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[ CAS No. 622-08-2 ] {[proInfo.proName]}

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Chemical Structure| 622-08-2
Chemical Structure| 622-08-2
Structure of 622-08-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 622-08-2 ]

CAS No. :622-08-2 MDL No. :MFCD00002868
Formula : C9H12O2 Boiling Point : -
Linear Structure Formula :- InChI Key :CUZKCNWZBXLAJX-UHFFFAOYSA-N
M.W : 152.19 Pubchem ID :12141
Synonyms :

Calculated chemistry of [ 622-08-2 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.33
Num. rotatable bonds : 4
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 43.27
TPSA : 29.46 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) : -6.44 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.92
Log Po/w (XLOGP3) : 1.11
Log Po/w (WLOGP) : 1.04
Log Po/w (MLOGP) : 1.26
Log Po/w (SILICOS-IT) : 1.87
Consensus Log Po/w : 1.44

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.62
Solubility : 3.63 mg/ml ; 0.0238 mol/l
Class : Very soluble
Log S (Ali) : -1.32
Solubility : 7.26 mg/ml ; 0.0477 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.76
Solubility : 0.264 mg/ml ; 0.00174 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.45

Safety of [ 622-08-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312+P330-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P403+P233-P405-P501 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 622-08-2 ]

* 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 [ 622-08-2 ]
  • Downstream synthetic route of [ 622-08-2 ]

[ 622-08-2 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 622-08-2 ]
  • [ 13807-91-5 ]
Reference: [1] Chemistry - A European Journal, 2012, vol. 18, # 22, p. 6907 - 6914
  • 2
  • [ 75-21-8 ]
  • [ 100-51-6 ]
  • [ 2050-25-1 ]
  • [ 622-08-2 ]
  • [ 55489-58-2 ]
  • [ 86259-87-2 ]
Reference: [1] ACH - Models in Chemistry, 1997, vol. 134, # 2-3, p. 241 - 252
[2] ACH - Models in Chemistry, 1997, vol. 134, # 2-3, p. 241 - 252
  • 3
  • [ 622-08-2 ]
  • [ 2050-25-1 ]
Reference: [1] ACH - Models in Chemistry, 1996, vol. 133, # 1-2, p. 21 - 26
  • 4
  • [ 75-21-8 ]
  • [ 100-51-6 ]
  • [ 2050-25-1 ]
  • [ 622-08-2 ]
Reference: [1] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 16, p. 2456
  • 5
  • [ 75-21-8 ]
  • [ 100-51-6 ]
  • [ 2050-25-1 ]
  • [ 622-08-2 ]
  • [ 55489-58-2 ]
  • [ 86259-87-2 ]
  • [ 57671-28-0 ]
Reference: [1] Tetrahedron Letters, 1997, vol. 38, # 4, p. 661 - 664
  • 6
  • [ 622-08-2 ]
  • [ 22539-93-1 ]
Reference: [1] Chemistry - A European Journal, 2012, vol. 18, # 22, p. 6907 - 6914
  • 7
  • [ 622-08-2 ]
  • [ 1462-37-9 ]
YieldReaction ConditionsOperation in experiment
56.2% With N-Bromosuccinimide; triphenylphosphine In dichloromethane at -10 - 23℃; for 1 h; Step 2: To a stirred solution of 2-(benzyloxy)ethanol (17.0 g, 1 1 1 .84 mmol) and PPh3 (35.0 g, 134.21 mmol) in DCM (170 mL) at -10 <C to -5 <C, NBS (23.88 g, 134.21 mmol) was added slowly in portions maintaining the temperature at -10 °C to -5 °C. After addition, the reaction mixture was allowed to stir at RT for 1 h until complete consumption starting material, as evidenced by TLC analysis. The reaction mixture was concentrated, the obtained crude compound was purified by CC using 5percent EtOAc in PE as eluent to afford ((2-bromoethoxy)methyl)benzene (13.5 g, 56.2percent) as pale yellow liquid (TLC solvent system: 30percent EtOAc in PE; Rf: 0.7).
Reference: [1] Journal of the American Chemical Society, 2011, vol. 133, # 4, p. 958 - 963
[2] Organic Letters, 2011, vol. 13, # 12, p. 3246 - 3249
[3] Synlett, 2001, # 9, p. 1428 - 1430
[4] Journal of Organic Chemistry, 1991, vol. 56, # 7, p. 2364 - 2370
[5] Nucleosides, Nucleotides and Nucleic Acids, 2009, vol. 28, # 5-7, p. 337 - 351
[6] Synlett, 2004, # 10, p. 1763 - 1764
[7] Patent: WO2013/68461, 2013, A1, . Location in patent: Page/Page column 118
[8] Journal of the Chemical Society - Dalton Transactions, 1996, # 23, p. 4379 - 4387
[9] Journal of Organic Chemistry, 1971, vol. 36, p. 3526 - 3532
[10] Journal of Medicinal Chemistry, 2009, vol. 52, # 8, p. 2493 - 2505
[11] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 18, p. 4075 - 4099
  • 8
  • [ 558-13-4 ]
  • [ 622-08-2 ]
  • [ 1462-37-9 ]
YieldReaction ConditionsOperation in experiment
76% With pyridine; triphenylphosphine In methanol; dichloromethane; ethyl acetate A.
To an ice-cooled mechanically stirred solution of 2-benzyloxyethanol (25 mL, 0.18 mole), triphenylphosphine (115.2 g, 0.44 mole) and pyridine (56.9 mL, 0.70 mole) in methylene chloride (1000 mL) was added, dropwise, carbon tetrabromide (61.3 g, 0.18 mole).
The mixture was stirred overnight at room temperature.
Methanol (130 mL) was then added and, after further stirring for 1 hour, the solvents were evaporated.
The residue was triturated with hexane and the hexane solution was concentrated to yield an oil which was set aside.
The residue remaining after trituration was taken up in ethyl acetate, washed with saturated sodium bicarbonate solution and brine and was concentrated to afford a brown oil.
This was triturated with hexane.
The resulting hexane solution was combined with the oil from the previous trituration and concentrated.
The residue was chromatographed twice on silica gel eluding with hexane and then 5percent ethyl acetate/hexane to afford (2-bromoethoxymethyl)benzene as an oil (28.8 g, 76percent yield).
Reference: [1] Patent: US5854275, 1998, A,
  • 9
  • [ 622-08-2 ]
  • [ 603-35-0 ]
  • [ 1462-37-9 ]
Reference: [1] Patent: US5886022, 1999, A,
[2] Patent: US5789434, 1998, A,
  • 10
  • [ 622-08-2 ]
  • [ 1462-37-9 ]
  • [ 100-39-0 ]
Reference: [1] Tetrahedron, 1999, vol. 55, # 31, p. 9405 - 9424
  • 11
  • [ 75-21-8 ]
  • [ 100-51-6 ]
  • [ 2050-25-1 ]
  • [ 622-08-2 ]
  • [ 55489-58-2 ]
  • [ 86259-87-2 ]
Reference: [1] ACH - Models in Chemistry, 1997, vol. 134, # 2-3, p. 241 - 252
[2] ACH - Models in Chemistry, 1997, vol. 134, # 2-3, p. 241 - 252
  • 12
  • [ 75-21-8 ]
  • [ 100-51-6 ]
  • [ 2050-25-1 ]
  • [ 622-08-2 ]
  • [ 55489-58-2 ]
  • [ 86259-87-2 ]
  • [ 57671-28-0 ]
Reference: [1] Tetrahedron Letters, 1997, vol. 38, # 4, p. 661 - 664
  • 13
  • [ 622-08-2 ]
  • [ 38336-04-8 ]
Reference: [1] Journal of Medicinal Chemistry, 1998, vol. 41, # 27, p. 5362 - 5374
[2] Tetrahedron, 1998, vol. 54, # 46, p. 13981 - 13996
[3] Journal of the American Chemical Society, 1994, vol. 116, # 12, p. 5057 - 5062
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