[ CAS No. 18243-41-9 ] {[proInfo.proName]}

Name: 18243-41-9|(Bromomethyl)trimethylsilane|98%
Brand: Ambeed
SKU: A368681
Rating: 91 (30 reviews)

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Quality Control of [ 18243-41-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 18243-41-9 ]

SDS Specification

Alternatived Products of [ 18243-41-9 ]

Product Details of [ 18243-41-9 ]

CAS No. :	18243-41-9	MDL No. :	MFCD00000167
Formula :	C₄H₁₁BrSi	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ACAUYCZBWABOLI-UHFFFAOYSA-N
M.W :	167.12	Pubchem ID :	87523
Synonyms :

Safety of [ 18243-41-9 ]

Signal Word:	Danger	Class:	3,8
Precautionary Statements:	P210-P280-P305+P351+P338-P310	UN#:	2924
Hazard Statements:	H225-H314	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 18243-41-9 ]

* 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 [ 18243-41-9 ]
Downstream synthetic route of [ 18243-41-9 ]

[ 18243-41-9 ] Synthesis Path-Upstream 1~4

1
[ 628-17-1 ]
[ 18243-41-9 ]
[ 110-53-2 ]
[ 4206-67-1 ]

Reference： [1] Tetrahedron Letters, 1981, vol. 22, # 14, p. 1295 - 1298

2
[ 542-69-8 ]
[ 18243-41-9 ]
[ 109-65-9 ]
[ 4206-67-1 ]

Reference： [1] Tetrahedron Letters, 1981, vol. 22, # 14, p. 1295 - 1298

3
[ 628-17-1 ]
[ 18243-41-9 ]
[ 110-53-2 ]
[ 4206-67-1 ]

Reference： [1] Tetrahedron Letters, 1981, vol. 22, # 14, p. 1295 - 1298

4
[ 18243-41-9 ]
[ 100-46-9 ]
[ 53215-95-5 ]

Reference： [1] Canadian Journal of Chemistry, 1977, vol. 55, p. 2589 - 2600

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Yield	Reaction Conditions	Operation in experiment
32%	With N-Bromosuccinimide In dichloromethane at 20℃; for 18h;	34 Silane compounds can be monobrominated, dibrominated and tribrominated in the presence of an excess amount of NBS and a Lewis acid catalyst such as AICI3, FeCI3 or ZrCI4. For example, as shown in Scheme 21 , (bromomethyl)trimethylsilane can be obtained as the major product in 32% isolated yield using NBS, AICI3 (5 mole %), in CH2CI2 at room temperature for 18 hours. As shown in Scheme 22, (1 ,1-dibromoethyl)triethylsilane can be obtained as the major product in 54% isolated yield using NBS, ZrCI4 (5 mole %), in CH2CI2 at room temperature for 18 hours. The major products were isolated by distillation.; Example 34: (Bromomethyl)trimethylsilane; CH3 CH3H3C-Si-CH3 - H3C-Si-CH2BrCH3 CH3[00158] To a suspension of NBS (50 mmol) and AICI3 (5 mol%) in CH2CI2 (400 mL) was added Me4Si (50 mmol) under nitrogen. The solution was stirred at room temperature for 18 h. The reaction was quenched by a saturated aqueous solution of NaHCOs, and the separated organic phase was EPO washed with brine. After drying over Na2SO4, the organic phase was distilled and (bromomethyl)trimethylsilane was obtained as major product.
	durch Photobromierung;
	durch Photobromierung;

Yield	Reaction Conditions	Operation in experiment
65%	In ethanol
	With ethanol

Yield	Reaction Conditions	Operation in experiment
72%	at 80℃; for 12h;
	at 140 - 150℃;

Yield	Reaction Conditions	Operation in experiment
82%	With sodium bromide In water for 264h; Heating;
47%	Stage #1: Chloromethyltrimethylsilane With magnesium In diethyl ether for 1.5h; Inert atmosphere; Reflux; Stage #2: With bromine In diethyl ether at -80 - 20℃; Inert atmosphere;
	(i) Mg, Et₂O, (ii) AgBr; Multistep reaction;

[ CAS No. 18243-41-9 ] {[proInfo.proName]}

Quality Control of [ 18243-41-9 ]

Related Doc. of [ 18243-41-9 ]

Product Details of [ 18243-41-9 ]

Safety of [ 18243-41-9 ]

Application In Synthesis of [ 18243-41-9 ]

[ 18243-41-9 ] Synthesis Path-Upstream 1~4

[ 18243-41-9 ] Synthesis Path-Downstream 1~88

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Yield	Reaction Conditions	Operation in experiment
66%	With lithium diisopropyl amide In tetrahydrofuran 1.) 0 deg C, 1h, 2.) reflux, 15 h;
	With lithium diisopropyl amide In tetrahydrofuran

Yield	Reaction Conditions	Operation in experiment
62%	With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; n-butyllithium In tetrahydrofuran; hexane -78 deg C up to RT;
	With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; n-butyllithium 1) THF, 10 min, -78 deg C, 2) to 25 deg C, overnight; Yield given. Multistep reaction;

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; diisopropylamine; lithium chloride In tetrahydrofuran; hexane at 23℃; for 22h; Yield given. Yields of byproduct given;
	With lithium chloride; lithium hexamethyldisilazane 1.) THF, 0 deg C, 20 min, 2.) 0 deg C, 23 h; Yield given; Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

Yield	Reaction Conditions	Operation in experiment
	With Cl₂ In not given
	With Cl₂ In not given
	With chlorine In not given

Yield	Reaction Conditions	Operation in experiment
80%	With CH₃MgBr In not given
80%	With CH₃MgBr In not given
80%	With methylmagnesium bromide In not given

Yield	Reaction Conditions	Operation in experiment
	With CH₃OH; KCN In methanol react. with KCN in boiling CH3OH;;
	With CH₃OH; KCN In methanol react. with KCN in boiling CH3OH;;
	With methanol; potassium cyanide In methanol react. with KCN in boiling CH3OH;;

Yield	Reaction Conditions	Operation in experiment
	With bromine In methanol (N2); monitored by (1)H NMR;
	With bromine In tetrachloromethane (N2); monitored by (1)H NMR;
	With bromine In dichloromethane (N2); monitored by (1)H NMR;

	With bromine In N,N-dimethyl-formamide (N2); monitored by (1)H NMR;
	With bromine In chloroform (N2); monitored by (1)H NMR;

Yield	Reaction Conditions	Operation in experiment
82%	Stage #1: methyl 4-hydroxylbenzoate With sodium hydride In N,N-dimethyl-formamide for 0.5h; Stage #2: (bromomethyl)trimethylsilane In N,N-dimethyl-formamide at 60℃; for 1h;	1.1 [0049]Stepl: Synthesis of 4-trimethyl silylmethyl methyl benzoate (CnH18OsSi).; [0050] Structure:[0051 ]NaH (4.4-g), supplied as 60% oily suspension, was washed over a glass filter with 2 x 50-ml absolute dimethylformamide to remove oil. In small portions, NaH was added slowly (over a 20 min time period) to 16.8-g of 4-hydroxymethylbenzoate previously dissolved in dimethylformamide (at room temperature with constant mixing with magnetic stirrer); mixing continued for 30 min after the last addition. The resulting suspension was placed on a 6O0C oil bath followed by drop-wise addition of 16.7-g of trimethylbromomethyl silane, previously dissolved in 50-ml dimethylformamide. The mixture was mixed for another 1-hour period and then taken off the oil bath. After the mixture reached the room temperature, the surplus NaH was reacted with 30-ml methanol to form NaOH and H2. The precipitated NaOH was removed by filtering on a glass filter and the filtrate was subjected to distillation (2-3 Hgmm). The resulting brown precipitate was dissolved in 200-ml of ethylacetate followed by washing with 2 x 150 ml distilled water. The organic phase was dried over water-free sodium sulfate followed by the removal of ethylacetate by distillation using a Rotadest equipment. The resulting light yellow oily substance (4-trimethyl silylmethyl methylbenzoate) was used for the next step as the starting material. The yield of this product was -82%. [0052]
82%	Stage #1: methyl 4-hydroxylbenzoate With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.833333h; Stage #2: (bromomethyl)trimethylsilane In N,N-dimethyl-formamide at 60℃; for 1h;	1.1 NaH (4.4-g), supplied as 60% oily suspension, was washed over a glass filter with 2×50-ml absolute dimethylformamide to remove oil. In small portions, NaH was added slowly (over a 20 min time period) to 16.8-g of 4-hydroxymethylbenzoate previously dissolved in dimethylformamide (at room temperature with constant mixing with magnetic stirrer); mixing continued for 30 min after the last addition. The resulting suspension was placed on a 60° C. oil bath followed by drop-wise addition of 16.7-g of trimethylbromomethyl silane, previously dissolved in 50-ml dimethylformamide. The mixture was mixed for another 1-hour period and then taken off the oil bath. After the mixture reached the room temperature, the surplus NaH was reacted with 30-ml methanol to form NaOH and H2. The precipitated NaOH was removed by filtering on a glass filter and the filtrate was subjected to distillation (2-3 Hgmm). The resulting brown precipitate was dissolved in 200-ml of ethylacetate followed by washing with 2×150 ml distilled water. The organic phase was dried over water-free sodium sulfate followed by the removal of ethylacetate by distillation using a Rotadest equipment. The resulting light yellow oily substance (4-trimethyl silylmethyl methylbenzoate) was used for the next step as the starting material. The yield of this product was 82%.

Yield	Reaction Conditions	Operation in experiment
30%	With calcium at -78℃; for 2h; Inert atmosphere; Schlenk technique;
	With calcium at 0℃; Inert atmosphere; Schlenk technique;

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