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544396

Sigma-Aldrich

4-Allyloxybenzaldehyde

97%

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About This Item

Linear Formula:
H2C=CHCH2OC6H4CHO
CAS Number:
40663-68-1
Molecular Weight:
162.19
EC Number:
255-027-2
MDL number:
MFCD00014133
UNSPSC Code:
12352100
PubChem Substance ID:
24878731
NACRES:
NA.22

Assay

97%

refractive index

n20/D 1.568 (lit.)

bp

150-152 °C/18 mmHg (lit.)

density

1.058 g/mL at 25 °C (lit.)

SMILES string

C=CCOc1ccc(C=O)cc1

InChI

1S/C10H10O2/c1-2-7-12-10-5-3-9(8-11)4-6-10/h2-6,8H,1,7H2

InChI key

TYNJQOJWNMZQFZ-UHFFFAOYSA-N

General description

4-Allyloxybenzaldehyde can be prepared by reacting 4-hydroxybenzaldehyde and allylbromide in the presence of a base.4 It can undergo chemoselective dithioacetalization in the presence of cobalt(II)chloride.[1]

Application

4-Allyloxybenzaldehyde may be used in the preparation of:
  • 4,6,4′,6′-O-di-4-allyloxybenzylidene-α,α-D-trehalose[2]
  • 3-allyl-4-hydroxybenzaldehyde[3]
  • (±)-4-allyloxymethamphetamine (ALLMA)[4]

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H317

Precautionary Statements

P280

Hazard Classifications

Skin Sens. 1

Storage Class Code

12 - Non 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

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Certificates of Analysis (COA)

Lot/Batch Number
BCBQ5773V
BCBH5424V
BCBF6609V
1438234V
1438234

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Selective mechanism-based inactivation of rat CYP2D by 4-allyloxymethamphetamine.
Lin LY, et al.
Journal of Pharmacology and Experimental Therapeutics, 277(2), 595-603 (1996)
Synthesis and properties of thermoplastic alternating copolymers containing trehalose and siloxane units by hydrosilylation reaction.
Teramoto N, et al.
Polymer Journal, 39(9), 975-975 (2007)
An isomerization-ring-closing metathesis strategy for the synthesis of substituted benzofurans.
van Otterlo WAL, et al.
Tetrahedron, 61(32), 7746-7755 (2005)
Cobalt (II) chloride catalyzed chemoselective thioacetalization of aldehydes.
De SK.
Tetrahedron Letters, 45(5), 1035-1036 (2004)

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