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[ CAS No. 954-16-5 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 954-16-5
Chemical Structure| 954-16-5
Structure of 954-16-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 954-16-5 ]

CAS No. :954-16-5 MDL No. :MFCD02685558
Formula : C16H16O Boiling Point : -
Linear Structure Formula :- InChI Key :HPAFOABSQZMTHE-UHFFFAOYSA-N
M.W : 224.30 Pubchem ID :70380
Synonyms :

Calculated chemistry of [ 954-16-5 ]

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.19
Num. rotatable bonds : 2
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 71.21
TPSA : 17.07 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.57 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.78
Log Po/w (XLOGP3) : 4.36
Log Po/w (WLOGP) : 3.84
Log Po/w (MLOGP) : 3.77
Log Po/w (SILICOS-IT) : 4.89
Consensus Log Po/w : 3.93

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.37
Solubility : 0.00962 mg/ml ; 0.0000429 mol/l
Class : Moderately soluble
Log S (Ali) : -4.43
Solubility : 0.00826 mg/ml ; 0.0000368 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -6.03
Solubility : 0.000208 mg/ml ; 0.000000929 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.74

Safety of [ 954-16-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 954-16-5 ]

* 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.

  • Downstream synthetic route of [ 954-16-5 ]

[ 954-16-5 ] Synthesis Path-Downstream   1~88

  • 1
  • [ 50-00-0 ]
  • [ 954-16-5 ]
  • 3-chloromethyl-2,4,6-trimethyl-benzophenone [ No CAS ]
  • 2
  • [ 60-29-7 ]
  • [ 583-04-0 ]
  • mesityl magnesium (1+); bromide [ No CAS ]
  • [ 4810-05-3 ]
  • [ 954-16-5 ]
  • [ 65-85-0 ]
  • 3
  • [ 142-96-1 ]
  • [ 954-16-5 ]
  • [ 858491-19-7 ]
  • [ 925-90-6 ]
  • [ 40777-50-2 ]
  • 4
  • [ 142-96-1 ]
  • [ 954-16-5 ]
  • [ 858491-19-7 ]
  • phenylmagnesium bromide [ No CAS ]
  • [ 40777-50-2 ]
  • 5
  • [ 954-16-5 ]
  • [ 4885-13-6 ]
  • [ 103397-53-1 ]
  • 6
  • [ 954-16-5 ]
  • [ 4885-10-3 ]
  • [ 854037-81-3 ]
  • 7
  • [ 954-16-5 ]
  • [ 858491-19-7 ]
  • [ 40777-50-2 ]
  • 10
  • [ 954-16-5 ]
  • 2-benzoyl-3,5-dimethyl-benzoic acid [ No CAS ]
  • 4-benzoyl-2,5-dimethyl-benzoic acid [ No CAS ]
  • 11
  • [ 954-16-5 ]
  • [ 103397-53-1 ]
  • 12
  • [ 954-16-5 ]
  • [ 855289-46-2 ]
  • 13
  • [ 954-16-5 ]
  • 2,4,6-trimethyl-benzophenone; nitrate [ No CAS ]
  • 15
  • [ 954-16-5 ]
  • [ 4453-79-6 ]
  • [ 108-67-8 ]
  • 16
  • [ 954-16-5 ]
  • [ 98-88-4 ]
  • [ 26086-67-9 ]
  • 17
  • [ 954-16-5 ]
  • [ 98-88-4 ]
  • 1,3,5-tribenzoyl-2,4,6-trimethyl-benzene [ No CAS ]
  • 18
  • [ 98-88-4 ]
  • [ 108-67-8 ]
  • [ 954-16-5 ]
YieldReaction ConditionsOperation in experiment
98% With copper(II) ferrite; In neat (no solvent); at 80℃; for 18h; General procedure: The FC acylation of various benzenes with acid chlorides was carried out in the presence of magnetic nano CuFe2O4 (particle size = 50 nm) by using one of the reaction condition (A-D) given below. Condition A: Anisole/arene (1 mmol), acid chloride (1.2 mmol), nano CuFe2O4 (20 mol %), 1,2-DCE (2 mL), 80 C and 24 h. Condition B: Anisole/arene (1 mmol), acid chloride (1.2 mmol), nano CuFe2O4 (20 mol %), 1,2-DCE (2 mL), rt (35-38 C) and 18 h. Condition C: Neat reaction, anisole/arene (3.3 mmol), acid chloride (1.2 mmol), nano CuFe2O4 (20 mol %), rt (35-38 C) and 18 h. Condition D: Neat reaction, arene/anisole (3.3 mmol), acid chloride (1.2 mmol), nano CuFe2O4 (20 mol %), 80 C and 18 h.
95% With bismuth(lll) trifluoromethanesulfonate; 1-(n-butyl)-3-methylimidazolium triflate; at 140℃; for 0.5h;Microwave irradiation; Green chemistry; General procedure: a glass tube was filled with Bi(OTf)3 (0.0328 g, 0.05 mmol), [BMIM]OTf (0.1 g), anisole (0.108 g, 1 mmol), and benzoyl chloride (0.281 g, 2 mmol) and reacted at 120 C for 30 min under microwave activation. After cooling, the mixture was extracted with Et2O (3 × 20 mL). The organic layer was decanted, washed with water (10 mL), aqueous NaHCO3 (2 × 20mL), brine (10 mL), and dried over MgSO4. The solvent was removed using a rotary evaporator. Conversion was determined by GC analysis using n-hexadecane as the internal standard. The isolated yield was determined after purification by flash chromatography (n-hexane, then 10 % EtOAc in n-hexane) to give 4-methoxybenzophenone (0.1993 g, 94 % yield). The purity and authenticity of the product were confirmed by GC-MS and 1H NMR spectroscopy. The same procedure was carried out under conventional heating method.
82% With bismuth(lll) trifluoromethanesulfonate; In neat (no solvent); at 100℃; for 0.166667h;Sealed tube; Microwave irradiation; General procedure: A 10-mL pressurized glass tube with Teflon-coated septum equipped with amagnetic stirrer was charged with substrate (1 mmol), benzoyl chloride (1 mmol),and metal triflate (0.1 equiv). The tube was sealed and placed into a CEM microwaveat the temperature for the appropriate time. The reaction mixture was allowed tocool to the room temperature in the MW oven. After cooling, water (15 mL) wasadded to the mixture and the product was extracted by ethyl acetate or dichloromethane,which gave similar results (315mL). The organic layer was decanted;washed with water, aqueous NaHCO3, and brine; and dried with MgSO4. Thesolvent was then removed on a rotary evaporator and subjected to flash chromatographyon silica gel (mixture of hexane and ethyl acetate solvent to elute theproduct). The fractions containing product were concentrated and dried undervacuum to yield pure product. All products are known compounds; the purity and identityof all products were confirmed by GC-MS and 1H and 13C NMR spectroscopy.
Al-Ga supported Si-MCM-41 catalyst; at 145℃; under 760.051 Torr; for 0.116667h;Conversion of starting material; EXAMPLES 8 to 25; These examples further illustrate the process of this invention for the acylation by different acyl halide of aromatic compounds with or without comprising nitro group(s). The acylation was carried out by the procedure same as that described in Example-1 except that, the reactants and the reaction conditions employed in the step (iii) were different, as given in Table-2 and, in Examples 10, 12, 15 and 16, the solid catalyst obtained from step (ii) was stored over water in a desiccator at room temperature for 12 h before using it for the acylation reaction in step (iii). The results are included in Table-2. The results show that aromatic compounds with or without comprising nitro group can be acylated by the process of this invention, even in the presence of moisture in the reactants, solvent and/or catalyst.
boron carbide; In benzene; for 24h;Heating / reflux;Product distribution / selectivity; A mixture of 2.4 gm (0.02 moles) of mesitylene and 2.8 gm (0.02 moles) of benzoyl chloride in 50 ml of benzene containing 0.1 gm of boron carbide was allowed to reflux for 24 hours. Upon cooling, the benzene was removed at reduced pressure. The remaining solid was dissolved in an ethanol-acetone mixture and filtered to remove the boron carbide. The filtrate was allowed to evaporate to dryness and the crystals that formed were identified by its infrared spectra as 2,4,6-trimethylbenzophenone.

Reference: [1]RSC Advances,2014,vol. 4,p. 36951 - 36958
[2]Chemische Berichte,1983,vol. 116,p. 1195 - 1208
[3]Tetrahedron Letters,2013,vol. 54,p. 1738 - 1742
[4]Tetrahedron Letters,2005,vol. 46,p. 2697 - 2700
[5]Synthetic Communications,2003,vol. 33,p. 3983 - 3988
[6]Tetrahedron Letters,2014,vol. 55,p. 205 - 208
[7]Dalton Transactions,2016,vol. 45,p. 7875 - 7880
[8]Chemistry Letters,2008,vol. 37,p. 844 - 845
[9]Chinese Chemical Letters,2010,vol. 21,p. 1395 - 1398
[10]Bulletin of the Korean Chemical Society,2010,vol. 31,p. 3156 - 3158
[11]Tetrahedron,2004,vol. 60,p. 10843 - 10850
[12]Tetrahedron Letters,2003,vol. 44,p. 2037 - 2040
[13]Synthetic Communications,2004,vol. 34,p. 479 - 485
[14]Synthetic Communications,2014,vol. 44,p. 2921 - 2929
[15]Journal of the American Chemical Society,1995,vol. 117,p. 2226 - 2235
[16]Tetrahedron Letters,2002,vol. 43,p. 1105 - 1107
[17]Tetrahedron Letters,2006,vol. 47,p. 6063 - 6066
[18]Synthetic Communications,2002,vol. 32,p. 2843 - 2848
[19]Tetrahedron Asymmetry,1992,vol. 3,p. 841 - 844
[20]Journal of Organic Chemistry,1967,vol. 32,p. 2283 - 2286
[21]Recueil des Travaux Chimiques des Pays-Bas,1908,vol. 27,p. 353
[22]Journal of the American Chemical Society,1953,vol. 75,p. 745
[23]Patent: US2005/222465,2005,A1 .Location in patent: Page/Page column 5; 6
[24]Patent: US2006/281940,2006,A1 .Location in patent: Page/Page column 2
[25]Journal of the Chinese Chemical Society,2013,vol. 60,p. 261 - 266
[26]Patent: BE850024,1978,
    Patent: US4124726,1978,
    Chem.Abstr.,1979,vol. 90
  • 20
  • [ 100-47-0 ]
  • [ 2633-66-1 ]
  • [ 954-16-5 ]
  • 21
  • [ 142-96-1 ]
  • [ 954-16-5 ]
  • [ 858491-19-7 ]
  • [ 925-90-6 ]
  • [ 108-88-3 ]
  • [ 40777-50-2 ]
  • 22
  • [ 65-85-0 ]
  • [ 108-67-8 ]
  • [ 954-16-5 ]
YieldReaction ConditionsOperation in experiment
90% With erbium(III) triflate; In neat (no solvent); at 180℃; for 0.333333h;Microwave irradiation; General procedure: mixture of Er(OTf)3 (0.0614 g, 0.1 mmol), anisole(0.5407 g, 5 mmol) and benzoic acid (0.1221 g, 1 mmol) was heated undermicrowave irradiation at 220 C for 30 min in a CEM Discover apparatus. Afterbeing cooled, the mixture was extracted with CH2Cl2 (3 15 mL). The organiclayer was decanted, washed with H2O (10 mL), aqueous NaHCO3 (2 20 mL),and brine (10 mL), and dried over MgSO4. The solvent was removed on a rotaryevaporator. The crude product was purified by flash chromatography (nhexane,then 10% EtOAc in n-hexane) to give 4-methoxybenzophenone(0.153 g, 72% yield). The purity and identity of the product were confirmedby GC-FID, and from GC-MS spectra which were compared with the spectra inthe NIST library, and by 1H and 13C NMR spectroscopy.
  • 23
  • [ 60-29-7 ]
  • phenylmagnesium bromide [ No CAS ]
  • [ 938-18-1 ]
  • [ 954-16-5 ]
  • 24
  • [ 60-29-7 ]
  • [ 583-04-0 ]
  • [ 2633-66-1 ]
  • [ 4810-05-3 ]
  • [ 954-16-5 ]
  • [ 65-85-0 ]
  • 25
  • [ 142-96-1 ]
  • [ 954-16-5 ]
  • [ 858491-19-7 ]
  • [ 2633-66-1 ]
  • [ 40777-50-2 ]
  • 27
  • [ 583-04-0 ]
  • [ 2633-66-1 ]
  • [ 4810-05-3 ]
  • [ 954-16-5 ]
  • 28
  • [ 917-64-6 ]
  • [ 954-16-5 ]
  • [ 1667-02-3 ]
  • 29
  • [ 94543-86-9 ]
  • [ 954-16-5 ]
  • 30
  • [ 592-41-6 ]
  • [ 1146-83-4 ]
  • [ 954-16-5 ]
  • [ 64357-89-7 ]
  • [ 29334-21-2 ]
  • [ 1517-60-8 ]
  • 4,4'-Bis(2,4,6-trimethylbenzoyl)biphenyl [ No CAS ]
  • 4-(n-Hexyl)-2',4',6'-trimethylbenzhydrol [ No CAS ]
  • 31
  • [ 10364-94-0 ]
  • [ 108-67-8 ]
  • [ 954-16-5 ]
  • 32
  • [ 5005-35-6 ]
  • [ 108-67-8 ]
  • [ 954-16-5 ]
  • 33
  • [ 954-16-5 ]
  • [ 917-54-4 ]
  • [ 59671-58-8 ]
  • 34
  • [ 954-16-5 ]
  • [ 594-19-4 ]
  • [ 32363-47-6 ]
  • 35
  • [ 954-16-5 ]
  • [ 86-73-7 ]
  • [ 1430-97-3 ]
  • [ 120-12-7 ]
  • [ 1556-99-6 ]
  • [ 610-48-0 ]
  • [ 2928-44-1 ]
  • 36
  • [ 954-16-5 ]
  • [ 4453-79-6 ]
  • [ 41174-45-2 ]
  • [ 81667-58-5 ]
  • 39
  • [ 954-16-5 ]
  • [ 93007-82-0 ]
  • 42
  • [ 954-16-5 ]
  • [ 3453-83-6 ]
  • [ 108-67-8 ]
  • 46
  • [ 6279-93-2 ]
  • [ 954-16-5 ]
  • [ 1517-60-8 ]
  • 2-Bromo-2',4',6'-trimethylbenzhydrol [ No CAS ]
  • 47
  • [ 1146-81-2 ]
  • [ 954-16-5 ]
  • [ 1517-60-8 ]
  • 3-Bromo-2',4',6'-trimethylbenzhydrol [ No CAS ]
  • 49
  • [ 100-47-0 ]
  • [ 108-67-8 ]
  • [ 954-16-5 ]
  • [ 493-77-6 ]
  • 51
  • [ 67598-47-4 ]
  • [ 108-67-8 ]
  • [ 954-16-5 ]
  • 52
  • [ 67598-46-3 ]
  • [ 108-67-8 ]
  • [ 954-16-5 ]
  • 53
  • [ 36967-85-8 ]
  • [ 108-67-8 ]
  • [ 954-16-5 ]
  • 54
  • [ 76339-61-2 ]
  • [ 108-67-8 ]
  • [ 954-16-5 ]
  • 55
  • [ 480-63-7 ]
  • [ 71-43-2 ]
  • [ 954-16-5 ]
  • 56
  • [ 93-58-3 ]
  • [ 2633-66-1 ]
  • [ 954-16-5 ]
  • 57
  • [ 954-16-5 ]
  • [ 677-22-5 ]
  • [ 32363-47-6 ]
  • 59
  • [ 6738-06-3 ]
  • [ 954-16-5 ]
  • [ 13124-90-8 ]
  • 61
  • [ 98-88-4 ]
  • [ 174279-18-6 ]
  • [ 954-16-5 ]
  • 62
  • [ 98-88-4 ]
  • [ 174279-18-6 ]
  • [ 954-16-5 ]
  • [ 72761-85-4 ]
  • 63
  • [ 108-31-6 ]
  • [ 33574-14-0 ]
  • [ 954-16-5 ]
  • (3aR,4S,9aR)-4-Hydroxy-5,7-dimethyl-4-phenyl-3a,4,9,9a-tetrahydro-naphtho[2,3-c]furan-1,3-dione [ No CAS ]
  • 64
  • [ 712-74-3 ]
  • [ 33574-14-0 ]
  • [ 954-16-5 ]
  • 5-(2-Benzoyl-3,5-dimethyl-benzyl)-benzene-1,2,4-tricarbonitrile [ No CAS ]
  • 66
  • [ 618-32-6 ]
  • [ 108-67-8 ]
  • [ 954-16-5 ]
  • 68
  • [ 60-29-7 ]
  • phenylmagnesium bromide [ No CAS ]
  • [ 938-18-1 ]
  • cobalt (II)-chloride [ No CAS ]
  • [ 954-16-5 ]
  • [ 4746-81-0 ]
  • 1,2-dimesityl-1,2-diphenyl-ethane-1,2-diol [ No CAS ]
  • 71
  • [ 4453-79-6 ]
  • chromic acid [ No CAS ]
  • [ 954-16-5 ]
  • 72
  • [ 60-29-7 ]
  • [ 6279-93-2 ]
  • [ 71-43-2 ]
  • magnesium [ No CAS ]
  • MgI2 [ No CAS ]
  • [ 954-16-5 ]
  • 73
  • [ 64-17-5 ]
  • [ 954-16-5 ]
  • sodium amalgam [ No CAS ]
  • [ 1517-60-8 ]
  • 74
  • [ 954-16-5 ]
  • zinc dust [ No CAS ]
  • KOH-solution [ No CAS ]
  • [ 1517-60-8 ]
  • 75
  • [ 142-96-1 ]
  • [ 954-16-5 ]
  • [ 858491-19-7 ]
  • magnesium [ No CAS ]
  • MgI2 [ No CAS ]
  • [ 40777-50-2 ]
  • 76
  • [ 142-96-1 ]
  • [ 954-16-5 ]
  • [ 858491-19-7 ]
  • sodium [ No CAS ]
  • [ 40777-50-2 ]
  • 77
  • [ 954-16-5 ]
  • chromic acid mixture [ No CAS ]
  • 2-benzoyl-3,5-dimethyl-benzoic acid [ No CAS ]
  • 4-benzoyl-2,5-dimethyl-benzoic acid [ No CAS ]
  • 78
  • [ 7664-93-9 ]
  • [ 954-16-5 ]
  • [ 3453-83-6 ]
  • [ 65-85-0 ]
  • 79
  • [ 86119-84-8 ]
  • [ 954-16-5 ]
  • [ 108-67-8 ]
  • 80
  • [ 64-17-5 ]
  • [ 954-16-5 ]
  • sodium [ No CAS ]
  • [ 4453-79-6 ]
  • [ 108-67-8 ]
  • 81
  • [ 954-16-5 ]
  • [ 10034-85-2 ]
  • phosphorus [ No CAS ]
  • [ 4453-79-6 ]
  • [ 108-88-3 ]
  • [ 108-67-8 ]
  • 82
  • [ 7647-01-0 ]
  • [ 954-16-5 ]
  • [ 65-85-0 ]
  • [ 108-67-8 ]
  • 83
  • [ 954-16-5 ]
  • [ 10035-10-6 ]
  • [ 65-85-0 ]
  • [ 108-67-8 ]
  • 84
  • [ 954-16-5 ]
  • potash [ No CAS ]
  • [ 65-85-0 ]
  • [ 108-67-8 ]
  • 85
  • [ 1517-60-8 ]
  • chromic acid mixture [ No CAS ]
  • [ 954-16-5 ]
  • 86
  • [ 101594-26-7 ]
  • [ 7722-84-1 ]
  • aqueous methanol. NaOH [ No CAS ]
  • [ 480-63-7 ]
  • [ 954-16-5 ]
  • 87
  • [ 142-96-1 ]
  • [ 954-16-5 ]
  • [ 858491-19-7 ]
  • [ 108-88-3 ]
  • sodium [ No CAS ]
  • [ 40777-50-2 ]
  • 88
  • [ 954-16-5 ]
  • [ 858491-19-7 ]
  • dibutyl ether +toluene [ No CAS ]
  • magnesium iodide [ No CAS ]
  • magnesium [ No CAS ]
  • [ 106-44-5 ]
  • [ 40777-50-2 ]
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