5-Bromofuran-2-carbaldehyde (HCID 600328)

Namen und Bezeichner

Bevorzugter Name: 5-Bromofuran-2-carbaldehyde
IUPAC: 5-bromofuran-2-carbaldehyde
Englischer Name: 5-Bromo-2-furaldehyde
Summenformel: C5H3BrO2
Molmasse: 174.98

Namen und Synonyme

5-bromofuran-2-carbaldehydeRefChem:534041628-757-85-Bromo-2-furaldehyde1899-24-75-Bromofurfural2-Furancarboxaldehyde, 5-bromo-5-bromo-2-furfural5-bromofuran-2-carboxaldehydeMFCD001595015-bromo-furfural2-Furaldehyde, 5-bromo-

Weitere Namen anzeigen

5-Bromo-2-furaldehyde acid5- Bromofural5-Bromo-2-furaL5-Bromofuraldehyde5-bromo-2-furaldehye

5-bromo-furan-2-carbaldehydeFurfural, 5-bromo-5-bromo-2-formylfuran2-Bromofuran-5-carboxaldehydeSTR06646AC-25746SY008053Z57041993

Datenbank-Bezeichner

CAS: 1899-24-7
PubChem CID: 600328
DTXSID: DTXSID40344910
ChEMBL: CHEMBL2335228
EC Number: 628-757-8
Nikkaji: J27.236A

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 1,8
Polarare Oberfläche (TPSA): 30,2 Å²
H-Brücken-Donoren: 0
H-Brücken-Akzeptoren: 2
Frei drehbare Bindungen: 1
Schwere Atome: 8
Formalladung: 0
Komplexität: 94

Physikochemische Eigenschaften

Schmelzpunkt: 82 · 82-85 °C (lit.)
Siedepunkt: 112 °C/16 · 112 °C/16 mmHg (lit.)
Dichte: 1.594 · 1.5940 (rough estimate)
Brechungsindex: 1.445 · 1.4450 (estimate)
Flammpunkt: 112 °C/6mm · 112°C/6mm
storage temp.: 2 · 2-8°C
Löslichkeit: Chloroform, Methanol
Aggregatzustand: Powder
Farbe: Slightly yellow
BRN: 108403 · 108403
Stabilität: Stable. Incompatible with strong oxidizing agents.
InChI: InChI=1S/C5H3BrO2/c6-5-2-1-4(3-7)8-5/h1-3H
InChIKey: WJTFHWXMITZNHS-UHFFFAOYSA-N
SMILES: O1C(Br)=CC=C1C=O
CAS Datenbank: 1899 · 1899-24-7(CAS DataBase Reference)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 5 Einträge

Warning

H302 (95.7%): Harmful if swallowed [Warning Acute toxicity, oral]；H312 (87.2%): Harmful in contact with skin [Warning Acute toxicity, dermal]；H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H332 (87.2%): Harmful if inhaled [Warning Acute toxicity, inhalation]；H335 (97.9%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 47 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Gefahrenhinweise

Hazard Classes and CategoriesAcute Tox. 4 (95.7%)；Acute Tox. 4 (87.2%)；Skin Irrit. 2 (100%)；Eye Irrit. 2 (100%)；Acute Tox. 4 (87.2%)；STOT SE 3 (97.9%)

Sicherheitsdaten

wgk: 3
hs_code: 29130000
risk_code: 20/21/22-36/37/38
hazard_code: Xn,Xi
hazard_note: Harmful
safety_code: 26-36-36/37/39
hazard_class: IRRITANT
Speicherklasse: 11 - Combustible Solids
Hazard Classifications: Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3

Chemie und Industrie

Anwendungen

Verwenden5-Bromo-2-furaldehyde is used in the preparation of isoindolinones from furfural. Also used in the preparation of brominated nitrovinylfuran which displays antibacterial activity.

Darstellung · 1 Eintrag

synthetischeA three-necked 50 mL round bottom flask was charged with [bmim]Br3 (20 mmol) followed by dropwise addition of freshly distilled 2-furfural (20 mmol) over a period of 0.5 h and the reaction mixture was stirred for at 40 ℃ 2.5 h under nitrogen atmosphere. The mixture was extracted with petroleum ether (30 mL × 3), the organic layer was washed with water, dried (sodium sulfate) and concentrated. The crude product was purified by distillation and recrystallization with 10 % ethyl acetate-ether solution. 5-Bromo-2-furfural of yellowish crystal in 88 % yield was obtained. Mp. 82-85 ℃, 1H NMR (CDCl3), δ: 9.55 (s, 1H), 7.25 (s, 1H), 6.57 (s, 1H).