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[ CAS No. 14002-33-6 ] {[proInfo.proName]}

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Chemical Structure| 14002-33-6
Chemical Structure| 14002-33-6
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Product Details of [ 14002-33-6 ]

CAS No. :14002-33-6 MDL No. :MFCD00046013
Formula : C6H15NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :CXMYWOCYTPKBPP-UHFFFAOYSA-N
M.W : 133.19 Pubchem ID :106986
Synonyms :

Calculated chemistry of [ 14002-33-6 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 6
Num. H-bond acceptors : 3.0
Num. H-bond donors : 3.0
Molar Refractivity : 36.08
TPSA : 52.49 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.72 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.53
Log Po/w (XLOGP3) : -0.86
Log Po/w (WLOGP) : -0.66
Log Po/w (MLOGP) : -0.27
Log Po/w (SILICOS-IT) : 0.1
Consensus Log Po/w : -0.03

Druglikeness

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

Water Solubility

Log S (ESOL) : 0.27
Solubility : 249.0 mg/ml ; 1.87 mol/l
Class : Highly soluble
Log S (Ali) : 0.24
Solubility : 231.0 mg/ml ; 1.73 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : -1.18
Solubility : 8.86 mg/ml ; 0.0665 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.01

Safety of [ 14002-33-6 ]

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 [ 14002-33-6 ]

* 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 [ 14002-33-6 ]
  • Downstream synthetic route of [ 14002-33-6 ]

[ 14002-33-6 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 156-87-6 ]
  • [ 627-30-5 ]
  • [ 14002-33-6 ]
YieldReaction ConditionsOperation in experiment
80%
Stage #1: for 24 h; Heating / reflux
Stage #2: With potassium hydroxide In water
Dipropanolamine (2)
A mixture of 3-amino-1-propanol (45 mL, 0.59 mol), 1-chloro-3-hydroxypropane (25 mL, 0.30 mol) and water (130 mL) was refluxed over 24 hours.
Potassium hydroxide was then added.
After dissolution, the whole of the water was evaporated to leave viscous oil and large quantities of potassium chloride.
These were filtered and washed with dried acetone.
The organic phase was dried over magnesium sulfate, filtered and evaporated to leave dark brown oil.
The desired dipropanolamine was obtained, by distillation of this oil, as a colorless or light yellow liquid (m=31.5 g; 0.24 mol, yield=80percent).
1H NMR δ (CDCl3): 1.73 (q, 4H, N-CH2-CH2-CH2-OH); 2.81 (t, 4H, N-CH2-CH2-CH2-OH); 3.20 (s, 3H, HN-CH2-CH2-CH2-OH), 3.75 (t, 4H, N-CH2-CH2-CH2-OH).
12.5 g for 24 h; Reflux Step 1:
Preparation of Intermediate 1: 3,3'-azanediylbis(propan-1-ol)
A mixture of 3-amino-1-propanol (14.5 mL, 19.0 mmol), 1-chloro-3-hydroxy propane (8.00 mL, 95.6 mmol) and H2O (˜50 mL) was refluxed over 24 hours.
Potassium hydroxide (5.40 g) was then added.
After dissolution, the whole of the water was evaporated to leave viscous oil and large quantities of potassium chloride.
These were filtered and washed with dry acetone and dichloromethane.
The organic phase was dried over Na2SO4, filtered and evaporated to leave an oil.
Purification by silica gel chromatography eluating with a DCM/MeOH gradient yielded 3,3'-azanediylbis(propan-1-ol) (12.5 g).
Reference: [1] Patent: US2006/69249, 2006, A1, . Location in patent: Page/Page column 3
[2] Tetrahedron, 1995, vol. 51, # 4, p. 1197 - 1208
[3] Patent: WO2012/170952, 2012, A2, . Location in patent: Page/Page column 47
[4] Patent: US2013/330401, 2013, A1, . Location in patent: Paragraph 0098; 0099
  • 2
  • [ 5279-23-2 ]
  • [ 14002-33-6 ]
Reference: [1] Journal of the Chemical Society - Perkin Transactions 1, 1996, # 13, p. 1553 - 1558
[2] Journal of Organic Chemistry, 2000, vol. 65, # 24, p. 8367 - 8371
  • 3
  • [ 3518-85-2 ]
  • [ 14002-33-6 ]
Reference: [1] Journal of the American Chemical Society, 1980, vol. 102, p. 5073
  • 4
  • [ 3518-88-5 ]
  • [ 14002-33-6 ]
Reference: [1] Chemische Berichte, 1991, vol. 124, # 3, p. 481 - 486
  • 5
  • [ 156-87-6 ]
  • [ 627-30-5 ]
  • [ 14002-33-6 ]
  • [ 14002-34-7 ]
Reference: [1] Journal of the Chemical Society, Dalton Transactions, 2001, # 12, p. 1863 - 1871
  • 6
  • [ 793-19-1 ]
  • [ 14002-33-6 ]
Reference: [1] Journal of Organic Chemistry, 2000, vol. 65, # 24, p. 8367 - 8371
  • 7
  • [ 10494-79-8 ]
  • [ 14002-33-6 ]
Reference: [1] Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999), 1985, p. 1361 - 1364
  • 8
  • [ 70-55-3 ]
  • [ 109-64-8 ]
  • [ 14002-33-6 ]
Reference: [1] Zhurnal Obshchei Khimii, 1938, vol. 8, p. 1547[2] Chem. Zentralbl., 1939, vol. 110, # I, p. 4951
  • 9
  • [ 14002-33-6 ]
  • [ 317336-73-5 ]
Reference: [1] Journal of Organic Chemistry, 2000, vol. 65, # 24, p. 8367 - 8371
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