Home Cart 0 Sign in  

[ CAS No. 3900-89-8 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 3900-89-8
Chemical Structure| 3900-89-8
Structure of 3900-89-8 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 3900-89-8 ]

Related Doc. of [ 3900-89-8 ]

Alternatived Products of [ 3900-89-8 ]

Product Details of [ 3900-89-8 ]

CAS No. :3900-89-8 MDL No. :MFCD00674012
Formula : C6H6BClO2 Boiling Point : -
Linear Structure Formula :- InChI Key :RRCMGJCFMJBHQC-UHFFFAOYSA-N
M.W :156.37 Pubchem ID :2734322
Synonyms :

Calculated chemistry of [ 3900-89-8 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 41.28
TPSA : 40.46 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) : -6.22 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 1.45
Log Po/w (WLOGP) : 0.02
Log Po/w (MLOGP) : 0.88
Log Po/w (SILICOS-IT) : -0.08
Consensus Log Po/w : 0.45

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.1
Solubility : 1.24 mg/ml ; 0.00792 mol/l
Class : Soluble
Log S (Ali) : -1.91
Solubility : 1.94 mg/ml ; 0.0124 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.89
Solubility : 2.01 mg/ml ; 0.0129 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.81

Safety of [ 3900-89-8 ]

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

Application In Synthesis of [ 3900-89-8 ]

* 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 [ 3900-89-8 ]
  • Downstream synthetic route of [ 3900-89-8 ]

[ 3900-89-8 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 3900-89-8 ]
  • [ 611-33-6 ]
Reference: [1] Chinese Chemical Letters, 2014, vol. 25, # 5, p. 779 - 782
  • 2
  • [ 5922-60-1 ]
  • [ 3900-89-8 ]
  • [ 2958-36-3 ]
Reference: [1] Organic and Biomolecular Chemistry, 2014, vol. 12, # 41, p. 8204 - 8211
  • 3
  • [ 3900-89-8 ]
  • [ 2905-23-9 ]
Reference: [1] Journal of the American Chemical Society, 2013, vol. 135, # 29, p. 10638 - 10641
  • 4
  • [ 694-80-4 ]
  • [ 3900-89-8 ]
YieldReaction ConditionsOperation in experiment
98% With n-butyllithium; Triisopropyl borate In tetrahydrofuran; hexane; toluene at -70℃; for 1.5 h; Inert atmosphere Procedure (f):n-BuLi (2.5 M in n-Hexane, 2.5 ml, 1.2 eq., 6.3 mmol) was added dropwise to a solution of Bromo chloro benzene (I) (ig, 0.6 ml, 5.2 mmol) and Triisopropylborate (1.44 ml, 1.2 eq., 6.27 mmol) in Toluene and THF (4:1, 10 ml)under nitrogen at -7 0°C over 1 hour. The reaction mixture was stirred for an additional 0.5 hour while the temperature was held at -70°C. The reaction mixture was allowed to warm to -20°C, before a 2 N HC1 solution (5 ml) was added to the reaction mixture. When the reaction mixture reached room temperature, it was extracted with Dichloromethane. Combined organic phase was dried and evaporatedto give a white solid, which was recrystallized from MeCN with a yield of 98percent (800mg).
56%
Stage #1: With n-butyllithium In tetrahydrofuran; hexaneInert atmosphere
Stage #2: With Trimethyl borate In tetrahydrofuran; hexaneInert atmosphere
General procedure: Under an argon atmosphere a solution of the appropriate bromobenzene (1 equivalent) dissolved in anhydrous THF (approximately 30 mL per mmol bromobenzene) is cooled to -78 °C using a nitrogen-ethanol-bath. A solution of 2.3 equivalents of n-butyllithium in hexane is added drop wise keeping the temperature below -78 °C. After completion the mixture is stirred for one hour at this temperature. Then 1.5 equivalents of trimethyl borate are added slowly and the reaction mixture is stirred at -78 °C for another hour. The cooling bath is then removed, the reaction mixture is stirred until room temperature is reached and quenched with a saturated solution of ammonium chloride. THF and the major part of the water is removed under reduced pressure, the residue is laced with 3M hydrochloric acid until a pH of 3 is reached. After extraction with DCM (3 x) the organic phases are collected, washed with brine, dried over sodium sulphate and filtered. DCM is removed under reduced pressure, the resulting solid is washed first with ice cold water and then with PE and dried.
Reference: [1] Patent: WO2013/90725, 2013, A1, . Location in patent: Page/Page column 68
[2] European Journal of Medicinal Chemistry, 2017, vol. 126, p. 590 - 603
[3] Journal of Organic Chemistry, 2002, vol. 67, # 15, p. 5394 - 5397
  • 5
  • [ 694-80-4 ]
  • [ 3900-89-8 ]
YieldReaction ConditionsOperation in experiment
86% With magnesium In water A.
2-Chlorobenzeneboronic acid
Borane-THF (100 mL, 100 mmol) was slowly added to a mixture of 2-bromochlorobenzene (5.4 mL, 46 mmol) and magnesium (ribbon, 1.12 g, 46 mmol).
The flask was placed in a water bath and sonicated overnight.
Water (30 mL) was slowly added to destroy excess borane.
The aqueous solution was refluxed for 2 hrs.
The solvent was evaporated and the residue was neutralized with aq HCl.
The aqueous solution was extracted with ether (2*50 mL), dried (Na2 SO4) and evaporated to afford Compound A (6.24 g, 86percent).
Reference: [1] Patent: US6011029, 2000, A,
  • 6
  • [ 870195-94-1 ]
  • [ 3900-89-8 ]
Reference: [1] Tetrahedron Letters, 2005, vol. 46, # 46, p. 7899 - 7903
  • 7
  • [ 36692-27-0 ]
  • [ 688-74-4 ]
  • [ 3900-89-8 ]
Reference: [1] Journal of the American Chemical Society, 1934, vol. 56, p. 937,938, 941
  • 8
  • [ 121-43-7 ]
  • [ 694-80-4 ]
  • [ 3900-89-8 ]
Reference: [1] Chemistry - A European Journal, 2017, vol. 23, # 9, p. 2005 - 2009
  • 9
  • [ 13675-18-8 ]
  • [ 615-41-8 ]
  • [ 3900-89-8 ]
Reference: [1] Journal of Organic Chemistry, 2018, vol. 83, # 4, p. 1842 - 1851
  • 10
  • [ 36692-27-0 ]
  • [ 13195-76-1 ]
  • [ 3900-89-8 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1930, vol. <2>128, p. 153,169,170
  • 11
  • [ 103-82-2 ]
  • [ 3900-89-8 ]
  • [ 79422-00-7 ]
Reference: [1] Chemical Science, 2018, vol. 9, # 4, p. 1058 - 1072
  • 12
  • [ 76-09-5 ]
  • [ 3900-89-8 ]
  • [ 870195-94-1 ]
Reference: [1] Organic Letters, 2013, vol. 15, # 11, p. 2806 - 2809
[2] Journal of Organic Chemistry, 2018, vol. 83, # 4, p. 1842 - 1851
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 3900-89-8 ]

Organoboron

Chemical Structure| 68716-47-2

[ 68716-47-2 ]

2,4-Dichlorophenylboronic acid

Similarity: 0.98

Chemical Structure| 1679-18-1

[ 1679-18-1 ]

(4-Chlorophenyl)boronic acid

Similarity: 0.91

Chemical Structure| 73852-17-2

[ 73852-17-2 ]

(2,6-Dichlorophenyl)boronic acid

Similarity: 0.90

Chemical Structure| 73852-18-3

[ 73852-18-3 ]

2,4,6-Trichlorophenylboronic acid

Similarity: 0.90

Chemical Structure| 63503-60-6

[ 63503-60-6 ]

3-Chlorophenylboronic acid

Similarity: 0.89

Aryls

Chemical Structure| 68716-47-2

[ 68716-47-2 ]

2,4-Dichlorophenylboronic acid

Similarity: 0.98

Chemical Structure| 1679-18-1

[ 1679-18-1 ]

(4-Chlorophenyl)boronic acid

Similarity: 0.91

Chemical Structure| 73852-17-2

[ 73852-17-2 ]

(2,6-Dichlorophenyl)boronic acid

Similarity: 0.90

Chemical Structure| 73852-18-3

[ 73852-18-3 ]

2,4,6-Trichlorophenylboronic acid

Similarity: 0.90

Chemical Structure| 63503-60-6

[ 63503-60-6 ]

3-Chlorophenylboronic acid

Similarity: 0.89

Chlorides

Chemical Structure| 68716-47-2

[ 68716-47-2 ]

2,4-Dichlorophenylboronic acid

Similarity: 0.98

Chemical Structure| 1679-18-1

[ 1679-18-1 ]

(4-Chlorophenyl)boronic acid

Similarity: 0.91

Chemical Structure| 73852-17-2

[ 73852-17-2 ]

(2,6-Dichlorophenyl)boronic acid

Similarity: 0.90

Chemical Structure| 73852-18-3

[ 73852-18-3 ]

2,4,6-Trichlorophenylboronic acid

Similarity: 0.90

Chemical Structure| 63503-60-6

[ 63503-60-6 ]

3-Chlorophenylboronic acid

Similarity: 0.89