[ CAS No. 104514-49-0 ] {[proInfo.proName]}

Name: 104514-49-0|1,2-Dibromo-3-chlorobenzene|97%
Brand: Ambeed
SKU: A601756
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Quality Control of [ 104514-49-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 104514-49-0 ]

SDS Specification

Alternatived Products of [ 104514-49-0 ]

Product Details of [ 104514-49-0 ]

CAS No. :	104514-49-0	MDL No. :	MFCD08752332
Formula :	C₆H₃Br₂Cl	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BDMRCAWYRXJKLK-UHFFFAOYSA-N
M.W :	270.35	Pubchem ID :	13932014
Synonyms :

Calculated chemistry of [ 104514-49-0 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	46.85
TPSA :	0.0 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.16 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.42
Log Po/w (XLOGP3) :	3.93
Log Po/w (WLOGP) :	3.87
Log Po/w (MLOGP) :	4.37
Log Po/w (SILICOS-IT) :	3.86
Consensus Log Po/w :	3.69

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.49
Solubility :	0.00884 mg/ml ; 0.0000327 mol/l
Class :	Moderately soluble
Log S (Ali) :	-3.63
Solubility :	0.0635 mg/ml ; 0.000235 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.72
Solubility :	0.00518 mg/ml ; 0.0000191 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.75

Safety of [ 104514-49-0 ]

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

Application In Synthesis of [ 104514-49-0 ]

* 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 [ 104514-49-0 ]
Downstream synthetic route of [ 104514-49-0 ]

[ 104514-49-0 ] Synthesis Path-Upstream 1~3

1
[ 124-38-9 ]
[ 104514-49-0 ]
[ 93224-85-2 ]
[ 56961-26-3 ]

Reference： [1] Synlett, 2006, # 12, p. 1948 - 1952
[2] Magnetic Resonance in Chemistry, 2006, vol. 44, # 11, p. 1041 - 1043

2
[ 104514-49-0 ]
[ 151-10-0 ]
[ 16932-45-9 ]
[ 1267964-61-3 ]

Reference： [1] European Journal of Organic Chemistry, 2011, # 2, p. 341 - 354

3
[ 124-38-9 ]
[ 104514-49-0 ]
[ 93224-85-2 ]
[ 56961-26-3 ]

Reference： [1] Synlett, 2006, # 12, p. 1948 - 1952
[2] Magnetic Resonance in Chemistry, 2006, vol. 44, # 11, p. 1041 - 1043

[ 104514-49-0 ] Synthesis Path-Downstream 1~32

1
3,4-dibromo-2-chloro-aniline [ No CAS ]
[ 104514-49-0 ]

Reference： [1]Journal of the Chemical Society,1901,vol. 79,p. 1303

2
3-chloro-2-bromo-aniline [ No CAS ]
[ 104514-49-0 ]

Reference： [1]Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti,1913,vol. <5> 22 I,p. 823
Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti,1914,vol. <5> 23 I,p. 283 Anm.

3
[ 108-37-2 ]
[ 104514-49-0 ]

Reference： [1]Journal of Organic Chemistry,2006,vol. 71,p. 2188 - 2191
[2]European Journal of Organic Chemistry,2011,p. 327 - 340

4
[ 124-38-9 ]
[ 104514-49-0 ]
[ 93224-85-2 ]
[ 56961-26-3 ]

Reference： [1]Synlett,2006,p. 1948 - 1952
[2]Magnetic Resonance in Chemistry,2006,vol. 44,p. 1041 - 1043

5
[ 104514-49-0 ]
[ 108-37-2 ]

Reference： [1]Synlett,2006,p. 1948 - 1952

6
[ 104514-49-0 ]
[ 108-37-2 ]
[ 694-80-4 ]

Reference： [1]Synlett,2006,p. 1948 - 1952

7
[ 24108-97-2 ]
[ 104514-49-0 ]

Reference： [1]Journal of the Chemical Society,1901,vol. 79,p. 1303

8
acetic acid-(3,4-dibromo-2-chloro-anilide) [ No CAS ]
[ 104514-49-0 ]

Reference： [1]Journal of the Chemical Society,1901,vol. 79,p. 1303

9
[ 104514-49-0 ]
[ 151-10-0 ]
[ 16932-45-9 ]
[ 1267964-61-3 ]

Reference： [1]European Journal of Organic Chemistry,2011,p. 341 - 354

10
indolo[2,3-b]indole [ No CAS ]
[ 104514-49-0 ]
C₂₀H₁₁ClN₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate; In toluene; for 6h;Inert atmosphere; Reflux;	Under an argon atmosphere, to a 500 ml, three neck flask, 10.00 g (48.5 mmol) of Intermediate IM-2, 0.84 g (0.03 equiv, 1.5 mmol) of Pd(dba)2, 11.65 g (2.5 equiv, 121.2 mmol) of NaOtBu, 242 ml of toluene, 13.11 g (1 equiv, 48.5 mmol) of <strong>[104514-49-0]1,2-dibromo-3-chlorobenzene</strong> and 0.98 g (0.1 equiv, 4.8 mmol) of tBu3P were added in that order, followed by heating, stirring and refluxing for about 6 hours. After cooling to room temperature, water was added to the reaction product, and an organic layer was separately taken. To an aqueous layer, toluene was added, and an organic layer was extracted once more. The organic layer thus collected was washed with a saline solution and dried with MgSO4. MgSO4 was separated, and the organic layer was concentrated and then, the crude product thus obtained was separated by silica gel column chromatography (using a mixture solvent of hexane and toluene as a developer) to obtain Intermediate IM-3 (11.45 g, yield 75%) as a white solid compound. A molecular ion peak of m/z=314 was observed by measuring FAB-MS, and from the result, the product was identified as Intermediate IM-3.

Reference： [1]Patent: US2019/372019,2019,A1 .Location in patent: Paragraph 0115; 0120; 0121

11
[ 104514-49-0 ]
[ 98-80-6 ]
2-bromo-3-chloro-1,1'-biphenyl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69.26%	With tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; potassium carbonate; In ethanol; water; toluene; at 75 - 80℃; for 12h;	Add 3-chloro-1.2-dibromobenzene (70g, 259.03mmol),Phenylboronic acid (31.58g, 259.02mmol),Tetrakis (triphenylphosphine) palladium 2.99g, 2.59mmol), potassium carbonate (78.6.g, 569.86mmol),Tetrabutylammonium bromide (16.7g, 51.80mmol), toluene (560mL),Ethanol (140mL) and deionized water (140mL) are added to the round bottom flask,Under the protection of nitrogen, the temperature is raised to 75-80C and stirred for 12 hours;The reaction solution was cooled to room temperature, and toluene (500 mL) was added for extraction, Combine the organic phases, use anhydrous magnesium sulfate to dry, filter,Remove the solvent under reduced pressure;The obtained crude product was purified by silica gel column chromatography using n-heptane as the mobile phase, and then recrystallized and purified using a dichloromethane/n-heptane system.A pale yellow solid was obtained, namely the starting material 4a (48 g, yield 69.26%).
53%	With tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; potassium carbonate; In ethanol; water; toluene; at 80℃; for 18h;Inert atmosphere;	1,2-Dibromo-3-chlorobenzene (80.0g; 298.7mmol),Phenylboronic acid (36.5g; 298.7mmol),Tetrakis(triphenylphosphine)palladium (6.9g; 6.0mmol),Potassium carbonate (103.2g; 746.7mmol),Tetrabutylammonium bromide (19.2g; 59.7mmol) was added to the flask,And add toluene (600mL),A mixed solvent of ethanol (150mL) and water (150mL),Under the protection of nitrogen, the temperature was raised to 80C, and the temperature was kept stirring for 18 hours;Cool to room temperature, stop stirring, wash the reaction solution with water and separate the organic phase,Dry with anhydrous magnesium sulfate and remove the solvent under reduced pressure to obtain crude product;Carry out silica gel column chromatography purification using dichloromethane/n-heptane as the mobile relative crude product,The intermediate I-G-1 was obtained as a white solid product (42.0 g; yield 53%)
53%	With tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; potassium carbonate; In ethanol; water; toluene; at 80℃; for 18h;Inert atmosphere;	Combine <strong>[104514-49-0]1,2-dibromo-3-chlorobenzene</strong> (80.0g, 298.7mmol), phenylboronic acid (36.5g, 298.7mmol), tetrakis(triphenylphosphine) palladium (6.9g, 6.0mmol), potassium carbonate (103.2 g, 746.7mmol), tetrabutylammonium bromide (19.2g, 59.7mmol) were added to the flask,And add a mixed solvent of toluene (600mL), ethanol (150mL) and water (150mL),Under the protection of nitrogen, heat up to 80C, keep the temperature and stir for 18 hours, then cool to room temperature,Stop stirring, separate the organic phase after washing the reaction solution, and dry it with anhydrous magnesium sulfate.The solvent was removed under reduced pressure to obtain a crude product; the crude product was purified by silica gel column chromatography using dichloromethane/n-heptane as the mobile phase to obtain a white solid product intermediate a-1 (42.0 g, 53%).

53%	With tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; potassium carbonate; In ethanol; water; toluene; at 80℃; for 18h;Inert atmosphere;	Combine <strong>[104514-49-0]1,2-dibromo-3-chlorobenzene</strong> (80.0g; 298.7mmol), phenylboronic acid (36.5g; 298.7mmol), tetrakis(triphenylphosphine) palladium (6.9g; 6.0mmol), potassium carbonate (103.2 g; 746.7mmol), tetrabutylammonium bromide (19.2g; 59.7mmol) were added to the flask, and a mixed solvent of toluene (600mL), ethanol (150mL) and water (150mL) was added,Under the protection of nitrogen, the temperature is increased to 80C, and the temperature is maintained and stirred for 18 hours;Cool to room temperature, stop stirring, wash the reaction solution with water, separate the organic phase, dry with anhydrous magnesium sulfate, and remove the solvent under reduced pressure to obtain the crude product; use dichloromethane/n-heptane as the mobile phase to purify the crude product by silica gel column chromatography.A white solid product intermediate IM-I-G-1 (42.0g; yield 53%) was obtained
53%	With tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; potassium carbonate; In ethanol; water; toluene; at 80℃; for 18h;Inert atmosphere;	Combine <strong>[104514-49-0]1,2-dibromo-3-chlorobenzene</strong> (80.8g; 298.7mmol), phenylboronic acid (36.5g; 298.7mmol), tetrakis(triphenylphosphine) palladium (6.9g; 6.0mmol), potassium carbonate (103.2 g; 746.7mmol), tetrabutylammonium bromide (19.2g; 59.7mmol) were added to the flask,And add a mixed solvent of toluene (600mL), ethanol (150mL) and water (150mL),Under the protection of nitrogen, heat up to 80C, keep the temperature and stir for 18 hours; cool to room temperature,Stop stirring, separate the organic phase after washing the reaction solution with water, and dry it with anhydrous magnesium sulfate.The solvent was removed under reduced pressure to obtain the crude product; the crude product was purified by silica gel column chromatography using dichloromethane/n-heptane as the mobile phase to obtain the white solid product intermediate IM-I-C(42.0g; yield 53%)
53%	With tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; potassium carbonate; In ethanol; water; toluene; at 75 - 85℃; for 18h;Inert atmosphere;	To be equipped with mechanical stirring, thermometer,The three-necked flask of the spherical condenser is filled with nitrogen (0.100L/min) for 15min,Sequentially add <strong>[104514-49-0]1,2-dibromo-3-chlorobenzene</strong> (80.0g, 298.7mmol) (reactant A-1),Phenylboronic acid (36.5g, 298.7mmol),Tetratriphenylphosphine palladium (6.9g, 6.0mmol),Potassium carbonate (103.2g, 746.7mmol),Tetrabutylammonium bromide (19.2g, 59.7mmol),And add toluene (600mL),Ethanol (150mL) andA mixed solvent of water (150 mL).Turn on the stirring, heat up to 75-85 and react for 18h,After the reaction, it was cooled to room temperature.After the reaction solution is washed with water, the organic phase is separated, the organic phase is dried with anhydrous magnesium sulfate, and the filtrate is filtered and distilled under reduced pressure to remove the solvent;The crude product was purified by silica gel column chromatography using a dichloromethane/n-heptane system to obtain a white solid product intermediate a-1 (42.0 g, 53%).
53%	With tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; potassium carbonate; In ethanol; water; toluene; at 80℃; for 18h;Inert atmosphere;	Combine <strong>[104514-49-0]1,2-dibromo-3-chlorobenzene</strong> (80.0g; 298.7mmol), phenylboronic acid (36.5g; 298.7mmol), palladium tetrakistriphenylphosphine (6.9g; 6.0mmol), potassium carbonate (103.2g; 746.7mmol), tetrabutylammonium bromide (19.2g; 59.7mmol) was added to the flask, and a mixed solvent of toluene (600mL), ethanol (150mL) and water (150mL) was added. Under nitrogen protection, the temperature was raised to 80C, Keep the temperature and stir for 18 hours;Cool to room temperature, stop stirring, wash the reaction solution with water, separate the organic phase, dry with anhydrous magnesium sulfate, and remove the solvent under reduced pressure to obtain the crude product; use dichloromethane/n-heptane as the mobile phase to purify the crude product by silica gel column chromatography to obtain a white The solid product intermediate a-1 (42.0 g; 53%).
53%	With tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; potassium carbonate; In ethanol; water; toluene; at 80℃; for 18h;Inert atmosphere;	Combine <strong>[104514-49-0]1,2-dibromo-3-chlorobenzene</strong> (80.0g, 298.7mmol), phenylboronic acid (36.5g, 298.7mmol), tetrakis(triphenylphosphine) palladium (6.9g, 6.0mmol), potassium carbonate (103.2 g, 746.7mmol), tetrabutylammonium bromide (19.2g, 59.7mmol) were added to the flask, and a mixed solvent of toluene (600mL), ethanol (150mL) and water (150mL) was added. Under the protection of nitrogen, the temperature was raised to 80 , keep the temperature and stir for 18 hours; Cool to room temperature, stop stirring, wash the reaction solution with water, separate the organic phase, dry with anhydrous magnesium sulfate, and remove the solvent under reduced pressure to obtain a crude product; use dichloromethane/n-heptane as the mobile phase to purify the crude product by silica gel column chromatography to obtain a white The solid product intermediate a-1 (42.0 g, yield 53%).

Reference： [1]Patent: CN112239475,2021,A .Location in patent: Paragraph 0218-0222
[2]Patent: CN111138298,2020,A .Location in patent: Paragraph 0226-0227
[3]Patent: CN111995564,2020,A .Location in patent: Paragraph 0136-0137
[4]Patent: CN112110825,2020,A .Location in patent: Paragraph 0234-0235
[5]Patent: CN112745230,2021,A .Location in patent: Paragraph 0277-0278
[6]Patent: CN112876486,2021,A .Location in patent: Paragraph 0142-0144
[7]Patent: CN113045434,2021,A .Location in patent: Paragraph 0135-0137
[8]Patent: CN113292566,2021,A .Location in patent: Paragraph 0155-0157

12
[ 104514-49-0 ]
C₂₂H₂₃ClO [ No CAS ]

Reference： [1]Patent: CN111995564,2020,A
[2]Patent: CN112239475,2021,A
[3]Patent: CN113045434,2021,A
[4]Patent: CN113292566,2021,A

13
[ 104514-49-0 ]
C₂₂H₂₁Cl [ No CAS ]

Reference： [1]Patent: CN111995564,2020,A
[2]Patent: CN112239475,2021,A
[3]Patent: CN113045434,2021,A
[4]Patent: CN113292566,2021,A

14
[ 104514-49-0 ]
C₂₈H₃₃BO₂ [ No CAS ]

Reference： [1]Patent: CN111995564,2020,A
[2]Patent: CN113045434,2021,A

15
[ 104514-49-0 ]
C₂₈H₂₅NO₂ [ No CAS ]

Reference： [1]Patent: CN111995564,2020,A

16
[ 104514-49-0 ]
C₂₈H₂₅N [ No CAS ]

Reference： [1]Patent: CN111995564,2020,A

17
[ 104514-49-0 ]
C₄₀H₃₃N [ No CAS ]

Reference： [1]Patent: CN111995564,2020,A

18
[ 104514-49-0 ]
[ 118-92-3 ]
C₁₃H₉BrClNO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; L-proline; In water; at 140℃;Inert atmosphere;	Step 1: A mixture of a (340 mg, 2.47 mmol, 1.0 eq), b (1.0 g, 3.70 mmol, 1.5 eq), potassium carbonate (1.03 g, 7.41 mmol, 3.0 eq), Cuprous iodide (141.0 mg, 0.74 mmol, 0.3 eq), and L- proline (85.0 mg, 0.74 mmol, 0.3 eq) in 2-pentanol (30.0 mL) was stirred at 140 C overnight under argon atmosphere, then cooled to room temperature. Water (50.0 mL) was added. The mixture was filtered through celite. The filtrate was acidified to pH=2 with 2 N HCl, then water (50.0 mL) was added. The resulting mixture was extracted with EtOAc (50.0 mL x 3). The combined organic layers were washed with brine (20.0 mL x 5), dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo to afford c (crude, 600 mg, 74.5%). LC/MS: 326.0 [M+H]+.

Reference： [1]Patent: WO2020/232375,2020,A1 .Location in patent: Page/Page column 141

19
[ 104514-49-0 ]
C₁₃H₇BrClNO [ No CAS ]