[ CAS No. 69189-19-1 ]

Name: 4-Bromo-1,2-bis(bromomethyl)benzene
Brand: Ambeed
SKU: A940641
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COA GC NMR CNMR HPLC/UPLC LC-MS SDS

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Product Details of [ 69189-19-1 ]

CAS No. :	69189-19-1	MDL No. :	MFCD16620247
Formula :	C₈H₇Br₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	342.85	Pubchem ID :	12496465
Synonyms :

Computed Properties of [ 69189-19-1 ]

TPSA :Topological Polar Surface Area	0	H-Bond Acceptor Count :	0
XLogP3 :	3.7	H-Bond Donor Count :	0
SP3 :	0.25	Rotatable Bond Count :	2

Safety of [ 69189-19-1 ]

Signal Word:	Warning	Class
Precautionary Statements:	P280-P305+P351+P338	UN#:
Hazard Statements:	H317-H319	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 69189-19-1 ]

Upstream synthesis route of [ 69189-19-1 ]
Downstream synthetic route of [ 69189-19-1 ]

[ 69189-19-1 ] Synthesis Path-Upstream 1~6

1
[ 171011-37-3 ]
[ 69189-19-1 ]

Yield	Reaction Conditions	Operation in experiment
95%	With phosphorus tribromide In diethyl ether at 0℃; for 7.00 h; Reflux	To a solution of 11 (103 mg, 0.474 mM) in Et2O (3 mL) was slowly added a solution of PBr3 (0.16 mL,1.66 mM) in Et2O (0.25 mL) at 0 °C. The whole was refluxed for 7 h, poured to ice (ca 30 mL), andextracted with Et2O (20 mL × 3). The organic solutions were washed with brine (10 mL), dried, andevaporated. Purification of the residue by column chromatography (SiO2, hexane) gave 12 (154 mg,95percent) as colorless plates, mp 42-44 °C (lit [20]. mp 40-44 °C).
84%	With N-Bromosuccinimide In dichloromethane at 20℃; for 6.00 h;	After dissolving Compound 3 (5.2 g, 23.9 mmol) in methylene chloride (50 milliliter), followed by adding N-bromosuccinimide (12.8 g, 71.7 mmol) at room temperature, and then the resultant solution was stirred for 6 hours. Water (200 milliliter) was poured in the resultant reaction solution, and the deposited solid was washed by ethanol, and as a result, Compound 4 was obtained. Product Amount: 6.9 g, Yield: 84 percent

Reference： [1] Synlett, 2013, vol. 24, # 19, p. 2510 - 2514
[2] Patent: EP1659129, 2006, A1. Location in patent: Page/Page column 100-101
[3] Patent: US6025370, 2000, A
[4] Research on Chemical Intermediates, 2013, vol. 39, # 1, p. 139 - 146

2
[ 583-71-1 ]
[ 69189-19-1 ]

Yield	Reaction Conditions	Operation in experiment
93%	With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 1.00 h; Heating / reflux	4-bromo-l,2-bis(bromomethyl)benzene (Q22). To a 1000 mL round bottom flask was added 4-brmo-oe-xylene <21) (0.0811 mol, 15.0Og), NBS (0.0426 mol, 7.580 g), 2,2 -azobisisobutyronitrile (0.00405 mol, 0.6650 g) and 500 mL of CCl₄. The reaction mixture was then heated under reflux for Ih. After this time another amount of NBS and AIBN was added and repeated over four times in total. The precipitate was filtered off from the warm reaction mixture and the filtrate concentrated. Crude material was crystallized from hexanes to form white crystals (23 g, 93percent). ¹H NMR (300 MHz, CDCl₃) δ 7.53 (d, IH, ArH, J=2.0 Hz), 7.44 (dd, IH, ArH, J-8.1 Hz, J =2.0 Hz), 7.24 (d, IH, ArH, J=8.10), 4.60 (d, 4H, CH₂, J=4.20 Hz)
56.7%	With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 70℃; for 1.00 h;	Step A : 4-bromo-l,2-bis(bromomethyl)benzene A solution of 4-bromo-l,2-dimethylbenzene (2.0 g, 10.81 mmol) in carbon tetrachloride (70 mL) in a 250 mL round bottom flask was stirred at room temperature until all solids were dissolved. N-bromosuccinimide (4.81 g, 27.0 mmol) and 2,2'- azobis(2-methylpropionitrile) (0.044 g, 0.270 mmol) were added and mixture was heated to 70°C for 1 h. After cooling to room temperature, the mixture was filtered through celite bed. Celite bed was rinsed with carbon tetrachloride (3x50 mL). Combined filtrate was dried (sodium sulphate), filtered and concentrated under reduced pressure. The crude material was purified by combi- flash column chromatography (Column: 120 gm Red- Sep; eluent: hexane). The fractions were collected and concentrated under reduced pressure to yield 4-bromo-l,2-bis(bromomethyl) benzene (2.1 g, 56.7percent yield) as colorless gummy oil. 1H NMR (400 MHz, CDC1₃): δ 7.56-7.51 (m, 1H), 7.44-7.41 (m, 1H), 7.25- 7.22 (m, 1H), 4.59 (s, 2H), 4.578 (s, 2H).

Reference： [1] Patent: WO2008/24435, 2008, A2. Location in patent: Page/Page column 98
[2] Journal of Organic Chemistry USSR (English Translation), 1985, p. 1418 - 1421[3] Zhurnal Organicheskoi Khimii, 1985, vol. 21, # 7, p. 1556 - 1560
[4] Patent: WO2015/103508, 2015, A1. Location in patent: Page/Page column 102
[5] Journal of Organic Chemistry, 1979, vol. 44, # 9, p. 1519 - 1533
[6] Patent: US2014/194386, 2014, A1. Location in patent: Paragraph 0460

3
[ 86-90-8 ]
[ 69189-19-1 ]

Reference： [1] Research on Chemical Intermediates, 2013, vol. 39, # 1, p. 139 - 146
[2] Synlett, 2013, vol. 24, # 19, p. 2510 - 2514

4
[ 171011-37-3 ]
[ 69189-19-1 ]

Yield	Reaction Conditions	Operation in experiment
95%	With phosphorus tribromide In diethyl ether at 0℃; for 7.00 h; Reflux	To a solution of 11 (103 mg, 0.474 mM) in Et2O (3 mL) was slowly added a solution of PBr3 (0.16 mL,1.66 mM) in Et2O (0.25 mL) at 0 °C. The whole was refluxed for 7 h, poured to ice (ca 30 mL), andextracted with Et2O (20 mL × 3). The organic solutions were washed with brine (10 mL), dried, andevaporated. Purification of the residue by column chromatography (SiO2, hexane) gave 12 (154 mg,95percent) as colorless plates, mp 42-44 °C (lit [20]. mp 40-44 °C).
84%	With N-Bromosuccinimide In dichloromethane at 20℃; for 6.00 h;	After dissolving Compound 3 (5.2 g, 23.9 mmol) in methylene chloride (50 milliliter), followed by adding N-bromosuccinimide (12.8 g, 71.7 mmol) at room temperature, and then the resultant solution was stirred for 6 hours. Water (200 milliliter) was poured in the resultant reaction solution, and the deposited solid was washed by ethanol, and as a result, Compound 4 was obtained. Product Amount: 6.9 g, Yield: 84 percent

5
[ 583-71-1 ]
[ 69189-19-1 ]

Yield	Reaction Conditions	Operation in experiment
93%	With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 1.00 h; Heating / reflux	4-bromo-l,2-bis(bromomethyl)benzene (Q22). To a 1000 mL round bottom flask was added 4-brmo-oe-xylene <21) (0.0811 mol, 15.0Og), NBS (0.0426 mol, 7.580 g), 2,2 -azobisisobutyronitrile (0.00405 mol, 0.6650 g) and 500 mL of CCl₄. The reaction mixture was then heated under reflux for Ih. After this time another amount of NBS and AIBN was added and repeated over four times in total. The precipitate was filtered off from the warm reaction mixture and the filtrate concentrated. Crude material was crystallized from hexanes to form white crystals (23 g, 93percent). ¹H NMR (300 MHz, CDCl₃) δ 7.53 (d, IH, ArH, J=2.0 Hz), 7.44 (dd, IH, ArH, J-8.1 Hz, J =2.0 Hz), 7.24 (d, IH, ArH, J=8.10), 4.60 (d, 4H, CH₂, J=4.20 Hz)
56.7%	With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 70℃; for 1.00 h;	Step A : 4-bromo-l,2-bis(bromomethyl)benzene A solution of 4-bromo-l,2-dimethylbenzene (2.0 g, 10.81 mmol) in carbon tetrachloride (70 mL) in a 250 mL round bottom flask was stirred at room temperature until all solids were dissolved. N-bromosuccinimide (4.81 g, 27.0 mmol) and 2,2'- azobis(2-methylpropionitrile) (0.044 g, 0.270 mmol) were added and mixture was heated to 70°C for 1 h. After cooling to room temperature, the mixture was filtered through celite bed. Celite bed was rinsed with carbon tetrachloride (3x50 mL). Combined filtrate was dried (sodium sulphate), filtered and concentrated under reduced pressure. The crude material was purified by combi- flash column chromatography (Column: 120 gm Red- Sep; eluent: hexane). The fractions were collected and concentrated under reduced pressure to yield 4-bromo-l,2-bis(bromomethyl) benzene (2.1 g, 56.7percent yield) as colorless gummy oil. 1H NMR (400 MHz, CDC1₃): δ 7.56-7.51 (m, 1H), 7.44-7.41 (m, 1H), 7.25- 7.22 (m, 1H), 4.59 (s, 2H), 4.578 (s, 2H).

6
[ 86-90-8 ]
[ 69189-19-1 ]

Reference： [1] Research on Chemical Intermediates, 2013, vol. 39, # 1, p. 139 - 146
[2] Synlett, 2013, vol. 24, # 19, p. 2510 - 2514

[ 69189-19-1 ] Synthesis Path-Downstream 1~10

1
[ 86-73-7 ]
[ 69189-19-1 ]
C₅₁H₃₄ [ No CAS ]

Reference： [1]Patent: KR2019/48005,2019,A

2
[ 86-73-7 ]
[ 69189-19-1 ]
C₂₁H₁₅Br [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%		1.66 g (10 mmol) of Compound 9 was placed in a round flask, and 20 mL of dimethyl sulfoxide was added to dissolve the solution. A solution of 2 g (50 mmol) of sodium hydroxide in water at a ratio of 50 wtpercent was added and heated to 80 ° C. After 30 minutes, when the reaction solution turned red, 3.77 g (11 mmol) of Compound 10 was added and the mixture was stirred at 80° C for 12 hours. After cooling to room temperature, 20 ml of water was added, extracted with dichloromethane in a separating funnel, and then the solvent was removed by a rotary evaporator. Column chromatography afforded 1.53 g (yield: 44percent) of Compound 11.

Reference： [1]Patent: KR2019/48005,2019,A.Location in patent: Paragraph 0314-0316

3
[ 112-35-6 ]
[ 69189-19-1 ]
1,1'-(4-bromo-1,2-phenylene)bis(2,5,8,11-tetraoxadodecane) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride; In 1,4-dioxane; at 20℃; for 0.333333h;	4-Bromo-l ,2-bis(bromomethyl)benzene (250 mg) and 2-(2-(2-methoxyethoxy)ethoxy)ethanol (263 mg) were dissolved in dioxane (8 mL). Sodium hydride (60percent, 64.2 mg) was added, and the solution was mixed at ambient temperature. After 20 minutes, the solvent was removed under vacuum. The residue was suspended in ethyl acetate (20 mL), washed with brine (5 mL) and dried over anhydrous sodium sulfate. The solution was concentrated and syringe filtered. The remaining solvent was then removed under vacuum, and the material was utilized without further purification. NMR (500 MHz, dimethylsulfoxide-efe) delta ppm 7.57 (d, IH), 7.48 (dd, IH), 7.33 (d, IH), 4.54 (s, 2H), 4.50 (s, 2H), 3.60- 3.55 (m, 8H), 3.53-3.50 (m, 12H), 3.44-3.40 (m, 4H), 3.24-3.23 (m, 6H). MS (ESI) m/z 526.2 (M+H)+.

Reference： [1]Patent: WO2019/35927,2019,A1.Location in patent: Paragraph 00982

4
[ 69189-19-1 ]
[ 1011-65-0 ]
(±)-methyl 5-bromo-1,3-dihydrospiro[indene-2,3'-indoline]-5'-carboxylate [ No CAS ]