1-Aminopyrene Chemical Properties

Melting point:

115-117 °C (lit.)

Boiling point:

347.82°C (rough estimate)

Density 

1.1227 (rough estimate)

refractive index 

1.8230 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Chloroform (Slightly), Methanol (Sparingly)

form 

Powder

pka

4.32±0.30(Predicted)

color 

Yellow to green

Water Solubility 

Insoluble in water (0.576 mg/L at 25°C).

BRN 

1875737

Stability:

Stable. Incompatible with strong oxidizing agents.

InChIKey

YZVWKHVRBDQPMQ-UHFFFAOYSA-N

CAS DataBase Reference

1606-67-3(CAS DataBase Reference)

NIST Chemistry Reference

1-Aminopyrene(1606-67-3)

EPA Substance Registry System

1-Pyrenamine (1606-67-3)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-40-21/22

Safety Statements 

45-36/37

WGK Germany 

3

RTECS 

UR2275000

TSCA 

Yes

HS Code 

29214990

Toxicity

mouse,LD50,intraperitoneal,250mg/kg (250mg/kg),Archives Internationales de Pharmacodynamie et de Therapie. Vol. 135, Pg. 376, 1962.

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

1-Aminopyrene Usage And Synthesis

Chemical Properties

yellow-green powder

Uses

It acts as a precursor molecule for production of other fluorescent probes such as 1-Azidopyrene, APTS, and N-(1-Pyrene)iodoacetamide.

Uses

1-Aminopyrene is used in the synthesis of novel fluorescent nanoscale ionic silicate platelets for use in bacterial detection and other biosensor applications.

General Description

Colorless crystals. Yellow needles from hexane, melting point 117-8°C.

Reactivity Profile

1-Aminopyrene neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. May generate hydrogen, a flammable gas, in combination with strong reducing agents such as hydrides.

Fire Hazard

1-Aminopyrene is probably combustible.

Synthesis

Under argon protection and magnetic stirring conditions, 1-nitropyrene (1.00 g, 4.0 mmol) was dissolved in 60 mL of ethyl acetate with tin(II) chloride dihydrate (4.35 g, 19.2 mmol) in a 250 mL three-necked round-bottomed flask. The reaction mixture was heated to reflux for 6 hours. After the reaction was completed, it was cooled to room temperature and the pH was adjusted to 8.0 by slowly adding 20% (m/v) aqueous sodium carbonate solution and continued stirring for 1 hour. The reaction mixture was extracted three times with ethyl acetate, the organic phases were combined and dried with anhydrous magnesium sulfate. The desiccant was removed by filtration and the solvent was evaporated under reduced pressure to give a light green solid product 1-aminopyrene 0.80 g (90% yield). The product was characterized by the following data: melting point 115-116 °C (literature value: 115-117 °C); IR (KBr) νmax/cm?1: 3345-3387 (N-H stretching vibration), 3036 (aromatic C-H stretching vibration), 1623-1512 (C=C stretching vibration); 1H NMR (400 MHz, DMSO-d?) δ: 8.24 (d, 1H, J=9.4 Hz, Ar-H), 7.97 (d, 2H, J=7.8 Hz, Ar-H), 7.94 (d, 1H, J=7.8 Hz, Ar-H), 7.89 (d, 1H, J=9.0 Hz, Ar-H), 7.86 (d, 1H, J=8.6 Hz, Ar-H), 7.85 (t, 1H, J=7.6 Hz, Ar-H), 7.69 (d, 1H, J=8.6 Hz, Ar-H), 7.34 (d, 1H, J=8.2 Hz, Ar-H), 6.33 (s, 2H, NH?).

Purification Methods

1-Aminopyrene [1606-67-3] M 217.3, m 117-118o, pK 1 2.91 (50% aqueous EtOH), pK 2 2.77 (50% aqueous EtOH). Crystallise it from hexane. [Beilstein 12 IV 3460.]

References

[1] Analytical Chemistry, 1988, vol. 60, # 3, p. 194 - 199
[2] Organic and Biomolecular Chemistry, 2018, vol. 16, # 41, p. 7663 - 7673
[3] Tetrahedron Letters, 1998, vol. 39, # 40, p. 7243 - 7246
[4] Synthetic Communications, 1991, vol. 21, # 2, p. 161 - 165
[5] Bioorganic and Medicinal Chemistry, 2001, vol. 9, # 3, p. 593 - 605

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