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[ CAS No. 16473-35-1 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 16473-35-1
Chemical Structure| 16473-35-1
Chemical Structure| 16473-35-1
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Product Details of [ 16473-35-1 ]

CAS No. :16473-35-1 MDL No. :MFCD03427011
Formula : C8H9ClO Boiling Point : -
Linear Structure Formula :- InChI Key :OGALXJIOJZXBBP-UHFFFAOYSA-N
M.W : 156.61 Pubchem ID :5107660
Synonyms :

Calculated chemistry of [ 16473-35-1 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 2
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 42.33
TPSA : 20.23 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) : -6.12 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.95
Log Po/w (XLOGP3) : 1.6
Log Po/w (WLOGP) : 1.61
Log Po/w (MLOGP) : 2.19
Log Po/w (SILICOS-IT) : 2.64
Consensus Log Po/w : 2.0

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.13
Solubility : 1.16 mg/ml ; 0.0074 mol/l
Class : Soluble
Log S (Ali) : -1.64
Solubility : 3.62 mg/ml ; 0.0231 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.23
Solubility : 0.0916 mg/ml ; 0.000585 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.13

Safety of [ 16473-35-1 ]

Signal Word:Danger Class:8
Precautionary Statements:P260-P264-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P321-P363-P405-P501 UN#:1759
Hazard Statements:H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 16473-35-1 ]

* 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 [ 16473-35-1 ]
  • Downstream synthetic route of [ 16473-35-1 ]

[ 16473-35-1 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 1642-81-5 ]
  • [ 16473-35-1 ]
YieldReaction ConditionsOperation in experiment
96% With borane-THF In tetrahydrofuran at 20℃; Example 1: (1) [4-CHLOROMETHYLBENZYL] Alcohol To a solution of 4-chloro-4-toluic acid in tetrahydrofuran (THF, 60 [ML)] was added 1 M borane THF solution (90 [ML).] The mixture was stirred at room temperature overnight and quenched by addition of methanol (50 ml). The solvent was evaporated off and the residue was purified by silica gel column chromatography (hexane/ethyl acetate = 4/1 to 3/1) to obtain 4-chloromethylbenzyl Alcohol (8.84 g, 96percent) as a colorless solid.
76% With borane-THF In tetrahydrofuran at 0 - 20℃; for 5 h; Into a 2000-mL round-bottom flask was placed a solution of 4-(chloromethyl)benzoic acid 9a (50 g, 293 mmol) in THF (200 mL). This was followed by the addition of 1 M BH3/THF (586 mL, 586 mmol) dropwise with stirring at 0 °C over 1 hr. The resulting solution was stirred for 4 h at rt. The reaction was then quenched by the addition of 600 mL of 1 N HCI. The solution was extracted with 500 ml of ethyl acetate. The organic layer was washed with 300 ml of sodium carbonate (aq.), and 300 ml of brine. The organic layer was dried over sodium sulfate and concentrated under vacuum giving 9b (35 g, 76percent) as a white solid. 1H NMR (400 MHz, CDCI3) 4.50 (d, J=4.8 Hz, 2 H), 4.75 (s, 2 H), 5.21 (t, J=4.8 Hz, 1 H), 7.32 (d, J=7.6 Hz, 2 H), 7.39 (d, J=7.6 Hz, 2 H).
76% With diborane In tetrahydrofuran at 0 - 20℃; for 5 h; 10611] Into a 2000-mE round-bottom flask was placed asolution of 4-(chloromethyl)benzoic acid 9a (50 g, 293mmol) in THF (200 mE). This was followed by the addition of1 M 13H3/THF (586 mE, 586 mmol) dropwise with stirring at00 C. over 1 hr. The resulting solution was stirred for 4 hat rt.The reaction was then quenched by the addition of 600 mE of1 N Rd. The solution was extracted with 500 ml of ethylacetate. The organic layer was washed with 300 ml of sodium carbonate (aq.), and 300 ml of brine. The organic layer was dried over sodium sulfate and concentrated under vacuum giving 9b (35 g, 76percent) as a white solid. ‘H NMR (400 MHz, CDC13) 4.50 (d, J=4.8 Hz, 2H), 4.75 (s, 2H), 5.21 (t, J=4.8 Hz, 1H), 7.32 (d, J=7.6 Hz, 2H), 7.39 (d, J=7.6 Hz, 2H).
Reference: [1] Patent: WO2003/106403, 2003, A1, . Location in patent: Page 23
[2] Patent: US5387709, 1995, A,
[3] Patent: WO2015/51045, 2015, A2, . Location in patent: Page/Page column 161-162
[4] Patent: US2016/215288, 2016, A1, . Location in patent: Paragraph 0602; 0611
[5] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 16, p. 4481 - 4486
[6] Patent: US2006/194850, 2006, A1, . Location in patent: Page/Page column 30
  • 2
  • [ 589-29-7 ]
  • [ 16473-35-1 ]
YieldReaction ConditionsOperation in experiment
75% With thionyl chloride; sodium hydrogencarbonate In chloroform EXAMPLE 1
p-Hydroxymethylbenzyl chloride
1,4-benzenedimethanol (13.8 g, 0.10 mole) was dispersed in chloroform (100 mL) in a 500 mL three-neck round bottom flask equipped with a magnetic stirring bar, an addition funnel, a nitrogen inlet and a gas scrubber.
The mixture was cooled to 0° C. in an ice bath.
Thionyl chloride (13.1 g, 0.11 mole) dissolved in chloroform (10 mL) was added dropwise over ten minutes with rapid stirring to the cooled mixture.
As the addition proceeded, the mixture largely cleared.
During the addition step, and for one hour thereafter, the reaction flask was swept with nitrogen which was then passed through the scrubber before venting to the atmosphere.
The nitrogen was turned off and the scrubber disconnected.
The mixture was allowed to come to room temperature and stirring was continued for 20 hours.
Sufficient sodium bicarbonate was added to neutralize any residual hydrogen chloride.
The mixture was filtered through a coarse glass frit and the solvent removed under reduced pressure at 35° C.
A sample of the residue was chromatographed on silica gel (200 g) with an ethyl acetate:hexane (2:3) solvent.
p-Hydroxymethyl-benzyl chloride was obtained in 75percent yield (11.64 g).
The product had a melting point of 58°-60° C. NMR spectral data were as follows: 1 H NMR (CDCl3, 300 MHz): δ7.3 (m, 4H), 4.70 (s, 2H), 4.59 (s, 2H), 1.67 (s, 1H); 13 C NMR (CDCl3, 75 MHz, ppm) 141.372, 135.995, 128.876, 127.366, 64.927, 46.121.
141 g With hydrogenchloride In toluene at 50℃; for 2 h; A round bottom flask was charged with 138 g (1 mol) of 1,4-benzene dimethanol, 690 g of toluene was added and stirred. 203 g of an aqueous HCl solution (concentration: 35percent to 37percent) was gradually added dropwise to the round bottom flask, and the temperature was raised to 50°C and further stirred for 2 hours. When the reaction was completed, the aqueous layer was removed and washed with 5percent NaHCO3 aqueous solution and water. Water was removed using MgSO4, filtered and concentrated to give 141 g of a compound of formula (i).
Reference: [1] Tetrahedron, 2013, vol. 69, # 30, p. 6203 - 6212
[2] Journal of Medicinal Chemistry, 2006, vol. 49, # 8, p. 2628 - 2639
[3] Journal of Organic Chemistry, 1996, vol. 61, # 2, p. 444 - 450
[4] Patent: US5637780, 1997, A,
[5] Journal of the American Chemical Society, 1967, vol. 89, p. 2304 - 2316
[6] Patent: KR2016/101335, 2016, A, . Location in patent: Paragraph 0144-0147
  • 3
  • [ 876-08-4 ]
  • [ 16473-35-1 ]
YieldReaction ConditionsOperation in experiment
66.9% With sodium tetrahydroborate In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 1 h; 53.2 g of sodium borohydride, 530 g of tetrahydrofuran and 266 g of N, N-dimethylformamide were added to a three-necked flask equipped with a stirrer, a reflux condenser and a dropping funnel, and a solution of 266 g of chloromethylbenzoyl chloride in 130 g of tetrahydrofuran And the mixture was stirred at room temperature for 1 hour. 530 g of water of manufacture, 293 g of 10percent hydrochloric acid aqueous solution and 1060 g of ethyl acetate were added to the reaction solution, and the mixture was separated, washed with 665 g of sodium carbonate aqueous solution, and then dried with anhydrous sodium sulfate. The crude product obtained by distilling off the solvent was purified with 100 g of toluene to obtain 147.7 g (yield 66.9percent) of the title compound as white crystals.
Reference: [1] RSC Advances, 2017, vol. 7, # 53, p. 33248 - 33256
[2] Patent: JP6222973, 2017, B2, . Location in patent: Paragraph 0070
  • 4
  • [ 34040-64-7 ]
  • [ 16473-35-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 13, p. 3736 - 3740
[2] Organic and Biomolecular Chemistry, 2015, vol. 13, # 31, p. 8556 - 8560
[3] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 16, p. 4481 - 4486
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