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[ CAS No. 609-14-3 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 609-14-3
Chemical Structure| 609-14-3
Chemical Structure| 609-14-3
Structure of 609-14-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 609-14-3 ]

CAS No. :609-14-3 MDL No. :MFCD00009164
Formula : C7H12O3 Boiling Point : -
Linear Structure Formula :- InChI Key :FNENWZWNOPCZGK-UHFFFAOYSA-N
M.W : 144.17 Pubchem ID :701
Synonyms :

Calculated chemistry of [ 609-14-3 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.71
Num. rotatable bonds : 4
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 37.25
TPSA : 43.37 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.53 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.8
Log Po/w (XLOGP3) : 0.91
Log Po/w (WLOGP) : 0.77
Log Po/w (MLOGP) : 0.64
Log Po/w (SILICOS-IT) : 0.96
Consensus Log Po/w : 1.02

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.04
Solubility : 13.1 mg/ml ; 0.0905 mol/l
Class : Very soluble
Log S (Ali) : -1.41
Solubility : 5.66 mg/ml ; 0.0392 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.11
Solubility : 11.2 mg/ml ; 0.0778 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.96

Safety of [ 609-14-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P210-P280-P370+P378-P403+P235-P501-P264-P337+P313-P305+P351+P338 UN#:N/A
Hazard Statements:H319-H227 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 609-14-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 609-14-3 ]
  • Downstream synthetic route of [ 609-14-3 ]

[ 609-14-3 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 609-14-3 ]
  • [ 67434-65-5 ]
Reference: [1] Journal of the Chemical Society, 1946, p. 362,365
  • 2
  • [ 609-14-3 ]
  • [ 1780-32-1 ]
Reference: [1] Patent: WO2013/123401, 2013, A1,
  • 3
  • [ 609-14-3 ]
  • [ 95-54-5 ]
  • [ 52099-72-6 ]
Reference: [1] Patent: US5652246, 1997, A,
  • 4
  • [ 609-14-3 ]
  • [ 106-49-0 ]
  • [ 16382-15-3 ]
YieldReaction ConditionsOperation in experiment
25%
Stage #1: With hydrogenchloride; sodium nitrite In water at -5℃; for 0.25 h;
Stage #2: With potassium hydroxide; sodium acetate In ethanol; water at 0℃; for 18 h;
Stage #3: With toluene-4-sulfonic acid In toluene at 110℃; for 5 h;
7.2 g (0.104 mol) of sodium nitrite dissolved in 40 ml of water are added, at 5 C., to a mixture of 10.7 g (0.1 mol) of 4-methylaniline, 74 ml of 12 N hydrochloric acid and 140 ml of water. The reaction mixture is stirred for 15 minutes at 5 C. and is neutralized by addition of 8.1 g of sodium acetate. 12.33 g (0.085 mol) of ethyl a-methyl acetoacetate and 80 ml of ethanol are introduced into a three-necked Uask, followed, at 0 C., by 4.8 g (0.085 mol) ofpotassium hydroxide dissolved in 20ml ofwater and 100 g of ice. The diazonium solution prepared above is added dropwise, at 0 C., to this reaction mixture and the resulting mixture is left for 18 hours at 0 C. The aqueous phase is extracted 4 times with 50 ml of ethyl acetate and the organic phases are combined and dried over anhydrous sodium sulphate. The residue is taken up in 100 ml of toluene and 16.3 g (0.085 mol) of para-toluene sulphonic acid monohy drate. The mixture is then heated slowly to 110 C. and maintained at this temperature for S hours. After cooling and then addition of saturated sodium carbonate solution, the insoluble material is removed by ltration and the organic phase is separated out after settling has taken place, dried over anhydrous sodium sulphate and concentrated. The residue is chromatographed on a column of silica gel, eluent:30/70 (v/v) dichloromethane/cyclohexane, to give beige coloured crystals; m.p.=94 C.; yield=25percent.
Reference: [1] Patent: US2004/43995, 2004, A1, . Location in patent: Page 13
  • 5
  • [ 609-14-3 ]
  • [ 29237-78-3 ]
  • [ 133-13-1 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1926, vol. <4> 39, p. 1012
  • 6
  • [ 609-14-3 ]
  • [ 6313-33-3 ]
  • [ 34916-78-4 ]
Reference: [1] Patent: EP1333029, 2003, A1,
  • 7
  • [ 609-14-3 ]
  • [ 2365-48-2 ]
  • [ 32822-84-7 ]
Reference: [1] Patent: US4904686, 1990, A,
[2] Patent: US5021449, 1991, A,
  • 8
  • [ 609-14-3 ]
  • [ 2365-48-2 ]
  • [ 32822-84-7 ]
Reference: [1] Patent: US4748183, 1988, A,
[2] Patent: EP249236, 1991, B1,
  • 9
  • [ 609-14-3 ]
  • [ 5345-54-0 ]
  • [ 366-99-4 ]
YieldReaction ConditionsOperation in experiment
21% With sodium hydroxide; sodium nitrite In hydrogenchloride; ethanol; water; ethyl acetate (i)
Ethyl 2-acetyl-2-N'-(3-chloro-methoxylphenyl)hydrazino)propionate
Ethereal HCl (60 ml) was added to a solution of 3-chloro-p-anisidine in ethyl acetate (300 ml) to precipitate the salt, which was isolated by filtration and air dried.
The salt (18.5 g) was suspended in 1.5 N HCl (230 ml) at -5° C. under argon.
A solution of sodium nitrite (6.9 g) in water (50 ml) was added over 15 minutes to form a solution/slurry, which was stirred at -5° C. for a further 1 hour. (solution A)
A solution of sodium hydroxide (5.36 g) in water (10 ml) was added to a solution of ethyl-2-methylacetoacetate (13.5 ml) in ethanol (80 ml) at 5° C.
The reaction was stirred at 5° C. for a further 1 hour and the pH was then adjusted to 4 by addition of sodium acetate (20 g).(solution B)
Solution B was added to solution A at -5° C. and the mixture was allowed to warm to ambient temperature over 3 hours before partitioning between water (250 ml) and ethylacetate (250 ml).
The organic phase was dried (MgSO4), concentrated under vacuo and purified by column chromatography using 15percent ethylacetate/isohexane as the eluant to yield the desired product (7 g, 21percent); NMR (CDCl3) δ 1.24 (t, 3H), 1.63 (s, 3H), 2.34 (s,3), 3.98 (s, 3H), 4.22-4.35 (m, 2H), 7.02 (d, 1H), 7.72 (dd, 1H), 7.83 (d, 1H) m/z 270(M-CH3COH)+
In a similar manner but starting from 3-fluoro-4-methoxyaniline was prepared:
Reference: [1] Patent: US2003/144339, 2003, A1,
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