-Miyaura Coupling; Microwave irradiation;	73%
With palladium diacetate; potassium carbonate In 2-methoxy-ethanol; water at 21℃; for 0.25h; Suzuki coupling;	98 %Chromat.

1,4-Phenyldiboronic acid (4612-26-4) + para-bromoacetophenone (99-90-1) → 1,1'-(1,1':4',1''-terphenyl-4,4''-diyl)diethanone (4191-07-5)

Conditions	Yield
With C37H28N8O*2Cl(1-)*Pd(2+); potassium carbonate In ethanol at 70℃; for 2h; Suzuki-Miyaura Coupling;	99%
With palladium; potassium carbonate In methanol; acetonitrile at 20℃; for 2h; Suzuki Coupling;	87%

C34H38O6 (1444011-04-4) + 1,4-Phenyldiboronic acid (4612-26-4) → C80H76B4O12 (1444011-06-6)

Conditions	Yield
In chloroform-d1; d(4)-methanol at 50℃; Inert atmosphere;	99%

C76H102O12 + 1,4-Phenyldiboronic acid (4612-26-4) → C164H204B4O24

Conditions	Yield
In methanol; chloroform at 50℃; Molecular sieve;	99%

1,4-Phenyldiboronic acid (4612-26-4) + 2,5-dibromo-N,N'-bis-(4-octyl-phenyl)-benzene-1,4-diamine (599575-85-6) → polymer, product of polymerization by Suzuki coupling, Mw 7900 Da, PDI 1.8; monomer(s): benzene-1,4-diboronic acid; 2,5-dibromo-N,N\-bis(4-octylphenyl)-1,4-phenylenediamine

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water at 80℃; Suzuki coupling;	98%

2-(2-bromo-6-fluoro-1H-indol-3-ylmethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (908015-73-6) + 1,4-Phenyldiboronic acid (4612-26-4) → 1,4-bis-[2-(6-fluoro-1H-indol-3-ylmethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester]benzene

Conditions	Yield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; water; toluene at 100℃; for 5h;	98%

1,4-Phenyldiboronic acid (4612-26-4) + 4-bromo-benzaldehyde (1122-91-4) → [1,1′:4′,1″-terphenyl]-4,4″-dicarbaldehyde (62940-38-9)

Conditions	Yield
With [PdCl2(2-pyridin-2-yl-benzo[b]thiophen-3-ol)]; potassium carbonate In water; N,N-dimethyl-formamide at 90℃; for 8h; Catalytic behavior; Reagent/catalyst; Temperature; Solvent; Suzuki-Miyaura Coupling;	98%
With palladium; potassium carbonate In methanol; acetonitrile at 20℃; for 2h; Suzuki Coupling;	82%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; N,N-dimethyl-formamide at 80℃; for 8.5h; Suzuki-Miyaura Coupling; Inert atmosphere;	72.5%
With tetrakis(triphenylphosphine) palladium(0); water; sodium carbonate In tetrahydrofuran; toluene at 80℃; for 48h; Suzuki coupling; Inert atmosphere;	34%
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; toluene at 80℃; for 7h; Suzuki-Miyaura cross-coupling;	32%

1,4-Phenyldiboronic acid (4612-26-4) + N-<1(S)-methyl-2(R)-phenyl-2-hydroxyethyl>sarcosine (143444-51-3) → (+)-(N->B)(N'->B')-1,4-phenylenebis{N-methyl-N-(1-(S)-methyl-2-(R)-phenyl-2-oxyethyl)aminoacetate-O,O',N}bisboron

Conditions	Yield
In ethanol; benzene addn. of boronic acid to a soln. of glycine derivate in C2H5OH/C6H6, reflux for 8 h; evapn. (vac.);	98%

p-nitrobenzene iodide + 4-iodo-biphenyl (1591-31-7) + 1,4-Phenyldiboronic acid (4612-26-4) → 4-nitro-1,1':4',1'':4'',1'''-quaterphenyl (25627-14-9)

Conditions	Yield
Stage #1: p-nitrobenzene iodide; 1,4-Phenyldiboronic acid With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In methanol; water; toluene Suzuki cross-coupling; Stage #2: 4-iodo-biphenyl With tetrakis(triphenylphosphine) palladium(0) In methanol; water; toluene for 32h; Reflux;	98%

1-bromo-2-methoxy-3-tert-butylbenzene (1007375-07-6) + 1,4-Phenyldiboronic acid (4612-26-4) → 3,3"-di-tert-butyl-2,2"-dimethoxy[1,1';4',1"]terphenyl (1205536-15-7)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; N,N-dimethyl-formamide at 100℃; for 20h; Suzuki coupling; Inert atmosphere;	98%

2,3-dimethyl-2,3-butane diol (76-09-5) + 1,4-Phenyldiboronic acid (4612-26-4) → benzene-1,4-diboronic acid bispinacol ester (99770-93-1)

Conditions	Yield
With magnesium sulfate In methanol at 30℃;	97%
In diethyl ether at 20℃; for 12h;	95%
In N,N-dimethyl-formamide at 20℃; for 12h;	93%

1-phenyl-1,2-propanedione 2-oxime 1-hydrazone (41939-99-5) + 1,4-Phenyldiboronic acid (4612-26-4) + iron(II) bromide → {{Fe(PMXY)3}2B2C6H4}Br2

Conditions	Yield
In ethanol Dissolving/suspending of PMXY in absolute EtOH, outgassing of mixt. with N2, and then addn. of FeBr2. B-compd. is added to resulting orange-brown suspn., and mixt. is stirred (2 h, N2).; Filtn. of pptd. solid via suction and washing with EtOH followed by ethyl ether.;	97%

1,4-Phenyldiboronic acid (4612-26-4) + diethyl 4-bromo-2,6-pyridinedicarboxylate (112776-83-7) → C28H28N2O8

Conditions	Yield
Stage #1: 1,4-Phenyldiboronic acid; diethyl 4-bromo-2,6-pyridinedicarboxylate With potassium carbonate In water; toluene at 60℃; for 1h; Suzuki Coupling; Inert atmosphere; Stage #2: With tris(dibenzylideneacetone)dipalladium; tri-tert-butyl phosphine In water; toluene at 80℃; for 0.25h;	97%

C42H42O6 + 1,4-Phenyldiboronic acid (4612-26-4) → C96H84B4O12

Conditions	Yield
In methanol; chloroform at 50℃; Molecular sieve;	97%

iodobenzene (591-50-4) + 1,4-Phenyldiboronic acid (4612-26-4) → [1,1';4',1'']terphenyl (92-94-4)

Conditions	Yield
With potassium carbonate In water; N,N-dimethyl-formamide at 20℃; for 2h; Catalytic behavior; Suzuki Coupling; Inert atmosphere; Irradiation;	97%
With potassium phosphate In ethanol; water at 80℃; for 1h; Suzuki-Miyaura Coupling; Inert atmosphere;	99 %Chromat.

1,4-Phenyldiboronic acid (4612-26-4) + 5-bromo-2-methoxybenzoate → methyl 4,4′′-dimethoxy-[1,1′:4′,1′′-terphenyl]-3,3′′-dicarboxylate

Conditions	Yield
With C45H58ClNPPd; potassium carbonate In tetrahydrofuran; water for 20h; Reflux;	96.4%

1,4-Phenyldiboronic acid (4612-26-4) + ethylene glycol (107-21-1) → 1,4-bis(1,3,2-dioxaborolanyl)benzene (94934-64-2)

Conditions	Yield
In toluene for 2h; Heating;	96%

1,4-Phenyldiboronic acid (4612-26-4) + (1S,2R,5S,6R)-3,3,7,7-Tetramethyl-1,2,3,5,6,7-hexahydro-s-indacene-1,2,5,6-tetraol → polymer; monomer(s): 1,4-benzenedi(boronic acid)

Conditions	Yield
In methanol at 20℃; for 3h;	96%

3-iodo-8-isobutyl-5,6,7-trimethoxy-2-methyl-4H-chromen-4-one (853577-63-6) + 1,4-Phenyldiboronic acid (4612-26-4) → C40H46O10 (943027-57-4)

Conditions	Yield
With sodium carbonate; Pd2(dpf)2Cl2*CH2Cl2 In ethanol; water; N,N-dimethyl-formamide at 90℃; for 10h; Suzuki coupling;	96%

1,4-Phenyldiboronic acid (4612-26-4) + (1S,2R,5S,6R)-3,3,7,7-Tetramethyl-1,2,3,5,6,7-hexahydro-s-indacene-1,2,5,6-tetraol → BC6H4BO2C12H6(CH3)4O2

Conditions	Yield
In methanol react. tetrol and 1,4-benzenedi(boronic acid) in 1:1 ratio in MeOH at room temp. for 3 h; elem. anal.;	96%

Upstream product

• 2425-81-2 phen-1,4-ylenbis(magnesiumbromid) 
• 13283-31-3 borane 
• 7732-18-5 water 
• 1012-73-3 1,4-bis(trimethylstannyl)benzene 
• 121-43-7 Trimethyl borate 
• 106-37-6 1.4-dibromobenzene 
• 7647-01-0 hydrogenchloride 
• 13675-18-8 tetrahydroxydiboron 
• 637-87-6 1-Chloro-4-iodobenzene 
• 2449-19-6 1,4-bis(di-n-butoxy)-boryl-phenylene 
• 93687-09-3 C₁₀H₁₆B₂O₄ 
• 7519-94-0 2,4,6-tris(4-bromophenyl)boroxin 
• 71258-12-3 1,4-bis(dichloroboryl)benzene 

Downstream Products

• 26076-49-3 2,2'-p-phenylene-bis-[1,3,6,2]dioxazaborocane 
• 92-69-3 4-Phenylphenol 
• 92-94-4 [1,1';4',1'']terphenyl 
• 96433-09-9 benzene-1,4-bis(boronic acid) propane-1,3-diol diester 
• 884654-71-1 3,5-di(pyrid-2-yl)-1,1′-biphenyl 
• 855308-50-8 C₆H₄(B(OC₆H₄C(C₆H₅)N(CH₂)3O))2 
• 1063745-98-1 4,4''-bis[tris(4-methoxyphenyl)methyl]-[1,1',4',1'']-terphenyl 
• 1073514-03-0 8-(4'-hydroxy-p-biphenyl)-4,4-difluoro-2,6-diethyl-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene 
• 1073514-04-1 4',4'''-di(4,4-difluoro-2,6-diethyl-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacen-8-yl)-p-terphenyl 
• 951657-74-2 1,4-bis-(2'-cyanopyridin-5'-yl)phenylene 
• 951657-88-8 1,4-bis-(2'-cyanopyrimidin-5'-yl)-phenylene 
• 951657-84-4 1,4-bis-(2'-cyanopyrazin-5'-yl)phenylene 
• 1374685-93-4 (4Z,4'Z)-tetramethyl 4,4'-(1,4-phenylenebis(methan-1-yl-1-ylidene))bis(3-(prop-1-en-2-yl)cyclopent-2-ene-1,1-dicarboxylate) 
• 1374686-18-6 tetramethyl 3,3'-(1,1'-(1,4-phenylene)bis(cyclohexane-1,1-diyl))bis(4-(hex-1-enylidene)cyclopent-2-ene-1,1-dicarboxylate) 

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Bedford-type palladacycle-catalyzed miyaura borylation of aryl halides with tetrahydroxydiboron in water

A mild aqueous protocol for palladium catalyzed Miyaura borylation of aryl iodides, aryl bromides and aryl chlorides with tetrahydroxydiboron (BBA) as a borylating agent is developed. The developed methodology requires low catalyst loading of Bedford-type palladacycle catalyst (0.05 mol %) and works best under mild reaction conditions at 40 °C in short time of 6 h in water. In addition, our studies show that for Miyaura borylation using BBA in aqueous condition, maintaining a neutral reaction pH is very important for reproducibility and higher yields of corresponding borylated products. Moreover, our protocol is applicable for a broad range of aryl halides, corresponding borylated products are obtained in excellent yields up to 93% with 29 examples demonstrating its broad utility and functional group tolerance.

Off-axis digital holographic microscope as described in any one of Claims 1 to 6, includes a light coupled to the target unit (Sa) fluorescence excitation source (17).

The invention belongs to the field of medicine synthesis and specifically relates to a preparation method of an anidulafungin side chain intermediate 4'-orthopentyloxy-1,1':4',1'-terphenyl-4-carboxylic acid. The preparation method comprises the following steps: initiating a 1,4-dibromo-benzene material which serves as a starting material to carry out Grignard reagent reaction with magnesium by iodine; then, preparing 1,4-benzene hypoboric acid by virtue of addition and hydrolysis with trimethyl borate; and preparing 4'-orthopentyloxy-1,1':4',1'- terphenyl-ethyl carboxylate by virtue of Suzuki reaction of 1,4-benzene hypoboric acid, 4-pentyloxy bromobenzene and 4-halogenated ethyl benzoate in dioxane-ethanol liquor under catalysis of [1,1'-bis(diphenyl phosphino) ferrocene] palladium dichloride, and then, hydrolyzing to obtain a target product. The preparation method disclosed by the invention can lower process cost, is simple, convenient, safe and reliable to operate, and suitable for industrial production.