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Sigma-Aldrich

Benzoylacetonitrile

99%

Synonym(s):

β-Oxohydrocinnamonitrile

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About This Item

Linear Formula:
C6H5COCH2CN
CAS Number:
Molecular Weight:
145.16
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

99%

form

solid

bp

160 °C/10 mmHg (lit.)

mp

82-83 °C (lit.)

SMILES string

O=C(CC#N)c1ccccc1

InChI

1S/C9H7NO/c10-7-6-9(11)8-4-2-1-3-5-8/h1-5H,6H2

InChI key

ZJRCIQAMTAINCB-UHFFFAOYSA-N

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Application

Benzoylacetonitrile was used in the synthesis of substituted naphtho[1,8-bc]pyrans. It was also used as building block in the preparation of 4H-pyrans, 2-pyridones, furans and carbocyclics.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Classifications

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

Target Organs

Respiratory system

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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Journal of the Chemical Society. Perkin Transactions 1, 1681-1681 (1985)
Xing Tan et al.
Journal of the American Chemical Society, 134(39), 16163-16166 (2012-09-20)
The cascade oxidative annulation reactions of benzoylacetonitrile with internal alkynes proceed efficiently in the presence of a rhodium catalyst and a copper oxidant to give substituted naphtho[1,8-bc]pyrans by sequential cleavage of C(sp(2))-H/C(sp(3))-H and C(sp(2))-H/O-H bonds. These cascade reactions are highly
Journal of Heterocyclic Chemistry, 15, 57-57 (1978)
Organic preparations and procedures international, 18, 85-85 (1986)
Heterocycles, 14, 639-639 (1980)

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