5-Aminoindan Chemical Properties

Melting point:

34-36 °C(lit.)

Boiling point:

247-249 °C745 mm Hg(lit.)

Density 

0.9222 (rough estimate)

refractive index 

1.4600 (estimate)

Flash point:

>230 °F

storage temp. 

0-10°C

pka

5.17±0.20(Predicted)

form 

Crystalline Solid

color 

Brown

Water Solubility 

SLIGHTLY SOLUBLE

BRN 

2082278

InChI

InChI=1S/C9H11N/c10-9-5-4-7-2-1-3-8(7)6-9/h4-6H,1-3,10H2

InChIKey

LEWZOBYWGWKNCK-UHFFFAOYSA-N

SMILES

C1C2=C(C=C(N)C=C2)CC1

CAS DataBase Reference

24425-40-9(CAS DataBase Reference)

NIST Chemistry Reference

5-Aminoindan(24425-40-9)

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22

Safety Statements 

36-36/37

WGK Germany 

3

PackingGroup 

III

HS Code 

29214900

MSDS

• Language:English Provider:5-Indanamine
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

5-Aminoindan Usage And Synthesis

Chemical Properties

brown crystalline mass

Uses

5-Aminoindan was used in the synthesis of ligand 18/18 (2-(5-aminoindan)-6-(5-aminoindan)-4-chloro-s-triazine).

Synthesis

General procedure for the synthesis of 5-aminoindan from 5-nitroindene: To a solution of EtOAc (20 mL) of 5-nitroindene (80.5 mg, 0.5 mmol) was added 10% Pd/C (catalyst dosage of 20% by mass of 5-nitroindene). The mixture was stirred overnight at room temperature in a hydrogen atmosphere. Upon completion of the reaction, the insoluble material was removed by filtration and washed with EtOAc. The filtrate was concentrated to dryness under reduced pressure to give 5-aminoindene (65 mg, 98% yield) as a brown oil. To a solution of 5-aminoindene (150 mg, 0.8 mmol) in thionyl chloride (4 mL) was added a drop of pyridine followed by reflux for 24 hours. At the end of the reaction, the thionyl chloride was removed by distillation to give 5-aminoindene chloride as a light yellow solid, and the product was used directly in the next step of the reaction. A dichloromethane (2 mL) solution of 5-aminoindene chloride was added dropwise to an anhydrous pyridine (2 mL) solution of 5-aminoindene (65 mg, 0.5 mmol) at 0°C. The mixture was stirred at room temperature for 7 h. Methanol was subsequently removed by distillation. The organic layer was treated sequentially with 1N HCl until acidic. The mixture was partitioned between water and EtOAc. The organic layer was washed with saturated brine, dried over anhydrous Na2SO4 and concentrated in vacuum. The residue was purified by silica gel column chromatography (eluent: hexane/EtOAc = 3/1) to afford the target compound 5-aminoindan (118 mg, 80% yield) as a light yellow solid. Melting point 138~142°C; 1H-NMR: δ8.15 (d, J=6.9Hz, 2H), 7.93 (d, J=8.1Hz, 2H), 7.60 (s, 1H), 7.30 (d, J=8.1Hz, 1H), 7.22 (d, J=7.9Hz, 1H), 3.96 (s, 3H), 2.95-2.89 (m. 4H), 2.13-2.07 (m, 2H); ESI-MS: m/z [M+H]+ 296.

Purification Methods

Distil the indane and then crystallise it from pet ether. [Beilstein 12 I 511, 12 III 2798.]

References

[1] Molecules, 2017, vol. 22, # 1,
[2] Justus Liebigs Annalen der Chemie, 1953, vol. 579, p. 133,151
[3] Journal of the Chemical Society, 1947, p. 95

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