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Sigma-Aldrich

2-Hydroxybenzonitrile

99%

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Synonym(s):
2-Cyanophenol, Salicylonitrile
Linear Formula:
NCC6H4OH
CAS Number:
611-20-1
Molecular Weight:
119.12
Beilstein:
1210029
EC Number:
210-259-3
MDL number:
MFCD00002145
PubChem Substance ID:
24848487
NACRES:
NA.22

Quality Level

100

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 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.
2-Hydroxybenzonitrile was used as starting reagent during the synthesis of:
  • mono-alkoxyphenyloxazoline
  • furanoside

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302 - H317 - H318

Hazard Classifications

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

Storage Class Code

11 - 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

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Reactivity of 1, 2-cyclic sulfite xylosides towards nucleophiles.
Batoux N, et al.
Tetrahedron, 65(43), 8858-8862 (2009)
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)
A microwave-assisted multicomponent protocol for the synthesis of benzofuran-2-carboxamides.
Vincetti P, et al.
Tetrahedron Letters, 57(13), 1464-1467 (2016)
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)
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