2-IODO-9H-FLUORENE Chemical Properties

Melting point:

126-129 °C

Boiling point:

375.6±21.0 °C(Predicted)

Density 

1.714±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder to crystal

color 

White to Orange to Green

InChI

InChI=1S/C13H9I/c14-11-5-6-13-10(8-11)7-9-3-1-2-4-12(9)13/h1-6,8H,7H2

InChIKey

VNYQUOAQPXGXQO-UHFFFAOYSA-N

SMILES

C1C2=C(C=CC=C2)C2=C1C=C(I)C=C2

Safety Information

Hazard Codes 

N,Xi

Risk Statements 

51/53

Safety Statements 

61

RIDADR 

UN 3077 9/PG 3

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

9

PackingGroup 

III

HS Code 

29039990

MSDS

• Language:English Provider:SigmaAldrich

2-IODO-9H-FLUORENE Usage And Synthesis

Chemical Properties

White powder

Synthesis

Example 1 Synthesis of 2-iodofluorene: 90 mL of glacial acetic acid and 90 mL of water were added to a 300 mL four-necked flask, followed by the addition of 41.6 g (0.25 mole) of fluorene. Under vigorous stirring, 12.7 g (0.10 mol) of iodine, 1.93 g (0.018 mol) of sodium chlorate and 4.5 mL of concentrated sulfuric acid were added sequentially. The reaction mixture was refluxed at 85 to 90 °C for 30 min, followed by warming to 95 to 100 °C to continue refluxing for 30 min. Upon completion of the reaction, the reaction mixture was extracted with 55 mL of toluene. The organic layer was washed sequentially with 5% aqueous sodium thiosulfate solution and 50 mL of 20% brine solution. 216 mL of methanol was added to the organic layer and the mixture was crystallized at an internal temperature of 25 to 30 °C for 2 h. The crystals were collected by filtration. The crude product was washed with 76 mL of methanol, and 24.8 g (yield: 84.8%) of 2-iodofluorene was obtained as white crystals after drying.HPLC analytical conditions: the column was YMC-A-312, the detection wavelength was 254 nm, the flow rate was 1.0 mL/min, the eluent was methanol/water (9:1, v/v/v), and the buffer was a solution containing 0.1% triethylamine and acetic acid. The analytical results showed that the product composition was 1.3% fluorene, 98.4% 2-iodofluorene and 0.02% 2,7-diiodofluorene.

References

[1] Bulletin of the Chemical Society of Japan, 1989, vol. 62, # 2, p. 439 - 443
[2] New Journal of Chemistry, 2015, vol. 39, # 5, p. 4086 - 4092
[3] Patent: US6437203, 2002, B1
[4] Organic Electronics: physics, materials, applications, 2014, vol. 15, # 7, p. 1324 - 1337
[5] Journal of Materials Chemistry, 2012, vol. 22, # 12, p. 5319 - 5329

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