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Pinacol

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Name

Pinacol

EINECS 200-933-5
CAS No. 76-09-5 Density 0.963 g/cm 3
PSA 40.46000 LogP 0.52820
Solubility Soluble in hot water, alcohol, and diethyl ether. Melting Point 40-43 °C(lit.)
Formula C6H14O2 Boiling Point 174.4 °C at 760 mmHg
Molecular Weight 118.176 Flash Point 77.2 °C
Transport Information UN 1325 4.1/PG 2 Appearance white solid
Safety 37-37/39-26 Risk Codes 38-36/37/38
Molecular Structure Molecular Structure of 76-09-5 (Pinacol) Hazard Symbols IrritantXi
Synonyms

1,1,2,2-Tetramethylethyleneglycol;2,3-Dihydroxy-2,3-dimethylbutane;2,3-Dimethyl-2,3-butanediol;2,3-Dimethyl-2,3-dihydroxybutane;NSC 25943;Pinacone;Tetramethylethylene glycol;2,3-Dimethyl-butane-2,3-diol;2,3-Butanediol,2,3-dimethyl-;

Article Data 250

Pinacol Synthetic route

5076-20-0

2,3-dimethyl-2,3-epoxybutane

A

75-97-8

3,3-dimethyl-butan-2-one

B

76-09-5

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

C

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;
67-64-1

acetone

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;
1600-27-7

mercury(II) diacetate

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

A

76-09-5

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

B

C2H3ClHgO6

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

mercury(II) diacetate

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

A

76-09-5

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

B

C4H5ClHg2O8

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

mercury(II) trifluoroacetate

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

A

76-09-5

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

B

C4H2ClF3Hg2O8

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

2,3-Dimethyl-2-butene

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%
1600-27-7

mercury(II) diacetate

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

A

76-09-5

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

B

C3H5ClHgO6

Conditions
ConditionsYield
In ethanol for 0.166667h; Heating; Yields of byproduct given;A n/a
B 97%
19424-29-4

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

A

67-56-1

methanol

B

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.
1600-27-7

mercury(II) diacetate

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

A

76-09-5

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

B

C5H7ClHg2O8

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

2,3-Dimethyl-2-butene

A

75-97-8

3,3-dimethyl-butan-2-one

B

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

Pinacol Specification

1. Introduction of Pinacol
Pinacol is a white solid organic compound. It is an alcohol that has -OH groups on adjacent carbon atoms on the same side.

2. Properties of Pinacol
The density of Pinacol(76-09-5) is 0.963 g/cm3 and it has a melting point of  40-43 °C(lit.). The boiling point is  174.4 °C at 760 mmHg. The refractive index is about  1.448. Its flash point is  77.2 °C.

3. Toxicity of Pinacol
LD50/LC50: RTECS:
CAS# 76-09-5: Draize test, rabbit, skin: 500 mg/24H Moderate;
Oral, mouse: LD50 = 3380 mg/kg;
Carcinogenicity: Pinacol - Not listed as a carcinogen by ACGIH, IARC, NTP, or CA Prop 65. 
Other: The toxicological properties have not been fully investigated. See actual entry in RTECS for complete information. 

4. Safety Information of Pinacol
Hazard Codes:IrritantXi
Risk Statements:  
R38:Irritating to skin. 
R36/37/38:Irritating to eyes, respiratory system and skin. 
Safety Statements: 
S37:Wear suitable gloves. 
S37/39:Wear suitable gloves and eye/face protection. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
RIDADR  UN: 1325 4.1/PG 2
WGK Germany: 2
RTECS  EK:1720000
F: 3

5. Preparation of Pinacol
Pinacol may be produced by the pinacol coupling reaction from acetone.

 

6. Use of Pinacol
Pinacol can be use with borane and boron trichloride to produce useful synthetic intermediate such as pinacolborane, bis(pinacolato)diboron, and pinacolchloroborane

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