CYCLOPENTEN-1-YLBORONIC ACID Chemical Properties

Melting point:

134-140°C

Boiling point:

246.7±33.0 °C(Predicted)

Density 

1.08±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

pka

9.44±0.20(Predicted)

form 

solid

color 

white to pale yellow

InChI

1S/C5H9BO2/c7-6(8)5-3-1-2-4-5/h3,7-8H,1-2,4H2

InChIKey

UZBHNSVUMGIKLU-UHFFFAOYSA-N

SMILES

OB(O)C1=CCCC1

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-41-37/38

Safety Statements 

26-36/37/39-39

WGK Germany 

WGK 3

Hazard Note 

Harmful/Irritant/Keep Cold

TSCA 

No

HS Code 

29319090

Storage Class

11 - Combustible Solids

Hazard Classifications

Acute Tox. 4 Dermal
Acute Tox. 4 Inhalation
Acute Tox. 4 Oral
Eye Dam. 1
Skin Irrit. 2
STOT SE 3

CYCLOPENTEN-1-YLBORONIC ACID Usage And Synthesis

Chemical Properties

Off-white powder

Uses

suzuki reaction

Synthesis

Cyclopenten-1-ylboronic acid is prepared as follows:

The first step of the raw material 1-chlorocyclopentene preparation: to a 2L four-necked bottle equipped with magnetic stirring, thermometer, condenser tube and exhaust gas alkali absorption device, add 374.2 (1.818mol, 1.05) phosphorus pentachloride, 863g of n-heptane, warming to 70 ??, drop 151.4g (1.803mol, 1eq) cyclopentanone, about 2 hours after the drop, and continue the reaction Half an hour, after cooling down to 0 ??, dropwise addition of 6 mol / L sodium hydroxide solution 0.69 kg, stirring for one hour, separation of the upper organic layer, the organic layer was washed once with saturated sodium bicarbonate, to obtain 1-chlorocyclopentene n-hexane solution 799 g, the internal standard yield of 81.1%;

The second step of preparation of cyclopenten-1-ylboronic acid: to a 5L four-necked flask equipped with mechanical stirring, thermometer, argon protection and reflux condenser tube was added T2215.5g (1.608mol, 1.1eq), lithium metal 22.6g (3.216mol, 2.2eq), tetrahydrofuran 678g, cooled down to -10??C, and dropwise addition of 1-chlorocyclopentene's Heptane solution (1eq), titration is completed insulation -10 ?? stirring 11 hours, GC control, the end of the reaction, add 1.3kg6N hydrochloric acid adjust PH = 2 ~ 3, stratification, the aqueous layer and then 400g of ethyl acetate extracted once, combined with the organic layer, 40 ?? distillation under reduced pressure, to not flow, precipitation of solids, add 200g of n-heptane-10 ?? pulp, filtration, drying to obtain the white solid cyclopentene -1-ylboronic acid 89.3g, yield 54.5%.

CYCLOPENTEN-1-YLBORONIC ACID(850036-28-1)Related Product Information

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• Cyclopentene
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• CYCLOPENTEN-1-YLBORONIC ACID