2-(3,4-Dichlorophenoxy)propionic acid

Akhtar, Tashfeen; Rauf, M. Khawar; Ebihara, Masahiro; Hameed, Shahid

doi:10.1107/s1600536807014249

Cited by 5 publications

(5 citation statements)

References 4 publications

(2 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The substituted phenols were converted into the corresponding phenoxy acids 1a-h, prepared previously in our laboratory, by the reaction with 2-bromoalkanoic acids in aqueous solution of NaOH (14), followed by Fischer esterfication (15) in acidic MeOH to give the esters 2a-h. Compounds 2a-h were used directly for the next step without further purification.…”

Section: Resultsmentioning

confidence: 99%

“…-These compounds were prepared previously in our laboratory (14) by the treatment of 2-bromopropanoic acid or 2-bromobutanoic acid with commercial substituted phenols in aqueous NaOH. 2-(Bromophenoxy)propanoic acid (1a), 2-(bromophenoxy)butanoic acid (1b), 2-(chlorophenoxy)propanoic acid (1c), 2-(chlorophenoxy)butanoic acid (1d), 2-(3,4-dichlorophenoxy)propanoic acid (1e), 2-(3,4-dichlorophenoxy)butanoic acid (1f), 2-(p-tolyloxy)propanoic acid (1g), 2-(p-tolyloxy)butanoic acid (1h) were prepared by condensation of p-bromophenol with 2-bromopropanoic acid, p-bromophenol with 2-bromobutanoic acid, …”

Section: Syntheses General Procedures For the Synthesis Of 4-alkyl- 4mentioning

confidence: 99%

See 1 more Smart Citation

In vitro antitumor and antiviral activities of new benzothiazole and 1,3,4-oxadiazole-2-thione derivatives

et al. 2008

Self Cite

View full text Add to dashboard Cite

A series of new benzothiazole derivatives 6a-h have been synthesized, in five steps, from substituted phenols via the 1,3,4-oxadiazole-2-thiones 5a-h. The in vitro antitumor activity of the compounds obtained was investigated and the benzothiazol derivatives 6d and 6e showed strong effects on leukaemia cell lines CCRF-CEM (CC50=12+/-2 micromol L(-1), 8+/-1 micromol L(-1), respectively). These compounds are leading candidates for further development. The title compounds were tested against representatives of several virus families containing single stranded RNA genomes, either positive-sense (ssRNA+), or negativesense (RNA-), and against double-stranded RNA genomes (dsRNA), as well as some Flaviviridae viruses

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Syntheses General Procedures For the Synthesis Of 4-alkyl- 4mentioning

confidence: 99%

In vitro antitumor and antiviral activities of new benzothiazole and 1,3,4-oxadiazole-2-thione derivatives

et al. 2008

Self Cite

View full text Add to dashboard Cite

show abstract

“…For carboxyhydrazide derivatives with biological activities, see: Belkadi & Othman (2006); Goswami et al (1984); Akhtar et al (2008); ; Ahmad et al (1996); Akhtar et al (2006); For related structures, see: Akhtar, Khawar Rauf et al (2007); Zheng (2008).…”

Section: Related Literaturementioning

confidence: 99%

2-(4-Bromophenoxy)propanohydrazide

et al. 2009

Self Cite

View full text Add to dashboard Cite

The title compound, C9H11BrN2O2, is an important intermediate for the synthesis of heterocyclic compounds such as azoles, 2,5-disubstituted-1,3,4-oxadiazoles and 5-substituted 2-mercapto-1,3,4-oxadiazoles. The bromophenoxy group subtends a dihedral angle of 82.81 (7)° with the plane passing through the propanohydrazide moiety. The crystal structure is stabilized by intermolecular N—H⋯O hydrogen bonds that form columns extending along the b axis.

show abstract

“…For the structures and properties of oxadiazoles, see: Almasirad et al, (2004); Aboraia et al (2006); Akhtar, Hameed, Al-Masoudi et al (2008); Khan et al (2005); ; Akhtar, Hameed, Khan et al (2008); Akhtar, Rauf et al (2007); Aydogan et al, 2002). For a related structure, see: Thamotharan et al (2005).…”

Section: Related Literaturementioning

confidence: 99%

“…ethyl]-1,3,4-oxadiazole-2(3H)-thione, derived from 3,4-dichlorophenoxy propionic acid (Akhtar & Rauf et al, 2007).…”

Section: Data Collectionmentioning

confidence: 99%

5-[1-(3,4-Dichlorophenoxy)ethyl]-1,3,4-oxadiazole-2(3H)-thione hemihydrate

et al. 2009

Self Cite

View full text Add to dashboard Cite

In the title compound, C10H8Cl2N2O2S·0.5H2O, the atoms in the oxadiazole ring are essentially coplanar (r.m.s. deviation 0.010 Å). The crystal structure is stabilized by intermolecular N—H⋯O hydrogen bonds involving the water molecule, which is situated on an a twofold rotation axis, and two organic molecules, leading to a thione tautomer in the solid state. The C atom attached to the oxadiazole ring adopts a typical sp3 hybridization. The dihedral angle between the mean plane of the benzene ring of the dichlorophenyl group and the mean plane of the oxadiazole ring is 74.18 (4)°. The crystal structure is stabilized by intermolecular N—H⋯O and O—H⋯S hydrogen bonds.

show abstract

2-(3,4-Dichlorophenoxy)propionic acid

Abstract: In the title compound, C9H8Cl2O3, the molecules are linked in dimers across centres of symmetry by O—H...O hydrogen bonds. The O...O distance and O—H...O angle compare well with values observed in other substituted phenoxy and benzoic acids.

Cited by 5 publications

References 4 publications

In vitro antitumor and antiviral activities of new benzothiazole and 1,3,4-oxadiazole-2-thione derivatives

In vitro antitumor and antiviral activities of new benzothiazole and 1,3,4-oxadiazole-2-thione derivatives

2-(4-Bromophenoxy)propanohydrazide

5-[1-(3,4-Dichlorophenoxy)ethyl]-1,3,4-oxadiazole-2(3H)-thione hemihydrate

Contact Info

Product

Resources

About