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13675-18-8

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13675-18-8 Usage

Reaction

Reagent used for the palladium-catalyzed aryl borylation of aryl halides. ?Reagent used for the copper-catalyzed β-boration of α,β-unsaturated carbonyl compounds. ?Reagent used for the nickel-catayzed (het)aryl borylation of aryl halides. ?Reagent used for the palladium-catalyzed borylation of allylic alcohols.

Uses

Different sources of media describe the Uses of 13675-18-8 differently. You can refer to the following data:
1. suzuki reaction
2. Tetrahydroxydiboron can be used as a lubricating oil composition.

Check Digit Verification of cas no

The CAS Registry Mumber 13675-18-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,6,7 and 5 respectively; the second part has 2 digits, 1 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 13675-18:
(7*1)+(6*3)+(5*6)+(4*7)+(3*5)+(2*1)+(1*8)=108
108 % 10 = 8
So 13675-18-8 is a valid CAS Registry Number.
InChI:InChI=1/B2H4O4/c3-1(4)2(5)6/h3-6H

13675-18-8 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
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  • Detail
  • TCI America

  • (T2953)  Tetrahydroxydiborane  

  • 13675-18-8

  • 5g

  • 1,100.00CNY

  • Detail
  • TCI America

  • (T2953)  Tetrahydroxydiborane  

  • 13675-18-8

  • 25g

  • 3,880.00CNY

  • Detail
  • Aldrich

  • (754242)  Tetrahydroxydiboron  95%

  • 13675-18-8

  • 754242-1G

  • 307.71CNY

  • Detail
  • Aldrich

  • (754242)  Tetrahydroxydiboron  95%

  • 13675-18-8

  • 754242-5G

  • 1,206.27CNY

  • Detail
  • Aldrich

  • (754242)  Tetrahydroxydiboron  95%

  • 13675-18-8

  • 754242-25G

  • 4,819.23CNY

  • Detail
  • Aldrich

  • (754242)  Tetrahydroxydiboron  95%

  • 13675-18-8

  • 754242-100G

  • 7,897.50CNY

  • Detail
  • Aldrich

  • (754242)  Tetrahydroxydiboron  95%

  • 13675-18-8

  • 754242-1KG

  • 35,708.40CNY

  • Detail

13675-18-8SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name hypodiboric acid

1.2 Other means of identification

Product number -
Other names Tetrahydroxydiborane

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:13675-18-8 SDS

13675-18-8Synthetic route

water
7732-18-5

water

diboron tetrachloride
13701-67-2

diboron tetrachloride

A

tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

B

boric acid
11113-50-1

boric acid

Conditions
ConditionsYield
In water byproducts: HCl; hydrolysis of B2Cl4; dissolution of crude solid in degassed H2O, slow evapn. at room temp.;A 70%
B n/a
tetramethoxydiborane
7318-94-7

tetramethoxydiborane

water
7732-18-5

water

A

methanol
67-56-1

methanol

B

tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

B2Br4(NH(CH3)2)2
67183-19-1

B2Br4(NH(CH3)2)2

water
7732-18-5

water

A

tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

B

boric acid
11113-50-1

boric acid

Conditions
ConditionsYield
In tetrahydrofuran; water addn. of aq. THF to a soln. of boron compd. in THF, stirring for 2 d; dissolution in H2O, slow evapn. at room temp.;
tetrakis(dimethylamido)diborane
1630-79-1

tetrakis(dimethylamido)diborane

water
7732-18-5

water

A

tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

B

dimethyl amine
124-40-3

dimethyl amine

water
7732-18-5

water

diboron tetrachloride
13701-67-2

diboron tetrachloride

A

hydrogenchloride
7647-01-0

hydrogenchloride

B

tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

tetramethoxydiborane
7318-94-7

tetramethoxydiborane

A

tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

B

boric acid
11113-50-1

boric acid

Conditions
ConditionsYield
With water In water at room temp. in vac.;
With hydrogenchloride In not given with dild. HCl at room temp. in vac.;
With H2O In water at room temp. in vac.;
With HCl In not given with dild. HCl at room temp. in vac.;
tetramethoxydiborane
7318-94-7

tetramethoxydiborane

tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

Conditions
ConditionsYield
by hydrolysis;
by hydrolysis;
H4B2O2

H4B2O2

tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

Conditions
ConditionsYield
With iodine
With I2
H2B2O2

H2B2O2

tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

Conditions
ConditionsYield
In water evapn.;
With iodine In water
With I2 In water
In water evapn.;
dichlorobis(dimethylamino)diborane(4)
64541-76-0

dichlorobis(dimethylamino)diborane(4)

tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

Conditions
ConditionsYield
With H2O
tetrakis(dimethylamido)diborane
1630-79-1

tetrakis(dimethylamido)diborane

A

tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

B

N,N-dimethylammonium chloride
506-59-2

N,N-dimethylammonium chloride

Conditions
ConditionsYield
With hydrogenchloride; water
With H2O; HCl
tetrakis(dimethylamido)diborane
1630-79-1

tetrakis(dimethylamido)diborane

A

tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

B

dimethyl amine
124-40-3

dimethyl amine

Conditions
ConditionsYield
With H2O distn. in high vac.;
diboron tetrachloride
13701-67-2

diboron tetrachloride

tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

Conditions
ConditionsYield
With iodine In water oxydation by I2 in acidic soln.;
With I2; acid In water oxydation by I2 in acidic soln.;
tris(dimethylamino)monochlorodiborane(4)
7360-75-0

tris(dimethylamino)monochlorodiborane(4)

tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

Conditions
ConditionsYield
With H2O in acidic soln.;
water
7732-18-5

water

tetrakis(tetrahydropyrrole)boron
158752-98-8

tetrakis(tetrahydropyrrole)boron

tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

Conditions
ConditionsYield
at 100℃; Inert atmosphere;8.5 g
dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 20℃;
2,2'-bis(1,3,2-benzodioxaborole)
13826-27-2

2,2'-bis(1,3,2-benzodioxaborole)

A

tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

B

benzene-1,2-diol
120-80-9

benzene-1,2-diol

Conditions
ConditionsYield
With water In N,N-dimethyl acetamide at 80℃; for 8h; Inert atmosphere; Sealed tube;
tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

3-[2-bromo-5-(hydroxymethyl)phenyl]propan-1-ol

3-[2-bromo-5-(hydroxymethyl)phenyl]propan-1-ol

(1-hydroxy-4,5-dihydro-3H-2,1-benzoxaborepin-7-yl)methanol

(1-hydroxy-4,5-dihydro-3H-2,1-benzoxaborepin-7-yl)methanol

Conditions
ConditionsYield
With chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); potassium acetate; XPhos In ethanol at 80℃; for 1h; Inert atmosphere;100%
potassium hydrogenfluoride
1279123-63-5

potassium hydrogenfluoride

tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

1-chloro-3,5-dimethoxybenzene
7051-16-3

1-chloro-3,5-dimethoxybenzene

potassium (3,4-dimethoxyphenyl)trifluoroborate

potassium (3,4-dimethoxyphenyl)trifluoroborate

Conditions
ConditionsYield
With PdCl(C6H4C6H4NH2)(Cy2PC6H4-2-C6H2-2',4',6'-i-Pr3); Cy2PC6H4-2-C6H2-2',4',6'-i-Pr3; K acetate In ethanol aryl chloride reacted with B2(OH)4 in EtOH in presence of catalyst (Pt-complex - ligand) and K acetate at 80°C for 2 h; subjected to aq. workup; treated with KHF2; purified by Soxlet extn.;99%
With NaOC(CH3)3; 2,4,6-(i-Pr)3C6H2C6H4[2-P(cyclo-C6H11)2]; KOAc In methanol; ethanol mixt. org. compound, B2(OH)4, Pd-complex, 2,4,6-(i-Pr)3C6H2C6H4-2-P(c-C6H11)2, KOAc in EtOH at 80°C for 18 h, cooled to room temp., filtered, concd. aq. KHF2 was added dropwise in MeOH at 0°C, mixt. wasstirred at room temp. for 30 min;92%
potassium hydrogenfluoride
1279123-63-5

potassium hydrogenfluoride

tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

4-methoxyphenyl triflate
66107-29-7

4-methoxyphenyl triflate

potassium 4-(methoxy)phenyltrifluoroborate

potassium 4-(methoxy)phenyltrifluoroborate

Conditions
ConditionsYield
With PdCl(C6H4C6H4NH2)(Cy2PC6H4-2-C6H2-2',4',6'-i-Pr3); Cy2PC6H4-2-C6H2-2',4',6'-i-Pr3; K acetate In ethanol aryl triflate reacted with B2(OH)4 in EtOH in presence of catalyst (Pt-complex - ligand) and K acetate at 80°C for 2 h; subjected to aq. workup; treated with KHF2; purified by Soxlet extn.;99%
tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

(R)-1,1-bis(3,5-dimethylphenyl)-2-phenylethane-1,2-diol

(R)-1,1-bis(3,5-dimethylphenyl)-2-phenylethane-1,2-diol

(5R,5'R)-4,4,4',4'-tetrakis(3,5-dimethylphenyl)-5,5'-diphenyl-2,2'-bi(1,3,2-dioxaborolane)

(5R,5'R)-4,4,4',4'-tetrakis(3,5-dimethylphenyl)-5,5'-diphenyl-2,2'-bi(1,3,2-dioxaborolane)

Conditions
ConditionsYield
In tetrahydrofuran at 70℃; for 3h; Molecular sieve;99%
tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

(R)-2-phenyl-1,1-di-o-tolylethane-1,2-diol

(R)-2-phenyl-1,1-di-o-tolylethane-1,2-diol

(5R,5'R)-5,5'-diphenyl-4,4,4',4'-tetra-o-tolyl-2,2'-bi(1,3,2-dioxaborolane)

(5R,5'R)-5,5'-diphenyl-4,4,4',4'-tetra-o-tolyl-2,2'-bi(1,3,2-dioxaborolane)

Conditions
ConditionsYield
In tetrahydrofuran at 70℃; for 3h; Molecular sieve;99%
In tetrahydrofuran at 70℃; for 4h; Molecular sieve; Schlenk technique; Inert atmosphere;95%
tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

(R)-1,1-bis(2,5-dimethylphenyl)-2-phenylethane-1,2-diol

(R)-1,1-bis(2,5-dimethylphenyl)-2-phenylethane-1,2-diol

(5R,5'R)-4,4,4',4'-tetrakis(2,5-dimethylphenyl)-5,5'-diphenyl-2,2'-bi(1,3,2-dioxaborolane)

(5R,5'R)-4,4,4',4'-tetrakis(2,5-dimethylphenyl)-5,5'-diphenyl-2,2'-bi(1,3,2-dioxaborolane)

Conditions
ConditionsYield
In tetrahydrofuran at 70℃; for 3h; Molecular sieve;99%
In tetrahydrofuran at 70℃; for 4h; Molecular sieve; Schlenk technique; Inert atmosphere;94%
tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

2-methoxy-4-(2H-1,2,3-triazol-2-yl)benzenediazonium trifluoromethanesulfonic salt

2-methoxy-4-(2H-1,2,3-triazol-2-yl)benzenediazonium trifluoromethanesulfonic salt

(2-methoxy-4-(2H-1,2,3-triazol-2-yl)phenyl)boronic acid

(2-methoxy-4-(2H-1,2,3-triazol-2-yl)phenyl)boronic acid

Conditions
ConditionsYield
In water at 25℃; for 3h;99%
potassium hydrogenfluoride
1279123-63-5

potassium hydrogenfluoride

tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

2-methyl-3-buten-2-ol
115-18-4

2-methyl-3-buten-2-ol

potassium trifluoro(3-methylbut-2-en-1-yl)borate

potassium trifluoro(3-methylbut-2-en-1-yl)borate

Conditions
ConditionsYield
[1,3-bis(phenylselenomethyl)phenyl]palladium(II) chloride In methanol; dimethyl sulfoxide react. (B(OH)2)2 with olefine at 50°C for 16 h in mixt. DMSO-MeOH, aq. KHF2 was added;98%
potassium hydrogenfluoride
1279123-63-5

potassium hydrogenfluoride

tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

(C6H5O2S)(CO2CH3)C3H3CHCH2

(C6H5O2S)(CO2CH3)C3H3CHCH2

(C6H5O2S)(CO2CH3)C5H7BF3(1-)*K(1+)=(C6H5O2S)(COOCH3)C5H7BF3K

(C6H5O2S)(CO2CH3)C5H7BF3(1-)*K(1+)=(C6H5O2S)(COOCH3)C5H7BF3K

Conditions
ConditionsYield
[1,3-bis(phenylselenomethyl)phenyl]palladium(II) chloride In water; dimethyl sulfoxide B complex treated with ligand in DMSO at 40°C in the presence ofPd catalyst (5 mol%), reacted for 5 h, treated with aq. KHF2;98%
potassium hydrogenfluoride
1279123-63-5

potassium hydrogenfluoride

tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

1-Chloro-4-fluorobenzene
352-33-0

1-Chloro-4-fluorobenzene

potassim 4-fluorophenyltrifluoroborate

potassim 4-fluorophenyltrifluoroborate

Conditions
ConditionsYield
With PdCl(C6H4C6H4NH2)(Cy2PC6H4-2-C6H2-2',4',6'-i-Pr3); Cy2PC6H4-2-C6H2-2',4',6'-i-Pr3; K acetate In ethanol aryl chloride reacted with B2(OH)4 in EtOH in presence of catalyst (Pt-complex - ligand) and K acetate at 80°C for 2.5 h; subjected to aq. workup; treated with KHF2; purified by Soxlet extn.;98%
With NaOC(CH3)3; 2,4,6-(i-Pr)3C6H2C6H4[2-P(cyclo-C6H11)2]; KOAc In methanol; ethanol mixt. org. compound, B2(OH)4, Pd-complex, 2,4,6-(i-Pr)3C6H2C6H4-2-P(c-C6H11)2, KOAc in EtOH at 80°C for 18 h, cooled to room temp., filtered, concd. aq. KHF2 was added dropwise in MeOH at 0°C, mixt. wasstirred at room temp. for 30 min;80%
potassium hydrogenfluoride
1279123-63-5

potassium hydrogenfluoride

tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

4-bromo-phenol
106-41-2

4-bromo-phenol

potassium (4-hydroxyphenyl)trifluoroborate

potassium (4-hydroxyphenyl)trifluoroborate

Conditions
ConditionsYield
With PdCl(C6H4C6H4NH2)(Cy2PC6H4-2-C6H2-2',4',6'-i-Pr3); Cy2PC6H4-2-C6H2-2',4',6'-i-Pr3; K acetate In ethanol aryl bromide reacted with B2(OH)4 in EtOH in presence of catalyst (Pt-complex - ligand) and K acetate at 80°C for 1 h; subjected to aq. workup; treated with KHF2; purified by Soxlet extn.;98%
potassium hydrogenfluoride
1279123-63-5

potassium hydrogenfluoride

tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

1-bromo-3,5-dimethoxybenzene
20469-65-2

1-bromo-3,5-dimethoxybenzene

potassium (3,4-dimethoxyphenyl)trifluoroborate

potassium (3,4-dimethoxyphenyl)trifluoroborate

Conditions
ConditionsYield
With PdCl(C6H4C6H4NH2)(Cy2PC6H4-2-C6H2-2',4',6'-i-Pr3); Cy2PC6H4-2-C6H2-2',4',6'-i-Pr3; K acetate In ethanol aryl bromide reacted with B2(OH)4 in EtOH in presence of catalyst (Pt-complex - ligand) and K acetate at 80°C for 4 h; subjected to aq. workup; treated with KHF2; purified by Soxlet extn.;98%
potassium hydrogenfluoride
1279123-63-5

potassium hydrogenfluoride

tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

3-monochlorophenol
108-43-0

3-monochlorophenol

potassium (3-hydroxyphenyl)trifluoroborate
871231-45-7

potassium (3-hydroxyphenyl)trifluoroborate

Conditions
ConditionsYield
With PdCl(C6H4C6H4NH2)(Cy2PC6H4-2-C6H2-2',4',6'-i-Pr3); Cy2PC6H4-2-C6H2-2',4',6'-i-Pr3; K acetate In ethanol aryl chloride reacted with B2(OH)4 in EtOH in presence of catalyst (Pt-complex - ligand) and K acetate at 80°C for 2 h; subjected to aq. workup; treated with KHF2; purified by Soxlet extn.;98%
5-bromobenzofuran
23145-07-5

5-bromobenzofuran

tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

2,3-dihydro-1-benzofuran-5-ylboronic acid
331834-13-0

2,3-dihydro-1-benzofuran-5-ylboronic acid

Conditions
ConditionsYield
In methanol at 15℃; for 3h; Microwave irradiation;98%
With potassium tert-butylate In methanol at 0 - 20℃;
5-bromobenzo[b]thiophene
4923-87-9

5-bromobenzo[b]thiophene

tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

benzo[b]thiophen-5-ylboronic acid
845872-49-3

benzo[b]thiophen-5-ylboronic acid

Conditions
ConditionsYield
In methanol at 15℃; for 3h; Microwave irradiation;98%
With potassium tert-butylate In methanol at 0 - 20℃;
tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

phenyltrimethylammonium iodide
98-04-4

phenyltrimethylammonium iodide

phenylboronic acid
98-80-6

phenylboronic acid

Conditions
ConditionsYield
In methanol at 15℃; for 3h; Microwave irradiation;98%
tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

trimethyl-p-tolylammonium iodide
6140-15-4

trimethyl-p-tolylammonium iodide

4-methylphenylboronic acid
5720-05-8

4-methylphenylboronic acid

Conditions
ConditionsYield
In methanol at 15℃; for 3h; Microwave irradiation;98%
tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

4-nitrobenzenediazonium trifluoromethanesulfonate

4-nitrobenzenediazonium trifluoromethanesulfonate

4-nitrophenylboronic acid
24067-17-2

4-nitrophenylboronic acid

Conditions
ConditionsYield
In water at 20℃; for 3.5h;98%
potassium hydrogenfluoride
1279123-63-5

potassium hydrogenfluoride

tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

1,1-diacetoxy-2-propene
869-29-4

1,1-diacetoxy-2-propene

potassium trifluoro(3-acetoxy-2-propenyl)borate

potassium trifluoro(3-acetoxy-2-propenyl)borate

Conditions
ConditionsYield
[1,3-bis(phenylselenomethyl)phenyl]palladium(II) chloride In water; dimethyl sulfoxide B complex treated with ligand in DMSO at 40°C in the presence ofPd catalyst (5 mol%), reacted for 36 h, treated with aq. KHF2;97%
potassium hydrogenfluoride
1279123-63-5

potassium hydrogenfluoride

tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

methyl 3-chlorobenzoate
2905-65-9

methyl 3-chlorobenzoate

potassium (meta-methoxycarbonylphenyl)trifluoroborate
1242733-94-3

potassium (meta-methoxycarbonylphenyl)trifluoroborate

Conditions
ConditionsYield
With PdCl(C6H4C6H4NH2)(Cy2PC6H4-2-C6H2-2',4',6'-i-Pr3); Cy2PC6H4-2-C6H2-2',4',6'-i-Pr3; K acetate In ethanol aryl chloride reacted with B2(OH)4 in EtOH in presence of catalyst (Pt-complex - ligand) and K acetate at 80°C for 2.5 h; subjected to aq. workup; treated with KHF2; purified by Soxlet extn.;97%
tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

4-fluoro-1-iodobenzene
352-34-1

4-fluoro-1-iodobenzene

4-fluoroboronic acid
1765-93-1

4-fluoroboronic acid

Conditions
ConditionsYield
In methanol at 15℃; for 1h; Microwave irradiation;97%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In dimethyl sulfoxide at 60℃; for 0.333333h; Temperature; Solvent; Reagent/catalyst;74%
In methanol; water at -5℃; for 0.166667h; UV-irradiation; Flow reactor; chemoselective reaction;100 %Spectr.
tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

1-bromo-4-(trifluoromethoxy)benzene
407-14-7

1-bromo-4-(trifluoromethoxy)benzene

4-trifluoromethoxyphenylboronic acid
139301-27-2

4-trifluoromethoxyphenylboronic acid

Conditions
ConditionsYield
In methanol at 15℃; for 3h; Microwave irradiation;97%
With potassium tert-butylate In methanol at 0 - 20℃;
tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

ethylene glycol
107-21-1

ethylene glycol

(2,2’-bi(1,3,2-dioxaborolane))
13826-24-9

(2,2’-bi(1,3,2-dioxaborolane))

Conditions
ConditionsYield
With magnesium sulfate In tetrahydrofuran at 20℃; for 24h; Sealed tube;97%
With magnesium sulfate In tetrahydrofuran at 20℃; for 48h; Inert atmosphere;74%
potassium hydrogenfluoride
1279123-63-5

potassium hydrogenfluoride

tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

4-chloromethoxybenzene
623-12-1

4-chloromethoxybenzene

potassium 4-(methoxy)phenyltrifluoroborate

potassium 4-(methoxy)phenyltrifluoroborate

Conditions
ConditionsYield
With Pd(O2CCH3)2; Cy2PC6H4-2-C6H2-2',4',6'-i-Pr3; K acetate In ethanol Pd acetate, ligand and K acetate stirred in EtOH at 80°C for 20 min; B2(OH)4 in EtOH and aryl chloride added; reacted at 80°C for 1 h; subjected to aq. workup; treated with KHF2;95%
With PdCl(C6H4C6H4NH2)(Cy2PC6H4-2-C6H2-2',4',6'-i-Pr3); Cy2PC6H4-2-C6H2-2',4',6'-i-Pr3; K acetate In ethanol aryl chloride reacted with B2(OH)4 in EtOH in presence of catalyst (Pt-complex - ligand) and K acetate at 80°C for 2 h; subjected to aq. workup; treated with KHF2; purified by Soxlet extn.;93%
With NaOC(CH3)3; 2,4,6-(i-Pr)3C6H2C6H4[2-P(cyclo-C6H11)2]; KOAc In methanol; ethanol mixt. org. compound, B2(OH)4, Pd-complex, 2,4,6-(i-Pr)3C6H2C6H4-2-P(c-C6H11)2, KOAc in EtOH at 80°C for 18 h, cooled to room temp., filtered, concd. aq. KHF2 was added dropwise in MeOH at 0°C, mixt. was stirred at room temp. for 30 min;90%
potassium hydrogenfluoride
1279123-63-5

potassium hydrogenfluoride

tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

2-methylchlorobenzene
95-49-8

2-methylchlorobenzene

potassium o-tolyltrifluoroborate

potassium o-tolyltrifluoroborate

Conditions
ConditionsYield
With PdCl(C6H4C6H4NH2)(Cy2PC6H4-2-C6H2-2',4',6'-i-Pr3); Cy2PC6H4-2-C6H2-2',4',6'-i-Pr3; K acetate In ethanol aryl chloride reacted with B2(OH)4 in EtOH in presence of catalyst (Pt-complex - ligand) and K acetate at 80°C for 3.5 h; subjected to aq. workup; treated with KHF2; purified by Soxlet extn.;95%
With NaOC(CH3)3; 2,4,6-(i-Pr)3C6H2C6H4[2-P(cyclo-C6H11)2]; KOAc In methanol; ethanol mixt. org. compound, B2(OH)4, Pd-complex, 2,4,6-(i-Pr)3C6H2C6H4-2-P(c-C6H11)2, KOAc in EtOH at 80°C for 18 h, cooled to room temp., filtered, concd. aq. KHF2 was added dropwise in MeOH at 0°C, mixt. wasstirred at room temp. for 30 min;75%
potassium hydrogenfluoride
1279123-63-5

potassium hydrogenfluoride

tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

para-bromoacetophenone
99-90-1

para-bromoacetophenone

potassium 4-acetylphenyltrifluoroborate

potassium 4-acetylphenyltrifluoroborate

Conditions
ConditionsYield
With PdCl(C6H4C6H4NH2)(Cy2PC6H4-2-C6H2-2',4',6'-i-Pr3); Cy2PC6H4-2-C6H2-2',4',6'-i-Pr3; K acetate In ethanol aryl bromide reacted with B2(OH)4 in EtOH in presence of catalyst (Pt-complex - ligand) and K acetate at 80°C for 2 h; subjected to aq. workup; treated with KHF2; purified by Soxlet extn.;95%
potassium hydrogenfluoride
1279123-63-5

potassium hydrogenfluoride

tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

1-Bromo-4-fluorobenzene
460-00-4

1-Bromo-4-fluorobenzene

potassim 4-fluorophenyltrifluoroborate

potassim 4-fluorophenyltrifluoroborate

Conditions
ConditionsYield
With PdCl(C6H4C6H4NH2)(Cy2PC6H4-2-C6H2-2',4',6'-i-Pr3); Cy2PC6H4-2-C6H2-2',4',6'-i-Pr3; K acetate In ethanol aryl bromide reacted with B2(OH)4 in EtOH in presence of catalyst (Pt-complex - ligand) and K acetate at 80°C for 4 h; subjected to aq. workup; treated with KHF2; purified by Soxlet extn.;95%
tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

(3aR,9bR)-tert-butyl 9b-((4- fluorophenyl)sulfonyl)-7-iodo-3a,4,5 ,9b-tetrahydro- 1H-benzo [e]indole-3 -carboxylate

(3aR,9bR)-tert-butyl 9b-((4- fluorophenyl)sulfonyl)-7-iodo-3a,4,5 ,9b-tetrahydro- 1H-benzo [e]indole-3 -carboxylate

((3aR,9bR)-3-(tert-butoxycarbonyl)-9b-((4-fluorophenyl)sulfonyl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indol-7-yl)boronic acid

((3aR,9bR)-3-(tert-butoxycarbonyl)-9b-((4-fluorophenyl)sulfonyl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indol-7-yl)boronic acid

Conditions
ConditionsYield
With chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); potassium acetate; XPhos In ethanol at 55℃; for 2.4h; Time; Inert atmosphere;95%
With chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); potassium acetate; XPhos In ethanol at 55℃; for 18h;80%
potassium hydrogenfluoride
1279123-63-5

potassium hydrogenfluoride

tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

(E)-trifluoro-(hex-2-en-1-yl)-λ4-borane potassium

(E)-trifluoro-(hex-2-en-1-yl)-λ4-borane potassium

Conditions
ConditionsYield
[1,3-bis(phenylselenomethyl)phenyl]palladium(II) chloride In methanol; dimethyl sulfoxide react. (B(OH)2)2 with olefine at 50°C for 16 h in mixt. DMSO-MeOH, aq. KHF2 was added;94%
potassium hydrogenfluoride
1279123-63-5

potassium hydrogenfluoride

tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

3-bromo-N,N-dimethylaniline
16518-62-0

3-bromo-N,N-dimethylaniline

potassium (3-(dimethylamino)phenyl)trifluoroborate
1386231-64-6

potassium (3-(dimethylamino)phenyl)trifluoroborate

Conditions
ConditionsYield
With PdCl(C6H4C6H4NH2)(Cy2PC6H4-2-C6H2-2',4',6'-i-Pr3); Cy2PC6H4-2-C6H2-2',4',6'-i-Pr3; K acetate In ethanol aryl bromide reacted with B2(OH)4 in EtOH in presence of catalyst (Pt-complex - ligand) and K acetate at 80°C for 3.5 h; subjected to aq.workup; treated with KHF2; purified by Soxlet extn.;94%

13675-18-8Relevant articles and documents

Ray, R. C.

, p. 1260 - 1266 (1937)

Virtues of Volatility: A Facile Transesterification Approach to Boronic Acids

Hinkes, Stefan P.A.,Klein, Christian D.P.

supporting information, p. 3048 - 3052 (2019/05/10)

Boronic acids are an increasingly important compound class for many applications, including C-C bond formation reactions, medicinal chemistry, and diagnostics. The deprotection of boronic ester intermediates is frequently a problematic and inefficient step in boronic acid syntheses. We describe an approach that highly facilitates this transformation by leveraging the volatility of methylboronic acid and its diol esters. The method is performed under mild conditions, provides high yields, and eliminates cumbersome and problematic purification steps.

The solid-state structure of diboronic acid, B2(OH)4

Baber, R. Angharad,Norman, Nicholas C.,Orpen, A. Guy,Rossi, Jean

, p. 773 - 775 (2007/10/03)

The crystal structure of diboronic acid contains molecules of B2(OH)4 hydrogen-bonded into two-dimensional sheets linked by B...O interactions.

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