2-IODO-1 3-DIMETHOXYBENZENE 97

2-IODO-1 3-DIMETHOXYBENZENE 97 Property

Melting point:

105-106 °C(lit.)

Boiling point:

287℃

Density 

1.655

Flash point:

127℃

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

crystalline powder

color 

Yellow

Safety

Hazard Codes 

T

Risk Statements 

25-36-43

Safety Statements 

26-36/37-45

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

HazardClass 

6.1

PackingGroup 

Ⅲ

HS Code 

2909309090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H301Toxic if swalloed

H317May cause an allergic skin reaction

H319Causes serious eye irritation

Precautionary statements

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.

2-IODO-1 3-DIMETHOXYBENZENE 97 Chemical Properties,Usage,Production

Synthesis

General procedure for the synthesis of 2-iodo-1,3-dimethoxybenzene from 1,3-dimethoxybenzene: To a solution of 1,3-dimethoxybenzene (25 g, 180 mmol) in ether (150 mL) was slowly added butyllithium (112.5 mL 1.6 M hexane solution, 180 mmol). The reaction mixture was stirred for 30 hours and then cooled to -35°C. Iodine (45.7 g, 180 mmol) was added and the reaction mixture was stirred at 20 °C for 24 h, then poured into 10% aqueous sodium bisulfite solution (60 mL). The aqueous phase was separated and extracted with ethyl acetate (2 x 60 mL). The organic extracts were combined, washed sequentially with saturated aqueous sodium thiosulfate (60 mL), brine (60 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuum. Purification of the product by crystallization (diethyl ether) afforded 2-iodo-1,3-dimethoxybenzene (34 g, 71%) as a white solid; melting point 105-106 °C (literature value 104 °C) [1]; 1H NMR (CDCl3): δ 3.80 (s, 6H), 6.43 (d, J=8.4 Hz, 2H), 7.17 (t, J=8.4 Hz, 1H) ; 13C NMR (CDCl3): δ 56.6, 76.3, 103.9, 129.8, 159.5; analytical calculated values for C8H9IO2: C, 36.39; H, 3.44; measured values: C, 36.40; H, 3.46.

References

[1] Tetrahedron, 2010, vol. 66, # 46, p. 8904 - 8910
[2] Journal of the American Chemical Society, 2007, vol. 129, # 49, p. 15102 - 15103
[3] Organic and Biomolecular Chemistry, 2007, vol. 5, # 15, p. 2433 - 2440
[4] Journal of the American Chemical Society, 2004, vol. 126, # 34, p. 10526 - 10527
[5] Journal of the American Chemical Society, 2007, vol. 129, # 7, p. 1921 - 1930