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141038

Sigma-Aldrich

2-Hydroxybenzonitrile

99%

Synonym(s):

2-Cyanophenol, Salicylonitrile

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About This Item

Linear Formula:
NCC6H4OH
CAS Number:
611-20-1
Molecular Weight:
119.12
Beilstein:
1210029
EC Number:
210-259-3
MDL number:
MFCD00002145
UNSPSC Code:
12352100
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

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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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)
Reactivity of 1, 2-cyclic sulfite xylosides towards nucleophiles.
Batoux N, et al.
Tetrahedron, 65(43), 8858-8862 (2009)
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)
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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