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[ CAS No. 4472-45-1 ] {[proInfo.proName]}

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Chemical Structure| 4472-45-1
Chemical Structure| 4472-45-1
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Product Details of [ 4472-45-1 ]

CAS No. :4472-45-1 MDL No. :MFCD00234197
Formula : C6H7ClN2 Boiling Point : -
Linear Structure Formula :- InChI Key :GSXFOGXQLRLSKK-UHFFFAOYSA-N
M.W : 142.59 Pubchem ID :3154199
Synonyms :

Calculated chemistry of [ 4472-45-1 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.33
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 36.97
TPSA : 25.78 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) : -5.96 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.05
Log Po/w (XLOGP3) : 1.7
Log Po/w (WLOGP) : 1.75
Log Po/w (MLOGP) : 0.89
Log Po/w (SILICOS-IT) : 2.42
Consensus Log Po/w : 1.76

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.29
Solubility : 0.734 mg/ml ; 0.00515 mol/l
Class : Soluble
Log S (Ali) : -1.86
Solubility : 1.98 mg/ml ; 0.0139 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.02
Solubility : 0.137 mg/ml ; 0.000959 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.6

Safety of [ 4472-45-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 4472-45-1 ]

* 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 [ 4472-45-1 ]
  • Downstream synthetic route of [ 4472-45-1 ]

[ 4472-45-1 ] Synthesis Path-Upstream   1~20

  • 1
  • [ 4472-45-1 ]
  • [ 14331-54-5 ]
Reference: [1] Chemische Berichte, 1902, vol. 35, p. 1577
[2] Yakugaku Zasshi, 1950, vol. 70, p. 137[3] Chem.Abstr., 1950, p. 5886
  • 2
  • [ 930-61-0 ]
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1431 - 1435
  • 3
  • [ 930-61-0 ]
  • [ 67-66-3 ]
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  • [ 123-32-0 ]
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  • [ 108-50-9 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1431 - 1435
  • 4
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  • [ 67-66-3 ]
  • [ 4994-86-9 ]
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  • [ 693-98-1 ]
  • [ 75712-73-1 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1431 - 1435
  • 5
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  • [ 123-32-0 ]
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1431 - 1435
  • 6
  • [ 6622-92-0 ]
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YieldReaction ConditionsOperation in experiment
82% With trichlorophosphate In toluene for 3 h; Reflux POCl3 (0.460 g, 3.0 mmol) was added to the solution of compound 13 (1.0 mmol) in 15 mL of toluene and the mixture was stirred at reflux for 3 hours. Redundant POCl3 was removed under reduced pressure and ice water (10mL) was added. The solution was adjusted to the pH 9-10 with sodium carbonate and then extracted with methyl tert-butyl ether (MTBE). The organic phase was dried over sodium sulfate, and the solvent was removed under reduced pressure to afford compound 14. (Yield: 82percent) MS (ESI) (m /z) [M+H]+ 143.1.
71% With ammonia In sodium chloride; dichloromethane; trichlorophosphate Part 1
Preparation of 2,4-dimethyl-6-chloropyrimidine.
METHOD:
20 g (16.1*10-2 mol) of 2,4-dimethyl-6-hydroxypyrimidine in suspension in 150 ml of phosphorus oxychloride are introduced into a 250 ml three-necked flask fitted with a thermometer, a condenser and a magnetic stirrer.
The mixture is heated at 90° C. for one and a half hours.
The mixture is then cooled and then evaporated to dryness.
The residue which crystallises at ambient temperature is added, in small portions, to a binary mixture consisting of dichloromethane (200 ml) and 10percent ammonia (300 ml), previously cooled to -5° C. in an ice bath containing sodium chloride.
The mixture is stirred cold for half an hour and the organic phase is then decanted off, washed with water until neutral and then dried over sodium sulphate, filtered and evaporated.
The yellow liquid obtained is filtered through a glass frit filled with silica using the dichloromethane/methanol (99/1) eluent system; the pure fractions collected are evaporated.
16.4 g of a colourless liquid which has a persistent odour and which crystallises in a refrigerator are obtained.
Yield: 71percent.
Elementary analysis for C6 H7 ClN2; molecular weight=142.5.
The 1 H and 13 C NMR and mass spectra are in accordance with the expected structure.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 10, p. 1769 - 1775
[2] Tetrahedron Letters, 1999, vol. 40, # 42, p. 7477 - 7478
[3] Patent: US5438058, 1995, A,
[4] Patent: US6093718, 2000, A,
  • 7
  • [ 1780-26-3 ]
  • [ 4472-45-1 ]
Reference: [1] Patent: WO2005/95357, 2005, A2, . Location in patent: Page/Page column 167; 168
  • 8
  • [ 6622-92-0 ]
  • [ 4472-45-1 ]
Reference: [1] Heterocycles, 2006, vol. 68, # 9, p. 1973 - 1979
[2] Helvetica Chimica Acta, 2001, vol. 84, # 5, p. 1112 - 1118
[3] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 22, p. 6439 - 6442
  • 9
  • [ 930-62-1 ]
  • [ 67-66-3 ]
  • [ 4472-45-1 ]
  • [ 95-89-6 ]
  • [ 75712-74-2 ]
  • [ 75712-73-1 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1427 - 1430
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1427 - 1430
  • 10
  • [ 930-61-0 ]
  • [ 67-66-3 ]
  • [ 14331-54-5 ]
  • [ 123-32-0 ]
  • [ 54198-89-9 ]
  • [ 4472-45-1 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1431 - 1435
  • 11
  • [ 930-61-0 ]
  • [ 67-66-3 ]
  • [ 4994-86-9 ]
  • [ 4472-45-1 ]
  • [ 693-98-1 ]
  • [ 75712-73-1 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1431 - 1435
  • 12
  • [ 930-61-0 ]
  • [ 67-66-3 ]
  • [ 14331-54-5 ]
  • [ 123-32-0 ]
  • [ 4472-45-1 ]
  • [ 108-50-9 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1431 - 1435
  • 13
  • [ 930-62-1 ]
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  • [ 95-89-6 ]
  • [ 38557-72-1 ]
  • [ 75712-73-1 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1427 - 1430
  • 14
  • [ 6622-92-0 ]
  • [ 10025-87-3 ]
  • [ 4472-45-1 ]
Reference: [1] Chemische Berichte, 1902, vol. 35, p. 1577
  • 15
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  • [ 461-98-3 ]
Reference: [1] Chemische Berichte, 1902, vol. 35, p. 1577
  • 16
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  • [ 7664-41-7 ]
  • [ 461-98-3 ]
Reference: [1] Chemische Berichte, 1902, vol. 35, p. 1577
  • 17
  • [ 930-62-1 ]
  • [ 67-66-3 ]
  • [ 4472-45-1 ]
  • [ 95-89-6 ]
  • [ 75712-74-2 ]
  • [ 75712-73-1 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1427 - 1430
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1427 - 1430
  • 18
  • [ 930-62-1 ]
  • [ 67-66-3 ]
  • [ 4472-45-1 ]
  • [ 95-89-6 ]
  • [ 38557-72-1 ]
  • [ 75712-73-1 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1427 - 1430
  • 19
  • [ 930-62-1 ]
  • [ 67-66-3 ]
  • [ 4472-45-1 ]
  • [ 95-89-6 ]
  • [ 38557-72-1 ]
  • [ 75712-73-1 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1427 - 1430
  • 20
  • [ 4472-45-1 ]
  • [ 14001-62-8 ]
Reference: [1] Gazzetta Chimica Italiana, 1951, vol. 81, p. 405,412
[2] Yakugaku Zasshi, 1942, vol. 62, p. 315,333; dtsch. Ref. S. 95, 106[3] Chem.Abstr., 1951, p. 5150
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