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[ CAS No. 620-72-4 ] {[proInfo.proName]}

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Type HazMat fee for 500 gram (Estimated)
Excepted Quantity USD 0.00
Limited Quantity USD 15-60
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Inaccessible (Haz class 6.1), International USD 150+
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Chemical Structure| 620-72-4
Chemical Structure| 620-72-4
Structure of 620-72-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 620-72-4 ]

CAS No. :620-72-4 MDL No. :MFCD00192391
Formula : C8H7BrO2 Boiling Point : -
Linear Structure Formula :- InChI Key :UEWYUCGVQMZMGY-UHFFFAOYSA-N
M.W : 215.04 Pubchem ID :564919
Synonyms :

Calculated chemistry of [ 620-72-4 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 45.81
TPSA : 26.3 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) : -5.99 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.96
Log Po/w (XLOGP3) : 2.28
Log Po/w (WLOGP) : 1.99
Log Po/w (MLOGP) : 2.4
Log Po/w (SILICOS-IT) : 2.23
Consensus Log Po/w : 2.17

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.82
Solubility : 0.329 mg/ml ; 0.00153 mol/l
Class : Soluble
Log S (Ali) : -2.47
Solubility : 0.73 mg/ml ; 0.00339 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.35
Solubility : 0.0961 mg/ml ; 0.000447 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.57

Safety of [ 620-72-4 ]

Signal Word:Danger Class:8
Precautionary Statements:P264-P270-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P363-P403+P233-P501 UN#:3261
Hazard Statements:H302-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 620-72-4 ]

* 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 [ 620-72-4 ]
  • Downstream synthetic route of [ 620-72-4 ]

[ 620-72-4 ] Synthesis Path-Upstream   1~9

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Reference: [1] Synthetic Communications, 1986, vol. 16, # 9, p. 1043 - 1048
[2] Journal of Organic Chemistry, 1989, vol. 54, # 16, p. 3916 - 3926
[3] Chemische Berichte, 1988, vol. 121, p. 431 - 442
[4] Chemische Berichte, 1898, vol. 31, p. 173
[5] Journal of the American Chemical Society, 1949, vol. 71, p. 2652,2654
[6] Organic Letters, 2007, vol. 9, # 16, p. 3195 - 3197
[7] Chemical Communications, 2012, vol. 48, # 42, p. 5076 - 5078
[8] Chemistry Letters, 2013, vol. 42, # 4, p. 355 - 357
[9] Journal of the American Chemical Society, 2013, vol. 135, # 33, p. 12160 - 12163
[10] Organic Syntheses, 2012, vol. 89, p. 501 - 509
[11] Organic Letters, 2014, vol. 16, # 23, p. 6264 - 6266
[12] Organic Letters, 2016, vol. 18, # 10, p. 2443 - 2446
[13] Tetrahedron, 2017, vol. 73, # 29, p. 4150 - 4159
[14] Journal of Organic Chemistry, 2017, vol. 82, # 18, p. 9291 - 9304
[15] Advanced Synthesis and Catalysis, 2018, vol. 360, # 7, p. 1510 - 1516
[16] Chemical Communications, 2018, vol. 54, # 28, p. 3516 - 3519
[17] Chinese Journal of Chemistry, 2018, vol. 36, # 9, p. 857 - 865
[18] Organic Letters, 2018, vol. 20, # 18, p. 5799 - 5802
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  • [ 106-41-2 ]
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Reference: [1] Patent: US5514711, 1996, A,
  • 3
  • [ 100-66-3 ]
  • [ 598-21-0 ]
  • [ 620-72-4 ]
Reference: [1] Synthetic Communications, 2002, vol. 32, # 5, p. 721 - 728
  • 4
  • [ 79-08-3 ]
  • [ 108-95-2 ]
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Reference: [1] Journal of the American Chemical Society, 1970, vol. 92, p. 1370 - 1378
  • 5
  • [ 7647-01-0 ]
  • [ 60-29-7 ]
  • [ 1600-27-7 ]
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Reference: [1] Journal of the American Chemical Society, 1942, vol. 64, p. 2635,2637
  • 6
  • [ 7732-18-5 ]
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Reference: [1] Journal of the American Chemical Society, 1945, vol. 67, p. 690
  • 7
  • [ 620-72-4 ]
  • [ 20989-17-7 ]
  • [ 491833-36-4 ]
YieldReaction ConditionsOperation in experiment
53%
Stage #1: With N-ethyl-N,N-diisopropylamine In acetonitrile at 5 - 20℃; for 4.5 h;
Stage #2: With hydrogenchloride In ethyl acetate at 15℃; for 0.333333 h;
(5S)-5-Phenylmorpholin-2-one HCl salt
A solution of phenyl bromoacetate (Aldrich, 862.17 g, 4.0 moles, 1.1 equivalents) in acetonitrile (reagent grade, 1500 ml) was cooled in an ice bath (internal temperature below 5° C.).
To this was added a cold slurry (internal temperature below 5° C.) of S-(+)-2-phenyl glycinol (Aldrich, 500 g, 3.65 moles, 1 equivalent) and diisopropylethylamine (DIPEA) (Aldrich, 1587 ml, 9.11 moles, 2.5 equivalents) in acetonitrile (2900 ml) in portions while keeping the internal temperature below 10° C.
The mixture was stirred at this temperature for 30 minutes before the ice bath was removed and the mixture was allowed to stir at room temperature for an additional 4 hours.
The solvent was removed in vacuo while maintaining the bath temperature at 25° C.
The mixture was coevaporated with ethyl acetate (2*500 ml) to produce a light yellow viscous oil.
To the reaction mixture, ethyl acetate (4500 ml) was added and the flask was immersed in an ice bath with agitation.
The mixture was allowed to cool below 8° C.
The solid was filtered and washed with ethyl acetate (3*250 ml). The solution was cooled to below 5° C. Dry HCl gas was passed slowly into the solution while maintaining the internal temperature below 15° C. until the pH was below 2 (wet pH paper). The mixture was allowed to stir at this temperature and pH for an additional 20 minutes before the solid was suction filtered. The solid was washed with ethyl acetate (3×200 ml) and dried under high vacuum for about 20 hours. The yield was 412 g (53percent). 1H NMR was consistent with the (5S)-5-phenylmorpholin-2-one HCl salt.
50%
Stage #1: With N-ethyl-N,N-diisopropylamine In acetonitrile at 10 - 20℃; Inert atmosphere
Stage #2: With hydrogenchloride In ethyl acetate
To a (S) + phenyl glycinol (100g) add N, N-diisopropylethylamine (314ml) and acetonitrile (2000ml) under nitrogen atmosphere at room temperature. It was cooled to 10- 15° C. Phenyl bromoacetate (172.4g) dissolved in acetonitrile (500ml) was added to the above solution at 15° C over a period of 30 min. The reaction mixture is allowed to room temperature and stirred for 16-20h. Progress of the reaction was monitored by thin layer chromatography. After completion of the reaction, the reaction mixture was concentrated under reduced pressure at a water bath temperature less than 25° C to get a residue. The residue was dissolved in ethyl acetate (1000ml) and stirred for 1 h at 15-20°C to obtain a white solid. The solid material obtained was filtered and washed with ethyl acetate (200ml). The filtrate was dried over anhydrous sodium sulphate (20g) and concentrated under reduced pressure at a water bath temperature less than 25° C to give crude compound (1000g) as brown syrup. The Crude brown syrup is converted to HCI salt by using HCI in ethyl acetate to afford 5-phenyl morpholine-2-one hydrochloride (44g) as a white solid. Yield: 50percent, Mass: m/z = 177.6; HPLC (percent Area Method): 90.5percent
Reference: [1] Patent: US9546161, 2017, B2, . Location in patent: Page/Page column 21
[2] Patent: WO2015/59679, 2015, A1, . Location in patent: Page/Page column 13; 14
  • 8
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Reference: [1] Patent: US2003/50299, 2003, A1,
  • 9
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  • [ 491833-29-5 ]
Reference: [1] Patent: WO2017/68496, 2017, A1,
[2] Patent: WO2017/68496, 2017, A1,
[3] Patent: WO2017/68496, 2017, A1,
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