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[ CAS No. 4377-33-7 ] {[proInfo.proName]}

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Chemical Structure| 4377-33-7
Chemical Structure| 4377-33-7
Structure of 4377-33-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 4377-33-7 ]

CAS No. :4377-33-7 MDL No. :MFCD05861645
Formula : C6H6ClN Boiling Point : -
Linear Structure Formula :- InChI Key :NJWIMFZLESWFIM-UHFFFAOYSA-N
M.W : 127.57 Pubchem ID :23393
Synonyms :

Calculated chemistry of [ 4377-33-7 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.17
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 34.0
TPSA : 12.89 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) : -6.13 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.57
Log Po/w (XLOGP3) : 1.33
Log Po/w (WLOGP) : 1.67
Log Po/w (MLOGP) : 1.15
Log Po/w (SILICOS-IT) : 2.37
Consensus Log Po/w : 1.62

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.96
Solubility : 1.41 mg/ml ; 0.011 mol/l
Class : Very soluble
Log S (Ali) : -1.2
Solubility : 8.01 mg/ml ; 0.0628 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.0
Solubility : 0.126 mg/ml ; 0.000989 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.36

Safety of [ 4377-33-7 ]

Signal Word:Danger Class:8
Precautionary Statements:P261-P280-P305+P351+P338-P310 UN#:3265
Hazard Statements:H302-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 4377-33-7 ]

* 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 [ 4377-33-7 ]
  • Downstream synthetic route of [ 4377-33-7 ]

[ 4377-33-7 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 4377-33-7 ]
  • [ 74-89-5 ]
  • [ 21035-59-6 ]
Reference: [1] Patent: WO2017/205534, 2017, A1, . Location in patent: Paragraph 00180
  • 2
  • [ 931-19-1 ]
  • [ 10025-87-3 ]
  • [ 18368-63-3 ]
  • [ 3678-63-5 ]
  • [ 4377-33-7 ]
Reference: [1] Yakugaku Zasshi, 1951, vol. 71, p. 217,218[2] Chem.Abstr., 1952, p. 4541
[3] Yakugaku Zasshi, 1955, vol. 75, p. 1233[4] Chem.Abstr., 1956, p. 8664
  • 3
  • [ 931-19-1 ]
  • [ 10025-87-3 ]
  • [ 18368-63-3 ]
  • [ 3678-63-5 ]
  • [ 4377-33-7 ]
Reference: [1] Yakugaku Zasshi, 1951, vol. 71, p. 217,218[2] Chem.Abstr., 1952, p. 4541
[3] Yakugaku Zasshi, 1955, vol. 75, p. 1233[4] Chem.Abstr., 1956, p. 8664
  • 4
  • [ 4377-33-7 ]
  • [ 2044-73-7 ]
Reference: [1] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1997, vol. 36, # 11, p. 1000 - 1004
  • 5
  • [ 4377-33-7 ]
  • [ 23579-92-2 ]
Reference: [1] Patent: US3966945, 1976, A,
  • 6
  • [ 4377-33-7 ]
  • [ 124-41-4 ]
  • [ 23579-92-2 ]
Reference: [1] Yakugaku Zasshi, 1959, vol. 79, p. 1277,1280[2] Chem.Abstr., 1960, p. 4566
[3] Pharmaceutical Bulletin, 1956, vol. 4, p. 211,212,214
[4] Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999), 1985, p. 731 - 736
  • 7
  • [ 4377-33-7 ]
  • [ 50-00-0 ]
  • [ 103-74-2 ]
YieldReaction ConditionsOperation in experiment
59%
Stage #1: With chloro-trimethyl-silane; ethylene dibromide; zinc In tetrahydrofuran at 70℃; for 2 h; Schlenk technique; Inert atmosphere
Stage #2: at 70℃; for 6 h; Schlenk technique; Inert atmosphere
General procedure: Phenethyl alcohol (3a) A two neck Schlenk flask equipped with a magnetic stirring bar and septum was heated with heat gun (~400 °C) for 10 min under high vacuum. After cooling to room temperature, the flask was flushed with argon (3 times). Zn-dust (654 mg, 2.0 equiv, 10.0 mmol) was added followed by THF (20 mL). 1,2-Dibromoethane (5 molpercent) was added and the reaction mixture was heated until ebullition occurs. After cooling to rt, chlorotrimethylsilane (1 molpercent) was added and the mixture was heated again till ebullition occurs. The flask was again cooled to rt and benzyl chloride (633 mg, 5.0 mmol, 1 equiv) was added as a solution in THF (10 mL) and it was heated at 70 °C for 2 h and cooled to rt. Paraformaldehyde (450 mg, 3.0 equiv. 15.0 mmol) was slowly added at rt and the flask was again heated at 70 °C for 6 h. The solution was cooled to rt and saturated NH4Cl solution was added. The phases were separated and the aqueous layer was extracted with ethyl acetate (100 mL). The combined organic layer was washed with water (20 mL), brine (10 mL) and then dried over Na2SO4. The solvents were evaporated under reduced pressure and the residue was purified by silica gel column chromatography using cyclohexane or cyclohexane/ethyl acetate as an eluent to obtain phenethyl alcohol (3a) (510 mg, 83percent) as a colourless liquid.
Reference: [1] Synthetic Communications, 2017, vol. 47, # 10, p. 968 - 974
  • 8
  • [ 4377-33-7 ]
  • [ 3731-51-9 ]
  • [ 16858-01-8 ]
Reference: [1] Journal of the American Chemical Society, 1993, vol. 115, # 7, p. 2677 - 2689
[2] Journal of Physical Chemistry, 1995, vol. 99, # 10, p. 3294 - 3302
[3] Patent: WO2012/97876, 2012, A1, . Location in patent: Page/Page column 14-15
[4] Bioconjugate Chemistry, 2012, vol. 23, # 7, p. 1415 - 1425
  • 9
  • [ 638-14-2 ]
  • [ 4377-33-7 ]
  • [ 16858-01-8 ]
Reference: [1] Dalton Transactions, 2015, vol. 44, # 17, p. 8021 - 8030
  • 10
  • [ 20979-34-4 ]
  • [ 4377-33-7 ]
  • [ 4377-35-9 ]
  • [ 10177-21-6 ]
  • [ 78846-88-5 ]
Reference: [1] Tetrahedron, 1982, vol. 38, # 22, p. 3277 - 3280
  • 11
  • [ 4377-33-7 ]
  • [ 524955-09-7 ]
Reference: [1] European Journal of Medicinal Chemistry, 2018, vol. 144, p. 330 - 348
  • 12
  • [ 4377-33-7 ]
  • [ 619-08-9 ]
  • [ 179687-79-7 ]
YieldReaction ConditionsOperation in experiment
52% With hydrogenchloride; caesium carbonate; sodium iodide In acetonitrile at 60℃; for 5 h; Example 71; 4-f [3-chloro-4-(pyridin-2-ylmethoxy)phenyl]amino) [1]benzothieno[2,3-d] pyrimidin-7-ol; Step 1. Preparation of 3-Chloro-4-(pyridin-2-ylmethoxy)-phenylamine; EPO <DP n="84"/> 2-chloro-4-nitro phenol (10 g, 57.6 mmol, 1 equiv), 2-pycolyl chloride hydrogen chloride (9.45 g, 57.6 mmol, 1 equiv) cesium carbonate 41.3 (126.8 mmol, 2.2 equiv) and sodium iodide (8.64 g, 57.6 mmol, 1 equiv) were suspended in 200 mL acetonitrile. The reaction mixture was stirred at 60°C for 5h. The resulted suspension was filtered and washed with water (400 mL), yielding 2-(2-chloro-4- nitro-phenoxymethyl)-pyridine (8 g, 52percent) as a red solid.2-(2-chloro-4-nitro-phenoxyrnethyl)-pyridine (8 g, 30.2mmol, 1 equiv) and iron (8.44 g, 151.1 mmol, 5 equiv) were mixed in acetic acid (100 mL ) and EtOAc (50 mL ) and were stirred at rt overnight. The reaction mixture was filtered through a pad of Celite.(R).. The filtrate was concentrated in vacuo and neutralized with saturated Na2CO3 solution. The solution was extracted with EtOAc and the organic layer was washed with brine and concentrated in vacuo. The resulting crude material was purified by flash chromatography eluting with EtOAc/hexane (3:7) to give 3-Chloro- 4-(pyridin-2-ylmethoxy)-phenylamine (3.2 g, 52percent) as a white solid. 1H-NMR (CDCl3) δ 5.18 (s, 2H), 6.50 (dd, 1H), 6.76 (d, 1H),. 6.80 (d, 1H), 7.22 (m, 1H), 7.64 (d, 1H), 7.73 (td, 1H), 8.55 (m, 1H); LCMS RT = 0.89 min, [M+H]+ = 235.1.
Reference: [1] Patent: WO2006/44524, 2006, A1, . Location in patent: Page/Page column 82-83
[2] European Journal of Medicinal Chemistry, 2018, vol. 144, p. 330 - 348
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