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141038

Sigma-Aldrich

2-Hydroxybenzonitrile

99%

Synonym(s):
2-Cyanophenol, Salicylonitrile
Linear Formula:
NCC6H4OH
CAS Number:
Molecular Weight:
119.12
Beilstein:
1210029
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

99%

form

powder

bp

149 °C/14 mmHg (lit.)

mp

92-95 °C (lit.)

SMILES string

Oc1ccccc1C#N

InChI

1S/C7H5NO/c8-5-6-3-1-2-4-7(6)9/h1-4,9H

InChI key

CHZCERSEMVWNHL-UHFFFAOYSA-N

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Application

2-Hydroxybenzonitrile was used as starting reagent during the synthesis of:
  • mono-alkoxyphenyloxazoline
  • furanoside
2-Hydroxybenzonitrile may be used in the preparation of:
  • methyl-(2-cyanophenoxy)acetate
  • 3-amino-N-phenylbenzofuran-2-carboxamide
  • 2-(2-oxo-2-phenylethoxy)benzonitrile
  • 3-amino-2-cyanobenzo[b]furane
It may also be used as a directing group for meta-selective C-H bond alkenylation.

Packaging

5, 25 g in glass bottle

Pictograms

CorrosionExclamation mark

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Skin Sens. 1B

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

Enantioselective Cu-catalyzed 1, 4-addition of Me3Al to a 4, 4-disubstituted cyclohexa-2, 5-dienone.
Takemoto Y, et al.
Tetrahedron, 52(45), 14177-14188 (1996)
Efficient New Synthesis of N-Arylbenzo [b] furo [3, 2-d] pyrimidin-4-amines and Their Benzo [b] thieno [3, 2-d] pyrimidin-4-amine Analogues via a Microwave-Assisted Dimroth Rearrangement.
Loidreau Y, et al.
Journal of Heterocyclic Chemistry, 50(5), 1187-1197 (2013)
A microwave-assisted multicomponent protocol for the synthesis of benzofuran-2-carboxamides.
Vincetti P, et al.
Tetrahedron Letters, 57(13), 1464-1467 (2016)
meta-Selective arene C-H bond olefination of arylacetic acid using a nitrile-based directing group.
Bera M, et al.
Organic Letters, 16(21), 5760-5763 (2014)
1, 3-Dipolar Cycloaddition in the Preparation of New Fused Heterocyclic Compounds via Thermal Initiation.
Porubsky M, et al.
Molecules (Basel), 21(2), 187-187 (2016)

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