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264598

Sigma-Aldrich

1,4-Benzodioxan-6-carboxaldehyde

98%

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About This Item

Empirical Formula (Hill Notation):
C9H8O3
CAS Number:
29668-44-8
Molecular Weight:
164.16
EC Number:
249-763-3
MDL number:
MFCD00010092
UNSPSC Code:
12352100
PubChem Substance ID:
24856027
NACRES:
NA.22

Assay

98%

form

solid

bp

105 °C/15 mmHg (lit.)

mp

50-52 °C (lit.)

functional group

aldehyde

SMILES string

[H]C(=O)c1ccc2OCCOc2c1

InChI

1S/C9H8O3/c10-6-7-1-2-8-9(5-7)12-4-3-11-8/h1-2,5-6H,3-4H2

InChI key

CWKXDPPQCVWXAG-UHFFFAOYSA-N

Application

1,4-Benzodioxan-6-carboxaldehyde has been used:
  • as building block in the synthesis of tetrahydroisoquinolinones[1]
  • in the preparation of benzofuran analog, a potential inhibitor of CAMP-specific phosphodiesterase type IV[2]
  • in the synthesis of (5Z)-5-(2,3-dihydro-1,4-benzodioxan-6-ylmethylene)-1-methyl-2-thioxoimidazolidin-4-one[3]

Storage Class Code

11 - Combustible Solids

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
16707CI
15611LQ
14128JG
12924MI
09613KZ

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Structure-activity relationships involving the catechol subunit of rolipram.
Stafford JA, et al.
Bioorganic & Medicinal Chemistry Letters, 4(15), 1855-1860 (1994)
Khadidja Bourahla et al.
Molecules (Basel, Switzerland), 16(9), 7377-7390 (2011-09-01)
A practical protocol for the preparation of (5Z)-2-alkylthio-5-arylmethylene-1-methyl-1,5-dihydro-4H-imidazol-4-one derivatives is reported. The new compounds were obtained in good yield and stereoselectivity in two steps, namely a solvent-free Knoevenagel condensation under microwave irradiation, followed by an S-alkylation reaction with various halogenoalkanes.
M Lebl
Bioorganic & medicinal chemistry letters, 9(9), 1305-1310 (1999-05-26)
A new technique for high throughput solid phase synthesis using the centrifuge based liquid removal from readily available standard microtiterplates is described. This technique eliminates the filtration step and is therefore applicable to simultaneous processing of an unlimited number of

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