[ CAS No. 137266-85-4 ]

Name: Ethyl 1-benzyl-3-(chloromethyl)azetidine-3-carboxylate
Brand: Ambeed
SKU: A353165
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Quality Control of [ 137266-85-4 ]

COA GC NMR CNMR HPLC LC-MS

Related Doc. of [ 137266-85-4 ]

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Product Details of [ 137266-85-4 ]

CAS No. :	137266-85-4	MDL No. :	MFCD16660804
Formula :	C₁₄H₁₈ClNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	267.75	Pubchem ID :	59526760
Synonyms :

Computed Properties of [ 137266-85-4 ]

TPSA :Topological Polar Surface Area	-	H-Bond Acceptor Count :	-
XLogP3 :	-	H-Bond Donor Count :	-
SP3 :	-	Rotatable Bond Count :	-

Safety of [ 137266-85-4 ]

Signal Word:	Danger	Class	6.1
Precautionary Statements:	P201-P202-P261-P264-P270-P271-P280-P302 P352-P304 P340-P308 P313-P310-P330-P361-P403 P233-P405-P501	UN#:	2811
Hazard Statements:	H301-H311-H331-H341	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 137266-85-4 ]

Downstream synthetic route of [ 137266-85-4 ]

[ 137266-85-4 ] Synthesis Path-Downstream 1~10

1
[ 137266-85-4 ]
[ 1078166-34-3 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In diethyl ether; dichloromethane;	Preparation 3 Ethyl 1-benzyl-3-(chloromethyl)azetidine-3-carboxylate hydrochloride A solution of sodium ethoxide (21% wt. in ethanol, 66.3 mL, 205.0 mmol) in ethanol (70 mL) was added to a solution of 1-benzyl-3,3-bis(chloromethyl)azetidin-2-one (50.4 g, 195.0 mmol) (Preparation 2) in ethanol (210 mL) at 0 C. The mixture was stirred at reflux for 20 hours and then partitioned between water (200 mL) and dichloromethane (300 mL). The aqueous layer was re-extracted with dichloromethane (100 mL) and the combined organic solution was dried over magnesium sulfate and concentrated under reduced pressure to afford an orange oil. A solution of the oil in dichloromethane (100 mL) was treated with a solution of hydrogen chloride in diethyl ether (1M, 250 mL) and the resulting gummy precipitate was triturated with ethyl acetate to afford the title compound as a white solid in 73.2% yield, 43.5 g. 1H NMR (400 MHz, CD3OD) delta: 1.32 (t, 3H), 4.11 (s, 2H), 4.31 (m, 4H), 4.47 (m, 4H), 7.51 (m, 5H); LRMS APCI m/z 268 [MH]+
	With hydrogenchloride; In diethyl ether; dichloromethane;	A solution of sodium ethoxide (21 % wt. in ethanol, 66.3 ml_, 205.0 mmol) in ethanol (70 ml_) was added to a solution of the compound described in Preparation 2 (50.4 g, 195.0 mmol) in ethanol (210 ml_) at 0C. The mixture was stirred at reflux for 20 hours and then partitioned between water (200 ml_) and dichloromethane (300 ml_). The aqueous layer was re-extracted with dichloromethane (100 ml_) and the combined organic solution was then dried over magnesium sulfate and concentrated under reduced pressure to afford an orange oil. A solution of the oil in dichloromethane (100 ml_) was treated with a solution of hydrogen chloride in diethyl ether (1 M, 250 ml_) and the resulting gummy precipitate was triturated with ethyl acetate to afford the title compound as a white solid in 73.2% yield, 43.5 g.1H NMR (400 MHz, CD3OD) delta: 1.32 (t, 3H), 4.11 (s, 2H), 4.31 (m, 4H), 4.47 (m, 4H), 7.51 (m, 5H); LRMS APCI m/z 268 [MH]+

Reference： [1]Patent: US2008/280877,2008,A1.Location in patent: Page/Page column 31
[2]Patent: WO2009/63365,2009,A1.Location in patent: Page/Page column 55

2
[ 64-17-5 ]
[ 141-52-6 ]
[ 137266-59-2 ]
[ 137266-85-4 ]

Yield	Reaction Conditions	Operation in experiment
	for 20h;Heating / reflux;	Preparation 3 Ethyl 1-benzyl-3-(chloromethyl)azetidine-3-carboxylate hydrochloride A solution of sodium ethoxide (21% wt. in ethanol, 66.3 mL, 205.0 mmol) in ethanol (70 mL) was added to a solution of 1-benzyl-3,3-bis(chloromethyl)azetidin-2-one (50.4 g, 195.0 mmol) (Preparation 2) in ethanol (210 mL) at 0 C. The mixture was stirred at reflux for 20 hours and then partitioned between water (200 mL) and dichloromethane (300 mL). The aqueous layer was re-extracted with dichloromethane (100 mL) and the combined organic solution was dried over magnesium sulfate and concentrated under reduced pressure to afford an orange oil. A solution of the oil in dichloromethane (100 mL) was treated with a solution of hydrogen chloride in diethyl ether (1M, 250 mL) and the resulting gummy precipitate was triturated with ethyl acetate to afford the title compound as a white solid in 73.2% yield, 43.5 g. 1H NMR (400 MHz, CD3OD) delta: 1.32 (t, 3H), 4.11 (s, 2H), 4.31 (m, 4H), 4.47 (m, 4H), 7.51 (m, 5H); LRMS APCI m/z 268 [MH]+

Reference： [1]Patent: US2008/280877,2008,A1.Location in patent: Page/Page column 31

3
[ 141-52-6 ]
[ 137266-59-2 ]
[ 137266-85-4 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; for 20h;Heating / reflux;	A solution of sodium ethoxide (21 % wt. in ethanol, 66.3 ml_, 205.0 mmol) in ethanol (70 ml_) was added to a solution of the compound described in Preparation 2 (50.4 g, 195.0 mmol) in ethanol (210 ml_) at 0C. The mixture was stirred at reflux for 20 hours and then partitioned between water (200 ml_) and dichloromethane (300 ml_). The aqueous layer was re-extracted with dichloromethane (100 ml_) and the combined organic solution was then dried over magnesium sulfate and concentrated under reduced pressure to afford an orange oil. A solution of the oil in dichloromethane (100 ml_) was treated with a solution of hydrogen chloride in diethyl ether (1 M, 250 ml_) and the resulting gummy precipitate was triturated with ethyl acetate to afford the title compound as a white solid in 73.2% yield, 43.5 g.1H NMR (400 MHz, CD3OD) delta: 1.32 (t, 3H), 4.11 (s, 2H), 4.31 (m, 4H), 4.47 (m, 4H), 7.51 (m, 5H); LRMS APCI m/z 268 [MH]+

Reference： [1]Tetrahedron Letters,1991,vol. 32,p. 4795 - 4798
[2]Patent: WO2009/63365,2009,A1.Location in patent: Page/Page column 55

4
[ 115-77-5 ]
[ 137266-85-4 ]

Reference： [1]Tetrahedron Letters,1991,vol. 32,p. 4795 - 4798

5
[ 137266-85-4 ]
[ 26096-30-0 ]