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Sigma-Aldrich

2-Amino-6-fluorobenzonitrile

99%

Sinônimo(s):

6-Fluoroanthranilonitrile

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About This Item

Fórmula linear:
H2NC6H3(F)CN
Número CAS:
77326-36-4
Peso molecular:
136.13
Número MDL:
MFCD00015477
Código UNSPSC:
12352100
ID de substância PubChem:
24866895
NACRES:
NA.22

Ensaio

99%

pf

125-128 °C (lit.)

grupo funcional

fluoro
nitrile

temperatura de armazenamento

2-8°C

cadeia de caracteres SMILES

Nc1cccc(F)c1C#N

InChI

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

chave InChI

IQUNZGOZUJITBJ-UHFFFAOYSA-N

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Descrição geral

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.[1]

Aplicação

2-Amino-6-fluorobenzonitrile, a medicinal chemistry intermediate, has been employed for the preparation of tacrine-related compounds.[2] It may be used for the synthesis of antifolate and antibacterial quinazoline derivatives.[3]
It may be used for the synthesis bis(4-oxoquinazolin-2-yl)pyridine and fluoro-containing quinazolin-4(1H)-ones.[4] It may be employed for the synthesis of the following novel huprines[5]:
  • 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

Pictogramas

Exclamation mark
GHS07

Palavra indicadora

Warning

Frases de perigo

H319

Classificações de perigo

Eye Irrit. 2

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 2

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

dust mask type N95 (US), Eyeshields, Gloves

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Certificados de análise (COA)

Lot/Batch Number
MKCT1484
MKCQ8791
MKCB1101V
MKBZ5509V
MKBV4819V

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Visite a Biblioteca de Documentos

European Journal of Medicinal Chemistry, 29, 205-205 (1994)
Synthesis of 5-and 7-fluoroquinazolin-4 (1H)-ones.
Layeva AA, et al.
Russian Chemical Bulletin, 56(9), 1821-1827 (2007)
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
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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