Allyl alcohol

Allyl alcohol

Names
Preferred IUPAC name Prop-2-en-1-ol
Other names Allyl alcohol 1-Propen-3-ol Vinyl carbinol
Identifiers
CAS Number	107-18-6 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:16605 Y
ChEMBL	ChEMBL234926 Y
ChemSpider	13872989 Y
ECHA InfoCard	100.003.156
KEGG	C02001 Y
PubChem	7858
UNII	3W678R12M0 N
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	58.08 g·mol−1
Appearance	colorless liquid
Odor	mustard-like
Density	0.854 g/ml
Melting point	−129 °C
Boiling point	97 °C (207 °F; 370 K)
Solubility in water	Miscible
Vapor pressure	17 mm Hg
Magnetic susceptibility (χ)	-36.70·10−6 cm3/mol
Hazards
Safety data sheet	External MSDS
EU classification (DSD)	Toxic (T) Dangerous for the environment (N)
R-phrases	R10, R23/24/25, R36/37/38, R50
S-phrases	(S1/2), S36/37/39, S38, S45, S61
NFPA 704	3 3 0
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):
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)
US health exposure limits (NIOSH):
PEL (Permissible)	2 ppm
REL (Recommended)	TWA 2 ppm (5 mg/m3) ST 4 ppm (10 mg/m3) [skin]
IDLH (Immediate danger)	20 ppm
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (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, but 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. Today allyl alcohol can be obtained by many methods. Allyl alcohol is the smallest representative of the allylic alcohols.

Allyl alcohol was first prepared in 1856 by Auguste Cahours and August Hofmann by saponification of allyl iodide. Today allyl alcohol is produced commercially by the Dow and Shell corporations through the hydrolysis of allyl chloride:

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:

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