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Merck

235202

4-Bromomethyl-7-methoxycoumarin

97%

Synonym(s):

BMC, Br-Mmc

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About This Item

Empirical Formula (Hill Notation):
C11H9BrO3
CAS Number:
35231-44-8
Molecular Weight:
269.09
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24854087
EC Number:
252-448-3
Beilstein/REAXYS Number:
187211
MDL number:
MFCD00006869
Assay:
97%
Form:
solid

Key Documents

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InChI key

CTENSLORRMFPDH-UHFFFAOYSA-N

InChI

1S/C11H9BrO3/c1-14-8-2-3-9-7(6-12)4-11(13)15-10(9)5-8/h2-5H,6H2,1H3

SMILES string

COc1ccc2C(CBr)=CC(=O)Oc2c1

assay

97%

form

solid

mp

213-215 °C (lit.)

solubility

chloroform: soluble 20 mg/mL, clear, colorless to faintly yellow

fluorescence

λex 322 nm; λem 395 nm (after derivatization)

functional group

bromo, ester

Quality Level

200

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Application

4-Bromomethyl-7-methoxycoumarin has been used:
  • as derivatization reagent in determination of 5-fluorouracil (5-FU) in human plasma by HPLC-tandem mass spectrometry
  • as derivatization reagent in fluorescence detection of sodium monofluoroacetate (MFA-Na) in biological samples by HPLC
  • in the synthesis of new caged derivatives of hydrolysis-resistant 8-bromoadenosine cyclic 3′,5′-monophosphate (8-Br-cAMP) and 8-bromoguanosine cyclic 3′,5′-monophosphate (8-Br-cGMP)
  • in TLC and HPLC separation and fluorometric analysis of a wide range of naturally occurring acids, including bile and thromboxane B2
Fluorescent label for fatty acids.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000316436
0000316436
0000131291
0000115676
0000115675

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Analytical Letters, 26, 429-429 (1993)
Brisa S Fernandes et al.
BMC medicine, 13, 289-289 (2015-12-02)
The neurotrophic hypothesis postulates that mood disorders such as bipolar disorder (BD) are associated with a lower expression of brain-derived neurotrophic factor (BDNF). However, its role in peripheral blood as a biomarker of disease activity and of stage for BD
V Hagen et al.
Journal of photochemistry and photobiology. B, Biology, 53(1-3), 91-102 (2000-02-15)
New caged derivatives of hydrolysis-resistant 8-bromoadenosine cyclic 3',5'-monophosphate (8-Br-cAMP) and 8-bromoguanosine cyclic 3',5'-monophosphate (8-Br-cGMP) are described. The compounds are the axial and equatorial isomers of the (7-methoxycoumarin-4-yl)methyl (MCM) esters of cyclic nucleotides. Synthesis is accomplished by treatment of 4-bromomethyl-7-methoxycoumarin with
Joan M Lappe et al.
Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research, 30(1), 156-164 (2014-08-19)
Childhood and adolescence are critical periods of bone mineral content (BMC) accrual that may have long-term consequences for osteoporosis in adulthood. Adequate dietary calcium intake and weight-bearing physical activity are important for maximizing BMC accrual. However, the relative effects of
S Yoshida et al.
Journal of chromatography, 383(1), 61-68 (1986-11-28)
Derivatization of the pyrimidine nucleobases and nucleosides with 4-bromomethyl-7-methoxycoumarin was studied with the aim of developing a sensitive and selective column liquid chromatographic method for these substances in serum. The labeling reactions and the nature of derivatives are discussed, together
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