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308188

Sigma-Aldrich

Benzoyl isocyanate

technical grade, 90%

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About This Item

Linear Formula:
C6H5CONCO
CAS Number:
4461-33-0
Molecular Weight:
147.13
EC Number:
224-717-5
MDL number:
MFCD00002032
UNSPSC Code:
12352100
PubChem Substance ID:
24858655
NACRES:
NA.22

grade

technical grade

Quality Level

100

Assay

90%

refractive index

n20/D 1.5514 (lit.)

bp

94-96 °C/21 mmHg (lit.)

density

1.171 g/mL at 25 °C (lit.)

storage temp.

−20°C

SMILES string

O=C=NC(=O)c1ccccc1

InChI

1S/C8H5NO2/c10-6-9-8(11)7-4-2-1-3-5-7/h1-5H

InChI key

LURYMYITPCOQAU-UHFFFAOYSA-N

General description

The reaction mechanism of benzoyl isocyanate with 6-benzyl-6-azabicyclo[2.2.1]hept-2-ene was studied.

Application

Benzoyl isocyanate was used as a capping reagent for low-reactivity hydroxy groups in the solid-phase-supported oligosaccharide synthesis.

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Resp. Sens. 1 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

161.6 °F - closed cup

Flash Point(C)

72 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Cong Zhang et al.
The journal of physical chemistry. A, 114(8), 2913-2919 (2010-02-09)
Reaction mechanisms of the 6-benzyl-6-azabicyclo[2.2.1]hept-2-ene with benzoyl isocyanate have been investigated using density functional theory (DFT) at the B3LYP/6-31G(d,p) level of theory. The reaction proceeding along six competitive channels includes two categories. That is, two channels are formally [3,3]-sigmatropic rearrangements
Xiangyang Wu et al.
The Journal of organic chemistry, 69(6), 1853-1857 (2004-04-03)
Solid-phase-supported oligosaccharide synthesis of a core N-glycan tetrasaccharide and of a trisaccharide containing the Galili antigen is reported. The synthesis is based on a hydroxymethylbenzyl benzoate spacer-linker system attached to the Merrifield resin, O-Fmoc-protected O-glycosyl trichloroacetimidates as glycosyl donors, and
P Madhusudhana Reddy et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 186, 8-16 (2017-06-11)
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