Home Cart 0 Sign in  
X

[ CAS No. 459-04-1 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
HazMat Fee +

There will be a HazMat fee per item when shipping a dangerous goods. The HazMat fee will be charged to your UPS/DHL/FedEx collect account or added to the invoice unless the package is shipped via Ground service. Ship by air in Excepted Quantity (each bottle), which is up to 1g/1mL for class 6.1 packing group I or II, and up to 25g/25ml for all other HazMat items.

Type HazMat fee for 500 gram (Estimated)
Excepted Quantity USD 0.00
Limited Quantity USD 15-60
Inaccessible (Haz class 6.1), Domestic USD 80+
Inaccessible (Haz class 6.1), International USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic USD 100+
Accessible (Haz class 3, 4, 5 or 8), International USD 200+
3d Animation Molecule Structure of 459-04-1
Chemical Structure| 459-04-1
Chemical Structure| 459-04-1
Structure of 459-04-1 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 459-04-1 ]

Related Doc. of [ 459-04-1 ]

Alternatived Products of [ 459-04-1 ]

Product Details of [ 459-04-1 ]

CAS No. :459-04-1 MDL No. :MFCD00674181
Formula : C8H6ClFO Boiling Point : -
Linear Structure Formula :- InChI Key :SIOJFYRPBYGHOO-UHFFFAOYSA-N
M.W : 172.58 Pubchem ID :3744988
Synonyms :

Calculated chemistry of [ 459-04-1 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 41.17
TPSA : 17.07 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.56 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.88
Log Po/w (XLOGP3) : 2.53
Log Po/w (WLOGP) : 2.55
Log Po/w (MLOGP) : 2.52
Log Po/w (SILICOS-IT) : 3.08
Consensus Log Po/w : 2.51

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.78
Solubility : 0.289 mg/ml ; 0.00168 mol/l
Class : Soluble
Log S (Ali) : -2.54
Solubility : 0.503 mg/ml ; 0.00292 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.64
Solubility : 0.0394 mg/ml ; 0.000229 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.27

Safety of [ 459-04-1 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338-P310 UN#:3261
Hazard Statements:H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 459-04-1 ]

* 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 [ 459-04-1 ]
  • Downstream synthetic route of [ 459-04-1 ]

[ 459-04-1 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 64-17-5 ]
  • [ 459-04-1 ]
  • [ 587-88-2 ]
Reference: [1] Organic Letters, 2007, vol. 9, # 21, p. 4203 - 4206
[2] Journal of the American Chemical Society, 2003, vol. 125, # 46, p. 13948 - 13949
[3] Journal of Organic Chemistry, 2009, vol. 74, # 6, p. 2571 - 2574
[4] Patent: WO2011/120153, 2011, A1, . Location in patent: Page/Page column 70-71
[5] Patent: WO2008/76427, 2008, A2, . Location in patent: Page/Page column 77
  • 2
  • [ 1066-54-2 ]
  • [ 459-04-1 ]
  • [ 13101-83-2 ]
YieldReaction ConditionsOperation in experiment
69% With trifluoroacetic acid In hexane; dichloromethane; ethyl acetate Step 3
6-Fluoro-2-naphthol
A solution of 2-(4-fluorophenyl)acetyl chloride (5.0g; 29 mmol) in CH2Cl2 was added to AlCl3 (7.73g;58 mmol) in CH2Cl2 at -20° C. over 30 min.
Trimethylsilyl acetylene (9.96g; 101.43 mmol) was added also over 30 min and stirred at -10° C. for 1h.
The mixture was poured in ice and extracted with EtOAc.
The organic phase was washed with water, NaHCO3 and brine.
After purification by gel silica chromatography (10percent EtOAc in hexane) 2.43 g (36percent) of 3-(trimethylsilyl)-6-chloro-2-naphthol was collected.
The desylilation was done with TFA in CH2Cl2 at rt overnight.
Purification by gel silica chromatography (10percent EtOAc in hexane) afforded the title compound in 69percent yield.
1H NMR (CDCl3) δ7.10-7.20 (3H, m), 7.37 (1H, dd) and 7.65 (2H, m).
Reference: [1] Patent: US6242493, 2001, B1,
  • 3
  • [ 459-04-1 ]
  • [ 13101-83-2 ]
Reference: [1] Australian Journal of Chemistry, 1970, vol. 23, p. 1921 - 1937
  • 4
  • [ 74-85-1 ]
  • [ 459-04-1 ]
  • [ 29419-14-5 ]
Reference: [1] Australian Journal of Chemistry, 1970, vol. 23, p. 1921 - 1937
[2] Journal of Medicinal Chemistry, 1993, vol. 36, # 17, p. 2485 - 2493
[3] Journal of Medicinal Chemistry, 1995, vol. 38, # 12, p. 2202 - 2216
[4] Synthetic Communications, 2003, vol. 33, # 13, p. 2215 - 2227
[5] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 22, p. 6160 - 6163
[6] Patent: EP1191008, 2002, A1, . Location in patent: Page 67
[7] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 9, p. 2637 - 2640
  • 5
  • [ 459-04-1 ]
  • [ 29419-14-5 ]
Reference: [1] Patent: US4431834, 1984, A,
  • 6
  • [ 67-56-1 ]
  • [ 459-04-1 ]
  • [ 34837-84-8 ]
Reference: [1] Patent: US2007/15923, 2007, A1, . Location in patent: Page/Page column 7; 8
[2] Patent: WO2008/54690, 2008, A2, . Location in patent: Page/Page column 13-14
  • 7
  • [ 459-04-1 ]
  • [ 34837-84-8 ]
Reference: [1] Tetrahedron Letters, 2015, vol. 56, # 31, p. 4634 - 4637
  • 8
  • [ 459-04-1 ]
  • [ 34547-28-9 ]
YieldReaction ConditionsOperation in experiment
86% With hydrazine hydrate; triethylamine In acetonitrile for 3 h; Reflux General procedure: Aralkanoic acid chlorides 2a-g were synthesized by the reaction of aralkanoic acid 1a-g (1 mmol) in the presence of 1,2-dichloroethane (12 mL) solvent and phosphorous oxychloride(0.4 mL) chlorinating agent under reflux for 3hours. Then, the resulting solution was cooled to room temperature, and the solvent was removed under reduced pressureto afford aralkanoic acid chloride 2a-g, which was directly used in the next step without further purification. Acid chloride 2a-g was dissolved in acetonitrile (80 mL), addeddropwise to a solution containing hydrazine hydrate(1 mmol), TEA (0.5 mL) and acetonitrile (20 mL) and allowed to reflux for 3 hours with monitoring by TLC. After consumption of the starting material, the reaction mixture was cooled to room temperature. Evaporation of the solvent under reduced pressure yielded crude acid hydrazide 3a-g as a white solid on cooling, which was purified by column chromatography and crystallized in methanol [46].
69% With hydrazine In dichloromethane at 0℃; for 0.666667 h; A cold (0 oC) solution of hydrazine (4. 5 ML, 144 mmol) in dichloromethane (50 mL) was treated with a dichloromethane solution of (4-fluorophenyl) acetyl chloride (1. 0 g, 5. 8 mmol). The resultant solution was stirred for 40 minutes and water was then added. The layers were separated and the aqueous layer was extracted with dichloromethane and the combined organics were dried over sodium sulfate. Filtration and concentration followed by purification by flash chromatography (5percent methanol-dichloromethane gradient elution) provided 2- (4-FLUOROPHENYL) acetic hydrazide (673 mg, 69percent) as a white solid. 1H NMR (DMSO-D6) : S 9. 18 (broad, 1 H), 7. 26 (dd, J= 8. 4, 5. 7 Hz, 2 H), 7. 09 (t, J= 8. 4 Hz, 2 H), 4. 21 (broad, 2 H), 3. 31 (s, 2 H) ; MS INTO 169 (M+1),
Reference: [1] Medicinal Chemistry, 2014, vol. 10, # 8, p. 810 - 823
[2] Patent: WO2004/101512, 2004, A2, . Location in patent: Page 55
[3] Patent: WO2007/50510, 2007, A2, . Location in patent: Page/Page column 38
[4] Patent: WO2011/46873, 2011, A1, . Location in patent: Page/Page column 29
[5] Patent: WO2011/120153, 2011, A1,
[6] Journal of Molecular Structure, 2017, vol. 1138, p. 177 - 191
  • 9
  • [ 459-04-1 ]
  • [ 1324397-22-9 ]
  • [ 34547-28-9 ]
Reference: [1] Patent: WO2011/120153, 2011, A1, . Location in patent: Page/Page column 70-71
  • 10
  • [ 459-04-1 ]
  • [ 459-28-9 ]
Reference: [1] Journal of the American Chemical Society, 2013, vol. 135, # 19, p. 7304 - 7311
[2] Patent: US2005/227959, 2005, A1,
  • 11
  • [ 459-04-1 ]
  • [ 75908-73-5 ]
Reference: [1] Journal of Medicinal Chemistry, 1994, vol. 37, # 11, p. 1704 - 1711
  • 12
  • [ 459-04-1 ]
  • [ 1052114-81-4 ]
Reference: [1] Patent: WO2014/713, 2014, A1,
[2] Patent: WO2014/145004, 2014, A1,
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 459-04-1 ]

Fluorinated Building Blocks

Chemical Structure| 121639-61-0

[ 121639-61-0 ]

3,4-Difluorophenyl acetyl chloride

Similarity: 0.92

Chemical Structure| 451-81-0

[ 451-81-0 ]

2-(2-Fluorophenyl)acetyl chloride

Similarity: 0.90

Chemical Structure| 116622-90-3

[ 116622-90-3 ]

2,6-Difluorophenylacetyl chloride

Similarity: 0.88

Chemical Structure| 141060-00-6

[ 141060-00-6 ]

2,4-Difluorophenylacetyl chloride

Similarity: 0.88

Chemical Structure| 157033-23-3

[ 157033-23-3 ]

2,5-Difluorophenylacetyl chloride

Similarity: 0.88

Aryls

Chemical Structure| 121639-61-0

[ 121639-61-0 ]

3,4-Difluorophenyl acetyl chloride

Similarity: 0.92

Chemical Structure| 451-81-0

[ 451-81-0 ]

2-(2-Fluorophenyl)acetyl chloride

Similarity: 0.90

Chemical Structure| 116622-90-3

[ 116622-90-3 ]

2,6-Difluorophenylacetyl chloride

Similarity: 0.88

Chemical Structure| 141060-00-6

[ 141060-00-6 ]

2,4-Difluorophenylacetyl chloride

Similarity: 0.88

Chemical Structure| 157033-23-3

[ 157033-23-3 ]

2,5-Difluorophenylacetyl chloride

Similarity: 0.88

Chlorides

Chemical Structure| 121639-61-0

[ 121639-61-0 ]

3,4-Difluorophenyl acetyl chloride

Similarity: 0.92

Chemical Structure| 451-81-0

[ 451-81-0 ]

2-(2-Fluorophenyl)acetyl chloride

Similarity: 0.90

Chemical Structure| 116622-90-3

[ 116622-90-3 ]

2,6-Difluorophenylacetyl chloride

Similarity: 0.88

Chemical Structure| 141060-00-6

[ 141060-00-6 ]

2,4-Difluorophenylacetyl chloride

Similarity: 0.88

Chemical Structure| 157033-23-3

[ 157033-23-3 ]

2,5-Difluorophenylacetyl chloride

Similarity: 0.88

Acyl Chlorides

Chemical Structure| 121639-61-0

[ 121639-61-0 ]

3,4-Difluorophenyl acetyl chloride

Similarity: 0.92

Chemical Structure| 451-81-0

[ 451-81-0 ]

2-(2-Fluorophenyl)acetyl chloride

Similarity: 0.90

Chemical Structure| 116622-90-3

[ 116622-90-3 ]

2,6-Difluorophenylacetyl chloride

Similarity: 0.88

Chemical Structure| 141060-00-6

[ 141060-00-6 ]

2,4-Difluorophenylacetyl chloride

Similarity: 0.88

Chemical Structure| 157033-23-3

[ 157033-23-3 ]

2,5-Difluorophenylacetyl chloride

Similarity: 0.88