[ CAS No. 185342-88-5 ] {[proInfo.proName]}

Name: 185342-88-5|1,3-Dibromo-2,4-dimethoxybenzene|95+%
Brand: Ambeed
SKU: A1061529
Rating: 98 (25 reviews)

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3d Animation Molecule Structure of 185342-88-5

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Quality Control of [ 185342-88-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 185342-88-5 ]

Product Details of [ 185342-88-5 ]

CAS No. :	185342-88-5	MDL No. :	MFCD09032322
Formula :	C₈H₈Br₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UZFUWYMMUGVSCE-UHFFFAOYSA-N
M.W :	295.96	Pubchem ID :	11645053
Synonyms :

Calculated chemistry of [ 185342-88-5 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.25
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	54.83
TPSA :	18.46 Å²

Pharmacokinetics

GI absorption :	High
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) :	-5.8 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.7
Log Po/w (XLOGP3) :	3.25
Log Po/w (WLOGP) :	3.23
Log Po/w (MLOGP) :	2.93
Log Po/w (SILICOS-IT) :	3.17
Consensus Log Po/w :	3.06

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.96
Solubility :	0.0324 mg/ml ; 0.00011 mol/l
Class :	Soluble
Log S (Ali) :	-3.31
Solubility :	0.144 mg/ml ; 0.000488 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.35
Solubility :	0.0133 mg/ml ; 0.0000449 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	1.83

Safety of [ 185342-88-5 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:
Hazard Statements:	H302-H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 185342-88-5 ]

* 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 [ 185342-88-5 ]
Downstream synthetic route of [ 185342-88-5 ]

[ 185342-88-5 ] Synthesis Path-Upstream 1~1

1
[ 151-10-0 ]
[ 17715-69-4 ]
[ 185342-88-5 ]

Reference： [1] Tetrahedron Letters, 1996, vol. 37, # 47, p. 8609 - 8612

[ 185342-88-5 ] Synthesis Path-Downstream 1~21

1
[ 18011-67-1 ]
[ 77-78-1 ]
2,4-dibromo-3-methoxy-phenol [ No CAS ]
[ 185342-88-5 ]

Reference： [1]Journal of the American Chemical Society,1926,vol. 48,p. 3127

2
[ 18011-67-1 ]
[ 77-78-1 ]
[ 185342-88-5 ]

Reference： [1]Journal of the American Chemical Society,1926,vol. 48,p. 3127

3
[ 151-10-0 ]
[ 17715-69-4 ]
[ 185342-88-5 ]

Reference： [1]Tetrahedron Letters,1996,vol. 37,p. 8609 - 8612

4
[ 151-10-0 ]
[ 185342-88-5 ]

Reference： [1]Tetrahedron Letters,1997,vol. 38,p. 4415 - 4416
[2]Patent: EP2436679,2012,A1
[3]Patent: JP2015/7036,2015,A
[4]Patent: US2017/54086,2017,A1

5
[ 16932-45-9 ]
[ 185342-88-5 ]

Yield	Reaction Conditions	Operation in experiment
95%	With N-Bromosuccinimide; In acetonitrile; at 20℃; for 15h;Cooling with ice;	(A-2) Synthesis of 1,3-dibromo-2,6-dimethoxybenzene 17.9g of <strong>[16932-45-9]1-bromo-2,6-dimethoxybenzene</strong> and 200 mL of acetonitrile were placed in a flask, and the resulting mixture was cooled on ice. Then, 14.7g of N-bromosuccinimide was added. Then, while heating the reaction solution to room temperature, stirring was conducted for 8 hours. 2.39g of N-bromosuccinimide was further added, and stirring was conducted at room temperature for 7 hours. After completion of the stirring, the solvent was distilled off under reduced pressure. Residues were dissolved in dichloromethane, and washed sequentially with sodium thiosulfate and saturated saline. An organic phase was dried with magnesium sulfate and concentrated. Residues were purified by means of silica gel column chromatography, whereby 23.2g (yield: 95%) of colorless oil of 1,3-bromo-2,6-dimethoxybenzene was obtained.
95%	With N-Bromosuccinimide; In acetonitrile; at 20℃; for 15h;Cooling with ice;	Intermediate 14 (17.9 g), was charged acetonitrile (200 mL) in a flask, after cooled with ice, was added N- bromosuccinimide (14.7 g). The reaction solution was stirred for 8 hours while raising the temperature to room temperature. Add N- bromosuccinimide (2.39 g) was further stirred at room temperature for 7 hours. After stirring stop, the solvent was evaporated under reduced pressure, after which the residue was dissolved in dichloromethane, sodium thiosulfate, washed successively with saturated brine. The organic layer was dried over magnesium sulfate, concentrated and the residue was purified by silica gel chromatography to give Intermediate 15 (23.2g). The yield was 95%.
80%	With N-Bromosuccinimide; In acetonitrile; at 0 - 20℃; for 16h;Inert atmosphere; Schlenk technique;	A solution of <strong>[16932-45-9]2-bromo-1,3-dimethoxybenzene</strong> (2.00 g, 9.21 mmols) in 20 mL of acetonitrile was brought to 0 C and N-bromosuccinimide (2.05 g, 11.52 mmols) was added. After the addition, the reaction mixture was brought to rt and stirred overnight. Subsequently, the reaction mixture was concentrated in vacuo and the resulting orange solid was redissolved in 70 mL of DCM and washed with half-saturated sodium thiosulfate solution (2 x 20 mL), 15 mL sat. sodium chloride solution and 30 mL of water in the stated order and subsequently dried over magnesium sulfate. The orange oil obtained was dried in a high vacuum and subsequently purified on silica gel by flash chromatography (10% EtOAc/PE). The product (2.17 g, 7.34 mmols, 80%) was obtained as a colorless oil. Rf: 0.48 (20% EtOAc/PE). 1H NMR (500 MHz, CDCl3) delta = 7.33 (d, 3J = 8.9 Hz, 1H), 6.50 (d, 3J = 8.9 Hz, 1H), 3.81 (s, 3H), 3.79 (s, 3H). 13C NMR (126 MHz, CDCl3) delta = 156.59, 154.82, 131.55, 108.59, 108.44, 108.14, 60.34, 56.55. GC-MS: tR = 6.02 min; m/z = 293.9, 295.9, 297.9 [M ]+. HRMS (EI): calculated for C8H8O2 79Br2: m/z = 293.88856 [M ]+, found: m/z = 293.88896 [M ]+. calculated for C8H8O2 79Br 81Br: m/z = 295.88651 [M ]+, found: m/z = 295.88582 [M ]+. calculated for C8H8O2 81Br2: m/z = 297.88446 [M ]+, found: m/z = 297.88565 [M ]+.

Reference： [1]Patent: EP2436679,2012,A1 .Location in patent: Page/Page column 46
[2]Patent: JP2015/7036,2015,A .Location in patent: Paragraph 0234; 0237
[3]Journal of Organic Chemistry,2006,vol. 71,p. 775 - 788
[4]Tetrahedron,2018,vol. 74,p. 4531 - 4537
[5]Advanced Synthesis and Catalysis,2018,vol. 360,p. 626 - 630
[6]Patent: US2017/54086,2017,A1 .Location in patent: Paragraph 0260

6
[ 185342-88-5 ]
[ 33513-42-7 ]
[ 875902-97-9 ]

Reference： [1]Journal of Organic Chemistry,2006,vol. 71,p. 775 - 788

7
[ 151-10-0 ]
4-methoxy-<i>trans</i>(?)-cinnamic acid [ No CAS ]
[ 185342-88-5 ]

Reference： [1]Journal of Organic Chemistry,2006,vol. 71,p. 775 - 788

8
[ 1993-03-9 ]
[ 185342-88-5 ]
[ 1256544-08-7 ]

Yield	Reaction Conditions	Operation in experiment
45%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; toluene; for 24.0h;Inert atmosphere; Reflux;	(A-3) Synthesis of 2,4-bis(2-fluorophenyl)-1,3-dimethoxybenzene In the atmosphere of argon, 23.2g of 1,3-dibromo-2,6-dimethoxybenzene, 32.9g of 2-fluorophenylboronic acid, 5.43g of tetrakis(triphenylphosphine)palladium(0), 150 mL of toluene, 150 mL of 1,2-dimethoxyethane and 150 mL of a 2M aqueous sodium carbonate solution were placed in a flask. The resulting mixture was stirred with heating under reflux for 24 hours. After being cooled to room temperature, an aqueous phase was removed, and an organic phase was washed with saturated saline. The organic phase was dried with magnesium sulfate and concentrated. Residues were purified by means of silica gel column chromatography. The resulting crystals were recrystallized from hexane, whereby 11.6g (yield: 45%) of white crystals of 2,4-bis(2-fluorophenyl)-1,3-dimethoxybenzene were obtained.
45%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; water; toluene; for 24.0h;Reflux; Inert atmosphere;	Under argon atmosphere Intermediate 15 (23.2g), 2-fluorophenylboronic acid (32.9 g), tetrakis triphenylphosphine palladium (0) (5.43g), toluene (150 mL), 1,2-dimethoxyethane ( 150 mL), 2M aqueous sodium carbonate (150 mL) were charged to a flask and stirred heated to reflux for 24 hours. After cooling to room temperature, the water layer was removed, and the organic layer was washed with saturated brine. The organic layer was dried over magnesium sulfate, concentrated, and the residue was purified by silica gel chromatography. The obtained crystals were recrystallized Intermediate 16 (11.6g) in hexane. The yield was 45%.
42%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; toluene; at 100℃; for 12.0h;	1,3-dibromo-2,6-dimethoxybenzene in the reactor, 50 g (169 mmol), fluorophenylboronic acid 52 g (372 mmol),Tetrakis (triphenylphosphine) palladium (0) 3.9 g (3 mmol), Potassium carbonate46.7 g (338 mmol), 1,4-dioxane 250 ml,Toluene250 ml, 50 ml of distilled water was put into the mixture and was stirred at100 for 12hours. When the reaction is completed it is cooled at room temperature, theorganic layer was extracted and concentrated under reduced pressure to obtain23 g of a compound represented by .4-a (Yield 42%)

Reference： [1]Patent: EP2436679,2012,A1 .Location in patent: Page/Page column 46
[2]Patent: JP2015/7036,2015,A .Location in patent: Paragraph 0234; 0238
[3]Patent: KR2015/114636,2015,A .Location in patent: Paragraph 0572-0577
[4]Patent: US2017/54086,2017,A1 .Location in patent: Paragraph 0260

9
[ 185342-88-5 ]
[ 1256544-09-8 ]

Reference： [1]Patent: EP2436679,2012,A1
[2]Patent: KR2015/114636,2015,A
[3]Patent: JP2015/7036,2015,A
[4]Patent: US2017/54086,2017,A1

10
[ 185342-88-5 ]
[ 1256544-10-1 ]

Reference： [1]Patent: EP2436679,2012,A1
[2]Patent: KR2015/114636,2015,A
[3]Patent: JP2015/7036,2015,A
[4]Patent: US2017/54086,2017,A1

11
[ 185342-88-5 ]
[ 1377187-97-7 ]

Reference： [1]Patent: EP2436679,2012,A1
[2]Patent: US2017/54086,2017,A1

12
[ 185342-88-5 ]
[ 1256544-69-0 ]

Reference： [1]Patent: EP2436679,2012,A1

13
[ 185342-88-5 ]
[ 1256544-11-2 ]

Reference： [1]Patent: EP2436679,2012,A1
[2]Patent: KR2015/114636,2015,A
[3]Patent: JP2015/7036,2015,A
[4]Patent: US2017/54086,2017,A1

14
[ 185342-88-5 ]
C₂₄H₁₃NO₄ [ No CAS ]

Reference： [1]Patent: JP2015/7036,2015,A

15
[ 185342-88-5 ]
C₂₄H₁₃NO₂ [ No CAS ]

Reference： [1]Patent: JP2015/7036,2015,A

16
[ 185342-88-5 ]
C₂₄H₁₃BrO₂ [ No CAS ]

Reference： [1]Patent: US2017/54086,2017,A1

17
[ 185342-88-5 ]
C₅₄H₃₂O₂ [ No CAS ]

Reference： [1]Patent: US2017/54086,2017,A1

18
[ 185342-88-5 ]
(±)-naphthalen-2-yl(2,2',4-trimethoxy-[1,1'-biphenyl]-3-yl)methanol [ No CAS ]

Reference： [1]Tetrahedron,2018,vol. 74,p. 4531 - 4537

19
[ 185342-88-5 ]
(±)-(3-(1-benzyl-1H-pyrazol-4-yl)-2,6-dimethoxyphenyl)(naphthalen-2-yl)methanol [ No CAS ]

Reference： [1]Tetrahedron,2018,vol. 74,p. 4531 - 4537

20
[ 185342-88-5 ]
(3-(1-benzyl-1H-pyrazol-4-yl)-2,6-dimethoxyphenyl)(naphthalen-2-yl)methanone [ No CAS ]

Reference： [1]Tetrahedron,2018,vol. 74,p. 4531 - 4537

21
[ 185342-88-5 ]
[ 66-99-9 ]
(±)-(3-bromo-2,6-dimethoxyphenyl)(naphthalen-2-yl)methanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%		To a solution of <strong>[185342-88-5]1,3-dibromo-2,4-dimethoxybenzene</strong> (230) (375 mg, 1.27 mmols) in 10 mL of abs. THF, n-BuLi (1.6 M in hexane, 792 μL, 1.27 mmols) was added slowly at -78 C and the mixture was stirred at this temperature for a further 2 h. Subsequently, at -78 C., a -78 C cold solution of 2-naphthalenehyde (495 mg, 3.17 mmols) in 2 mL of abs. THF was added. The reaction mixture was stirred at the same temperature for 1 h and slowly brought to rt overnight. The reaction mixture was washed successively with 4 mL of water, 4 mL of sat. amMonium chloride solution and 30 mL EtOAc. After stirring for 10 min, the organic layer was separated off and the aqueous phase was extracted three times with in each case 10 mL of EtOAc. The combined organic layers were washed with 15 mL sat. sodium chloride solution and then dried over anhydrous magnesium sulfate. The solvent was completely removed in vacuo and the residue was purified by flash chromatography on silica gel (10% EtOAc/PE). The product (404 mg, 1.08 mmols, 85%) was obtained as a colorless oil. Rf: 0.14 (10% EtOAc/PE). 1H NMR (400 MHz, CDCl3) δ = 7.82 - 7.78 (m, 4H), 7.50 - 7.45 (m, 4H), 6.65 (d, 3J = 8.9 Hz, 1H), 6.44 (s, 1H), 3.74 (s, 3H), 3.63 (s, 3H). 13C NMR (101 MHz, CDCl3) δ = 157.57, 155.50, 141.88, 133.28, 132.91, 132.60, 128.10, 127.87, 127.64, 127.31, 126.05, 125.71, 124.42, 123.71, 109.06, 108.83, 69.34, 61.67, 56.17. ESI-MS: m/z = 354.90, 356.90 [(M-H2O)+H]+. HRMS (ESI): calculated for C19H16O2 79Br: m/z = 355.03282 [M+H]+, found: m/z = 355.03317 [M+H]+. calculated for C19H16O2 81Br: m/z = 357.03077 [M+H]+, found: m/z = 357.03049 [M+H]+.

Reference： [1]Tetrahedron,2018,vol. 74,p. 4531 - 4537

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H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 185342-88-5 ] {[proInfo.proName]}

Quality Control of [ 185342-88-5 ]

Related Doc. of [ 185342-88-5 ]

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[ 185342-88-5 ] Synthesis Path-Upstream 1~1

[ 185342-88-5 ] Synthesis Path-Downstream 1~21

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