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Cyclopropane information


Cyclopropane[1]
Cyclopropane - displayed formula
Cyclopropane - displayed formula
Cyclopropane - skeletal formula
Cyclopropane - skeletal formula
Names
Preferred IUPAC name
Cyclopropane[2]
Identifiers
CAS Number
  • 75-19-4 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:30365 checkY
ChEMBL
  • ChEMBL1796999 ☒N
ChemSpider
  • 6111 checkY
ECHA InfoCard 100.000.771 Edit this at Wikidata
KEGG
  • D03627 checkY
PubChem CID
  • 6351
UNII
  • 99TB643425 checkY
UN number 1027
CompTox Dashboard (EPA)
  • DTXSID4058786 Edit this at Wikidata
InChI
  • InChI=1S/C3H6/c1-2-3-1/h1-3H2 checkY
    Key: LVZWSLJZHVFIQJ-UHFFFAOYSA-N checkY
  • InChI=1/C3H6/c1-2-3-1/h1-3H2
    Key: LVZWSLJZHVFIQJ-UHFFFAOYAL
SMILES
  • C1CC1
Properties
Chemical formula
C3H6
Molar mass 42.08 g/mol
Appearance Colorless gas
Odor Sweet, ethereal
Density 1.879 g/L (1 atm, 0 °C)
680 g/L (liquid)
Melting point −128 °C (−198 °F; 145 K)
Boiling point −32.9 °C (−27.2 °F; 240.2 K)
Solubility in water
502 mg/L
Vapor pressure 640 kPa (20 °C)
1350 kPa (50 °C)
Acidity (pKa) ~46
Magnetic susceptibility (χ)
-39.9·10−6 cm3/mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Highly flammable
Asphyxiant
GHS labelling:
Pictograms
GHS02: FlammableGHS04: Compressed Gas
Signal word
Danger
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g. propaneInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazard SA: Simple asphyxiant gas. E.g. nitrogen, helium
1
4
0
SA
Autoignition
temperature
495 °C (923 °F; 768 K)
Explosive limits 2.4 % (lower)
10.4 % (upper)
Safety data sheet (SDS) Air Liquide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Cyclopropane is the cycloalkane with the molecular formula (CH2)3, consisting of three methylene groups (CH2) linked to each other to form a triangular ring. The small size of the ring creates substantial ring strain in the structure. Cyclopropane itself is mainly of theoretical interest but many of its derivatives - cyclopropanes - are of commercial or biological significance.[3]

Cyclopropane was used as a clinical inhalational anesthetic from the 1930s through the 1980s. The substance's high flammability poses a risk of fire and explosions in operating rooms due to its tendency to accumulate in confined spaces, as its density is higher than that of air.

  1. ^ Merck Index, 11th Edition, 2755.
  2. ^ "Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 137. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
  3. ^ Faust, Rüdiger (2001). "Fascinating Natural and Artificial Cyclopropane Architectures". Angewandte Chemie International Edition. 40 (12): 2251–2253. doi:10.1002/1521-3773(20010618)40:12<2251::AID-ANIE2251>3.0.CO;2-R. PMID 11433485.

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Cyclopropane

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Cyclopropane is the cycloalkane with the molecular formula (CH2)3, consisting of three methylene groups (CH2) linked to each other to form a triangular...

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Cyclopropanes

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Cyclopropanes are a family of organic compounds containing the cyclopropyl group. The parent is cyclopropane (C3H6). Most cyclopropanes are not prepared...

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Cyclopropanation

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chemistry, cyclopropanation refers to any chemical process which generates cyclopropane ((CH2)3) rings. It is an important process in modern chemistry as many...

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Ring strain

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abnormal. Strain is most commonly discussed for small rings such as cyclopropanes and cyclobutanes, whose internal angles are substantially smaller than...

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Cyclopropane fatty acid

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Cyclopropane fatty acids (CPA) are a subgroup of fatty acids that contain a cyclopropane group. Although they are usually rare, the seed oil from lychee...

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Activation of cyclopropanes by transition metals

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In organometallic chemistry, the activation of cyclopropanes by transition metals is a research theme with implications for organic synthesis and homogeneous...

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Bent bond

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resembling a similar "bent" structure within small ring molecules, such as cyclopropane (C3H6) or as a representation of double or triple bonds within a compound...

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Cycloalkane

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side chains (also known as monocycloalkanes) are classified as small (cyclopropane and cyclobutane), common (cyclopentane, cyclohexane, and cycloheptane)...

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Lindemann mechanism

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Lindemann mechanism, because once the cyclopropane, the reactant, is excited by collision it becomes an energized cyclopropane. And then, this molecule can be...

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Methylcyclopropane

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colorless gas is the monomethyl derivative of cyclopropane. Methylcyclopropane, like many other cyclopropanes, undergoes ring-opening reactions. Bond cleavage...

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Flumethrin

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the cyclopropane ring and the cis-configuration at the olefinic carbon-carbon double bond and 8% of the isomer with cis geometry on the cyclopropane ring...

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Alicyclic compound

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attached. The simplest alicyclic compounds are the monocyclic cycloalkanes: cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, and...

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Methylenecyclopropane

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is derived from the addition of a methylene (=CH2) substituent to a cyclopropane ring. It is a colourless, easily condensed gas that is used as a reagent...

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Inhalational anesthetic

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countries: Acetylene Chloroethane (ethyl chloride) Chloroform Cryofluorane Cyclopropane Diethyl ether Divinyl ether Enflurane Ethylene Fluroxene Halothane (still...

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Ketamine

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Levonorgestrel cyclopropylcarboxylate

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Levonorgestrel cyclopropylcarboxylate (developmental code name HRP-003), or levonorgestrel 17β-cyclopropylcarboxylate, is a progestin and a progestogen...

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Strain energy

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the form of mechanical work. For example, the heat of combustion of cyclopropane (696 kJ/mol) is higher than that of propane (657 kJ/mol) for each additional...

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Cycloeucalenol cycloisomerase

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lyases. The systematic name of this enzyme class is cycloeucalenol lyase (cyclopropane-decyclizing). This enzyme is also called cycloeucalenol---obtusifoliol...

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Zinc

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allosteric modulators: Barbiturates (e.g., pentobarbital, sodium thiopental) Cyclopropane Enflurane Ethanol (alcohol) Evans blue GYKI-52466 GYKI-53655 Halothane...

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NMDA receptor

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allosteric modulators: Barbiturates (e.g., pentobarbital, sodium thiopental) Cyclopropane Enflurane Ethanol (alcohol) Evans blue GYKI-52466 GYKI-53655 Halothane...

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Sterculic acid

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reactive intermediate, followed by cyclization via loss of H+ mediated by a cyclopropane-fatty-acyl-phospholipid synthase enzyme. The product, dihydrosterculic...

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Nitrous oxide

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are a novel target for the anesthetic gases xenon, nitrous oxide, and cyclopropane". Molecular Pharmacology. 65 (2): 443–52. doi:10.1124/mol.65.2.443. PMID 14742687...

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Permethrin

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(two enantiomeric pairs), arising from the two stereocenters in the cyclopropane ring. The trans enantiomeric pair is known as transpermethrin. (1R,3S)-trans...

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Neighbouring group participation

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In organic chemistry, neighbouring group participation (NGP, also known as anchimeric assistance) has been defined by the International Union of Pure and...

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C3H6

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C3H6 (molar mass: 42.08 g/mol, exact mass: 42.0470 u) may refer to: Cyclopropane Propylene, also known as propene This set index page lists chemical structure...

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Dextromethorphan

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allosteric modulators: Barbiturates (e.g., pentobarbital, sodium thiopental) Cyclopropane Enflurane Ethanol (alcohol) Evans blue GYKI-52466 GYKI-53655 Halothane...

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