Allyl alcohol

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
Identifiers
CAS Number	107-18-6 Y
3D model (JSmol)	Interactive image
3DMet	B00381
ChEBI	CHEBI:16605 Y
ChEMBL	ChEMBL234926 Y
ChemSpider	13872989 Y
ECHA InfoCard	100.003.156
EC Number	203-470-7
KEGG	C02001 Y
PubChem CID	7858
RTECS number	BA5075000
UNII	3W678R12M0 N
UN number	1098
CompTox Dashboard (EPA)	DTXSID8020044
InChI InChI=1S/C3H6O/c1-2-3-4/h2,4H,1,3H2 Y Key: XXROGKLTLUQVRX-UHFFFAOYSA-N Y InChI=1/C3H6O/c1-2-3-4/h2,4H,1,3H2 Key: XXROGKLTLUQVRX-UHFFFAOYAC
SMILES C=CCO
Properties
Chemical formula	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
Boiling point	97 °C (207 °F; 370 K)
Solubility in water	Miscible
Vapor pressure	17 mmHg[1]
Acidity (pKa)	15.5 (H2O)[2]
Magnetic susceptibility (χ)	-36.70·10−6 cm3/mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Highly toxic, lachrymator
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H225, H301, H302, H311, H315, H319, H331, H335, H400
Precautionary statements	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)	3 3 1
Flash point	21 °C (70 °F; 294 K)
Autoignition temperature	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 their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Allyl alcohol (IUPAC name: prop-2-en-1-ol) is an organic compound with the structural formula CH₂=CHCH₂OH. Like many alcohols, it is a water-soluble, colourless liquid. It is more toxic than typical small alcohols. Allyl alcohol is used as a raw material for the production of glycerol, but is also used as a precursor to many specialized compounds such as flame-resistant materials, drying oils, and plasticizers.^[5] Allyl alcohol is the smallest representative of the allylic alcohols.

Production

Allyl alcohol can be obtained by many methods. It was first prepared in 1856 by Auguste Cahours and August Hofmann by hydrolysis of allyl iodide.^[5] Today allyl alcohol is produced commercially by the Olin and Shell corporations through the hydrolysis of allyl chloride:

${\displaystyle {\ce {CH2=CHCH2Cl + NaOH -> CH2=CHCH2OH + NaCl))}$

Allyl alcohol can also be made by the rearrangement of propylene oxide, a reaction that is catalyzed by potassium 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" of propylene to allyl acetate:

${\displaystyle {\ce {CH2=CHCH3 + 1/2 O2 + CH3COOH -> CH2=CHCH2OCOCH3 + H2O))}$

Hydrolysis of this acetate gives allyl alcohol. In alternative fashion, propylene can be oxidized to acrolein, which upon hydrogenation gives the alcohol.

Other methods

In principle, allyl alcohol can be obtained by dehydrogenation of propanol. In the laboratory, it has been prepared by the reaction of glycerol with oxalic or formic acids.^[6][7] Allyl alcohols in general can be prepared by allylic oxidation of allyl compounds by selenium dioxide.

Applications

Allyl alcohol is converted mainly to glycidol, which is a chemical intermediate in the synthesis of glycerol, glycidyl ethers, esters, and amines. Also, a variety of polymerizable esters are prepared from allyl alcohol, e.g. diallyl phthalate.^[5]

Safety

Allyl alcohol is more toxic than related alcohols. Its threshold limit value (TLV) is 2 ppm. It is a lachrymator.^[5]

It is classified as an extremely hazardous substance in the United States as defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.^[8]