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499749

Sigma-Aldrich

2-Benzyloxybenzaldehyde

98%

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About This Item

Linear Formula:
C6H5CH2OC6H4CHO
CAS Number:
5896-17-3
Molecular Weight:
212.24
MDL number:
MFCD00016583
UNSPSC Code:
12352100
PubChem Substance ID:
24873296
NACRES:
NA.22

assay

98%

refractive index

n20/D 1.6 (lit.)

bp

326 °C (lit.)

density

1.339 g/mL at 25 °C (lit.)

SMILES string

O=Cc1ccccc1OCc2ccccc2

InChI

1S/C14H12O2/c15-10-13-8-4-5-9-14(13)16-11-12-6-2-1-3-7-12/h1-10H,11H2

InChI key

PBEJTRAJWCNHRS-UHFFFAOYSA-N

General description

2-Benzyloxybenzaldehyde is a benzaldehyde derivative. It undergoes enantioselective cyanoformylation with ethyl cyanoformate in the presence of a vanadium(V) chiral salen complex and imidazole to form the corresponding cyanohydrin carbonate.[1]

Application

2-Benzyloxybenzaldehyde may be used in the synthesis of:
  • 2-benzyloxy-2′-hydroxy-3′,4′,6′-trimethoxychalcone[2]
  • N2-(2-benzyloxy)benzylidenyl isonicotinic acid hydrazide[3]
  • 2-hydroxy-2′-methoxybenzophenone[4]
  • 2′-hydroxy-5,6,7-trimethoxyflavone[5]

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
08823MH
09909BH
01831CE
03618MD
15409CD

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The synthesis of 5, 2'-dihydroxy-6, 8-dimethoxyflavone and its isomers: A revised structure of skullcapflavone I.
Horie T, et al.
Bulletin of the Chemical Society of Japan, 52(10), 2950-2952 (1979)
Synthesis of 3-ureido derivatives of coumarin and 2-quinolone as potent acyl-CoA: cholesterol acyltransferase inhibitors.
Tawada H, et al.
Chemical & Pharmaceutical Bulletin, 43(4), 616-625 (1995)
Vanadium(V) salen complex catalyzed highly enantioselective cyanoformylation of aldehydes in the presence of imidazole as a cocatalyst.
Khan NH, et al.
European Journal of Organic Chemistry, 2008(26), 4511-4515 (2008)
Michael J Hearn et al.
European journal of medicinal chemistry, 44(10), 4169-4178 (2009-06-16)
Structural modification of the frontline antitubercular isonicotinic acid hydrazide (INH) provides lipophilic adaptations (3-46) of the drug in which the hydrazine moiety of the parent compound has been chemically blocked from the deactivating process of N(2)-acetylation by N-arylaminoacetyl transferases. As
Synthesis and structure-activity relationship of cytotoxic 5,2',5'-trihydroxy-7,8-dimethoxyflavanone analogues.
Min BS, et al.
Archives of Pharmacal Research, 19(6), 543-550 (1996)

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