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Key Documents

630748

Sigma-Aldrich

7,8-Dihydroxy-4-methylcoumarin

97%

Synonym(s):

4-Methyldaphnetin

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About This Item

Empirical Formula (Hill Notation):
C10H8O4
CAS Number:
Molecular Weight:
192.17
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Assay

97%

form

solid

mp

242-246 °C (lit.)

storage temp.

2-8°C

SMILES string

CC1=CC(=O)Oc2c(O)c(O)ccc12

InChI

1S/C10H8O4/c1-5-4-8(12)14-10-6(5)2-3-7(11)9(10)13/h2-4,11,13H,1H3

InChI key

NWQBYMPNIJXFNQ-UHFFFAOYSA-N

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Application

Can be used as a fluorescent sensor to monitor the consumption of a boronic acid in a Suzuki cross-coupling reaction. Fluorescence is easily detectable to the naked eye using a standard hand-held long-wave UV lamp (365 nm).

Pictograms

Health hazard

Signal Word

Danger

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Resp. Sens. 1

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Timothy E Barder et al.
Organic letters, 9(1), 137-139 (2006-12-29)
[reaction: see text] Although boronic acids are widely used in metal-catalyzed reactions, it is difficult to assay their consumption. As such, we developed a reversible fluorescent sensor that is activated upon binding a boronic acid. The sensor can be used

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