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Sigma-Aldrich

5-Bromo-2-furaldehyde

97%

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About This Item

Empirical Formula (Hill Notation):
C5H3BrO2
CAS Number:
1899-24-7
Molecular Weight:
174.98
MDL number:
MFCD00159501
UNSPSC Code:
12352100
PubChem Substance ID:
24867161
NACRES:
NA.22

Assay

97%

bp

112 °C/16 mmHg (lit.)

mp

82-85 °C (lit.)

storage temp.

2-8°C

SMILES string

Brc1ccc(C=O)o1

InChI

1S/C5H3BrO2/c6-5-2-1-4(3-7)8-5/h1-3H

InChI key

WJTFHWXMITZNHS-UHFFFAOYSA-N

Application

5-Bromo-2-furaldehyde may be employed for the following syntheses:
  • 5-substituted 2-furaldehydes
  • anilines, through a novel one-pot, two-step amination/Diels-Alder procedure
  • 5-(5′,8′-dimethyl-9′-tert-butoxycarbonyl-9′H-carbazol-3′-yl)-furan-2-carbaldehyde
  • 5-(6-hydroxyhexyl)-2-furaldehyde
  • 5-methylsulfonyl-2-furaldehyde
  • 5-phenylsulfonyl-2-furaldehyde
  • 5-(4-acetamidobenzylsulfonyl)-2-furaldehyde
  • 5-iodo-2-furaldehyde

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Classifications

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

Target Organs

Respiratory system

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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Efficient coupling of heteroaryl bromides with arylboronic acids in the presence of a palladium-tetraphosphine catalyst.
Feuerstein M, et al.
Tetrahedron Letters, 42(23), 5659-5662 (2001)
Photochemical coupling between halogenoheterocyclic and heterocyclic derivatives.
D'Agostini A and D'Auria M.
Journal of the Chemical Society. Perkin Transactions 1, 9, 1245-1249 (1994)
Raouf Medimagh et al.
The Journal of organic chemistry, 73(6), 2191-2197 (2008-02-28)
Selective metal-free amination and Diels-Alder reactions are described in the furan series, leading to polysubstituted anilines or to stable oxabicyclic adducts in high yield. Interestingly, anilines are conveniently prepared through a novel one-pot, two-step amination/Diels-Alder procedure from commercially available 5-bromo-2-furaldehyde.
Aminomethylations via cross-coupling of potassium organotrifluoroborates with aryl bromides.
Molander GA and Sandrock DL.
Organic Letters, 9(8), 1597-1600 (2007)
A synthesis strategy yielding skeletally diverse small molecules combinatorially.
Burke MD, et al.
Journal of the American Chemical Society, 126(43), 14095-14104 (2004)
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