1-tert-butyl-4-iodobenzene Chemical Properties

Melting point:

78°C (estimate)

Boiling point:

140 °C

Density 

1.468 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.57(lit.)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder to lump to clear liquid

color 

White or Colorless to Yellow

Specific Gravity

1.468

Sensitive 

Light Sensitive

BRN 

1931810

InChI

InChI=1S/C10H13I/c1-10(2,3)8-4-6-9(11)7-5-8/h4-7H,1-3H3

InChIKey

WQVIVQDHNKQWTM-UHFFFAOYSA-N

SMILES

C1(C(C)(C)C)=CC=C(I)C=C1

CAS DataBase Reference

35779-04-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36

Safety Statements 

26-36

WGK Germany 

3

HazardClass 

LIGHT SENSITIVE

HS Code 

29039990

MSDS

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

1-tert-butyl-4-iodobenzene Usage And Synthesis

Uses

1-T-butyl-3-iodobenzene has wide applications in organic synthesis. It is commonly used as an important intermediate in drug synthesis. For example, it can be used as a key raw material in the synthesis of antiepileptic drugs, antibiotics, and other drugs. Furthermore, 1-tert-butyl-3-iodobenzene can also be used to synthesize aromatic ethers, aromatic amines, and halogenated aromatic hydrocarbons.

Chemical Properties

Clear orange to red liquid

General Description

4-tert-Butyliodobenzene is an electron-rich aryl iodide. Heck reaction between 2-methylprop-2-en-1-ol and 4-tert-butyliodobenzene catalyzed by ionic liquids has been studied. It participates in the one-pot Heck-reductive amination reaction pathway during the synthesis of fungicide fenpropimorph.

Synthesis

GENERAL METHOD: 4-tert-butylphenylboronic acid (0.067 g, 0.4 mmol), copper powder (0.0052 g, 0.08 mmol), (CF3)2CFI (0.178 g, 0.6 mmol), and DMF (2 mL) were added to a hermetically sealed reaction tube with a rubber stopper. The reaction mixture was stirred at room temperature for 24 hours. Upon completion of the reaction, the resulting suspension was poured into water and extracted with ethyl acetate. The organic layers were combined and dried with anhydrous Na2SO4 and subsequently concentrated to dryness under reduced pressure. The crude product was purified by silica gel fast column chromatography using petroleum ether/ethyl acetate (20:1, v/v) as eluent to afford 1-tert-butyl-4-iodobenzene (0.086 g, 0.35 mmol, 87% yield) as a light yellow solid.

References

[1] Journal of Fluorine Chemistry, 2016, vol. 189, p. 59 - 67
[2] Catalysis Communications, 2013, vol. 32, p. 15 - 17
[3] Tetrahedron Letters, 2015, vol. 56, # 9, p. 1122 - 1123

1-tert-butyl-4-iodobenzene(35779-04-5)Related Product Information

• Butylbenzene
• Iodobenzene
• 1-tert-Butyl-2-iodobenzene,1-Iodo-2-tert-butylbenzene
• 3-(TERT-BUTYL DIMETHYLSILOXY) IODOBENZENE
• BIS(4-TERT-BUTYLPHENYL)IODONIUM PERFLUORO-1-BUTANESULFONATE
• BIS(4-TERT-BUTYLPHENYL)IODONIUM P-TOLUENESULFONATE
• BIS(4-TERT-BUTYLPHENYL)IODONIUM TRIFLATE
• 3,5-Dibromo-4-iodo-tert-butylbenzene
• 5-(TERT-BUTYL)-2-IODO-1,3-DIMETHYLBENZENE
• Bis(4-tert-butylphenyl)iodonium perfluoro-1-butanesulfonate
• Bis(4-tert-butylphenyl)iodonium hexafluorophosphate
• 3-Bromo-4-iodo-tert-butylbenzene
• 1-tert-butyl-4-iodobenzene