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Sigma-Aldrich

4-Bromomethyl-7-methoxycoumarin

97%

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Synonym(s):
BMC, Br-Mmc
Empirical Formula (Hill Notation):
C11H9BrO3
CAS Number:
35231-44-8
Molecular Weight:
269.09
Beilstein:
187211
EC Number:
252-448-3
MDL number:
MFCD00006869
UNSPSC Code:
12352100
PubChem Substance ID:
24854087
NACRES:
NA.22

Quality Level

200

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)

SMILES string

COc1ccc2C(CBr)=CC(=O)Oc2c1

InChI

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

InChI key

CTENSLORRMFPDH-UHFFFAOYSA-N

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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

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

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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Analytical Letters, 26, 429-429 (1993)
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
Muhammad R Afzal et al.
Circulation research, 117(6), 558-575 (2015-07-15)
Notwithstanding the uncertainties about the outcomes of bone marrow cell (BMC) therapy for heart repair, further insights are critically needed to improve this promising approach. To delineate the true effect of BMC therapy for cardiac repair and gain insights for
Marcelo Sobral-Leite et al.
BMC medicine, 13, 156-156 (2015-07-04)
Annexin A1 (ANXA1) is a protein related with the carcinogenesis process and metastasis formation in many tumors. However, little is known about the prognostic value of ANXA1 in breast cancer. The purpose of this study is to evaluate the association
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
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