[ CAS No. 863870-87-5 ] {[proInfo.proName]}

Name: 863870-87-5|3-Bromo-2-chlorophenol|98%
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SKU: A213231
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Quality Control of [ 863870-87-5 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 863870-87-5 ]

CAS No. :	863870-87-5	MDL No. :	MFCD08166321
Formula :	C₆H₄BrClO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DUKKNDLIWRYBCT-UHFFFAOYSA-N
M.W :	207.45	Pubchem ID :	6455237
Synonyms :

Calculated chemistry of [ 863870-87-5 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	41.18
TPSA :	20.23 Å²

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) :	-5.51 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.01
Log Po/w (XLOGP3) :	2.9
Log Po/w (WLOGP) :	2.81
Log Po/w (MLOGP) :	2.84
Log Po/w (SILICOS-IT) :	2.7
Consensus Log Po/w :	2.65

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.45
Solubility :	0.0742 mg/ml ; 0.000358 mol/l
Class :	Soluble
Log S (Ali) :	-2.99
Solubility :	0.215 mg/ml ; 0.00103 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.3
Solubility :	0.105 mg/ml ; 0.000506 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.55

Safety of [ 863870-87-5 ]

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 [ 863870-87-5 ]

* 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 [ 863870-87-5 ]
Downstream synthetic route of [ 863870-87-5 ]

[ 863870-87-5 ] Synthesis Path-Upstream 1~10

1
[ 591-20-8 ]
[ 13659-24-0 ]
[ 183802-98-4 ]
[ 863870-87-5 ]

Reference： [1] Organic Letters, 2016, vol. 18, # 21, p. 5476 - 5479
[2] Organic Letters, 2016, vol. 18, # 21, p. 5476 - 5479
[3] ACS Catalysis, 2018, vol. 8, # 5, p. 4033 - 4043

2
[ 591-20-8 ]
[ 13659-24-0 ]
[ 183802-98-4 ]
[ 863870-87-5 ]

Reference： [1] Organic Letters, 2016, vol. 18, # 21, p. 5476 - 5479
[2] Organic Letters, 2016, vol. 18, # 21, p. 5476 - 5479
[3] ACS Catalysis, 2018, vol. 8, # 5, p. 4033 - 4043

3
[ 591-20-8 ]
[ 13659-24-0 ]
[ 183802-98-4 ]
[ 863870-87-5 ]

Reference： [1] Organic Letters, 2016, vol. 18, # 21, p. 5476 - 5479
[2] Organic Letters, 2016, vol. 18, # 21, p. 5476 - 5479
[3] ACS Catalysis, 2018, vol. 8, # 5, p. 4033 - 4043

4
[ 863870-81-9 ]
[ 863870-87-5 ]

Reference： [1] Journal of Organic Chemistry, 2005, vol. 70, # 16, p. 6548 - 6551
[2] Journal of Organic Chemistry, 2011, vol. 76, # 9, p. 3416 - 3437

5
[ 95-57-8 ]
[ 139-66-2 ]
[ 863870-87-5 ]

Reference： [1] Patent: US4210766, 1980, A,
[2] Patent: US4210766, 1980, A,

6
[ 863870-72-8 ]
[ 863870-87-5 ]

Reference： [1] Journal of Organic Chemistry, 2005, vol. 70, # 16, p. 6548 - 6551
[2] Journal of Organic Chemistry, 2011, vol. 76, # 9, p. 3416 - 3437

7
[ 95-57-8 ]
[ 863870-87-5 ]

Reference： [1] Patent: US4210766, 1980, A,

8
[ 591-20-8 ]
[ 863870-87-5 ]

Reference： [1] Journal of the Indian Chemical Society, 1989, vol. 66, # 5, p. 301 - 303
[2] Journal of the Indian Chemical Society, 1989, vol. 66, # 5, p. 301 - 303
[3] Journal of Organic Chemistry, 2005, vol. 70, # 16, p. 6548 - 6551

9
[ 116435-77-9 ]
[ 863870-87-5 ]

Reference： [1] Journal of the Chemical Society, 1934, p. 137

10
[ 863870-87-5 ]
[ 56131-46-5 ]

Reference： [1] Journal of Organic Chemistry, 2011, vol. 76, # 9, p. 3416 - 3437

[ 863870-87-5 ] Synthesis Path-Downstream 1~88

1
[ 863870-87-5 ]
[ 872277-20-8 ]

Reference： [1]Journal of the Chemical Society,1934,p. 137

2
[ 591-20-8 ]
[ 863870-87-5 ]

Reference： [1]Journal of the Indian Chemical Society,1989,vol. 66,p. 301 - 303
[2]Journal of the Indian Chemical Society,1989,vol. 66,p. 301 - 303
[3]Journal of Organic Chemistry,2005,vol. 70,p. 6548 - 6551

3
[ 863870-72-8 ]
[ 863870-87-5 ]

Reference： [1]Journal of Organic Chemistry,2005,vol. 70,p. 6548 - 6551
[2]Journal of Organic Chemistry,2011,vol. 76,p. 3416 - 3437

4
[ 95-57-8 ]
[ 863870-87-5 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 5 257 g (2 moles) of 2-chlorophenol is brominated, in the manner described in Example 1, with the use of a variety of catalyst mixtures. Chlorobromophenol is thus obtained in yields of 99.5 to 99.8% of theory.

Reference： [1]Patent: US4210766,1980,A

5
[ 95-57-8 ]
[ 139-66-2 ]
[ 863870-87-5 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen bromide; bromine;Zinc chloride;	EXAMPLE 2 326.4 g (2.04 moles) of bromine is added dropwise, within 6 hours, to a mixture of 257.2 g (2 moles) of 2-chlorophenol, 2.0 g of zinc chloride and 2.0 g of diphenyl sulfide, the reaction temperature being held continuously just above the crystallisation point of the mixture. The following amounts of bromine are added at the individual reaction temperatures: After the total amount of bromine has been added, the mixture is stirred for 30 minutes at 50 C., and is then freed at 60 C. under a pressure of 18 Torr from dissolved hydrogen bromide to yield 414.2 g (99.7% of theory) of chlorobromophenol which, according to gas-chromatographical determination, has the following composition:
	With hydrogen bromide; bromine;Zinc chloride;	EXAMPLE 3 326.4 g (2.04 moles) of bromine is added dropwise in the course of 6 hours with vigorous stirring, within a temperature range of between 20 and 45 C., to a mixture of 257.2 g (2 moles) of 2-chlorophenol, 1.0 g of zinc chloride and 1.0 g of diphenyl sulfide. After the addition of 70 ml of bromine, the temperature rises to 35 C. To avoid crystallisation, the reaction mixture is afterwards heated to 40 C. and a further 20 ml of bromine is added dropwise. The remaining bromine is finally added at 45 C. After the addition of bromine is complete, stirring is maintained for 30 minutes at 50 C., and subsequently the reaction product is freed at 60 C. under reduced pressure from dissolved hydrogen bromide to leave 414.5 g (99.8% of theory) of chlorobromophenol which, according to gas-chromatographical analysis, has the following composition:

Reference： [1]Patent: US4210766,1980,A
[2]Patent: US4210766,1980,A

6
[ 5720-07-0 ]
[ 863870-87-5 ]
[ 1014625-95-6 ]

Reference： [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 1344 - 1351

7
[ 863870-87-5 ]
[ 106-95-6 ]
[ 1014625-97-8 ]

Reference： [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 1344 - 1351

8
[ 863870-87-5 ]
[ 75-36-5 ]
[ 1111084-93-5 ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 858 - 867

9
[ 863870-87-5 ]
[ 56131-46-5 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 3416 - 3437

10
[ 863870-87-5 ]
[ 1287791-79-0 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 3416 - 3437

11
[ 4704-77-2 ]
[ 863870-87-5 ]
3-(3-bromo-2-chlorophenoxy)propane-1,2-diol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In N,N-dimethyl-formamide; at 20 - 70℃;Inert atmosphere;	Intermediate: 3-(3-bromo-2-chlorophenoxy)propane-1,2-diol To a solution of <strong>[863870-87-5]3-bromo-2-chlorophenol</strong> (500 mg, 2.410 mmol) in anhydrous DMF (8 mL) was added cesium carbonate (4.0 g, 12.28 mmol), followed by 3-bromo-1,2-propanediol (650 muL, 7.42 mmol). The reaction was flushed briefly with N2, and stirred at room temp for 3.5 h. The reaction was heated to 70 C. for 3.5 h, then stirred at room temp for 18 h. Additional 3-bromo-1,2-propanediol (200 muL, 2.284 mmol) was added and reaction heated to 70 C. for several hours. The solvent was evaporated under a gentle stream of N2, and the residue dissolved in a mixture of EtOAc (200 mL) and ice cold aq 1N NaOH (20 mL). The organic layer was extracted with water (220 mL), brine (120 mL) and dried over Na2SO4, filtered and evaporated to dryness to give the title compound (530 mg, 78%) that was used "as is" without further purification in subsequent reactions. 1H NMR (500 MHz, CHLOROFORM-d) delta 7.32-7.29 (m, 1H), 7.12 (t, J=8.2 Hz, 1H), 6.92 (d, J=8.4 Hz, 1H), 4.22-4.07 (m, 3H), 3.96-3.80 (m, 2H), 2.74 (d, J=4.7 Hz, 1H), 2.11 (t, J=6.1 Hz, 1H)

Reference： [1]Patent: US2017/107202,2017,A1 .Location in patent: Paragraph 1179; 1180; 1181

12
[ 115-77-5 ]
[ 863870-87-5 ]
2-((3-bromo-2-chlorophenoxy)methyl)(hydroxymethyl)propane-1,3-diol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
25%	With diamide; triphenylphosphine; In tetrahydrofuran; at 20℃; for 36h;Inert atmosphere; Sealed tube;	Intermediate: 2-((3-bromo-2-chlorophenoxy)methyl)(hydroxymethyl)propane-1,3-diol To a solution of <strong>[863870-87-5]3-bromo-2-chlorophenol</strong> (500 mg, 2.410 mmol), pentaerythritol (1 mL, 7.35 mmol) and triphenylphosphine (1.3 g, 4.96 mmol) in anhydrous THF (8 mL) was added diamide (625 mg, 3.63 mmol). The reaction turned bright yellow. The reaction was flushed with N2, capped and stirred at room temp for 18 h. The reaction was treated with additional TMAD (155 mg, 0.9 mmol) and triphenylphosphine (250 mg, 0.95 mmol), and stirred at room temp for 18 h. The white solid was filtered off through a disposable frit, washed with THF and the filtrate evaporated to dryness in vacuo. The residue was dissolved in CH2Cl2 (35 mL) and apply to the head of a 80 g Teledyne Isco Silica Flash Column. The column was eluted with a linear gradient from 100% CH2Cl2 to 100% EtOAc over 12 column volumes. The fractions containing the desired product were pooled and evaporated to dryness to give the title compound (194 mg, 25%). LC/MS Condition A: ret time 0.920 min; m/e=325(M+H)+. 1H NMR (500 MHz, METHANOL-d4) delta 7.27 (dd, J=8.1, 1.4 Hz, 1H), 7.18 (t, J=8.2 Hz, 1H), 7.09 (dd, J=8.2, 1.4 Hz, 1H), 4.08 (s, 2H), 3.76 (s, 6H)

Reference： [1]Patent: US2017/107202,2017,A1 .Location in patent: Paragraph 1193; 1194; 1195; 1196

13
[ 96-21-9 ]
[ 863870-87-5 ]
[ 104706-47-0 ]
(3R)-1-(3-(3-bromo-2-chlorophenoxy)-2-hydroxypropyl)pyrrolidin-3-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
8%		Intermediate: (3R)-1-(3-(3-bromo-2-chlorophenoxy)-2-hydroxypropyl)pyrrolidin-3-ol To a mixture of <strong>[863870-87-5]3-bromo-2-chlorophenol</strong> (494 mg, 2.381 mmol) and cesium carbonate (1.9 g, 5.83 mmol) was added dry DMF (4 mL). The reaction was flushed with argon, treated with 1,3-dibromopropan-2-ol (1.16 g, 5.32 mmol), capped and stirred at room temp for 18 h. The reaction was then diluted with DMF (4.5 mL), treated with (R)-pyrrolidin-3-ol, HCl (1.58 g, 12.79 mmol), N,N-diisopropylethylamine (2.4 mL, 13.74 mmol) and heated at 65 C. for 18 h. The reaction was partitioned with ethyl acetate (150 mL) and 1 N aq NaOH (20 mL). The organic layer was extracted with 1 N aq NaOH (10 mL), water (320 mL) and brine (50 mL), dried over Na2SO4 filtered and evaporated to dryness. The crude material was purified via preparative LC/MS with the following conditions: Column: XBridge C18, 50250 mm, 5-mum particles; Mobile Phase A: 5:95 acetonitrile: water with 10-mM ammonium acetate; Mobile Phase B: 95:5 acetonitrile: water with 10-mM ammonium acetate; Gradient: 5-60% B over 30 minutes, then a 7-minute hold at 100% B; Flow: 100 mL/min to give the title compound (64 mg, 8%). LC/MS Condition E: ret time 1.32 min; m/e=350 (M+H)+. LC/MS Condition F: ret time 1.18 min; m/e=350 (M+H)+.

Reference： [1]Patent: US2017/107202,2017,A1 .Location in patent: Paragraph 1208; 1209; 1210

14
[ 863870-87-5 ]
[ 138108-72-2 ]
tert-butyl (S)-3-((3-bromo-2-chlorophenoxy)methyl)pyrrolidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With diamide; triphenylphosphine; In tetrahydrofuran; at 20 - 45℃; for 116.5h;Inert atmosphere; Sealed tube;	Intermediate: tert-butyl (S)-3-((3-bromo-2-chlorophenoxy)methyl)pyrrolidine-1-carboxylate To a mixture of (R)-3-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (500 mg, 2.48 mmol), <strong>[863870-87-5]3-bromo-2-chlorophenol</strong> (532 mg, 2.56 mmol), and triphenylphosphine (841 mg, 3.21 mmol) in tetrahydrofuran (12 mL) under a gentle stream of argon was added solid TMAD (500 mg, 2.90 mmol). The reaction was capped, stirred at room temp for 2 h, then heated to 45 C. for 2.5 h, then stirred at room temp for 18 h. The reaction was charged with additional triphenylphosphine (420 mg, 1.6 mmol) and TMAD (250 mg, 1.45 mmol) and stirred at room temp for 94 h. The reaction was filtered, the filtrate evaporated to dryness in vacuo, and crude product applied to the head of a 80 g Teledyne Isco Silica Flash Column. The column was eluted with a linear gradient 100% hexanes to 100% EtOAc over 12 col vols and the fractions containing the desired product were pooled and evaporated to dryness to give the title compound (830 mg, 86%). 1H NMR (500 MHz, CHLOROFORM-d) delta 7.27 (br d, J=8.1 Hz, 1H), 7.09 (t, J=8.2 Hz, 1H), 6.87 (dd, J=8.2, 1.1 Hz, 1H), 3.99 (br dd, J=14.3, 6.5 Hz, 2H), 3.74-3.35 (m, 3H), 3.27 (br d, J=5.3 Hz, 1H), 2.76 (br s, 1H), 2.13 (br d, J=6.1 Hz, 1H), 1.96-1.80 (m, 1H), 1.49 (s, 9H).

Reference： [1]Patent: US2017/107202,2017,A1 .Location in patent: Paragraph 1402; 1403; 1404

15
[ 863870-87-5 ]
[ 83948-53-2 ]
tert-butyl (3-(3-bromo-2-chlorophenoxy)propyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 20 - 50℃; for 19h;Inert atmosphere;	To a mixture of tert-butyl (3-bromopropyl)carbamate (4.29 g, 18.02 mmol) and <strong>[863870-87-5]3-bromo-2-chlorophenol</strong> (3.74 g, 18.02 mmol) in anhydrous DMF (25 mL) was added solid potassium carbonate (5 g, 36.2 mmol). The reaction was flushed with argon, stirred at room temp for 5 min, then heated at 50 C for 19h. The reaction was cooled to room temp, diluted with EtOAc (600 mL) and the organic layer was washed with water ( 4 x 150 mL), sat. aq NaCl (100 mL), dried over anhydrous Na2SO4, filtered and concentrated. The crude product (6.5 g, 94%) was used?as is? without further purification in subsequent reactions. 1H NMR (500 MHz, CHLOROFORM-d) delta 7.26 (dd, J=8.1, 1.2 Hz, 1H), 7.10 (t, J=8.2 Hz, 1H), 6.88 (dd, J=8.3, 1.1 Hz, 1H), 5.17 (br s, 1H), 4.13 (t, J=5.8 Hz, 2H), 3.40 (q, J=5.8 Hz, 2H), 2.14 - 2.01 (m, 2H), 1.46 (s, 9H).
	With potassium carbonate; In N,N-dimethyl-formamide; at 50 - 55℃; for 19h;Inert atmosphere;	Intermediate: tert-butyl (3-(3-bromo-2-chlorophenoxy)propyl)carbamate To a solution of tert-butyl (3-bromopropyl)carbamate (4.29 g, 18.02 mmol) and <strong>[863870-87-5]3-bromo-2-chlorophenol</strong> (3.74 g, 18.02 mmol) in DMF (25 mL) under argon was added potassium carbonate (5 g, 36.2 mmol) and the reaction was heated at 50-55 C for 19 h. The reaction was diluted with EtOAc (600 mL). The organic layer was washed with water (4*150 mL), brine (100 mL), dried over Na2SO4, filtered and the solvent was removed in vacuo to give the title compound (6.5 g, 94%) that was used "as is" without further purification. 1H NMR (500 MHz, CHLOROFORM-d) ? 7.26 (dd, J=8.1, 1.2 Hz, 1H), 7.10 (t, J=8.2 Hz, 1H), 6.88 (dd, J=8.3, 1.1 Hz, 1H), 5.17 (br.s., 1H), 4.13 (t, J=5.8 Hz, 2H), 3.40 (q, J=5.8 Hz, 2H), 2.10-2.04 (m, 2H), 1.46 (s, 9H).

Reference： [1]Patent: WO2018/44963,2018,A1 .Location in patent: Page/Page column 130-131
[2]Patent: US2017/107202,2017,A1 .Location in patent: Paragraph 1220; 1221; 1222

16
[ 863870-87-5 ]
5-((4-chloro-5-((2'-chloro-3'-(2,3-dihydroxypropoxy)-2-methyl-[1,1'-biphenyl]-3-yl)methoxy)-2-formylphenoxy)methyl)nicotinonitrile [ No CAS ]