[ CAS No. 20248-86-6 ] {[proInfo.proName]}

Name: 20248-86-6|4,4-Bis(bromomethyl)biphenyl|95%
Brand: Ambeed
SKU: A415093
Rating: 96 (27 reviews)

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COA NMR CNMR HPLC LC-MS

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CAS No. :	20248-86-6	MDL No. :	MFCD00094419
Formula :	C₁₄H₁₂Br₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HMUGRILXVBKBID-UHFFFAOYSA-N
M.W :	340.05	Pubchem ID :	621238
Synonyms :

Safety of [ 20248-86-6 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P273	UN#:	3261
Hazard Statements:	H302-H314-H410	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 20248-86-6 ]

* 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 [ 20248-86-6 ]
Downstream synthetic route of [ 20248-86-6 ]

[ 20248-86-6 ] Synthesis Path-Upstream 1~3

1
[ 20248-86-6 ]
[ 1667-12-5 ]

Reference： [1] Patent: US2789969, 1953, ,

2
[ 92-52-4 ]
[ 2567-29-5 ]
[ 20248-86-6 ]

Reference： [1] Chemische Berichte, 1937, vol. 70, p. 983

3
[ 20248-86-6 ]
[ 122-52-1 ]
[ 17919-34-5 ]

Yield	Reaction Conditions	Operation in experiment
96%	at 150℃; for 12 h; Inert atmosphere	A mixture of 4,4’-bis(bromoethyl)biphenyl (1) (0.204 g, 0.592 mmol) and P(OEt)3 (1 mL, 6.27mmol) was heated at 150°C for 12 h under N2. The mixture was purified over silica gel columnchromatography using ethyl acetate as eluant, giving 258 mg of 3.Yield : 96 percent. 1H NMR (CDCl3, 400 MHz)δ 7.53 (d, J = 8.3 Hz, 4H), 7.36 (d, J = 8.3 Hz, 4H), 4.04(q, J = 7.1 Hz, 8H), 3.19 (d, J = 21.7 Hz, 4H), 1.27 (t, J = 7.1 Hz, 12H).
96%	at 150℃; for 12 h;	4,4’-bis(bromoethyl)-1,1’-biphenyl (0.204 g, 0.592 mmol) and P(OEt)₃ (1 ml, 6.27 mmol) were stirred at 150 for 12 hours. The mixture was then cooled to room temperature and the product was purified by column chromatography on silica gel (ethyl acetate). The product was isolated as a colorless solid (0.258 g, 96).

Reference： [1] Bulletin of the Chemical Society of Japan, 2016, vol. 89, # 8, p. 911 - 913
[2] Bulletin of the Chemical Society of Japan, 2017, vol. 90, # 12, p. 1337 - 1339
[3] Tetrahedron, 2003, vol. 59, # 25, p. 4673 - 4685
[4] Organic Letters, 2002, vol. 4, # 5, p. 719 - 722
[5] Chemistry - A European Journal, 2007, vol. 13, # 5, p. 1481 - 1498
[6] Patent: JP2016/166190, 2016, A, . Location in patent: Paragraph 0087

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Yield	Reaction Conditions	Operation in experiment
31%	With phosphoric acid; hydrogen bromide; acetic acid at 80 - 120℃; for 6h;
31%	With phosphoric acid; hydrogen bromide; acetic acid at 70 - 130℃; for 6h; Inert atmosphere;
30%	With hydrogen bromide; acetic acid In tetrachloromethane for 20h; Ambient temperature;

Yield	Reaction Conditions	Operation in experiment
37%	In acetonitrile Heating;
37%	In acetonitrile for 72h; Heating;

Yield	Reaction Conditions	Operation in experiment
	With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane;	(1) To 150 ml of carbon tetrachloride, 10 g of <strong>[613-33-2]4,4'-dimethylbiphenyl</strong> (a product of ALDRICH Co.), 20 g of N-bromosuccinimide (a product of HIROSHIMA WAKO Co., Ltd.), and 0.9 g of benzoyl peroxide (a product of HIROSHIMA WAKO Co., Ltd.) were added, and the reaction was allowed to proceed in the resultant mixture at 90 C. for 2 hours while the mixture was stirred. After the reaction product was cooled, the precipitated crystal was washed with 100 ml of methanol to obtain 13.2 g of 4,4'-dibromomethyl-biphenyl.
	With hydrogen bromide; dihydrogen peroxide; In 1,2-dichloro-ethane; for 12h;Cooling with ice; Irradiation;	82 g (1.2 mol) of 50% hydrogen peroxide was slowly added into a mixture of 100 g (0.55 mol) of 4,4'-dimethyl-1,1'-biphenyl and 370 g (2.2 mol) of hydrobromic acid in 1000 g of DCE under ice bath. The resulting mixture was irradiated by a visible light lamp (with a wavelength of about 400 nm) for 12 hours to form a crude product (in an organic layer). 4,4'-bis(bromomethyl)-1,1'-biphenyl was obtained with a yield of 75% after removing the solvent from the crude product by evaporation.

Yield	Reaction Conditions	Operation in experiment
92.2%	With sulfuric acid; hydrogen bromide; In water;	b) Preparation of 4,4'-Bis (Bromomethyl) Biphenyl. 11.6g (54.13 mmoles) of 4,4'-bis (hydroxymethyl) biphenyl, 35.3 ml of HBr at 48% by weight in H2O (649.6 mmoles) and 19.11 ml of H2SO4 at 96% are placed in a three-necked 500ml flask which has a mechanical agitator, cooler and oil heating bath. The mixture is heated to 135oC under vigorous agitation for 4 hours, after the first two hours adding to the very dense mixture an additional 7.4ml of HBr at 48% and 2ml of H2SO4 at 96%. On completion the cooled mixture is filtered on a Gooch G2 and the precipitate recovered is washed with iced water until the washings are neutral (about 1 litre). The solid residue is extracted with three 100ml-portions of hot toluene (50oC) and the extract is filtered hot. The toluene solution is concentrated dry at a reduced pressure and the residue dried at 40oC using a high-vacuum pump. 16.97g of 4,4'-bis (bromomethyl) biphenyl are obtained with a molar yield of 92.2%.
89%	With phosphorus tribromide; In tetrahydrofuran; water; at 0 - 20℃; for 3h;Inert atmosphere;	To a solution of 4,4?-biphenyldimethanol (3.01 g, 14 mmol) in dry THF (30 mL) at 0 was addedwith stirring under N2 a solution containing PBr3 (0.9 mL, 9.48 mmol) in dry THF (5 mL). Afterstirring for 2.5 h at room temperature, water (50 mL) was added at 0 and the solution was furtherstirred for 30 min at room tempetarure. THF was removed, and the residue was extracted into ethylacetate. This solution was washed with brine, dried over MgSO4 and evaporated. The residue waspurified by recrystallization from ethyl acetate.Yield : 89%. 1H NMR (CDCl3, 270 MHz)delta 7.56 (d, J = 8.1 Hz, 4H), 7.46 (d, J = 8.1 Hz, 4H), 4.52 (s,4H).
89%	With phosphorus tribromide; In tetrahydrofuran; at 0 - 20℃; for 2.5h;	4,4?-Bis(bromoethyl)biphenyl. 4,4?-Biphenyldimethanol (3.01 g, 14.0 mmol) was dissolved in THF (30 ml). PBr3 (0.9 ml, 9.48 mmol) was then introduced at 0 . The mixture was stirred for 2.5 hours at room temperature. Upon completion, the reaction was quenched with water (50 ml). The organic layer was diluted with ethyl acetate (20 ml) and washed with water. The organic layer was dried over MgSO4 and evaporated under reduced pressure. The product was purified by recrystallization from ethyl acetate. The product was isolated as colorless crystals (4.19 g, 89).

[ CAS No. 20248-86-6 ] {[proInfo.proName]}

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[ 20248-86-6 ] Synthesis Path-Upstream 1~3

[ 20248-86-6 ] Synthesis Path-Downstream 1~88