Cyclopropylacetylene
ETHYNYLCYCLOPROPANE · CYCLOPROPYLACETYLENE · CPAC · Cylopropylethylnen · Cylopropyl acetylene · Cyclopropyl acetylen · Cyclopropylacethylene · Cyclopropane,ethynyl-
Identifiers & Physical Properties
| CAS No. | 6746-94-7 |
|---|---|
| Molecular formula | C5H6 |
| Average molar mass | 66.1 g/mol |
| Monoisotopic mass | 66.04695019 g/mol |
| SMILES | C#CC1CC1 |
| InChIKey | NPTDXPDGUHAFKC-UHFFFAOYSA-N |
| PubChem CID | 138823 |
| EC No. | 425-430-1 |
| DTXSID | DTXSID80217795 |
Chemical & Physical Properties
| XLogP | 1.5 |
|---|---|
| Topological polar surface area | 0 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 0 |
| Rotatable bonds | 0 |
| Heavy atoms | 5 |
| Formal charge | 0 |
| Complexity | 69.3 |
| SpringerMaterials Properties | Coriolis coupling |
| Melting point | 294 °C (decomp) |
| Boiling point | 79-80 °C |
| Density | 0.7801 |
| Refractive index | n20/D 1.4480 |
| Flash point | -5 °F |
| Storage conditions | 2-8°C |
| Solubility | Chloroform, Ethyl AcetateSlightly soluble in water. |
| Physical state | Liquid |
| Specific gravity | 0.797 |
| Color | Clear colorless to light yellow |
| 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) |
| UNSPSC Code | 12352100 |
| NACRES | NA.22 |
| GHS pictogram | GHS02,GHS05 |
| Signal word | Danger |
| GHS hazard statements | H225-H315-H318-H412 |
| GHS precautionary statements | P210-P233-P273-P280-P303+P361+P353-P305+P351+P338 |
| Personal protective equipment (PPE) | Eyeshields, Faceshields, Gloves |
| Hazard symbols | F,Xn,Xi |
| Risk statements (R) | 11-36/37/38-48/20-63-65-67-52/53-41-38-4-37/38-22 |
| Safety statements (S) | 26-36/37-62-37/39-16-61-33-9-36/37/39-39 |
| UN transport number | UN 1294 3/PG 2 |
| Water hazard class (WGK) | 2 |
| Hazard class | IRRITANT, FLAMMABLEAquatic Chronic 3Eye Dam. 1Flam. Liq. 2Skin Irrit. 2 |
| Packing group | II |
| Customs code | 29021990 |
| Storage class | 3 - Flammable liquids |
| REACH registrations | Inactive |
Safety & Regulations
| GHS classification | DangerH225: Highly Flammable liquid and vapor [Danger Flammable liquids]P210, P233, P240, P241, P242, P243, P264, P264+P265, P273, P280, P302+P352, P303+P361+P353, P305+P354+P338, P317, P321, P332+P317, P362+P364, P370+P378, P403+P235, and P501 (click each P-code to see the statement)H225 (96.1%): Highly Flammable liquid and vapor [Danger Flammable liquids] |
|---|---|
| Regulatory information | Status: Active Update: 05-09-2011 https://echa.europa.eu/registration-dossier/-/registered-dossier/1000 |
| Hazard Classes and Categories | Flam. Liq. 2 (96.1%)Flam. Liq. 2 (85.7%)Flammable liquid - category 2 |
| Personal protective equipment (PPE) | Eyeshields, Faceshields, Gloves |
| Water hazard class (WGK) | 2 |
| UN transport number | UN 1294 3/PG 2 |
| Customs code | 29021990 |
| Risk statements (R) | 11-36/37/38-48/20-63-65-67-52/53-41-38-4-37/38-22 |
| Signal word | Danger |
| GHS pictogram | GHS02,GHS05 |
| Hazard symbols | F,Xn,Xi |
| Safety statements (S) | 26-36/37-62-37/39-16-61-33-9-36/37/39-39 |
| Hazard class | 3Aquatic Chronic 3Eye Dam. 1Flam. Liq. 2Skin Irrit. 2 |
| Storage class | 3 - Flammable liquids |
| Packing group | II |
| GHS hazard statements | H225-H315-H318-H412 |
| REACH registrations | Inactive |
| GHS precautionary statements | P210-P233-P273-P280-P303+P361+P353-P305+P351+P338 |
Applications & Uses
Uses
Cyclopropylacetylene is used as an organic chemical synthesis intermediate.
Preparation & 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.