| Identification | More | [Name]
1-PYRENEBUTYRIC ACID | [CAS]
3443-45-6 | [Synonyms]
1-PYRENEBUTANOIC ACID
1-PYRENEBUTYRIC ACID
4-(1-PYRENYL)BUTYRIC ACID
4-(PYRENE-1-YL)-N-BUTYRIC ACID
1-pyrenebutyrate
pyrene-1-butyric acid
1-PYRENEBUTYRIC ACID, FOR FLUORESCENCE
1-Pyrenebutyricacid,97%
Pyrene-3-butyric acid.
1-Pyrenylbutyric acid
4-(Pyren-1-yl)butyric acid
4-(Pyrene-1-yl)butanoic acid
4-(Pyrene-3-yl)butanoic acid | [EINECS(EC#)]
222-354-7 | [Molecular Formula]
C20H16O2 | [MDL Number]
MFCD00004141 | [Molecular Weight]
288.34 | [MOL File]
3443-45-6.mol |
| Chemical Properties | Back Directory | [Appearance]
Pale yellow or yellow-beige crystalline powder | [Melting point ]
184-186 °C (lit.) | [Boiling point ]
370.57°C (rough estimate) | [density ]
1.1742 (rough estimate) | [refractive index ]
1.4800 (estimate) | [storage temp. ]
Store below +30°C. | [solubility ]
DMSO (Slightly), Methanol (Slightly, Heated) | [form ]
Crystalline Powder | [pka]
4.76±0.10(Predicted) | [color ]
Pale yellow or yellow-beige | [Water Solubility ]
Partially soluble in water. | [BRN ]
2140554 | [InChI]
InChI=1S/C20H16O2/c21-18(22)6-2-3-13-7-8-16-10-9-14-4-1-5-15-11-12-17(13)20(16)19(14)15/h1,4-5,7-12H,2-3,6H2,(H,21,22) | [InChIKey]
QXYRRCOJHNZVDJ-UHFFFAOYSA-N | [SMILES]
C1(CCCC(O)=O)=C2C3=C4C(C=C2)=CC=CC4=CC=C3C=C1 | [CAS DataBase Reference]
3443-45-6(CAS DataBase Reference) | [EPA Substance Registry System]
1-Pyrenebutanoic acid (3443-45-6) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [RIDADR ]
UN 3077 9/PG 3 | [WGK Germany ]
3
| [TSCA ]
Yes | [HS Code ]
29163990 |
| Hazard Information | Back Directory | [Description]
Pyrenylbutyric acid is a derivative of pyrene hydrocarbon with a free carboxylic acid function. The reagent is useful as a control for experiments with other reactive pyrene derivatives such as pyrene NHS ester and pyrene azide. Carboxylic acid function can be activated by carbodiimides and other activating reagents. | [Chemical Properties]
Pale yellow or yellow-beige crystalline powder | [Uses]
1-Pyrenebutyric Acid is a fluorescent probe used to study proteins, lipids, nucleic acids and other biological systems. The fluorescence lifetime of 1-Pyrenebutyric Acid depends on local oxygen and fr
ee radical concentration. | [General Description]
1-Pyrenebutyric acid (PBA) is a conjugated polymer that has a large π system and a carboxylic group. It is majorly used in surface functionalization. It has a high fluorescence efficiency and stability that make it useful in optoelectronic applications. | [Synthesis]
General procedure for the synthesis of 1-pyrenylbutyric acid from 4-oxo-4-(pyren-1-yl)butyric acid: 1 g (2.78 mmol) of 4-oxo-4-(pyren-1-yl)butyric acid was dissolved in 30 mL of diethylene glycol, to which were added 0.59 g (10 mmol) of hydrazine hydrate and 0.56 g (10 mmol) of KOH.The reaction mixture was heated and refluxed for 2 h. The reaction mixture was subsequently poured into ice hydrochloric acid (25%) to produce a yellow precipitate. The solid was collected by filtration and recrystallized from ethanol to give 570 mg (71% yield) of 4-(pyrene-1-yl)butanoic acid. Molecular formula C20H16O2, molecular weight 288 g/mol. EI-MS: m/z (%) = 289 (16) [MH+], 288 (62) [M], 216 (20), 215 (100), 213 (11). High-resolution EI-MS (C20H16O2): calculated value 288.1150; measured value 288.1150.1H-NMR ([D6]-DMSO): δ (ppm) = 8.50-7.92 (9H, m, CHarom), 3.36 (2H, m, CH2C16H9), 2.41 (2H, m, CH2CO2H), 2.04 (2H, m, CH2CO2H), 2.04 (2H, m, CH2CO2H). 2.04 (2H, m, CH2).1H-NMR (CDCl3): δ (ppm) = 8.32-7.86 (9H, m, CHarom), 3.42 (2H, t, CH2C16H9, 3JHH = 7.57 Hz), 2.51 (2H, t, CH2CO2H, 3JHH = 7.00 Hz), 2.23 (2H, m, CH2, 3JHH = 7.00 Hz), 2.23 (2H, m, CH2, 3JHH = 3JHH). m, CH2, 3JHH = 7.57Hz, 3JHH = 7.00Hz).13C-NMR ([D6]-DMSO): δ (ppm) = 174.74 (1CO), 136.39-123.39 (9 CHarom, 7 Carom), 33.64-26.98 (1CH2CO2H, 2CH2).13C- NMR (CDCl3): δ (ppm) = 177.48 (1CO), 135.25-123.04 (9 CHarom, 7 Carom), 33.21-26.46 (1CH2CO2H, 2CH2).IR (KBr): ν (cm-1) = 3447w, 3037w, 2950m, 2934w, 2874w, 1695s, ν (cm-1) 2874w, 1695s, 1431w, 1275m, 1206m, 918w, 846s, 711w. | [Purification Methods]
Crystallise the butyric acid from *benzene, EtOH, EtOH/water (7:3 v/v) or *C6H6/AcOH. Dry it over P2O5. [Chu & Thomas J Am Chem Soc 108 6270 1986, Beilstein 9 IV 2731.] | [References]
[1] Patent: US7301043, 2007, B2. Location in patent: Page/Page column 7-8
[2] ACS Catalysis, 2016, vol. 6, # 11, p. 7398 - 7408
[3] New Journal of Chemistry, 2008, vol. 32, # 8, p. 1438 - 1448
[4] Journal of the American Chemical Society, 1941, vol. 63, p. 1682,1684
[5] Justus Liebigs Annalen der Chemie, 1937, vol. 531, p. 1,128 | [Abs/Em Maxima]
343; 326; 313; 276; 265; 242; 234/377; 397 nm |
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