17642-18-1|Methyl 2-bromobut-2-enoate| Ambeed

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Structure of 17642-18-1

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Quality Control of [ 17642-18-1 ] Purity: 95% SDS Specification

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Product Details of [ 17642-18-1 ]

CAS No. :	17642-18-1
Formula :	C₅H₇BrO₂
M.W :	179.01
SMILES Code :	C/C=C(Br)/C(OC)=O
MDL No. :	MFCD00042891
InChI Key :	DMKWWKUPZZAUQL-ARJAWSKDSA-N
Pubchem ID :	6372571

Safety of [ 17642-18-1 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H302-H314
Precautionary Statements:	P260-P264-P270-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P405-P501
Class:	8
UN#:	3265
Packing Group:	Ⅱ

Application In Synthesis of [ 17642-18-1 ]

* 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.

Downstream synthetic route of [ 17642-18-1 ]

[ 17642-18-1 ] Synthesis Path-Downstream 1~35

1
[ 17642-18-1 ]
[ 98024-96-5 ]

References: [1]Journal of the Chemical Society,1960,p. 1262 - 1268.

2
[ 17642-18-1 ]
[ 108-95-2 ]
[ 92016-89-2 ]

References: [1]Journal of the Chemical Society,1963,p. 4210 - 4218.
[2]Organic Letters,2017,vol. 19,p. 2869 - 2872.

3
[ 930-68-7 ]
[ 17642-18-1 ]
[ 61111-41-9 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1980,p. 963 - 977.

4
[ 78-59-1 ]
[ 17642-18-1 ]
[ 61111-44-2 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1980,p. 963 - 977.

5
[ 930-30-3 ]
[ 17642-18-1 ]
endo-6-(Carbomethyloxy)-6-vinylbicyclo<3.1.0>hexan-2-one [ No CAS ]
exo-6-(Carbomethyloxy)-6-vinylbicyclo<3.1.0>hexan-2-one [ No CAS ]

References: [1]Journal of the American Chemical Society,1989,vol. 111,p. 6691 - 6707.

6
[ 1193-18-6 ]
[ 17642-18-1 ]
[ 61111-42-0 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1980,p. 963 - 977.

7
[ 74-93-1 ]
[ 17642-18-1 ]
methyl 2-(ethylthio)but-2-enoate [ No CAS ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1986,p. 629 - 632.

8
[ 17642-18-1 ]
(-)-Carvone [ No CAS ]
[ 61111-43-1 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1980,p. 963 - 977.

9
[ 17642-18-1 ]
[ 137207-24-0 ]
[ 137207-25-1 ]

References: [1]Tetrahedron Letters,1991,vol. 32,p. 4695 - 4698.
[2]Tetrahedron Letters,1991,vol. 32,p. 4695 - 4698.
[3]Tetrahedron Letters,1991,vol. 32,p. 4695 - 4698.

10
[ 17642-18-1 ]
methyl (Z)-2,4-dibromobut-2-enoate [ No CAS ]

References: [1]Journal of Chemical Research, Miniprint,1980,p. 4658 - 4667.

11
[ 17642-18-1 ]
C₆H₁₃C₃H₄B(OH)2 [ No CAS ]
(E)-2-((1S,2S)-2-Hexyl-cyclopropyl)-but-2-enoic acid methyl ester [ No CAS ]

References: [1]Synlett,1998,p. 198 - 200.

13
[ 17642-18-1 ]
[ 107-11-9 ]
(2S,3S)-1-Allyl-3-methyl-aziridine-2-carboxylic acid methyl ester [ No CAS ]
(2S,3R)-1-Allyl-3-methyl-aziridine-2-carboxylic acid methyl ester [ No CAS ]

References: [1]Tetrahedron Letters,2002,vol. 43,p. 4329 - 4331.

14
[ 17642-18-1 ]
[ 100-46-9 ]
(2S,3S)-1-Benzyl-3-methyl-aziridine-2-carboxylic acid methyl ester [ No CAS ]
(±)-methyl 1-benzyl-3-methylaziridine-2-carboxylate [ No CAS ]

References: [1]Tetrahedron Letters,2002,vol. 43,p. 4329 - 4331.

15
[ 17642-18-1 ]
[ 344406-33-3 ]

References: [1]Journal of Chemical Research, Miniprint,1980,p. 4658 - 4667.

16
[ 17642-18-1 ]
[ 74285-20-4 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1980,p. 963 - 977.

17
[ 17642-18-1 ]
[ 98139-94-7 ]

References: [1]Journal of the Chemical Society,1960,p. 1262 - 1268.

18
[ 17642-18-1 ]
[ 2296-23-3 ]
methyl 4-[4-cyano-2-iodo-phenoxy]-but-2-enoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; NaH; In tetrahydrofuran; mineral oil;	Methyl 4-[4-Cyano-2-Iodo-Phenoxy]-But-2-enoate To a cooled (0 C.) suspension of NaH (1.5 g of 60% suspension in mineral oil, 38 mmol) in THF (80 mL) was added a solution comprised of <strong>[2296-23-3]4-hydroxy-3-iodo-benzonitrile</strong> (8.4 g, 34 mmol) (reference example 12), methyl bromo-crotonate (6.65 mL tech. grade, approx. 51 mmol) and DMPU (10 mL) in THF (20 mL). On complete addition, the cold bath was removed and replaced with an oil bath. The reaction mixture was heated to 55 C. and stirred at this temperature for 4.5 hr, cooled to room temperature and acidified with 2M aqueous HCl. The mixture was then diluted with ethyl acetate, washed sequentially with water and brine, dried over MgSO4 and concentrated. The residue was triturated with hexane several times, leaving 8.6 g of the title compound as a solid. 1H NMR (CDCl3) d 3.78 (s, 3H), 4.80 (dd, J=4, 1 Hz, 1H), 6.35 (dt, J=16, 1 Hz, 1H), 6.79 (d, J=8 Hz, 1H), 7.05 (dt, J=16, 4 Hz, 1H), 7.60 (dd, J=8, 1 Hz, 1H), 8.06 (d, J=1 Hz, 1H). MS (EI) m/z 343 (M)+.

References: [1]Patent: US2002/193410,2002,A1 .

19
[ 17642-18-1 ]
[ 620-24-6 ]
[ 1139688-74-6 ]

References: [1]Organic Process Research and Development,2009,vol. 13,p. 525 - 534.

20
methyl crotonate [ No CAS ]
[ 17642-18-1 ]

References: [1]Organic Process Research and Development,2009,vol. 13,p. 525 - 534.
[2]Patent: WO2021/160649,2021,A1 .

21
[ 908094-01-9 ]
[ 17642-18-1 ]
4-methyl-1⁽²⁾<i>H</i>-pyrazole-3-carboxylic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Intermediate 6Methyl 4-methyl-1 H-pyrazole-5-carboxylate To a solution of diazomethane (nominally 0.68g - generated from DIAZALD (5g) in diethyl ether (45ml)) at -78 C was added a solution of E/Z methyl-2-bromo-2-butenoate(3.58g) (available from Fluka) in diethyl ether (15ml), dropwise, over 15min. The mixture was maintained at -78C for 1 h then allowed to warm to 20C with stirring overnight. Acetic acid (1 ml) was added to destroy excess diazomethane and the mixture evaporated under reduced pressure. The residue was co-evaporated with toluene. Purification of the residue by column chromatography on silica gel eluting with ethyl acetate:cyclohexane (1 :1 ) gave the title compound (1.12g) as an orange solid. <n="92"/>TLC Rf 0.33 (ethyl acetate:cyclohexane 1 :1 )

References: [1]Patent: WO2009/147188,2009,A1 .Location in patent: Page/Page column 89-90.

22
[ 17642-18-1 ]
[ 10292-61-2 ]
[ 1574541-77-7 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In acetonitrile; at 20℃; for 16h;	Step-I: Methyl 2-(4-cyclopropylphenoxy)but-2-enoate (intermediate Bl-1) [00221] To a stirring solution of 4-cyclopropylphenol (6.81 g, 50.8 mmol) in acetonitrile (150 mL) at 0 C, K2C03 (21.06 g, 152 mmol) was added. Methyl 2-bromo- 2-butenoate (10 g, 55.9 mmol) was subsequently added dropwise. The reaction was stirred for 16 h at room temperature. The reaction mixture was filtered through Celite, washed with acetonitrile and concentrated in vacuo to afford the crude product, methyl 2-(4-cyclopropylphenoxy)but-2-enoate (15 g, 64.6 mmol, -100% yield), as a light- brownish oil. The crude was taken to the next step without further purification. NMR (400 MHz, chloroform-d) δ lH NMR (400 MHz, chloroform-d) δ 7.39 (d, J= 6.75 Hz, 0.5H), 6.93 - 7.04 (m, 2H), 6.75 - 6.85 (m, 2H), 6.68 (d, J= 7.25 Hz, 0.5H), 3.67 - 3.86 (m, 3H), 1.70 - 2.00 (m, 4H), 0.81 - 0.95 (m, 2H), 0.61 (dd, J= 1.50, 5.00 Hz, 2H).

References: [1]Patent: WO2014/39412,2014,A1 .Location in patent: Paragraph 00221.

23
[ 17642-18-1 ]
[ 92-69-3 ]
[ 1574542-10-1 ]