[ CAS No. 71-91-0 ] {[proInfo.proName]}

Name: 71-91-0|Tetraethylammonium bromide|97%
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Quality Control of [ 71-91-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 71-91-0 ]

Product Details of [ 71-91-0 ]

CAS No. :	71-91-0	MDL No. :	MFCD00011825
Formula :	C₈H₂₀BrN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HWCKGOZZJDHMNC-UHFFFAOYSA-M
M.W :	210.16	Pubchem ID :	6285
Synonyms :

Calculated chemistry of [ 71-91-0 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	4
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	51.87
TPSA :	0.0 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-9.7 cm/s

Lipophilicity

Log Po/w (iLOGP) :	-2.17
Log Po/w (XLOGP3) :	-2.98
Log Po/w (WLOGP) :	-1.11
Log Po/w (MLOGP) :	-0.99
Log Po/w (SILICOS-IT) :	1.2
Consensus Log Po/w :	-1.21

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	1.0
Solubility :	2090.0 mg/ml ; 9.96 mol/l
Class :	Highly soluble
Log S (Ali) :	3.54
Solubility :	731000.0 mg/ml ; 3480.0 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	-3.07
Solubility :	0.181 mg/ml ; 0.000859 mol/l
Class :	Soluble

Medicinal Chemistry

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

Safety of [ 71-91-0 ]

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 [ 71-91-0 ]

* 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 [ 71-91-0 ]
Downstream synthetic route of [ 71-91-0 ]

[ 71-91-0 ] Synthesis Path-Upstream 1~18

1
[ 71-91-0 ]
[ 937-14-4 ]
[ 108-85-0 ]
[ 1128-76-3 ]

Reference： [1] Chemistry Letters, 1998, # 11, p. 1085 - 1086

2
[ 71-91-0 ]
[ 555-21-5 ]
[ 74-88-4 ]
[ 71825-51-9 ]

Reference： [1] Patent: US2009/137595, 2009, A1,

3
[ 74-96-4 ]
[ 121-44-8 ]
[ 71-91-0 ]

Reference： [1] Zeitschrift fuer Physikalische Chemie, Stoechiometrie und Verwandtschaftslehre, 1890, vol. 5, p. 592
[2] Zeitschrift fuer Kristallographie, Kristallgeometrie, Kristallphysik, Kristallchemie, 1907, vol. 43, p. 151
[3] Journal fuer Praktische Chemie (Leipzig), 1903, vol. <2>67, p. 348
[4] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1984, p. 711 - 716
[5] Chemical Communications, 2012, vol. 48, # 6, p. 916 - 918
[6] Journal of Chemical and Engineering Data, 2013, vol. 58, # 6, p. 1505 - 1515
[7] Patent: JP5789397, 2015, B2, . Location in patent: Paragraph 0088
[8] New Journal of Chemistry, 2017, vol. 41, # 19, p. 10712 - 10722

4
[ 2509-16-2 ]
[ 121-44-8 ]
[ 71-91-0 ]
[ 996-85-0 ]

Reference： [1] Journal of Organic Chemistry USSR (English Translation), 1985, vol. 21, # 3, p. 594[2] Zhurnal Organicheskoi Khimii, 1985, vol. 21, # 3, p. 655 - 656

5
[ 91-22-5 ]
[ 120782-58-3 ]
[ 120782-61-8 ]
[ 71-91-0 ]

Reference： [1] Polyhedron, [2] Polyhedron, 1988, vol. 7, p. 1067 - 1070

6
[ 120782-58-3 ]
[ 120782-68-5 ]
[ 71-91-0 ]

Reference： [1] Polyhedron, [2] Polyhedron, 1988, vol. 7, p. 1067 - 1070

7
[ 120782-58-3 ]
[ 33136-93-5 ]
[ 71-91-0 ]

Reference： [1] Polyhedron, [2] Polyhedron, 1988, vol. 7, p. 1067 - 1070

8
[ 110-85-0 ]
[ 77-98-5 ]
[ 79-08-3 ]
[ 71-91-0 ]

Reference： [1] Synthesis, 2005, # 20, p. 3555 - 3564

9
[ 1392488-19-5 ]
[ 100-39-0 ]
[ 946-80-5 ]
[ 71-91-0 ]
[ 108-95-2 ]

Reference： [1] Journal of the American Chemical Society, 2012, vol. 134, # 32, p. 13415 - 13429

10
[ 64-67-5 ]
[ 121-44-8 ]
[ 71-91-0 ]

Reference： [1] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 18, p. 2983
[2] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 18, p. 2984

11
[ 5437-45-6 ]
[ 71-91-0 ]

Reference： [1] Synthesis, 2005, # 20, p. 3555 - 3564

12
[ 20688-29-3 ]
[ 121-44-8 ]
[ 71-91-0 ]
[ 996-85-0 ]

Reference： [1] Journal of Organic Chemistry USSR (English Translation), 1985, vol. 21, # 3, p. 594[2] Zhurnal Organicheskoi Khimii, 1985, vol. 21, # 3, p. 655 - 656

13
[ 51575-86-1 ]
[ 121-44-8 ]
[ 71-91-0 ]
[ 996-85-0 ]

Reference： [1] Journal of Organic Chemistry USSR (English Translation), 1985, vol. 21, # 3, p. 594[2] Zhurnal Organicheskoi Khimii, 1985, vol. 21, # 3, p. 655 - 656

14
[ 121-44-8 ]
[ 535-11-5 ]
[ 82614-48-0 ]
[ 71-91-0 ]
[ 636-70-4 ]

Reference： [1] Danske Vid.Selsk.Mat.fys.Medd., 1943, vol. 20, # 13, p. 8,9[2] Chem.Abstr., 1945, p. 1844

15
[ 121-44-8 ]
[ 108-88-3 ]
[ 535-11-5 ]
[ 82614-48-0 ]
[ 71-91-0 ]
[ 636-70-4 ]

Reference： [1] Danske Vid.Selsk.Mat.fys.Medd., 1943, vol. 20, # 13, p. 8,9[2] Chem.Abstr., 1945, p. 1844

16
[ 540-49-8 ]
[ 121-44-8 ]
[ 71-91-0 ]
[ 109-89-7 ]

Reference： [1] Chemische Berichte, 1881, vol. 14, p. 1822

17
[ 71-91-0 ]
[ 665-46-3 ]

Reference： [1] Zeitschrift fuer Chemie (Stuttgart, Germany), 1980, vol. 20, # 8, p. 309 - 310
[2] Patent: CN103992275, 2016, B, . Location in patent: Paragraph 0264; 0265; 0266; 0267; 0268; 0269; 0285-86

18
[ 621-50-1 ]
[ 71-91-0 ]
[ 74-88-4 ]
[ 915394-28-4 ]

Reference： [1] Patent: US2009/137595, 2009, A1,

[ 71-91-0 ] Synthesis Path-Downstream 1~88

1
[ 71-91-0 ]
[ 665-46-3 ]

Reference： [1]Zeitschrift fur Chemie,1980,vol. 20,p. 309 - 310
[2]Patent: CN103992275,2016,B .Location in patent: Paragraph 0264; 0265; 0266; 0267; 0268; 0269; 0285-86

2
[ 71-91-0 ]
[ 937-14-4 ]
[ 108-85-0 ]
[ 1128-76-3 ]

Reference： [1]Chemistry Letters,1998,p. 1085 - 1086

3
[ 71-91-0 ]
[ 6735-55-3 ]

Yield	Reaction Conditions	Operation in experiment
95.89%	With sulfuric acid; dihydrogen peroxide; potassium bromide;molybdic acid; In water; at 0 - 20℃; for 0.916667h;	Molybdic acid monohydrate, H2MO04. H20 (0.24mmol, 0.043g), potassium bromide, KBr (47.56mmol, 5.66g) and <strong>[71-91-0]tetraethylammonium bromide</strong>, TEAB (23.79mmol, 5g) were powdered separately, mixed together smoothly and thoroughly. The whole was transferred to a boat kept on ice-water bath and 30% hydrogen peroxide, HZO2 (23.81mmol, 2.7mL) was added drop wise with continuous grinding for 15 min, followed by drop wise addition of 10M H2S04 (23. 80MMOL, 2. 38ML) leading to the formation of a yellow colored solution. It was stirred smoothly with glass rod for 10 min and then at room temperature for 30min. An exothermic reaction set in to form orange-yellow crystalline compound of tetraethylammonium tribromide, TEATB. The compound was dried over fused CaCl2 and extracted with ethyl acetate by dissolving in minimum amount of solvent followed by filtration through Whatman No. 42 filter paper. Aqueous phase, if present, could be separated using anhydrous sodium sulphate. The organic layer was concentrated to get yellow-orange tetraethylammonium tribromide, TEATB and the latter was recrystallized from acetonitrile. Yield: 8.44g (95.89%) Mp: 86-87 C. The chemical analyses, IR and conductance of the compound match very well with those reported in literature. Analytical data: The compound analyzed correctly C8H2ONBR3 : Calc. C, 25.97 ; H, 5.45 ; N, 3.79 ; Br, 64.79%. Found. C, 25.99 ; H, 5.82 ; N, 3.67 ; Br, 64.52 %.
94.99%		A sample of molybdic acid monohydrate, H2MO04. H20 (0. 24MMOL, 0.043g) was taken in a 250mL glass beaker and 30% hydrogen peroxide, H202 (23. 81MMOL, 2. 7ML) was added to it. The mixture was stirred for 30min at room temperature. The solution, which was slightly turbid, was filtered through Whatman No. L filter paper on a glass funnel. The clear filtrate was collected in a 250ML glass beaker and kept in an ice-water bath. <strong>[71-91-0]Tetraethylammonium bromide</strong>, TEAB (23. 79MMOL, 5G) and potassium bromide, KBr (47. 56MMOL, 5. 66g) dissolved in (0. 5M) H2S04 (23. 79MMOL, 47. 58ML) was added to this solution slowly with continuous stirring leading to the formation of a yellow precipitate. The mixture was continued to stir in ice-water bath for ANOTHER-LH and then kept standing in ice- water bath for 2h to get an orange yellow compound of Tetraethylammonium tribromide, TEATB. The compound was separated by filtration under suction using Whatman No. 1 filter paper. It was dried in vacuo over fused CACL2 and was recrystallized from acetonitrile. Y=8.36g (94.99%) MP : 86-87C. The chemical analyses, IR and conductance of the compound match very well with those reported in literature. Analytical data: The compound analyzed correctly CSH2ONBR3 : Calc. C, 25.97 ; H, 5. 45 ; N, 3.79 ; Br, 64.79 %. Found. C, 25.99 ; H, 5.82 ; N, 3. 67 ; Br, 64.52 %.
92%	With sodium hypochlorite; sulfuric acid; potassium bromide; for 0.05h;Green chemistry;	<strong>[71-91-0]Tetraethylammonium bromide</strong>, 2.l g (10 mmol) was added to a solution of 2.4 g (20 mmol) of KBr in 10 mL of 4N H2SO4. To the resulting solution was added 10 mL of 4 % sodium hypochlorite. The solution was stirred for ca. 3 mins and then the bright orange-yellow colored crystalline TEATB which had separated out was isolated by suction filtration and washed with water (5 mL) three to four times and dried under vacuum over anhydrous CaCl2 to obtain 3.40 g of TEATB as orange crystals (yield 92%).Mp: 84 C.

92%

With 3-chloro-benzenecarboperoxoic acid; potassium bromide; In water; for 0.05h;

3. Synthesis of tetraethyl ammonium tribromide, TEATB: 1 equiv of tetraethyl ammonium bromide (1mmol, 0.210 g), 2 equiv of KBr (2 mmol, 0.238 g) and 2 equiv of MCPBA (2 mmol, 0.346 g) were mixedtogether in 10 mL of water and stirred for ca. 3 min. The orange coloured product formed was washedwith NaHCO3 solution (10 % solution) for several times to remove unreacted substrate. After that thecrude product was again washed with water to remove by-products. The compound was dried in vacuoand recrystallized with EtOAc; mp: 87oC. Yield: 0.340 g; 92 %.

Reference： [1]Patent: WO2004/54962,2004,A1 .Location in patent: Page 11
[2]Patent: WO2004/54962,2004,A1 .Location in patent: Page 9-10
[3]Chemistry Letters,2014,vol. 43,p. 631 - 633
[4]Synthetic Communications,2015,vol. 45,p. 724 - 736
[5]Synthetic Communications,2013,vol. 43,p. 1734 - 1742
[6]Inorganic Chemistry,2010,vol. 49,p. 8684 - 8689

4
[ 71-91-0 ]
tetraethylammonium tribromide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94.99 - 95.89%	With sulfuric acid; dihydrogen peroxide; potassium bromide;molybdic acid; In water; at 0 - 20℃; for 0.916667 - 3.5h;Product distribution / selectivity;	A sample of molybdic acid monohydrate, H2MoO4.H2O (0.24 mmol 0.043 g) was taken in a 250 mL glass beaker and 30% hydrogen peroxide, H2O2 (23.81 mmol, 2.7 mL) was added to it. The mixture was stirred for 30 min at room temperature. The solution, which was slightly turbid, was filtered through Whatman No. 1 filter paper on a glass funnel. The clear filtrate was collected in a 250 mL glass beaker and kept in an ice-water bath. <strong>[71-91-0]Tetraethylammonium bromide</strong>, TEAB (23.79 mmol, 5 g) and potassium bromide, KBr (47.56 mmol. 5.66 g) dissolved in (0.5M) H2SO4 (23.79 mmol. 47.58 mL) was added to this solution slowly with continuous stirring leading to the formation of a yellow precipitate. The mixture was continued to stir in ice-water bath for another ~1 h and then kept standing in ice-water bath for 2 h to get an orange yellow compound of Tetraethylammonium tribromide, TEATB. The compound was separated by filtration under suction using Whatman No. 1 filter paper. EXAMPLE 6Synthesis of Tetraethylammonium Tribromide, TEATB (from TEAB)Molybdic acid monohydrate, H2 MoO4.H2O (0.24 mmol, 0.043 g), potassium bromide, KBr (47.56 mmol, 5.66 g) and <strong>[71-91-0]tetraethylammonium bromide</strong>, TEAB (23.79 mmol, 5 g) were powdered separately, mixed together smoothly and thoroughly. The whole was transferred to a boat kept on ice-water bath and 30% hydrogen peroxide, H2O2 (23.81 mmol, 2.7 mL) was added drop wise with continuous grinding for 15 min, followed by drop wise addition of 10M H2SO4 (23.80 mmol, 2.38 mL) leading to the formation of a yellow colored solution. It was stirred smoothly with glass rod for 10 min and then at room temperature for 30 min. An exothermic reaction set in to form orange-yellow crystalline compound of tetraethylammonium tribromide, TEATB. The compound was dried over fused CaCl2 and extracted with ethyl acetate by dissolving in minimum amount of solvent followed by filtration through Whatman No. 42 filter paper. Aqueous phase, if present, could be separated using anhydrous sodium sulphate. The organic layer was concentrated to get yellow-orange tetraethylammonium tribromide, TEATB and the latter was recrystallized from acetonitrile.Yield: 8.44 g (95.89%) Mp: 86-87 C. The chemical analyses, IR and conductance of the compound match very well with those reported in literature. Analytical data: The compound analyzed correctly C8H20NBr3: Calc. C, 25.97; H, 5.45; N, 3.79; Br, 64.79%. Found. C, 25.99; H, 5.82; N, 3.67; Br, 64.52%.

Reference： [1]Patent: US7005548,2006,B2 .Location in patent: Page/Page column 7-8; 9

5
[ 71-91-0 ]
[ 429-06-1 ]

Yield	Reaction Conditions	Operation in experiment
	With tetrafluoroboric acid; In methanol; for 0.5h;	Comparative Example 17; Tetraethylammonium tetrafluoroborate (TEA); A 120 g quantity of tetraethylammonium bromide (reagent, product of Tokyo Kasei Co., Ltd.) was dissolved in 120 g of methanol, and 172 g of methanol solution of 30 wt. % HBF4 was added to the solution. The mixture was stirred for 30 minutes whereupon crystals of tetraethylammonium tetrafluoroborate separated out. The solution was filtered, the crystals were then washed with isopropyl alcohol, thereafter dried in a nitrogen stream with heating at 130C to remove hydrogen bromide produced as a by-product, an excess of HBF4, methanol and isopropyl alcohol, giving 118 g of the desired product (white solid). 1H-NMR (CD3OD) delta ppm: 1.28(m 12H), 3.29(q 8H).

Reference： [1]Patent: EP1642894,2006,A1 .Location in patent: Page/Page column 33
[2]Russian Journal of Physical Chemistry,2009,vol. 83,p. 2069 - 2073

6
[ 110-52-1 ]
[ 6306-60-1 ]
[ 71-91-0 ]
[ 61023-75-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In dichloromethane;	1. alpha,alpha-tetramethylene-2,4-dichlorobenzyl cyanide Into a 500 ml three-necked flask is placed 200 ml of 25% sodium hydroxide solution and 4 g of tetraethyl ammonium bromide. To this suspension is added dropwise a solution of 33.5g (0.2 mole) of 2,4-dichlorobenzyl cyanide and 43g (0.2 mole) of 1,4-dibromobutane in 200 ml of methylene chloride under nitrogen. When the addition is over, the reaction mixture is heated to reflux for 1.5 hours. It is then poured into water and the layers are separated. The aqueous layer is extracted with 100 ml of methylene chloride. The combined organic extracts are washed with water, saturated sodium chloride solution and dried over magnesium sulfate. Solvent is evaporated to give a light yellow oil. Vacuum distillation (130-140/0.2 mm) gives 30.4g (63%) of pure product, which is identified by nmr.

Reference： [1]Patent: US4115578,1978,A

7
[ 71-91-0 ]
[ 13939-06-5 ]
C₅BrMoO₅^(1-)*C₈H₂₀N⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	In tetrahydrofuran; at 85 - 90℃; for 2.5h;Heating / reflux;	A solution containing Mo(CO)6 was prepared by dissolving 6.60 g (25.00 mmol) and 6.7Og (31.9 mmol) OfEt4NBr in 75 ml of THF. The mixture was refluxed for 2 hours, 30 minutes (Temp. = 85-9O0C). Afterwards, the solution was immediately filtered (yellow solution) and half the solvent was evaporated under vacuum. A precipitate started to form and 60 ml of hexane were added to the solution to induce more precipitation. The schlenk tube was kept at <n="21"/>-3O0C for 1 hour. After that time, the solution was filtered and the yellow compound obtained was dried in vacuum. Yield: 89%. LR-(KBr) (v 2069 (S), 1912 (S); 1871 (S); S=strong. Elemental Analysis C13H20BrMoNO5:= 446.1496. % experimental (% calculated): C 34.88 (35.00); H 4.82 (4.52); N 3.06 (3.14)

Reference： [1]Patent: WO2007/73225,2007,A1 .Location in patent: Page/Page column 19-20

8
[ 71-91-0 ]
[ 7705-08-0 ]
[ 7704-34-9 ]
[ 108-98-5 ]
(Et₄N)2(Fe₄S₄(SPh)4) [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1984,vol. 106,p. 1523 - 1524
[2]Journal of the American Chemical Society,1984,vol. 106,p. 1523 - 1524

9
sodium hexachloroplatinate [ No CAS ]
[ 201230-82-2 ]
[ 71-91-0 ]
[ 10025-83-9 ]
(NEt₄)4(PtIr₄(CO)14) [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1989,vol. 111,p. 165 - 173

10
2Na⁽¹⁺⁾*C₂B₁₀H₁₂^(2-)=Na₂C₂B₁₀H₁₂ [ No CAS ]
[ 71-91-0 ]
[ 3264-82-2 ]
2{N(C₂H₅)4}⁽¹⁺⁾*{(C₂B₁₀H₁₂)2Ni}^(2-)={N(C₂H₅)4}2{(C₂B₁₀H₁₂)2Ni} [ No CAS ]

Reference： [1]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Ni: Org.Verb.1, 1.2.2.1.2.4, page 409 - 410
[2]Journal of the American Chemical Society,1973,vol. 95,p. 1109 - 1115

11
[ 12304-98-2 ]
[ 71-91-0 ]
{N(C₂H₅)4}2{(1.2-C₂B₉H₁₁)2Ni} [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1968,vol. 90,p. 879 - 896
[2]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Ni: Org.Verb.1, 1.2.2.1.2.2.1, page 394 - 400

12
[ 75-15-0 ]
[ 71-91-0 ]
[ 7646-85-7 ]
[ 72022-68-5 ]

Reference： [1]Organic Letters,2017,vol. 19,p. 360 - 363
[2]Helvetica Chimica Acta,2006,vol. 89,p. 2040 - 2057
[3]Chemistry - A European Journal,2014,vol. 20,p. 17443 - 17453
[4]Organic Syntheses,1996,vol. 73,p. 270 - 270

13
[ 137941-29-8 ]
[ 71-91-0 ]
[ 62637-93-8 ]
Ru₂Br₂(CO)3((CH₃O)2PN(C₂H₅)P(OCH₃)2)2 [ No CAS ]