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260630

Sigma-Aldrich

tert-Butyl isocyanide

98%

Synonym(s):

1,1-Dimethylethyl isocyanide, 1-tert-Butylisonitrile, 2-Isocyano-2-methylpropane, t-Butylisonitrile, tert-Butylisonitrile

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About This Item

Linear Formula:
(CH3)3CNC
CAS Number:
7188-38-7
Molecular Weight:
83.13
Beilstein:
1903156
EC Number:
230-553-5
MDL number:
MFCD00000002
UNSPSC Code:
12352100
PubChem Substance ID:
24855763
NACRES:
NA.22
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Assay

98%

form

liquid

refractive index

n20/D 1.376 (lit.)

bp

91 °C (lit.)

density

0.735 g/mL at 25 °C (lit.)

functional group

amine
isonitrile

SMILES string

CC(C)(C)[N+]#[C-]

InChI

1S/C5H9N/c1-5(2,3)6-4/h1-3H3

InChI key

FAGLEPBREOXSAC-UHFFFAOYSA-N

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General description

Carbon dative bond formation by tert-butyl isocyanide on the germanium (100) surface has been reported[1]. It also forms complexes with metals and inserts into metal-carbon bonds to form iminoacyls[2].

Application

tert-Butyl isocyanide was used in the synthesis of coumarines, 4H-chromenes[3] and isoxazolines[4]. It was also used to trap 2-cyclopropylidene-1,3-diones[5].

Pictograms

FlameSkull and crossbones
GHS02,GHS06

Signal Word

Danger

Hazard Statements

H225,H330

Hazard Classifications

Acute Tox. 2 Inhalation - Flam. Liq. 2

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

28.4 °F - closed cup

Flash Point(C)

-2 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCJ3717
BCCB0126
BCBZ6961
BCBS1379V
BCBM8296V

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Graham A Bowmaker et al.
Dalton transactions (Cambridge, England : 2003), (13)(13), 1710-1720 (2008-03-21)
Single-crystal structural characterizations confirm the existence of the unusual 1 : 4 copper(I) halide : unidentate ligand adducts [Cu(CNt-Bu)4]X for X = Cl, Br (two forms), I (the chloride and one form of the bromide being solvated) with crystal packing
Synthesis of coumarines and 4H-chromenes through the reaction of tert-butyl isocyanide and dialkyl acetylenedicarboxylates in presence of 2-hydroxybenzaldehydes.
Yavari I, et al.
Synthesis, 5, 679-682 (2004)
Journal of the Chemical Society. Chemical Communications, 189-189 (1987)
Habib Nasri et al.
Inorganic chemistry, 43(9), 2932-2942 (2004-04-27)
The addition of the strongly pi-bonding ligands CO or tert-butyl isocyanide to the low-spin five-coordinate iron(II) nitrite species [Fe(TpivPP)(NO2)]- (TpivPP = picket fence porphyrin) gives two new six-coordinate species [Fe(TpivPP)(NO2)(CO)]- and [Fe(TpivPP)(NO2)(t-BuNC)]-. These species have been characterized by single-crystal structure
D Bandyopadhyay et al.
Biochemistry, 35(5), 1500-1505 (1996-02-06)
The kinetics of tert-butyl isocyanide binding to the heme protein horseradish peroxidase (HRP) at 22 degrees C was examined on all time scales, from minutes to picoseconds, in aqueous borate buffer at pH 9.08. Unlike myoglobin (Mb) or hemoglobin, HRP
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Questions

1–3 of 3 Questions  

  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  3. Is the product sealed under an inert atmosphere?

    1 answer

    1. The product 260630-tert-Butyl-isocyanide is packaged in an amber glass bottle with a PTFE liner cap and is sealed under Argon.

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