Cyclopropylacetylene Chemical Properties

Melting point:

294 °C (decomp)

Boiling point:

79-80 °C

Density 

0.7801

refractive index 

n20/D 1.4480

Flash point:

-5 °F

storage temp. 

2-8°C

solubility 

Chloroform, Ethyl Acetate

form 

Liquid

Specific Gravity

0.797

color 

Clear colorless to light yellow

Water Solubility 

Slightly soluble in water.

InChI

InChI=1S/C5H6/c1-2-5-3-4-5/h1,5H,3-4H2

InChIKey

NPTDXPDGUHAFKC-UHFFFAOYSA-N

SMILES

C1(C#C)CC1

CAS DataBase Reference

6746-94-7(CAS DataBase Reference)

NIST Chemistry Reference

Cyclopropylacetylene(6746-94-7)

Safety Information

Hazard Codes 

F,Xn,Xi

Risk Statements 

11-36/37/38-48/20-63-65-67-52/53-41-38-4-37/38-22

Safety Statements 

26-36/37-62-37/39-16-61-33-9-36/37/39-39

RIDADR 

UN 1294 3/PG 2

WGK Germany 

2

HazardClass 

IRRITANT, FLAMMABLE

HazardClass 

3

PackingGroup 

II

HS Code 

29021990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

Cyclopropylacetylene Usage And Synthesis

Preparation

Cyclopropylacetylene was prepared in a two-step procedure by dichlorination of cyclopropyl methyl ketone with phosphorus pentachloride (PCl5) followed by double dehydrohalogenation with a strong base. This sequence presented significant scale-up problems with low overall yields (20-25%).
Similarly, cyclopropylacetylene has been prepared by base-induced dehydrohalogenation of bromovinylcyclopropane . Cyclopropylacetylene has also been prepared from the 1-trimethylsilyl derivative of cyclopropylacetylene, which was prepared by treatment of 5-chloro-1-trimethylsilyl-1-pentyne with lithium diisopropylamide at ?78°C followed by warming to room temperature.

Chemical Properties

clear colorless to light yellow liquid

Uses

Cyclopropylacetylene is used as an organic chemical synthesis intermediate.

Synthesis

The general procedure for synthesizing cyclopropylacetylene from (1,1-dichloroethyl)cyclopropane was as follows: 1) 80 g of sodium hydroxide was mixed with 300 mL of ethoxyethanol and stirred at -60 °C, followed by the slow addition of 100 g of chlorocyclopropylacetylene at the same temperature. After the reaction was completed (the reaction process was monitored by gas chromatography analysis), atmospheric pressure distillation was performed to collect the 55 °C-65 °C fraction to obtain crude cyclopropylacetylene; 2) The crude cyclopropylacetylene was purified by distillation with continuous stirring. Finally, 59 g of cyclopropylacetylene with a purity greater than 98% was obtained, with a yield of 89%.

References

[1] Patent: CN105985223, 2016, A. Location in patent: Paragraph 0049; 0050; 0051; 0052
[2] Journal of Organic Chemistry, 1976, vol. 41, # 7, p. 1237 - 1240
[3] Synthesis, 1972, p. 703
[4] Journal of the American Chemical Society, 1972, vol. 94, p. 1158 - 1163
[5] Synlett, 1999, # 12, p. 1948 - 1950

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