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7188-38-7 - tert-Butyl isocyanide, 98% - L19747 - Alfa Aesar

L19747 tert-Butyl isocyanide, 98%

CAS Number
7188-38-7
Synonyms

Size Price ($) Quantity Availability
1g 38.90
5g 115.00
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tert-Butyl isocyanide, 98%

MDL
MFCD00000002
EINECS
230-553-5

Chemical Properties

Formula
C5H9N
Formula Weight
83.13
Boiling Point
90-92°
Flash Point
-2°(28°F)
Density
0.735
Refractive Index
1.3755
Solubility
Soluble in organic solvents such as ethanol, methanol, ether, toluene and dichloromethane.

Applications

tert-Butyl isocyanide is used in a tin-free procedure for alkyl radical reactions in the presence of a free-radical initiator. It is a useful intermediate in multicomponent reactions. It is also used in the synthesis of coumarines, 4H-chromenes, isoxazolines and to trap 2-cyclopropylidene-1,3-diones.

Notes

Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Incompatible with oxidizing agents.

Literature References

Bonggeun Shong.; Keith T Wong.; Stacey F Bent. Strong carbon-surface dative bond formation by tert-butyl isocyanide on the Ge(100)-2 × 1 surface. Journal of the American Chemical Society. 2014, 136 (16), 5848-5851.

Jack E. Baldwin.; Stephen B. Haber, Carolyn Hoskins, Lawrence I. Kruse. Synthesis of .beta.,.gamma.-unsaturated amino acids. J. Org. Chem. 1977, 42 (7), 1239-1241.

In the presence of a free-radical initiator, can be used in a tin-free procedure for alkyl radical reactions: Angew. Chem. Int. Ed., 43, 3598 (2004).

Useful intermediate in multicomponent reactions. For example, forms a reactive 1 : 1 adduct with acetylenic esters, e.g. Dimethyl­ acetyl­enedicarboxyl­ate, A11437, which can be trapped with strong C-H acids, such as 4-Hydroxy-6-methyl-2-pyrone, L11457:

GHS Hazard and Precautionary Statements

Hazard Statements: H225-H330

Highly flammable liquid and vapour. Fatal if inhaled.

Precautionary Statements: P210-P303+P361+P353-P304+P340-P320-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Specific treatment is urgent (see label). Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
1903156
Hazard Class
3
Packing Group
II
Harmonized Tariff Code
2929.10
TSCA
No
RTECS
EQ7102500

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