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433985

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
Pricing and availability is not currently available.

Quality Level

200

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[1]
  • anilines, through a novel one-pot, two-step amination/Diels-Alder procedure[2]
  • 5-(5′,8′-dimethyl-9′-tert-butoxycarbonyl-9′H-carbazol-3′-yl)-furan-2-carbaldehyde[3]
  • 5-(6-hydroxyhexyl)-2-furaldehyde[4]
  • 5-methylsulfonyl-2-furaldehyde[5]
  • 5-phenylsulfonyl-2-furaldehyde[5]
  • 5-(4-acetamidobenzylsulfonyl)-2-furaldehyde[5]
  • 5-iodo-2-furaldehyde[6]

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL3898
BCCG3182
BCCC6222
BCBL4639V
BCBG9585V

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Aminomethylations via cross-coupling of potassium organotrifluoroborates with aryl bromides.
Molander GA and Sandrock DL.
Organic Letters, 9(8), 1597-1600 (2007)
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.
A synthesis strategy yielding skeletally diverse small molecules combinatorially.
Burke MD, et al.
Journal of the American Chemical Society, 126(43), 14095-14104 (2004)
Efficient and Simple Synthesis of 6-Aryl-1,4-dimethyl-9H-carbazoles.
Caruso A, et al.
Molecules (Basel), 13(6), 1312-1320 (2008)
Furan derivatives. LXXXV11. The synthesis and ultraviolet spectra of 5-(4-X-phenyIsulfonyI)-2-furaldehydes and 2-cyano-3-[5-(4-X-phenyl-sulfonyl)-2-furyl] acrylonitriles.
Kada R and Kovac J.
Chemical Papers, 30(4), 502-507 (1976)
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