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76-09-5

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76-09-5 Usage

Chemical Properties

white solid

Occurrence

Has apparently not been reported to occur in nature.

Uses

Different sources of media describe the Uses of 76-09-5 differently. You can refer to the following data:
1. pinacol be used as organic intermediates.The pinacol coupling reaction with the inorganic electride [Ca2N](+)·e(−) as an electron donor in organic solvents was studied. Pinacol is used in the synthesis of organic reagents such as alkenylphenylphosphonates and alkenylboronates.
2. Pinacol is used in the preparation of synthetic intermediates like pinacolborane, bis(pinacolato)diboron and pinacolchloroborane by reaction with boron trichloride. Further, it plays an important role as an intermediate for biologically active compounds like antiviral, antibacterial, antifungal and antituberculous.

Preparation

By the bimolecular reduction of acetone.

Definition

ChEBI: A glycol that is ethylene glycol in which all four methylene hydrogens have been replaced by methyl groups.

Synthesis Reference(s)

Chemistry Letters, 10, p. 1469, 1981Journal of the American Chemical Society, 98, p. 1986, 1976 DOI: 10.1021/ja00423a067Tetrahedron Letters, 21, p. 449, 1980 DOI: 10.1016/S0040-4039(00)71429-8

Toxicity evaluation

Both the acute oral LD50 value in rats and the acute dermal LD50 value in rabbits exceeded 5 g/kg (Moreno, 1975). The acute oral LD50 of pinacol for male albino mice was found to be 28-6 mmol/kg (Wenzel & Koff, 1956). Pinacol showed anticonvulsant activity for electroshock seizures and Metrazol? convulsions; the PD 50 values (a measure of the protective dose) determined 15 min after oral administration of pinacol to mice were found to be 16-4 and 3-44 mmol/kg for electroshock and Metrazol convulsions, respectively (Wenzel & Koff, 1956).

General Description

The pinacol coupling reaction with the inorganic electride [Ca2N](+)·e(?) as an electron donor in organic solvents was studied.

Metabolism

Pinacol forms a glucuronide in the rabbit (Williams, 1959), and was found highly conjugated with glucuronic acid in the urine of chinchilla rabbits following oral administration of 1.0-1.5 g pinacol/kg body weight (Gessner, Parke & Williams, 1960). Pinacol was not utilized to any significant extent by endocrine tissues from human placenta, rat ovary, rat testis or rat adrenal gland (Ferguson, Baillie, Caiman & Hart, 1966).

Purification Methods

The hydrate is rendered anhydrous by azeotropic distillation of water with *benzene. Recrystallise it from *benzene or toluene/pet ether, absolute EtOH or dry diethyl ether. It recrystallises from water to give the hexahydrate. [Beilstein 1 IV 2575.]

Check Digit Verification of cas no

The CAS Registry Mumber 76-09-5 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 7 and 6 respectively; the second part has 2 digits, 0 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 76-09:
(4*7)+(3*6)+(2*0)+(1*9)=55
55 % 10 = 5
So 76-09-5 is a valid CAS Registry Number.
InChI:InChI=1/C6H14O2/c1-5(2,7)6(3,4)8/h7-8H,1-4H3

76-09-5 Well-known Company Product Price

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  • Aldrich

  • (221171)  Pinacol  98%

  • 76-09-5

  • 221171-500G

  • 3,267.81CNY

  • Detail

76-09-5SDS

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 2,3-dimethylbutane-2,3-diol

1.2 Other means of identification

Product number -
Other names 1,1,2,2-Tetramethylethylene glycol

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:76-09-5 SDS

76-09-5Synthetic route

2,3-dimethyl-2,3-epoxybutane
5076-20-0

2,3-dimethyl-2,3-epoxybutane

A

3,3-dimethyl-butan-2-one
75-97-8

3,3-dimethyl-butan-2-one

B

2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

C

2,3-dimethyl-1-buten-3-ol
10473-13-9

2,3-dimethyl-1-buten-3-ol

Conditions
ConditionsYield
With perchloric acid; sodium perchlorate at 25℃; Yields of byproduct given;A n/a
B 99.93%
C n/a
With perchloric acid; sodium perchlorate at 25℃; Product distribution; heterogeneous reaction;
acetone
67-64-1

acetone

2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

Conditions
ConditionsYield
With methanol; gallium nitride at 20℃; for 12h; Irradiation; Sealed tube;99%
With potassium bromate; hydrogenchloride; mercury(II) diacetate at 35℃; for 0.666667h; Equilibrium constant;
durch elektrolytische Reduktion;
mercury(II) diacetate
1600-27-7

mercury(II) diacetate

2-methyl-4,4,5,5-tetramethyl-1,3-dioxolanium perchlorate

2-methyl-4,4,5,5-tetramethyl-1,3-dioxolanium perchlorate

A

2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

B

C2H3ClHgO6

C2H3ClHgO6

Conditions
ConditionsYield
In ethanol for 0.166667h; Heating; Yields of byproduct given;A n/a
B 99%
mercury(II) diacetate
1600-27-7

mercury(II) diacetate

2-methyl-4,4,5,5-tetramethyl-1,3-dioxolanium perchlorate

2-methyl-4,4,5,5-tetramethyl-1,3-dioxolanium perchlorate

A

2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

B

C4H5ClHg2O8

C4H5ClHg2O8

Conditions
ConditionsYield
In ethanol for 0.25h; Heating; Yields of byproduct given;A n/a
B 99%
mercury(II) trifluoroacetate
13257-51-7

mercury(II) trifluoroacetate

2-methyl-4,4,5,5-tetramethyl-1,3-dioxolanium perchlorate

2-methyl-4,4,5,5-tetramethyl-1,3-dioxolanium perchlorate

A

2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

B

C4H2ClF3Hg2O8

C4H2ClF3Hg2O8

Conditions
ConditionsYield
In ethanol for 0.25h; Heating; Yields of byproduct given;A n/a
B 99%
2,3-Dimethyl-2-butene
563-79-1

2,3-Dimethyl-2-butene

2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

Conditions
ConditionsYield
With K2; (DHQD)2 quinuclidine; potassium hexacyanoferrate(III) In water; tert-butyl alcohol at 25℃; for 5h; pH=12; Oxidation;98%
With 1,4-diaza-bicyclo[2.2.2]octane; K2; oxygen In water; tert-butyl alcohol at 50℃; under 750.075 Torr; for 18h; pH=12.0;94%
With Nafion NR50; dihydrogen peroxide at 70℃; for 20h;86%
mercury(II) diacetate
1600-27-7

mercury(II) diacetate

2-ethyl-4,4,5,5-tetramethyl-1,3-dioxolan-2-ylium perchlorate

2-ethyl-4,4,5,5-tetramethyl-1,3-dioxolan-2-ylium perchlorate

A

2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

B

C3H5ClHgO6

C3H5ClHgO6

Conditions
ConditionsYield
In ethanol for 0.166667h; Heating; Yields of byproduct given;A n/a
B 97%
4,4,5,5-tetramethyl-1,3-dioxolan-2-one
19424-29-4

4,4,5,5-tetramethyl-1,3-dioxolan-2-one

A

methanol
67-56-1

methanol

B

2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

Conditions
ConditionsYield
With [carbonylchlorohydrido{bis[2-(diphenylphosphinomethyl)ethyl]amino}ethylamino] ruthenium(II); potassium tert-butylate; hydrogen In tetrahydrofuran at 140℃; for 20h; Autoclave;A 95 %Chromat.
B 96%
With (bis[(2-diisopropylphosphino)ethyl]amine)Mn(CO)2Br; hydrogen; sodium t-butanolate In tetrahydrofuran at 120℃; under 22502.3 Torr; for 26h; Schlenk technique; Glovebox; Autoclave;A 66%
B 76%
With potassium phosphate; C62H63N5OPRu(1+)*Cl(1-); hydrogen In tetrahydrofuran at 140℃; under 38002.6 Torr; for 24h; Glovebox; Autoclave;A 93 %Chromat.
B 99 %Chromat.
mercury(II) diacetate
1600-27-7

mercury(II) diacetate

2-ethyl-4,4,5,5-tetramethyl-1,3-dioxolan-2-ylium perchlorate

2-ethyl-4,4,5,5-tetramethyl-1,3-dioxolan-2-ylium perchlorate

A

2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

B

C5H7ClHg2O8

C5H7ClHg2O8

Conditions
ConditionsYield
In ethanol for 0.25h; Heating; Yields of byproduct given;A n/a
B 95%
2,3-Dimethyl-2-butene
563-79-1

2,3-Dimethyl-2-butene

A

3,3-dimethyl-butan-2-one
75-97-8

3,3-dimethyl-butan-2-one

B

2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

Conditions
ConditionsYield
With C34H32N4O2RuSe4 In 1,1,1,3',3',3'-hexafluoro-propanol at 23℃; for 4h; Inert atmosphere;A 94%
B n/a
4,4,5,5-tetramethyl-2-[(4-methylphenyl)methyl]-1,3,2-dioxaborolane
356570-52-0

4,4,5,5-tetramethyl-2-[(4-methylphenyl)methyl]-1,3,2-dioxaborolane

A

2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

B

trifluoro(4-methylbenzyl)-λ4-borane potassium salt

trifluoro(4-methylbenzyl)-λ4-borane potassium salt

Conditions
ConditionsYield
With potassium hydrogen difluoride In tetrahydrofuran; water at 20℃;A n/a
B 90%
2-[(4-chlorophenyl)methyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
517920-59-1

2-[(4-chlorophenyl)methyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

A

2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

B

(4-chlorobenzyl)trifluoro-λ4-borane potassium salt

(4-chlorobenzyl)trifluoro-λ4-borane potassium salt

Conditions
ConditionsYield
With potassium hydrogen difluoride In tetrahydrofuran; water at 20℃;A n/a
B 89%
Methyl 2,3-dichloro-2,3,3-trifluoropropanoate
16329-89-8

Methyl 2,3-dichloro-2,3,3-trifluoropropanoate

A

2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

B

Methyl 3-chloro-2,3,3-trifluoropropanoate
684-50-4

Methyl 3-chloro-2,3,3-trifluoropropanoate

C

2,3-Difluor-2,3-bis(chlordifluormethyl)bernsteinsaeuredimethylester

2,3-Difluor-2,3-bis(chlordifluormethyl)bernsteinsaeuredimethylester

Conditions
ConditionsYield
With isopropyl alcohol at 18 - 20℃; for 1.5h; Irradiation;A n/a
B 88.9%
C n/a
nonafluorobutanesulfonyl 2-(6-chloroquinolin-2-yl)thiazol-4-ol

nonafluorobutanesulfonyl 2-(6-chloroquinolin-2-yl)thiazol-4-ol

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

A

2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

B

2-(6-chloroquinolin-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole
1449748-82-6

2-(6-chloroquinolin-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole

Conditions
ConditionsYield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 80℃; for 4h; Inert atmosphere; Overall yield = 700 mg;A n/a
B 87%
O-acetyl-α-hydroxyisobutyric acid
15805-98-8

O-acetyl-α-hydroxyisobutyric acid

A

diethylacetamide
685-91-6

diethylacetamide

B

2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

C

Essigsaeure-2-hydroxy-1,1,2-trimethylpropylester
20127-81-5

Essigsaeure-2-hydroxy-1,1,2-trimethylpropylester

D

acetic anhydride
108-24-7

acetic anhydride

Conditions
ConditionsYield
With triethylamine In acetonitrile Ambient temperature; electrolysis; Further byproducts given;A 47%
B 86.8%
C 4.7%
D n/a
O-acetyl-α-hydroxyisobutyric acid
15805-98-8

O-acetyl-α-hydroxyisobutyric acid

triethylamine
121-44-8

triethylamine

A

diethylacetamide
685-91-6

diethylacetamide

B

2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

C

Essigsaeure-2-hydroxy-1,1,2-trimethylpropylester
20127-81-5

Essigsaeure-2-hydroxy-1,1,2-trimethylpropylester

D

acetic anhydride
108-24-7

acetic anhydride

Conditions
ConditionsYield
In acetonitrile Ambient temperature; electrolysis; Further byproducts given;A 47%
B 86.8%
C 4.7%
D n/a
mercury(II) diacetate
1600-27-7

mercury(II) diacetate

2-methyl-4,4,5,5-tetramethyl-1,3-dioxolanium perchlorate

2-methyl-4,4,5,5-tetramethyl-1,3-dioxolanium perchlorate

A

2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

B

C6H7ClHg3O10

C6H7ClHg3O10

Conditions
ConditionsYield
In ethanol for 0.416667h; Heating; Yields of byproduct given;A n/a
B 85%
9-fluorenone
486-25-9

9-fluorenone

A

2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

B

9-Fluorenol
1689-64-1

9-Fluorenol

Conditions
ConditionsYield
With samarium; 1,2-Diiodoethane In 1,2-dimethoxyethane for 24h; Ambient temperature;A 84%
B 13%
4,4,5,5-tetramethyl-1,3-dioxolan-2-one
19424-29-4

4,4,5,5-tetramethyl-1,3-dioxolan-2-one

2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

Conditions
ConditionsYield
With potassium tert-butylate; hydrogen; C16H18BrCoINO2 In dibutyl ether at 160℃; under 45004.5 Torr; for 20h; Sealed tube; Autoclave;82%
Methyl 2,3,3-trichloro-3,3-difluoropropanoate
20621-19-6

Methyl 2,3,3-trichloro-3,3-difluoropropanoate

A

2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

B

methyl 2,3-dichloro-3,3-difluoropropanoate
86011-99-6

methyl 2,3-dichloro-3,3-difluoropropanoate

C

2,3-Difluor-2,3-bis(chlordifluormethyl)bernsteinsaeuredimethylester

2,3-Difluor-2,3-bis(chlordifluormethyl)bernsteinsaeuredimethylester

Conditions
ConditionsYield
With isopropyl alcohol at 18 - 20℃; for 1.66667h; Irradiation;A n/a
B 81.3%
C n/a
spirothiophene-2(3H),1'-cyclopropan>-3-one 1,1-dioxide
65172-43-2

spirothiophene-2(3H),1'-cyclopropan>-3-one 1,1-dioxide

isopropyl alcohol
67-63-0

isopropyl alcohol

A

2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

B

3,3''-bithiophene-2(3H),1'-cyclopropane>>3,3''-diol 1,1,1'',1''-tetraoxide

3,3''-bithiophene-2(3H),1'-cyclopropane>>3,3''-diol 1,1,1'',1''-tetraoxide

Conditions
ConditionsYield
for 16h; Irradiation;A 72%
B 78%
isoquinoline
119-65-3

isoquinoline

acetone
67-64-1

acetone

A

2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

B

1-(1-hydroxy-1-methylethyl)-1,2,3,4-tetrahydroisoquinoline
77796-18-0

1-(1-hydroxy-1-methylethyl)-1,2,3,4-tetrahydroisoquinoline

C

isopropyl alcohol
67-63-0

isopropyl alcohol

Conditions
ConditionsYield
In sulfuric acid at 30℃; electrolysis;A n/a
B 78%
C n/a
9-fluorenone
486-25-9

9-fluorenone

A

2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

B

9H-fluorene
86-73-7

9H-fluorene

C

9-Fluorenol
1689-64-1

9-Fluorenol

Conditions
ConditionsYield
With samarium; 1,2-Diiodoethane In 1,2-dimethoxyethane for 4h; Product distribution; Ambient temperature; reversibility, further rare earth metals, different molar ratios;A 18%
B 5%
C 76%
With samarium; 1,2-Diiodoethane In 1,2-dimethoxyethane for 4h; Ambient temperature;A 18%
B 5%
C 76%
2-chloro-2,3,3,3-tetrafluoro methylpropanoate
28509-44-6

2-chloro-2,3,3,3-tetrafluoro methylpropanoate

A

2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

B

methyl 2,3,3,3-tetrafluoropropanoate
382-93-4

methyl 2,3,3,3-tetrafluoropropanoate

C

2,3-Difluor-2,3-bis(chlordifluormethyl)bernsteinsaeuredimethylester

2,3-Difluor-2,3-bis(chlordifluormethyl)bernsteinsaeuredimethylester

Conditions
ConditionsYield
With isopropyl alcohol at 18 - 20℃; for 1.08333h; Irradiation;A n/a
B 75.5%
C n/a
acetophenone
98-86-2

acetophenone

A

2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

B

1-acetyl-2-<2'-(α-hydroxyethyl)phenyl-1'>-2-cyclohexene

1-acetyl-2-<2'-(α-hydroxyethyl)phenyl-1'>-2-cyclohexene

Conditions
ConditionsYield
With potassium sulfate In ethanol; water Product distribution; electrolysis; other reagent;A 15%
B 70%
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

methyl 2-iodo 5-fluorobenzoate

methyl 2-iodo 5-fluorobenzoate

A

2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

B

methyl 3-fluorobenzoate
455-68-5

methyl 3-fluorobenzoate

C

5-fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid methyl ester
1293284-58-8

5-fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid methyl ester

Conditions
ConditionsYield
With triethylamine; palladium diacetate; tris-(o-tolyl)phosphine In tetrahydrofuran at 65℃; for 1h; Inert atmosphere;A 14%
B 4%
C 70%
mercury(II) trifluoroacetate
13257-51-7

mercury(II) trifluoroacetate

2-methyl-4,4,5,5-tetramethyl-1,3-dioxolanium perchlorate

2-methyl-4,4,5,5-tetramethyl-1,3-dioxolanium perchlorate

A

2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

B

C6HClF6Hg3O10

C6HClF6Hg3O10

Conditions
ConditionsYield
In ethanol for 0.416667h; Heating; Yields of byproduct given;A n/a
B 63%
isopropyl alcohol
67-63-0

isopropyl alcohol

A

2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

B

acetone
67-64-1

acetone

Conditions
ConditionsYield
With air; 2,2'-thiobis(2,4-di-tert-butylphenol); triethylamine; copper(l) chloride In tetrahydrofuran at 20℃; for 12h;A 61%
B n/a
With water; zinc sulfide for 4h; Quantum yield; Irradiation;A 0.056 mmol
B n/a
With mercury for 20h; Heating; Irradiation; Yields of byproduct given;A 97 % Chromat.
B n/a
allyl iodid
556-56-9

allyl iodid

acetophenone
98-86-2

acetophenone

A

2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

B

2-phenylpent-4-en-2-ol
4743-74-2

2-phenylpent-4-en-2-ol

Conditions
ConditionsYield
With samarium diiodide In various solvent(s) at 0℃; for 2h;A 57%
B 9 % Chromat.
2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

3,3-dimethyl-butan-2-one
75-97-8

3,3-dimethyl-butan-2-one

Conditions
ConditionsYield
With aluminium phosphate aluminium oxide catalyst Heating;100%
With silica-supported orthophosphoric acid In neat (no solvent) at 180℃; for 0.5h; Catalytic behavior; Temperature; Time; Pinacol Rearrangement; Green chemistry;100%
With [Fe3O(OOCC6H5)6(H2O)3]4[α-SiW12O40] In toluene at 99.84℃; for 6h;80%
2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

C8H19BN2S
77896-83-4

C8H19BN2S

4,4,5,5-Tetramethyl-2-((Z)-3-methylsulfanyl-allyl)-[1,3,2]dioxaborolane
77896-84-5

4,4,5,5-Tetramethyl-2-((Z)-3-methylsulfanyl-allyl)-[1,3,2]dioxaborolane

Conditions
ConditionsYield
100%
2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

acetone
67-64-1

acetone

Conditions
ConditionsYield
With N-Bromosuccinimide; water; potassium carbonate; triphenylbismuthane In acetonitrile for 2h;100%
With tert.-butylhydroperoxide; bis(acetylacetonato)dioxidomolybdenum(VI) In chlorobenzene at 60℃; for 24h;99%
With tert.-butylhydroperoxide; chromium tetra(tert-butoxide) In benzene at 20℃; for 24h;90%
2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

4-formylphenylboronic acid,
87199-17-5

4-formylphenylboronic acid,

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde
128376-64-7

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde

Conditions
ConditionsYield
In tetrahydrofuran; toluene100%
In diethyl ether at 20℃; cyclocondensation;100%
Inert atmosphere;100%
2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

3-Formylphenylboronic acid
87199-16-4

3-Formylphenylboronic acid

3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarboxaldehyde
380151-86-0

3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarboxaldehyde

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 18h; Inert atmosphere;100%
In ethyl acetate for 4h;90%
With 4 A molecular sieve In dichloromethane for 120h;77%
2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

4-acetylphenylboronic acid
149104-90-5

4-acetylphenylboronic acid

1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethanone
171364-81-1

1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethanone

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 1h;100%
In tetrahydrofuran at 40℃;98%
In tetrahydrofuran at 40℃; Reduced pressure;98%
2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

Conditions
ConditionsYield
With tetrakis(dimethylamido)diborane In diethyl ether at 20℃; for 18h; Conversion of starting material;100%
With tetrakis(dimethylamido)diborane at 50 - 100℃; for 0.616667h; Conversion of starting material;94.2%
With tetrakis(dimethylamido)diborane In n-heptane at 40 - 98℃; for 0.6h; Conversion of starting material;90.5%
2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

2-Cyanophenylboronic acid
138642-62-3

2-Cyanophenylboronic acid

2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

Conditions
ConditionsYield
100%
2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

4-carboxyphenylboronic acid
14047-29-1

4-carboxyphenylboronic acid

4-carboxyphenylboronic acid pinacol ester
180516-87-4

4-carboxyphenylboronic acid pinacol ester

Conditions
ConditionsYield
In tetrahydrofuran; toluene100%
In tetrahydrofuran; toluene at 45℃;100%
In hexane at 70℃; for 3h; Temperature; Time; Concentration;93.7%
2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

(4-fluoro-3-formylphenyl)boronic acid
374538-01-9

(4-fluoro-3-formylphenyl)boronic acid

2-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde
443776-94-1

2-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde

Conditions
ConditionsYield
With 4 A molecular sieve In tetrahydrofuran at 20℃; for 16h;100%
In tetrahydrofuran Molecular sieve;
With magnesium sulfate In methanol at 20℃; for 6h;
2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

(2E)-3-(dihydroxyboryl)acrolein

(2E)-3-(dihydroxyboryl)acrolein

(2E)-3-(4,4,5,5-tetramethyl-1,2,3-dioxaborolan-2-yl)prop-2-enal
153725-01-0

(2E)-3-(4,4,5,5-tetramethyl-1,2,3-dioxaborolan-2-yl)prop-2-enal

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 0.5h;100%
In pentane N2, pinacol added at room temp. to the suspended B-compound, 3 h; dried (MgSO4), filtered, solvent removed under vacuo, distd.; elem. anal.;80%
In diethyl ether at 20℃; for 12h;75%
2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

(E)-2-(4-methylphenyl)ethenylboronic acid
72316-17-7

(E)-2-(4-methylphenyl)ethenylboronic acid

2-[(E)-2-p-tolylethenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
149777-84-4

2-[(E)-2-p-tolylethenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions
ConditionsYield
With diethyl ether at 20℃;100%
2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

phenylboronic acid
98-80-6

phenylboronic acid

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

Conditions
ConditionsYield
at 0℃; for 1h;100%
In pentane at 0 - 20℃; for 3h;100%
In tetrahydrofuran at 20℃; for 1h;95%
2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

trans-2-phenylvinylboronic acid
6783-05-7

trans-2-phenylvinylboronic acid

4,4,5,5-tetramethyl-2-((E)-styryl)-[1,3,2]dioxaborolane
83947-56-2

4,4,5,5-tetramethyl-2-((E)-styryl)-[1,3,2]dioxaborolane

Conditions
ConditionsYield
In tetrahydrofuran at 23℃; for 3h;100%
In tetrahydrofuran at 20℃; for 3h;100%
In tetrahydrofuran at 20℃; for 3h; Inert atmosphere;100%
C11H13BCl2O

C11H13BCl2O

2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

2-(2-benzyloxymethyl-cyclopropyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

2-(2-benzyloxymethyl-cyclopropyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

Conditions
ConditionsYield
Stage #1: C11H13BCl2O With methanol for 0.166667h;
Stage #2: 2,3-dimethyl-2,3-butane diol In methanol for 15h;
100%
2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

(2-chloropyrimidin-5-yl)boronic acid
1003845-06-4

(2-chloropyrimidin-5-yl)boronic acid

2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine
1003845-08-6

2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine

Conditions
ConditionsYield
With magnesium sulfate In toluene at 20℃; for 15h;100%
With magnesium sulfate In toluene at 20℃; for 15h;100%
2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

4-Vinylphenylboronic acid
2156-04-9

4-Vinylphenylboronic acid

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)styrene
870004-04-9

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)styrene

Conditions
ConditionsYield
With magnesium sulfate In tetrahydrofuran at 20℃; for 2h;100%
With magnesium sulfate In tetrahydrofuran at 20℃; for 3h; Inert atmosphere;100%
With magnesium sulfate In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;99%
4-(dihydroxyboranyl)-2-fluorobenzoic acid
120153-08-4

4-(dihydroxyboranyl)-2-fluorobenzoic acid

2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid
867256-77-7

2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid

Conditions
ConditionsYield
In ethanol; toluene for 24h; Reflux;100%
In ethanol; toluene Heating / reflux;
In ethanol; toluene Heating;
In toluene for 20h; Reflux;
2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

2,6-difluoro-4-carboxylphenylboronic acid
1031857-98-3

2,6-difluoro-4-carboxylphenylboronic acid

2,6-difluoro-4-(4,4,5,5-tetramethyl-1,3,2-bioxaborolan-2-yl)benzoic acid
1031857-96-1

2,6-difluoro-4-(4,4,5,5-tetramethyl-1,3,2-bioxaborolan-2-yl)benzoic acid

Conditions
ConditionsYield
In tetrahydrofuran; toluene at 40℃;100%
2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

4-mercaptophenylboronic acid
237429-33-3

4-mercaptophenylboronic acid

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenethiol
1029438-23-0

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenethiol

Conditions
ConditionsYield
With sodium sulfate at 20℃; for 16h; Inert atmosphere;100%
With magnesium sulfate In diethyl ether at 20℃;98%
With magnesium sulfate In cyclohexane at 20℃;98%
2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

2-(diethylcarbamoyloxy)-3,5-dimethoxyphenylboronic acid
1135822-19-3

2-(diethylcarbamoyloxy)-3,5-dimethoxyphenylboronic acid

3,5-dimethoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl diethylcarbamate
1032189-97-1

3,5-dimethoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl diethylcarbamate

Conditions
ConditionsYield
In ethyl acetate100%
2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

diisopropyl (iodomethyl)boronate
167967-38-6

diisopropyl (iodomethyl)boronate

2-(iodomethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
70557-99-2

2-(iodomethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions
ConditionsYield
In pentane at 20℃; Inert atmosphere; Schlenk technique;100%
In pentane at 20℃;
In diethyl ether; pentane at 20℃; for 16h; Inert atmosphere;4.91 g
2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

4-chloro-4'-iodo-1,1'-biphenyl
60200-91-1

4-chloro-4'-iodo-1,1'-biphenyl

2-(4'-chloro-[1,1'-biphenyl]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
942589-53-9

2-(4'-chloro-[1,1'-biphenyl]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions
ConditionsYield
Stage #1: 4-chloro-4'-iodo-1,1'-biphenyl With n-butyllithium In diethyl ether; hexane at -78℃; Inert atmosphere;
Stage #2: With Trimethyl borate In diethyl ether; hexane at -78 - 20℃;
Stage #3: 2,3-dimethyl-2,3-butane diol Further stages;
100%
2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

5-(1,3-dioxolan-2-yl)-2-fluoropyridin-3-ylboronic acid
1253569-20-8

5-(1,3-dioxolan-2-yl)-2-fluoropyridin-3-ylboronic acid

5-(1,3-dioxolan-2-yl)-2-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
1253571-13-9

5-(1,3-dioxolan-2-yl)-2-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Conditions
ConditionsYield
With magnesium sulfate In toluene at 22℃; for 72h; Inert atmosphere;100%
With magnesium sulfate In toluene at 20℃; Inert atmosphere;
2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

[((4-carboxyphenyl)methanesulfonyl)amino]methaneboronic acid

[((4-carboxyphenyl)methanesulfonyl)amino]methaneboronic acid

C15H22BNO6S
1254692-14-2

C15H22BNO6S

Conditions
ConditionsYield
In tetrahydrofuran Inert atmosphere;100%
2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

(2-ethoxy-naphthalene-1-sulfonylamino)methaneboronic acid

(2-ethoxy-naphthalene-1-sulfonylamino)methaneboronic acid

C19H26BNO5S

C19H26BNO5S

Conditions
ConditionsYield
In tetrahydrofuran Inert atmosphere;100%
2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

3,4-dichlophenylboronic acid
151169-75-4

3,4-dichlophenylboronic acid

2-(3,4-dichlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
401797-02-2

2-(3,4-dichlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions
ConditionsYield
In diethyl ether at 20℃; for 17h;100%
2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

(2-(trimethylsilyl)phenyl)boronic acid
1160757-30-1

(2-(trimethylsilyl)phenyl)boronic acid

trimethyl(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane
910875-07-9

trimethyl(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane

Conditions
ConditionsYield
In diethyl ether at 20℃; Inert atmosphere; Molecular sieve;100%
With magnesium sulfate In tetrahydrofuran at 20℃;
2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

4-biphenylboronic acid
5122-94-1

4-biphenylboronic acid

2-(biphenyl-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
144432-80-4

2-(biphenyl-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions
ConditionsYield
With potassium phosphate; water In tetrahydrofuran at 90℃; for 1h; Inert atmosphere;100%
With air In dichloromethane at 25℃; for 16h; Molecular sieve;46%
In diethyl ether at 20℃; Inert atmosphere; Molecular sieve;
2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

9,9-didodecylfluorene-2,7-diboronic acid
480424-86-0

9,9-didodecylfluorene-2,7-diboronic acid

2,2'-(9,9-didodecyl-9H-fluorene-2,7-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
749900-93-4

2,2'-(9,9-didodecyl-9H-fluorene-2,7-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

Conditions
ConditionsYield
In toluene Reflux; Inert atmosphere;100%

76-09-5Relevant articles and documents

Reductive coupling of phthalic anhydrides with aliphatic ketones by low-valent titanium: Unusual two-to-one coupling for preparation of 3,3-disubstituted phthalides

Kise, Naoki,Yamamoto, Shota,Sakurai, Toshihiko

, (2020)

The reductive coupling of phthalic anhydrides with acetone by Zn-TiCl4 in THF gave two-to-one and one-to-one coupled products. The coupled products were transformed to 3,3-diisopropyl-, 3-isopropylidene-, and 3-isopropylphthalides. In addition, the reductive coupling of phthalic anhydrides with acetonylacetone by Zn-TiCl4 in THF gave 3-spirocyclopentanylphtalides stereoselectively.

Duran et al.

, p. 442 (1977)

Synthesis of Layered Carbonitrides from Biotic Molecules for Photoredox Transformations

Yang, Can,Wang, Bo,Zhang, Linzhu,Yin, Ling,Wang, Xinchen

, p. 6627 - 6631 (2017)

The construction of layered covalent carbon nitride polymers based on tri-s-triazine units has been achieved by using nucleobases (adenine, guanine, cytosine, thymine and uracil) and urea to establish a two-dimensional semiconducting structure that allows band-gap engineering applications. This biomolecule-derived binary carbon nitride polymer enables the generation of energized charge carrier with light-irradiation to induce photoredox reactions for stable hydrogen production and heterogeneous organosynthesis of C?O, C?C, C?N and N?N bonds, which may enrich discussion on chemical reactions in prebiotic conditions by taking account of the photoredox function of conjugated carbonitride semiconductors that have long been considered to be stable HCN-derived organic macromolecules in space.

Well-defined Cp*Co(III)-catalyzed Hydrogenation of Carbonates and Polycarbonates

Dahiya, Pardeep,Gangwar, Manoj Kumar,Sundararaju, Basker

, p. 934 - 939 (2020/12/15)

We herein report the catalytic hydrogenation of carbonates and polycarbonates into their corresponding diols/alcohols using well-defined, air-stable, high-valent cobalt complexes. Several novel Cp*Co(III) complexes bearing N,O-chelation were isolated for the first time and structurally characterized by various spectroscopic techniques including single crystal X-ray crystallography. These novel Co(III) complexes have shown excellent catalytic activity to produce value added diols/alcohols from carbonate and polycarbonates through hydrogenation using molecular hydrogen as sole reductant or iPrOH as transfer hydrogenation source. To demonstrate the developed methodology's practical applicability, we have recycled the bisphenol A monomer from compact disc (CD) through hydrogenation under the established reaction conditions using phosphine-free, earth-abundant, air- and moisture-stable high-valent cobalt catalysts.

GaN nanowires as a reusable photoredox catalyst for radical coupling of carbonyl under blacklight irradiation

Botton, Gianluigi,Cen, Yunen,Cheng, Shaobo,Li, Chao-Jun,Liu, Mingxin,Mi, Zetian,Rashid, Roksana T.,Tan, Lida

, p. 7864 - 7870 (2020/08/19)

Employing photo-energy to drive the desired chemical transformation has been a long pursued subject. The development of homogeneous photoredox catalysts in radical coupling reactions has been truly phenomenal, however, with apparent disadvantages such as the difficulty in separating the catalyst and the frequent requirement of scarce noble metals. We therefore envisioned the use of a hyper-stable III-V photosensitizing semiconductor with a tunable Fermi level and energy band as a readily isolable and recyclable heterogeneous photoredox catalyst for radical coupling reactions. Using the carbonyl coupling reaction as a proof-of-concept, herein, we report a photo-pinacol coupling reaction catalyzed by GaN nanowires under ambient light at room temperature with methanol as a solvent and sacrificial reagent. By simply tuning the dopant, the GaN nanowire shows significantly enhanced electronic properties. The catalyst showed excellent stability, reusability and functional tolerance. All reactions could be accomplished with a single piece of nanowire on Si-wafer. This journal is

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