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133299

Sigma-Aldrich

Benzyl isocyanide

98%

Synonym(s):

(Isocyanomethyl)benzene, Benzyl isonitrile

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About This Item

Linear Formula:
C6H5CH2NC
CAS Number:
10340-91-7
Molecular Weight:
117.15
EC Number:
233-738-9
MDL number:
MFCD00000004
UNSPSC Code:
12352100
PubChem Substance ID:
24848098
NACRES:
NA.22

assay

98%

refractive index

n20/D 1.521 (lit.)

bp

105-106 °C/75 mmHg (lit.)

density

0.962 g/mL at 25 °C (lit.)

storage temp.

−20°C

SMILES string

[C-]#[N+]Cc1ccccc1

InChI

1S/C8H7N/c1-9-7-8-5-3-2-4-6-8/h2-6H,7H2

InChI key

RIWNFZUWWRVGEU-UHFFFAOYSA-N

Related Categories

General description

Benzyl isocyanide forms phosphaalkene-containing complexes.

Application

Benzyl isocyanide was used in the synthesis of Ru(II) complexes containing hydrazine and benzyl isocyanide ligands. It was used in a three-component coupling process leading to O- and N-arylamides.

Other Notes

May darken in storage

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

174.2 °F - closed cup

flash_point_c

79 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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p-Toluenesulfonylmethyl isocyanide 98%

Sigma-Aldrich

188204

p-Toluenesulfonylmethyl isocyanide

Samantha N MacMillan et al.
Chemical communications (Cambridge, England), (40)(40), 4172-4174 (2007-10-11)
Reaction of (N(3)N)ZrPHPh (N(3)N=N(CH(2)CH(2)NSiMe(3))(3)(3-)) with PhCH(2)N[triple bond]C affords the 1,1-insertion product (N(3)N)Zr[C(PHPh)=NCH(2)Ph], which thermally rearranges to the phosphaalkene-containing complex, (N(3)N)Zr[N(CH(2)Ph)C(H)=PPh].
Laurent El Kaïm et al.
The Journal of organic chemistry, 72(11), 4169-4180 (2007-04-26)
The use of Smiles rearrangement in Ugi- and Passerini-type couplings with electron-deficient phenols allows very straightforward multicomponent formation of O-aryl- and N-arylamides. Best yields were observed with the highly activated o- and p-nitrophenols, salicylic derivatives giving adducts in lower yields.
Synthesis and X-ray studies of ruthenium (II) complexes containing hydrazine and benzyl isocyanide ligands.
Owalude SO, et al.
Bulletin of the Chemical Society of Ethiopia, 27(3), 405-411 (2013)
Zeinab Faghih et al.
Iranian journal of pharmaceutical research : IJPR, 19(3), 134-143 (2021-03-09)
The complex [(PhCH2NC)AuCl], 1, was prepared by the reaction of [(Me2S)AuCl], A, with an equimolar amount of benzyl isocyanide (PhCH2NC) ligand. Through a salt metathesis reaction, the chloride ligand in 1 was replaced by potassium benzothiazole-2-thiolate (Kbt) and potassium benzoimidazole-2-thiolate
Ben J Tickner et al.
Chemical science, 10(20), 5235-5245 (2019-06-14)
We report the formation of a series of novel [Ir(H)2(IMes)(α-13C2-carboxyimine)L] complexes in which the identity of the coligand L is varied. When examined with para-hydrogen, complexes in which L is benzylamine or phenethylamine show significant 1H hydride and 13C2 imine
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