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Key Documents

133280

Sigma-Aldrich

Butyl isocyanide

97%

Synonym(s):

1-Butylisonitrile, 1-Isocyanobutane, Butyl isonitrile, n-Butyl isocyanide, n-Butyl isonitrile

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About This Item

Linear Formula:
CH3(CH2)3NC
CAS Number:
Molecular Weight:
83.13
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

97%

form

liquid

refractive index

n20/D 1.396 (lit.)

density

0.795 g/mL at 25 °C (lit.)

functional group

amine
isonitrile

storage temp.

2-8°C

SMILES string

CCCC[N+]#[C-]

InChI

1S/C5H9N/c1-3-4-5-6-2/h3-5H2,1H3

InChI key

FSBLVBBRXSCOKU-UHFFFAOYSA-N

Application

Butyl isocyanide was used to study the crystal structure of carbon monoxide dehydrogenases-II isolated from Carboxydothermus hydrogenoformans. It was used to probe the mechanism of NO activation of the hemoprotein soluble guanylate cyclase. .

Biochem/physiol Actions

Butyl isocyanide forms complex with ferric and ferrous iron of the heme in cytochrome P450.

Other Notes

May form haziness and/or precipitate with no loss in purity.

Pictograms

FlameExclamation mark

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Flam. Liq. 2

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

69.8 °F - closed cup

Flash Point(C)

21 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Y Imai et al.
Biochimica et biophysica acta, 1337(1), 66-74 (1997-01-04)
Heme-external ligand interactions of P-450nor were examined spectrophotometrically and compared with those of other P-450s. Most nitrogenous ligands induced type II spectral changes on binding to ferric P-450nor, as did other P-450s. In contrast with other P-450s, 2-methylpyridine and 1-butanol
Akira Ikezaki et al.
Chemical communications (Cambridge, England), (19)(19), 2257-2259 (2008-05-09)
Addition of tert-butylisocyanide (tBuNC) to a CD2Cl2 solution of the bis(perchlorato)(meso-tetramesitylporphyrinato) iron(III) cation radical leads to the formation of the corresponding bis(adduct), [Fe(TMP)(tBuNC)2]2+, whose electronic structure is in sharp contrast to that of the corresponding imidazole(HIm) complex, [Fe(TMP)(HIm)2]2+; the former
T H Tahirov et al.
Nature structural biology, 3(5), 459-464 (1996-05-01)
We have determined the structure of n-butylisocyanide-bound Rhodobacter capsulatus cytochrome c'. This is the first example of a ligand-bound structure of a class IIa cytochrome c. Compared with the structure of native cytochrome c', there are significant conformational changes of
C Mouro et al.
European journal of biochemistry, 267(1), 216-221 (1999-12-22)
An 1H-NMR study of ferric cytochrome P450cam in different paramagnetic states was performed. Assignment of three heme methyl resonances of the isocyanide adduct of cytochrome P450 in the ferric low-spin state was recently performed using electron exchange in the presence
D Barrick et al.
Biochemistry, 40(13), 3780-3795 (2001-04-13)
The linkage between the proximal histidines and the proximal polypeptide in normal adult human hemoglobin (Hb A) has been proposed to play a major role in transmitting allosteric effects between oxygen binding sites [Perutz, M. F. (1970) Nature 228, 726-734].

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