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Cyclopropylacetylene

Product NameCyclopropylacetylene
CAS6746-94-7
MFC5H6
MW66.1
EINECS425-430-1
MOL File6746-94-7.mol

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
Storage Class	3 - Flammable liquids
Hazard Classifications	Aquatic Chronic 3 Eye Dam. 1 Flam. Liq. 2 Skin Irrit. 2

MSDS

Provider	Language
ACROS	English
SigmaAldrich	English

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

40459-85-6

6746-94-7

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

Cyclopropylacetylene

Chemical Properties

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MSDS

Usage And Synthesis

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