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| Names | |
|---|---|
| Preferred IUPAC name Prop-2-en-1-ol | |
| Other names Allyl alcohol 2-Propen-1-ol 1-Propen-3-ol[1] Vinyl carbinol[1] Allylic alcohol Weed drench[citation needed] | |
| Identifiers | |
| |
3D model (JSmol) | |
| ChEBI | |
| ChEMBL | |
| ChemSpider |
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| ECHA InfoCard | 100.003.156 |
| EC Number |
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| KEGG |
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| RTECS number |
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| UNII | |
| UN number | 1098 |
| |
| |
| Properties | |
| C3H6O | |
| Molar mass | 58.080 g·mol−1 |
| Appearance | colorless liquid[1] |
| Odor | mustard-like[1] |
| Density | 0.854 g/ml |
| Melting point | −129 °C (−200 °F; 144 K) |
| Boiling point | 97 °C (207 °F; 370 K) |
| Miscible | |
| Vapor pressure | 17 mmHg[1] |
| Acidity (pKa) | 15.5 (H2O)[2] |
| −36.70·10−6 cm3/mol | |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards | Highly toxic, lachrymator |
| GHS labelling: | |
    | |
| Danger | |
| H225,H301,H302,H311,H315,H319,H331,H335,H400 | |
| P210,P233,P240,P241,P242,P243,P261,P264,P270,P271,P273,P280,P301+P310,P302+P352,P303+P361+P353,P304+P340,P305+P351+P338,P311,P312,P321,P322,P330,P332+P313,P337+P313,P361,P362,P363,P370+P378,P391,P403+P233,P403+P235,P405,P501 | |
| NFPA 704 (fire diamond) | |
| Flash point | 21 °C (70 °F; 294 K) |
| 378 °C (712 °F; 651 K) | |
| Explosive limits | 2.5–18.0% |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose) | 80 mg/kg (rat, orally)[3] |
LC50 (median concentration) | 1000 ppm (mammal, 1 hr) 76 ppm (rat, 8 hr) 207 ppm (mouse, 2 hr) 1000 ppm (rabbit, 3.5 hr) 1000 ppm (monkey, 4 hr) 1060 ppm (rat, 1 hr) 165 ppm (rat, 4 hr) 76 ppm (rat, 8 hr)[4] |
| NIOSH (US health exposure limits): | |
PEL (Permissible) | 2 ppm[1] |
REL (Recommended) | TWA 2 ppm (5 mg/m3) ST 4 ppm (10 mg/m3) [skin][1] |
IDLH (Immediate danger) | 20 ppm[1] |
| Safety data sheet (SDS) | External MSDS |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Allyl alcohol (IUPAC name:prop-2-en-1-ol) is anorganic compound with thestructural formulaCH2=CHCH2OH. Like manyalcohols, it is a water-soluble, colourless liquid. It is more toxic than typical small alcohols. Allyl alcohol is used as aprecursor to many specialized compounds such as flame-resistant materials,drying oils, andplasticizers.[5] Allyl alcohol is the smallest representative of theallylicalcohols.
Allyl alcohol is produced commercially by theOlin andShellcorporations through the hydrolysis ofallyl chloride:
Allyl alcohol can also be made by the rearrangement ofpropylene oxide, a reaction that is catalyzed bypotassium alum at high temperature. The advantage of this method relative to the allyl chloride route is that it does not generate salt. Also avoiding chloride-containing intermediates is the "acetoxylation" ofpropylene toallyl acetate:
Hydrolysis of this acetate gives allyl alcohol. In alternative fashion,propylene can be oxidized toacrolein, which uponhydrogenation gives the alcohol.
In principle, allyl alcohol can be obtained bydehydrogenation ofpropanol.
In the laboratory,glycerol reacts withoxalic orformic acids to give (respectively)dioxalin or glyceric formate, either of whichdecarboxylate anddehydrate to allylol.[6][7]
Allyl alcohols in general are prepared byallylic oxidation ofallyl compounds, usingselenium dioxide ororganic peroxides. Other methods include carbon-carbon bond-forming reactions such as thePrins reaction, theMorita-Baylis-Hillman reaction, or a variant of theRamberg-Bäcklund reaction. Hydrogenation ofenones is another route. Some of these methods are achieved by theLuche reduction,Wharton reaction, and theMislow-Evans rearrangement.
Allyl alcohol was first prepared in 1856 byAuguste Cahours andAugust Hofmann byhydrolysis ofallyl iodide.[5] Today aAllyl alcohol can be formed aftertrituration ofgarlic (Allium sativum) cloves (producing from garlic in two ways: firstly by aself-condensation reaction ofallicin and itsdecomposition products such asdiallyl trisulphide anddiallyl disulphide and secondly by thereaction betweenalliin, theprecursor ofallicin, andwater).[8]
Allyl alcohol is converted mainly toglycidol, which is achemical intermediate in the synthesis ofglycerol, glycidyl ethers,esters, andamines. Also, a variety ofpolymerizable esters are prepared from allyl alcohol, e.g. diallylphthalate.[5]
Allyl alcohol hasherbicidal activity and can be used as aweed eradicant[9]) andfungicide.[8]
Allyl alcohol is the precursor in the commercial synthesis ofallyl bromide:[10]
Allyl alcohol ishepatotoxic. Inrats,in vivo, allyl alcohol ismetabolized byliveralcohol dehydrogenase toacrolein, which can causedamage to themicrotubules of rathepatocytemitochondria and depletion ofglutathione.[8] It is significantly more toxic than related alcohols.[5][11] Its threshold limit value (TLV) is 2 ppm. It is alachrymator.[5]
Practical Organic Chemistry Cohen Julius.
