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[ CAS No. 99-03-6 ] {[proInfo.proName]}

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Chemical Structure| 99-03-6
Chemical Structure| 99-03-6
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Product Details of [ 99-03-6 ]

CAS No. :99-03-6 MDL No. :MFCD00007796
Formula : C8H9NO Boiling Point : -
Linear Structure Formula :- InChI Key :CKQHAYFOPRIUOM-UHFFFAOYSA-N
M.W :135.16 Pubchem ID :7417
Synonyms :

Calculated chemistry of [ 99-03-6 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 41.04
TPSA : 43.09 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) : -6.54 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.25
Log Po/w (XLOGP3) : 0.83
Log Po/w (WLOGP) : 1.48
Log Po/w (MLOGP) : 1.12
Log Po/w (SILICOS-IT) : 1.44
Consensus Log Po/w : 1.22

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.58
Solubility : 3.56 mg/ml ; 0.0264 mol/l
Class : Very soluble
Log S (Ali) : -1.32
Solubility : 6.51 mg/ml ; 0.0482 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.34
Solubility : 0.615 mg/ml ; 0.00455 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 99-03-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 99-03-6 ]

* 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 [ 99-03-6 ]
  • Downstream synthetic route of [ 99-03-6 ]

[ 99-03-6 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 99-03-6 ]
  • [ 5000-65-7 ]
Reference: [1] Patent: CN106242957, 2016, A,
  • 2
  • [ 99-03-6 ]
  • [ 121-89-1 ]
Reference: [1] Organic and Biomolecular Chemistry, 2011, vol. 9, # 16, p. 5863 - 5870
  • 3
  • [ 99-03-6 ]
  • [ 14452-30-3 ]
Reference: [1] RSC Advances, 2017, vol. 7, # 86, p. 54881 - 54891
[2] Organic and Biomolecular Chemistry, 2011, vol. 9, # 16, p. 5863 - 5870
[3] Journal of Organic Chemistry, 1947, vol. 12, p. 617,680
[4] Journal of the Chemical Society, 1934, p. 1167,1169
[5] Organic Letters, 2006, vol. 8, # 4, p. 617 - 619
  • 4
  • [ 99-03-6 ]
  • [ 5400-78-2 ]
Reference: [1] Organic and Biomolecular Chemistry, 2011, vol. 9, # 16, p. 5863 - 5870
  • 5
  • [ 99-03-6 ]
  • [ 56773-33-2 ]
Reference: [1] Chemistry - A European Journal, 2015, vol. 21, # 48, p. 17220 - 17223
  • 6
  • [ 99-03-6 ]
  • [ 121-71-1 ]
YieldReaction ConditionsOperation in experiment
88.3%
Stage #1: With sulfuric acid In water at 45 - 50℃; for 0.5 h;
Stage #2: With water; urea; sodium nitrite In water at 0 - 5℃; for 0.5 h;
Stage #3: With sulfuric acid In 5,5-dimethyl-1,3-cyclohexadiene; water at 90℃; for 2 h;
In the reactor,Add 590g of water,270g mass fraction of 98percent concentrated sulfuric acid,135 g (1 mol) of 3-aminoacetophenone prepared by S2 was added thereto at a controlled temperature of 45 to 50 ° C,Insulation stirring 0.5h,Control the temperature at 0 ~ 5 ,Dropping sodium nitrite solution (sodium nitrite 77g and 190g water preparation,The mass fraction is 28.8percentAll drops),After the addition is completed,Add 2.8g of urea,Insulation diazotization reaction 0.5h,After completion of the reaction was added to the reaction solution from xylene,Water and concentrated sulfuric acid mixture of hydrolyzate (380g of xylene, 80g of water and 16g concentrated sulfuric acid),Heated to 90 hydrolysis reaction,Nitrogen release,Reflux 2h,After the completion of the hydrolysis reaction was cooled to 10 ~ 15 ,Insulation stirring 0.5h,filter,Washed,Dried to give pale yellow powder 3-hydroxyacetophenone 120g,The yield was 88.3percentThe tested melting point of 95-98 ;
80%
Stage #1: With sodium nitrite In water at 20℃; Milling; Green chemistry
Stage #2: at 80℃; for 0.5 h; Neutral conditions; Green chemistry
General procedure: Aniline (1mmol, 0.095mL), silica sulfuric acid (0.75g) and sodium nitrite (1.7mmol, 0.12g) were ground in a mortar with a pestle for a few minutes to obtain a homogeneous mixture. Then, four drops of water were gradually added and the mixture was ground for 10min to give phenyl diazonium silica sulfate. Five drops of water were added to phenyl diazonium silica sulfate (1mmol) and the resulting mixture was simply blended and then placed into a covered petri dish. Then, the petri dish was placed in an oven at 60°C for 15min. After that, the reaction mixture was diluted with EtOAc (15mL) and filtered after vigorous stirring. The residue was extracted with EtOAc (2×10mL) and the combined organic layer was dried over anhydrous Na2SO4. The solvent was evaporated under reduced pressure to afford the crude product. Further purification was performed by flash column chromatography and the pure phenol was obtained in 81percent (0.076g).
Reference: [1] Patent: CN106242957, 2016, A, . Location in patent: Paragraph 0030; 0037; 0044
[2] Tetrahedron, 2017, vol. 73, # 49, p. 6954 - 6961
[3] Journal of the Chemical Society, 1936, p. 1649,1651
[4] Journal of the Chemical Society, 1945, p. 646,655
[5] Journal of the American Chemical Society, 1932, vol. 54, p. 1114,1116
[6] Pr.S.Dakota Acad., 1945, vol. 25, p. 64
[7] Journal of the American Chemical Society, 1945, vol. 67, p. 2089,2090
  • 7
  • [ 99-03-6 ]
  • [ 33852-43-6 ]
Reference: [1] Journal of the Chemical Society, 1945, p. 646,655
  • 8
  • [ 99-03-6 ]
  • [ 67500-19-0 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1987, vol. 24, # 6, p. 1509 - 1520
  • 9
  • [ 99-03-6 ]
  • [ 2454-37-7 ]
YieldReaction ConditionsOperation in experiment
84%
Stage #1: With sodium tetrahydroborate In ethanol at 0℃; for 3 h;
Stage #2: With hydrogenchloride In ethanol; water
<Example 38> Synthesis of 8-[1-(Dimethylamino)ethyl]-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridine-5(6H)-one dihydrochloride Step 1: Synthesis of 1-(3-aminophenyl)ethanol [Show Image] 3-aminoacetophenon (2.0 g, 14.80 mmol) was dissolved in ethanol (25 ml) and added with sodium borohydride (1.4 g, 36.99 mmol) at 0 °C. The resulting mixture was stirred for 3 hours and poured into ice water. The mixture was neutralized with 2 N hydrochloric acid acqueous solution and extracted with chloroform. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain the title compound (1.7 g, yield:84percent, white solid). 1H NMR(400MHz, CDCl3); δ 7.13(t, J=8.0Hz, 1H), 6.76-6.72(m, 2H), 6.60(dd, J=8.0Hz, 2.4Hz, 1H), 4.81(m, 1H), 1.46(d, J=6.8Hz, 3H)
84%
Stage #1: With sodium tetrahydroborate In ethanol at 0℃; for 3 h;
Stage #2: With water In ethanol
Step 1:
Synthesis of 1-(3-aminophenyl)ethanol
3-aminoacetophenon (2.0 g, 14.80 mmol) was dissolved in ethanol (25 ml) and added with sodium borohydride (1.4 g, 36.99 mmol) at 0° C.
The resulting mixture was stirred for 3 hours and poured into ice water.
The mixture was neutralized with 2 N hydrochloric acid aqueous solution and extracted with chloroform.
The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain the title compound (1.7 g, yield:84percent, white solid).
1H NMR(400 MHz, CDCl3); δ 7.13(t, J=8.0 Hz, 1H), 6.76-6.72(m, 2H), 6.60(dd, J=8.0 Hz, 2.4 Hz, 1H), 4.81(m, 1H), 1.46(d, J=6.8 Hz, 3H)
76% With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; sodium formate In water at 30℃; for 24 h; Inert atmosphere; Schlenk technique General procedure: In a schlenk tube, the chiral ligand (0.05 mmol) and the metallicprecursor (0.025 mmol) are dissolved in the water (4 mL). After 1 hof stirring at 30 °C, the sodium formate (10 mmol) and the ketone (1 mmol) were added to the aqueous solution. The biphasic solution was stirred at 30 for the indicated time and follow by TLC untilthe total reduction of ketone. The formed alcohol was separated from the catalyst by simple extraction with pentane (2 8 mL) and the organic layer was dried over MgSO4 and concentrated in vacuo.The crude residue was distilled in order to purify the alcohol.
Reference: [1] Dalton Transactions, 2018, vol. 47, # 29, p. 9889 - 9896
[2] Patent: EP2364983, 2011, A2, . Location in patent: Page/Page column 53
[3] Patent: US2011/218193, 2011, A1, . Location in patent: Page/Page column 43
[4] Journal of Organometallic Chemistry, 2018, vol. 868, p. 95 - 101
[5] Tetrahedron Letters, 2004, vol. 45, # 9, p. 2003 - 2007
[6] ChemCatChem, 2015, vol. 7, # 1, p. 107 - 113
[7] Organic and Biomolecular Chemistry, 2016, vol. 14, # 13, p. 3404 - 3408
[8] Tetrahedron Letters, 1987, vol. 28, # 40, p. 4725 - 4728
[9] Journal of the Chemical Society, Dalton Transactions, 2001, # 20, p. 2989 - 2995
[10] Organic Letters, 2002, vol. 4, # 24, p. 4297 - 4300
[11] Organic and Biomolecular Chemistry, 2011, vol. 9, # 16, p. 5863 - 5870
[12] Organometallics, 2011, vol. 30, # 17, p. 4720 - 4729
[13] Biocatalysis and Biotransformation, 2012, vol. 30, # 5-6, p. 469 - 475
[14] Chemistry - A European Journal, 2014, vol. 20, # 3, p. 839 - 845
[15] Organic and Biomolecular Chemistry, 2017, vol. 15, # 43, p. 9169 - 9175
  • 10
  • [ 121-89-1 ]
  • [ 1314911-01-7 ]
  • [ 2454-37-7 ]
  • [ 99-03-6 ]
Reference: [1] Applied Catalysis A: General, 2013, vol. 462-463, p. 121 - 128
  • 11
  • [ 99-03-6 ]
  • [ 98-80-6 ]
  • [ 23699-65-2 ]
Reference: [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 12, p. 3212 - 3219
  • 12
  • [ 99-03-6 ]
  • [ 23699-65-2 ]
Reference: [1] Journal of the Chemical Society, 1931, p. 2381,2386
  • 13
  • [ 99-03-6 ]
  • [ 7440-44-0 ]
  • [ 98-86-2 ]
  • [ 74-88-4 ]
  • [ 42865-75-8 ]
Reference: [1] Patent: US3954734, 1976, A,
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