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3-Thienylmethylamine

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3-Thienylmethylamine Basic information

Product Name:
3-Thienylmethylamine
Synonyms:
  • RARECHEM AL BW 0778
  • BUTTPARK 121\50-76
  • C-THIOPHEN-3-YL-METHYLAMINE
  • 3-(Aminomethyl)thiophene
  • (3-thienylmethyl)amine(SALTDATA: HCl)
  • Thiophen-3-yl-methylamine
  • (Thien-3-yl)methylamine
  • 3-ThiopheneMethylaMine
CAS:
27757-86-4
MF:
C5H7NS
MW:
113.18
Product Categories:
  • CHIRAL CHEMICALS
Mol File:
27757-86-4.mol
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3-Thienylmethylamine Chemical Properties

Boiling point:
102°C (15 mmHg)
Density 
1.130
refractive index 
1.5660
storage temp. 
under inert gas (nitrogen or Argon) at 2–8 °C
form 
clear liquid
pka
9.57±0.29(Predicted)
color 
Colorless to Light yellow
Water Solubility 
Slightly soluble in water.
Sensitive 
Air Sensitive
InChI
InChI=1S/C5H7NS/c6-3-5-1-2-7-4-5/h1-2,4H,3,6H2
InChIKey
DUDAKCCDHRNMDJ-UHFFFAOYSA-N
SMILES
C1SC=CC=1CN
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Safety Information

Hazard Codes 
C
Risk Statements 
34
Safety Statements 
26-36/37/39-45
RIDADR 
2735
Hazard Note 
Corrosive
HazardClass 
IRRITANT
HazardClass 
8
PackingGroup 
HS Code 
29349990
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3-Thienylmethylamine Usage And Synthesis

Chemical Properties

Colorless liquid

Uses

3-Thiophenemethylamineis an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff.

Synthesis

1641-09-4

27757-86-4

General procedure for the synthesis of 3-aminomethylthiophene from 3-cyanothiophene: Ruthenium(II) complex (1 M) and 2-butanol (5 mL) were added to a 25 mL flask under argon protection and stirred for 5 min at room temperature. Subsequently, KOtBu (0.05 mM) was added and stirring was continued for 5 minutes. Next, 3-cyanothiophene (0.5 mM) was added and the reaction mixture was heated on a hot plate at 120°C for 30 minutes. Upon completion of the reaction, the catalyst was removed by addition of petroleum ether followed by filtration. The filtrate was neutralized with 1 M HCl. The ether layer was purified by short path silica gel column chromatography. Hexadecane was added to the purified filtrate as an internal standard and the yield of the product 3-aminomethylthiophene was determined by gas chromatography (GC).

References

[1] Organic Process Research and Development, 2012, vol. 16, # 1, p. 109 - 116
[2] Chemistry - A European Journal, 2016, vol. 22, # 14, p. 4991 - 5002
[3] Angewandte Chemie - International Edition, 2016, vol. 55, # 47, p. 14653 - 14657
[4] Angew. Chem., 2016, vol. 128, # 47, p. 14873 - 14877,5
[5] Journal of Coordination Chemistry, 2015, vol. 68, # 2, p. 321 - 334

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