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Allyl chloride information


Allyl chloride
Names
Preferred IUPAC name
3-Chloroprop-1-ene
Other names
3-Chloropropene
1-Chloro-2-propene[1]
3-Chloropropylene[1]
Identifiers
CAS Number
  • 107-05-1 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:82379
ChEMBL
  • ChEMBL451126 checkY
ChemSpider
  • 13836674 checkY
ECHA InfoCard 100.003.144 Edit this at Wikidata
EC Number
  • 209-675-8
KEGG
  • C19316
PubChem CID
  • 7850
RTECS number
  • UC7350000
UNII
  • V2RFT0R50S ☒N
UN number 1100
CompTox Dashboard (EPA)
  • DTXSID4039231 Edit this at Wikidata
InChI
  • InChI=1S/C3H5Cl/c1-2-3-4/h2H,1,3H2 checkY
    Key: OSDWBNJEKMUWAV-UHFFFAOYSA-N checkY
  • InChI=1/C3H5Cl/c1-2-3-4/h2H,1,3H2
    Key: OSDWBNJEKMUWAV-UHFFFAOYAQ
SMILES
  • C=CCCl
Properties
Chemical formula
C3H5Cl
Molar mass 76.52 g·mol−1
Appearance Colorless, brown, yellow, or purple liquid[1]
Odor pungent, unpleasant[1]
Density 0.94 g/mL
Melting point −135 °C (−211 °F; 138 K)
Boiling point 45 °C (113 °F; 318 K)
Solubility in water
0.36 g/100 ml (20 °C)
Solubility soluble in ether, acetone, benzene, chloroform
Vapor pressure 295 mmHg[1]
Refractive index (nD)
1.4055
Viscosity 0.3130 mPa·s[2]
Hazards
GHS labelling:
Pictograms
GHS02: FlammableGHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Signal word
Danger
Hazard statements
H225, H302, H312, H315, H319, H332, H335, H341, H351, H373, H400
Precautionary statements
P201, P202, P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P273, P280, P281, P301+P312, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P308+P313, P312, P314, P321, P322, P330, P332+P313, P337+P313, P362, P363, P370+P378, P391, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
3
3
1
Flash point −32 °C (−26 °F; 241 K)
Autoignition
temperature
390 °C (734 °F; 663 K)
Explosive limits 2.9–11.2%
Lethal dose or concentration (LD, LC):
LC50 (median concentration)
11000 mg/m3 (rat, 2 hr)
11500 mg/m3 (mouse, 2 hr)
5800 mg/m3 (guinea pig, 2 hr)
22500 mg/m3 (rabbit, 2 hr)
10500 mg/m3 (cat, 2 hr)[3]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 1 ppm (3 mg/m3)[1]
REL (Recommended)
TWA 1 ppm (3 mg/m3)
ST 2 ppm (6 mg/m3)[1]
IDLH (Immediate danger)
250 ppm[1]
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

Allyl chloride is the organic compound with the formula CH2=CHCH2Cl. This colorless liquid is insoluble in water but soluble in common organic solvents. It is mainly converted to epichlorohydrin, used in the production of plastics. It is a chlorinated derivative of propylene. It is an alkylating agent, which makes it both useful and hazardous to handle.[4]

  1. ^ a b c d e f g h NIOSH Pocket Guide to Chemical Hazards. "#0018". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ Viswanath, D.S.; Natarajan, G. (1989). Data Book on the Viscosity of Liquids. Hemisphere Publishing Corporation. ISBN 0-89116-778-1.
  3. ^ "Allyl chloride". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  4. ^ Cite error: The named reference Ullmann was invoked but never defined (see the help page).

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Allyl chloride

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Allyl chloride is the organic compound with the formula CH2=CHCH2Cl. This colorless liquid is insoluble in water but soluble in common organic solvents...

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Allyl group

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or of everyday importance, for example, allyl chloride. Allylation is any chemical reaction that adds an allyl group to a substrate. A site adjacent to...

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Allyl bromide

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alkylating agent. Allyl bromide is more reactive but more expensive than allyl chloride, and these considerations guide its use. Allyl bromide is produced...

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Allyl alcohol

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allyl chloride route is that it does not generate salt. Also avoiding chloride-containing intermediates is the "acetoxylation" of propylene to allyl acetate:...

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Cyclopropene

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the adduct of cycloheptatriene and dimethyl acetylenedicarboxylate. Allyl chloride undergoes dehydrohalogenation upon treatment with the base sodium amide...

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Allyl isothiocyanate

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extender in food packaging.: 118–120  Allyl isothiocyanate is produced commercially by the reaction of allyl chloride and potassium thiocyanate: CH2=CHCH2Cl...

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Epichlorohydrin

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and elastomers. Epichlorohydrin is traditionally manufactured from allyl chloride in two steps, beginning with the addition of hypochlorous acid, which...

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Allyl acetate

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and a green chemical. Allyl alcohol is also produced primarily from allyl chloride, but production via the hydrolysis of allyl acetate route avoids the...

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Allyl methyl sulfide

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breath" is attributed to its presence. It is prepared by the reaction of allyl chloride with sodium hydroxide and methanethiol. CH2=CHCH2Cl + NaOH (aq) + CH3SH...

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Allylpalladium chloride dimer

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tetrachloropalladate (prepared from palladium(II) chloride and sodium chloride), and allyl chloride. 2 Na2PdCl4   +   2 CH2=CHCH2Cl   +   2 CO   +   2 H2O...

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Chlorine

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methylene chloride, chloroform, vinylidene chloride, trichloroethylene, perchloroethylene, allyl chloride, epichlorohydrin, chlorobenzene, dichlorobenzenes...

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Allyl halide

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Allyl halides are organic halides containing an allyl group. Allyl halides include: Allyl chloride Allyl bromide Allyl iodide Allyl fluoride [Wikidata]...

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Propargyl chloride

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lacrymator. It is an alkylating agent that is used in organic synthesis. Allyl chloride Propargyl Propargyl alcohol *Merck Index, 11th Edition, 7820 M. Olomucki...

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Allylamine

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are produced by the treating allyl chloride with ammonia followed by distillation. Or by the reaction of allyl chloride with Hexamine. Pure samples can...

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Petrochemical

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ethers – from the condensation of glycols acrylic acid acrylic polymers allyl chloride epichlorohydrin – chloro-oxirane; used in epoxy resin formation epoxy...

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Sorbic acid

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hexadienoic acids, which are available via a nickel-catalyzed reaction of allyl chloride, acetylene, and carbon monoxide. The route used commercially, however...

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PolyDADMAC

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Calgon Corp. The monomer DADMAC is formed by reacting two equivalents of allyl chloride with dimethylamine. PolyDADMAC is then synthesized by radical polymerization...

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Hydrogen bromide

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precursors to fatty amine derivatives. Related free radical additions to allyl chloride and styrene give 1-bromo-3-chloropropane and phenylethylbromide, respectively...

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Amphetamine

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reactions. One example is the Friedel–Crafts alkylation of benzene by allyl chloride to yield beta chloropropylbenzene which is then reacted with ammonia...

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Allylmagnesium bromide

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hexadiene. Allyl chloride can also be used in place of the bromide to give allylmagnesium chloride. These reagents are used to prepare metal allyl complexes...

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Allyl iodide

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before decomposition into free iodine becomes apparent. Allyl Allyl alcohol Allyl bromide Allyl chloride Bertleff, Werner (2000). "Carbonylation". Ullmann's...

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Methallyl chloride

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colorless liquid and a lacrymator. Its properties are similar to those of allyl chloride. It is a strong alkylating agent used to install isobutenyl groups....

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Zinc chloride

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Zinc chloride is the name of inorganic chemical compounds with the formula ZnCl2·nH2O, with n ranging from 0 to 4.5, forming hydrates. Zinc chloride, anhydrous...

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Glycerol

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Epichlorohydrin is the most important precursor. chlorination of propylene gives allyl chloride, which is oxidized with hypochlorite to dichlorohydrin, which reacts...

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Vinyl group

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vinylogous: In allyl compounds, where the next carbon is saturated but substituted once, allylic rearrangement and related reactions are observed. Allyl Grignard...

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Molybdenum hexacarbonyl

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serves as a source of "Mo(CO)3". For instance treatment with allyl chloride gives [MoCl(allyl)(CO)2(MeCN)2], whereas treatment with KTp and sodium cyclopentadienide...

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