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460532

Sigma-Aldrich

2-Iodo-5-methylthiophene

97%

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About This Item

Empirical Formula (Hill Notation):
C5H5IS
CAS Number:
16494-36-3
Molecular Weight:
224.06
MDL number:
MFCD00022492
UNSPSC Code:
12352100
PubChem Substance ID:
24869708
NACRES:
NA.22

Quality Level

100

Assay

97%

refractive index

n20/D 1.626 (lit.)

bp

81-83 °C/10 mmHg (lit.)

density

1.852 g/mL at 25 °C (lit.)

functional group

iodo

storage temp.

2-8°C

SMILES string

Cc1ccc(I)s1

InChI

1S/C5H5IS/c1-4-2-3-5(6)7-4/h2-3H,1H3

InChI key

NAZNQEXKAPLVKC-UHFFFAOYSA-N

General description

2-Iodo-5-methylthiophene is a halogenated thiophene.

Application

2-Iodo-5-methylthiophene may be used for the preparation of:
  • methylbis[2-(5-methyl)thienyl]borane
  • dimethyl-terthienyl
  • 5,5′-dimethy-2,2′-bithienyl

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

192.2 °F - closed cup

Flash Point(C)

89 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCQ3128
MKCP8512
MKCD5989
MKBS7845V
MKBR6610V

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Chromatographic and spectral characteristics of some polythienyls.
Sease JW and Zechmeister L.
Journal of the American Chemical Society, 69(2), 270-273 (1947)
Studies on the Electronic Absorption Spectra of 2, 2'-Bithienyl and Some of Its Derivatives. A Molecular Orbital Treatment.
Abu-Eittah RH and Al-Sugeir FA.
Bulletin of the Chemical Society of Japan, 58(7), 2126-2132 (1985)
Synthesis and Properties of Bis (2-heteroaryl) borane Derivatives.
Kohler T, et al.
European Journal of Inorganic Chemistry, 2002(11), 2942-2946 (2002)
Synthesis and pharmacological evaluation of (Z)-9-(heteroarylmethylene)-7-azatricyclo [4.3. 1.0 3, 7] decanes: Thiophene analogues as potent norepinephrine transporter inhibitors.
Zhou J, et al.
Bioorganic & Medicinal Chemistry Letters, 13(20), 3565-3569 (2003)
Alexander Koch et al.
Dalton transactions (Cambridge, England : 2003), 47(36), 12534-12539 (2018-05-05)
The reduction of 2-bromo- and 3-bromothiophene with calcium powder gives impure thienylcalcium complexes due to interference of various subsequent metalation and calcium-halogen exchange reactions as well as ether degradation. Therefore, calcium-iodine exchange succeeds via the reaction of trimethylsilylmethylcalcium halide with

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