161160

Sigma-Aldrich

α-Bromocinnamaldehyde

98%

Linear Formula:
C6H5CH=C(Br)CHO
CAS Number:
Molecular Weight:
211.06
EC Number:
MDL number:
PubChem Substance ID:
Pricing and availability is not currently available.

Quality Level

assay

98%

mp

66-68 °C (lit.)

storage temp.

2-8°C

SMILES string

Br\C(C=O)=C/c1ccccc1

InChI

1S/C9H7BrO/c10-9(7-11)6-8-4-2-1-3-5-8/h1-7H/b9-6-

InChI key

WQRWNOKNRHCLHV-TWGQIWQCSA-N

General description

α-Bromocinnamaldehyde is commonly employed as an anti-mildew agent in commercial products.

Application

α-Bromocinnamaldehyde was used in the synthesis of 3,4-diaryl 1H-pyrazoles. It was also used in the preparation of spiro imidazolidine-oxazolidine intermediate via guanidinium ylide mediated aziridination.

Packaging

50 g in glass bottle

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Target Organs

Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN 3335

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

S Kojima et al.
Eisei Shikenjo hokoku. Bulletin of National Institute of Hygienic Sciences, (107)(107), 21-25 (1989-01-01)
The amount of alpha-bromocinnamaldehyde (BCA), an anti-mildew agent, in some commercial products, was examined by high performance liquid chromatography (HPLC) using the following conditions: column, Nucleosil 50-5 (Nagel, 250 mm x 4.6 mm i.d.); mobile phase, hexane-chloroform (12:5); flow rate...
Ya Zhang et al.
International immunopharmacology, 14(1), 107-113 (2012-06-20)
Early experiments showed cinnamaldehyde had obvious therapeutic effect on viral myocarditis, but cinnamaldehyde was unstable in vivo. To overcome this limitation, we used cinnamaldehyde as a lead compound to synthesize α-bromo-4-chlorocinnamaldehyde (BCC). In the present study, we compared the therapeutic...
Boris O A Tasch et al.
Organic & biomolecular chemistry, 11(36), 6113-6118 (2013-08-09)
The Masuda borylation-Suzuki coupling (MBSC) sequence was successfully extended to the challenging coupling of vinylhalides with various (hetero)arylhalides using sterically hindered phosphane ligands. Starting from (hetero)arylhalides and α-bromocinnamaldehyde, the sequentially Pd-catalyzed process selectively furnishes α,β-substituted cinnamaldehydes without affecting the reactivity...
J Momma et al.
Eisei Shikenjo hokoku. Bulletin of National Institute of Hygienic Sciences, (107)(107), 29-36 (1989-01-01)
Bromocinnamic aldehyde (BCA), an antibacterial/antifungal agent, was tested for its chronic toxicity/carcinogenicity in female Slc:ddY mice. The animals received 0.25%, 1.0% and 4.0% of BCA dissolved in olive oil applied to the shaved back skin area twice a week for...
Wannaporn Disadee et al.
The Journal of organic chemistry, 71(17), 6600-6603 (2006-08-12)
We successfully isolated a spiro imidazolidine-oxazolidine intermediate in the reaction of guanidinium ylide mediated aziridination using alpha-bromocinnamaldehyde. X-ray crystallographic analysis unambiguously revealed that the stereogenic centers of the spiro intermediate were in a trans configuration. The role of the spiro...

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