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Sigma-Aldrich

2-Amino-6-fluorobenzonitrile

99%

Synonym(s):

6-Fluoroanthranilonitrile

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About This Item

Linear Formula:
H2NC6H3(F)CN
CAS Number:
77326-36-4
Molecular Weight:
136.13
MDL number:
MFCD00015477
UNSPSC Code:
12352100
PubChem Substance ID:
24866895
NACRES:
NA.22

Assay

99%

mp

125-128 °C (lit.)

storage temp.

2-8°C

SMILES string

Nc1cccc(F)c1C#N

InChI

1S/C7H5FN2/c8-6-2-1-3-7(10)5(6)4-9/h1-3H,10H2

InChI key

IQUNZGOZUJITBJ-UHFFFAOYSA-N

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General description

2-Amino-6-fluorobenzonitrile can be prepared by treatment of 2,6- difluorobenzonitrile with ammonia, which involves displacement of one of the activated fluorine atoms.

Application

2-Amino-6-fluorobenzonitrile, a medicinal chemistry intermediate, has been employed for the preparation of tacrine-related compounds. It may be used for the synthesis of antifolate and antibacterial quinazoline derivatives.
It may be used for the synthesis bis(4-oxoquinazolin-2-yl)pyridine and fluoro-containing quinazolin-4(1H)-ones. It may be employed for the synthesis of the following novel huprines:
  • 12-amino-3-chloro-6,7,10,11-tetrahydro-9-isopropyl-7,11-methanocycloocta[b]quinoline hydrochloride
  • 9-allyl-12-amino-3-chloro-6,7,10,11-tetrahydro-7,11-methanocycloocta[b]quinoline hydrochloride
  • 12-amino-1-fluoro-6,7,10,11-tetrahydro-9-isopropyl-7,11-methanocycloocta[b]quinoline hydrochloride
  • 9-allyl-12-amino-1-fluoro-6,7,10,11-tetrahydro-7,11-methanocycloocta[b]quinoline hydrochloride

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H319

Hazard Classifications

Eye Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

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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European Journal of Medicinal Chemistry, 29, 205-205 (1994)
N V Harris et al.
Journal of medicinal chemistry, 33(1), 434-444 (1990-01-01)
A series of 5-substituted 2,4-diaminoquinazolines (3) has been synthesized and evaluated as inhibitors of the enzyme dihydrofolate reductase (DHFR) from both bacterial and mammalian sources. The best compounds (e.g. 53) show good activity against Escherichia coli DHFR, but there is
Synthesis of 5-and 7-fluoroquinazolin-4 (1H)-ones.
Layeva AA, et al.
Russian Chemical Bulletin, 56(9), 1821-1827 (2007)
N-(aminophenyl)oxamic acids and esters as potent, orally active antiallergy agents.
D H Klaubert et al.
Journal of medicinal chemistry, 24(6), 742-748 (1981-06-01)
Julien Defaux et al.
Bioorganic & medicinal chemistry, 19(5), 1702-1707 (2011-02-15)
A series of 19 huprines has been evaluated for their activity against cultured bloodstream forms of Trypanosoma brucei and Plasmodium falciparum. Moreover, cytotoxicity against rat myoblast L6 cells was assessed for selected huprines. All the tested huprines are moderately potent

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