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Sigma-Aldrich

1-(4-Methylphenyl)-3-buten-1-ol

97%

Synonym(s):

1-p-Tolyl-but-3-en-1-ol

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About This Item

Linear Formula:
CH3C6H4CH(OH)CH2CH=CH2
CAS Number:
24165-63-7
Molecular Weight:
162.23
MDL number:
MFCD03427119
UNSPSC Code:
12352100
PubChem Substance ID:
24879206
NACRES:
NA.22

Assay

97%

refractive index

n20/D 1.5270 (lit.)

bp

253 °C (lit.)

density

0.983 g/mL at 25 °C (lit.)

SMILES string

Cc1ccc(cc1)C(O)CC=C

InChI

1S/C11H14O/c1-3-4-11(12)10-7-5-9(2)6-8-10/h3,5-8,11-12H,1,4H2,2H3

InChI key

RCKGDEZXTBRGHR-UHFFFAOYSA-N

General description

1-(4-Methylphenyl)-3-buten-1-ol (1-p-tolyl-but-3-en-1-ol) is a homoallylic alcohol derivative. It can be prepared by the allylation of 4-methylbenzaldehyde using potassium allyltrifluoroborate in the presence of 18-crown-6. It can undergo Prins cyclization with in the presence of cellulose-sulfonic acid to form the corresponding tetrahydropyran-4-ol.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Cellulose-SO3H as a recyclable catalyst for the synthesis of tetrahydropyranols via Prins cyclization.
Reddy BVS, et al.
Tetrahedron Letters, 51(50), 6511-6515 (2010)
Fernanda C G Barbosa et al.
Molecules (Basel, Switzerland), 17(12), 14099-14110 (2012-11-30)
An efficient method for the allylation of aldehydes containing a broad range of functional groups using potassium allyltrifluoroborate is described. The reaction utilizes a catalytic amount of 18-C-6 in biphasic media under open atmosphere and room temperature to provide the

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