Cyclopropyl cyanide

Names
Preferred IUPAC name

Cyclopropanecarbonitrile

Other names

Cyanocyclopropane

Identifiers

CAS Number

* 5500-21-0 Y

3D model (JSmol)

* Interactive image

ChemSpider |

* 71940

ECHA InfoCard | 100.024.397
EC Number |

* 226-836-8

PubChem CID

* 79637

UNII |

* AFU99GZS5D Y

CompTox Dashboard (EPA)

* DTXSID1063936

InChI

* InChI=1S/C4H5N/c5-3-4-1-2-4/h4H,1-2H2

Key: AUQDITHEDVOTCU-UHFFFAOYSA-N

SMILES

* N#CC1CC1

Properties

Chemical formula

| C4H5N
Molar mass | 67.0892g/mol[1]
Appearance  | clear to light yellow liquid
Density | 0.911g/mL
Melting point | −25 °C (−13 °F; 248 K)
Boiling point | 135 °C (275 °F; 408 K)

Solubility in water

| soluble in water[2]
log P | 1.196
Hazards
Occupational safety and health (OHS/OSH):

Main hazards

| Toxic, hazardous if inhaled, contacted with skin, or swallowed
GHS labelling:

Pictograms

Signal word

| Danger

Hazard statements

| H226, H301, H311, H315, H319, H330, H331, H335

Precautionary statements

| P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P280, P284, P301+P310, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P311, P312, P320, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P370+P378, P403+P233, P403+P235, P405, P501
Flash point | 40 °C (104 °F; 313 K)
Thermochemistry

Std enthalpy of
combustion (ΔcH⦵298)

| 182.7

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Infobox references

Chemical compound

Cyclopropyl cyanide is an organic compound consisting of a nitrile group as a substituent on a cyclopropane ring. It is the smallest cyclic compound containing a nitrile.

## Structure

[edit]

The structure of cyclopropyl cyanide has been determined by a variety of experiments, including microwave spectroscopy, rotational spectroscopy and photodissociation. In 1958, cyclopropyl cyanide was first studied for its rotational spectra, by Friend and Dailey.[citation needed] An additional experiment involving cyclopropyl cyanide was the determination of the molecular dipole moment through spectroscopy experiments, by Carvalho in 1967.[3]

## Production

[edit]

Cyclopropyl cyanide is prepared by the reaction of 4-chlorobutyronitrile with a strong base, such as sodium amide in liquid ammonia.[4]

## Reactions

[edit]

Hydrolysis gives cyclopropane carboxylic acid]. Cyclopropyl cyanide, when heated to 660-760K and under pressure of 2-89torr, becomes cis and trans crotonitrile and allyl cyanide molecules, with some presence of methacrylonitrile. This is an isomerization reaction that is homogeneous with rate of first order. The reaction result is due to the biradical mechanism, which involves the formation of carbon radicals as the three carbon ring opens up. The radicals then react to yield carbon=carbon double bonds.[5]

## References

[edit]

1. ^ "cyclopropanecarbonitrile - Compound Summary". PubChem.
2. ^ "Cyclopropyl cyanide". Chemical Book.
3. ^ Bizzocchi, Luca; Claudio Degli Esposti; Luca Dore; Zbigniew Kisiel (September–October 2008). "Submillimetre-wave spectrum, 14N-hyperfine structure, and dipole moment of cyclopropyl cyanide". Journal of Molecular Spectroscopy. 251 (1–2): 138–144\. Bibcode:2008JMoSp.251..138B. doi:10.1016/j.jms.2008.02.009.1–2&rft.pages=138-144&rft.date=2008-09/2008-10&rft_id=info:doi/10.1016/j.jms.2008.02.009&rft_id=info:bibcode/2008JMoSp.251..138B&rft.aulast=Bizzocchi&rft.aufirst=Luca&rft.au=Claudio+Degli+Esposti&rft.au=Luca+Dore&rft.au=Zbigniew+Kisiel&rfr_id=info:sid/en.wikipedia.org:Cyclopropyl+cyanide" class="Z3988">
4. ^ Schlatter, M. J. (1943). "Cyclopropyl Cyanide". Organic Syntheses. 23: 20. doi:10.15227/orgsyn.023.0020.
5. ^ Luckraft; Robinson (1973). "Kinetics of the reactions of cyclopropane derivatives. III. Gas-phase unimolecular isomerization of cyclopropyl cyanide to the cyanopropenes". International Journal of Chemical Kinetics. 5: 137–147\. doi:10.1002/kin.550050112.

*[CID]: Compound ID
*[EPA]: U.S. Environmental Protection Agency
*[H226]: H226: Flammable liquid and vapour
*[H301]: H301: Toxic if swallowed
*[H311]: H311: Toxic in contact with skin
*[H315]: H315: Causes skin irritation
*[H319]: H319: Causes serious eye irritation
*[H330]: H330: Fatal if inhaled
*[H331]: H331: Toxic if inhaled
*[H335]: H335: May cause respiratory irritation
*[P210]: P210: Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking.
*[P233]: P233: Keep container tightly closed.
*[P240]: P240: Ground and bond container and receiving equipment.
*[P241]: P241: Use explosion-proof electrical/ventilating/light/.../equipment.
*[P242]: P242: Use only non-sparking tools.
*[P243]: P243: Take precautionary measures to prevent static discharges.
*[P260]: P260: Do not breathe dust/fume/gas/mist/vapours/spray.
*[P261]: P261: Avoid breathing dust/fume/gas/mist/vapours/spray.
*[P264]: P264: Wash ... thoroughly after handling.
*[P270]: P270: Do not eat, drink or smoke when using this product.
*[P271]: P271: Use only outdoors or in a well-ventilated area.
*[P280]: P280: Wear protective gloves/protective clothing/eye protection/face protection.
*[P284]: P284: Wear respiratory protection.
*[P301+P310]: P301+P310: IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
*[P302+P352]: P302+P352: IF ON SKIN: Wash with soap and water.
*[P303+P361+P353]: P303+P361+P353: IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water [or shower].
*[P304+P340]: P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
*[P305+P351+P338]: P305+P351+P338: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing.
*[P310]: P310: Immediately call a POISON CENTER or doctor/physician.
*[P311]: P311: Call a POISON CENTER or doctor/physician.
*[P312]: P312: Call a POISON CENTER or doctor/physician if you feel unwell.
*[P320]: P320: Specific treatment is urgent (see ... on this label).
*[P321]: P321: Specific treatment (see ... on this label).
*[P322]: P322: Specific measures (see ... on this label).
*[P330]: P330: Rinse mouth.
*[P332+P313]: P332+P313: If skin irritation occurs: Get medical advice/attention.
*[P337+P313]: P337+P313: If eye irritation persists: Get medical advice/attention.
*[P361]: P361: Remove/Take off immediately all contaminated clothing.
*[P362]: P362: Take off contaminated clothing.
*[P363]: P363: Wash contaminated clothing before reuse.
*[P370+P378]: P370+P378: In case of fire: Use ... to extinguish.
*[P403+P233]: P403+P233: Store in a well ventilated place. Keep container tightly closed.
*[P403+P235]: P403+P235: Store in a well ventilated place. Keep cool.
*[P405]: P405: Store locked up.
*[P501]: P501: Dispose of contents/container to ...