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 -10C, 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

• CYCLOHEXYLHYDRAZINE HYDROCHLORIDE
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• 1-Octylboronic acid
• Cyclopentene
• 2-BORONO-2-CYCLOPENTENONE
• (1S)-1,7,7-TRIMETHYLBICYCLO[2.2.1]HEPT-2-EN-2-YLBORONIC ACID
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• 2-CYCLOPENTENYL-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE
• CYCLOPENTEN-1-YLBORONIC ACID