1-PYRENEBUTYRIC ACID

1-PYRENEBUTYRIC ACID Property

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

Appearance

off white solid

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

Hazard Codes 

Xi

Risk Statements 

36/37/38-50

Safety Statements 

26-36-61

RIDADR 

UN 3077 9/PG 3

WGK Germany 

3

TSCA 

Yes

HS Code 

2916 39 90

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

1-PYRENEBUTYRIC ACID Chemical Properties,Usage,Production

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 free 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