[ CAS No. 95924-34-8 ] {[proInfo.proName]}

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Quality Control of [ 95924-34-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 95924-34-8 ]

SDS Specification

Alternatived Products of [ 95924-34-8 ]

Product Details of [ 95924-34-8 ]

CAS No. :	95924-34-8	MDL No. :	MFCD14635870
Formula :	C₇H₁₀O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JALDGRUZXZRJGJ-UHFFFAOYSA-N
M.W :	126.15	Pubchem ID :	15186997
Synonyms :

Safety of [ 95924-34-8 ]

Signal Word:	Danger	Class:	3
Precautionary Statements:	P210-P233-P240-P241-P242-P243-P280-P303+P361+P353-P370+P378-P403+P235-P501	UN#:	1993
Hazard Statements:	H225	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 95924-34-8 ]

* 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 [ 95924-34-8 ]

[ 95924-34-8 ] Synthesis Path-Downstream 1~79

1
[ 67-56-1 ]
[ 56663-76-4 ]
[ 95924-34-8 ]

Reference： [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 1831 - 1836

2
[ 95924-34-8 ]
[ 164411-52-3 ]
[ 254990-24-4 ]

Reference： [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 1831 - 1836

3
[ 186581-53-3 ]
[ 56663-76-4 ]
[ 95924-34-8 ]

Yield	Reaction Conditions	Operation in experiment
	at 0 - 20℃;	To a solution of diazomethane (10 g) in ether (400 mL) was added dropwise <strong>[56663-76-4]2,2-dimethyl-but-3-ynoic acid</strong> (10.5 g, 93.7 mmol) at 0° C. The mixture was warmed to room temperature and stirred overnight. The mixture was distilled under atmospheric pressure to give crude methyl 2,2-dimethylbut-3-ynoate (14 g), which was used directly in the next step. 1H NMR (400 MHz, CDCl3) delta 3.76 (s, 3H), 2.28 (s, 1H), 1.50 (s, 6H).
		Methyl 2,2-dimethylbut-3-ynoateTo a solution of diazomethane (~10 g) in ether (400 mL) was added dropwise <strong>[56663-76-4]2,2-dimethyl-but-3-ynoic acid</strong> (10.5 g, 93.7 mmol) at 0° C.The mixture was warmed to room temperature and stirred overnight.The mixture was distilled under atmospheric pressure to give crude methyl 2,2-dimethylbut-3-ynoate (14 g), which was used directly in the next step. 1H NMR (400 MHz, CDCl3) delta 3.76 (s, 3H), 2.28 (s, 1H), 1.50 (s, 6H).
	In diethyl ether; at 0 - 20℃;	To a solution of diazomethane (?0.10 g) in ether (400 mL) was added dropwise <strong>[56663-76-4]2,2-dimethyl-but-3-ynoic acid</strong> (10.5 g, 93.7 mmol) at 0° C. The mixture was warmed to room temperature and stirred overnight. The mixture was distilled under atmospheric pressure to give crude methyl 2,2-dimethylbut-3-ynoate (14 g), which was used directly in the next step. 1H NMR (400 MHz, CDCl3) delta 3.76 (s, 3H), 2.28 (s, 1H), 1.50 (s, 6H).

Reference： [1]Journal of the American Chemical Society,1997,vol. 119,p. 3802 - 3806
[2]Patent: US2007/244159,2007,A1 .Location in patent: Page/Page column 130
[3]Patent: US2011/98311,2011,A1
[4]Patent: US2015/231142,2015,A1 .Location in patent: Paragraph 1712

4
[ 117068-71-0 ]
[ 95924-34-8 ]
[ 188990-86-5 ]

Reference： [1]Journal of the American Chemical Society,1997,vol. 119,p. 3802 - 3806

5
[ 95924-34-8 ]
[ 557757-32-1 ]
[ 557757-33-2 ]

Reference： [1]Tetrahedron Letters,2003,vol. 44,p. 3281 - 3284

6
[ 597-04-6 ]
[ 95924-34-8 ]

Reference： [1]Journal of the American Chemical Society,1997,vol. 119,p. 3802 - 3806

7
[ 56663-75-3 ]
[ 95924-34-8 ]

Reference： [1]Journal of the American Chemical Society,1997,vol. 119,p. 3802 - 3806
[2]Patent: US2011/98311,2011,A1
[3]Patent: US2015/231142,2015,A1

8
[ 95924-34-8 ]
2,2-Dimethyl-4-(6-oxo-1,6-dihydro-pyridin-2-yl)-but-3-ynoic acid [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1997,vol. 119,p. 3802 - 3806

9
[ 95924-34-8 ]
[ 188990-87-6 ]

Reference： [1]Journal of the American Chemical Society,1997,vol. 119,p. 3802 - 3806

10
[ 97987-62-7 ]
[ 95924-34-8 ]

Reference： [1]Journal of the American Chemical Society,1997,vol. 119,p. 3802 - 3806

11
[ 95924-34-8 ]
(E)-9-(1-naphthalenyl)-2,2,8-trimethyl-5-nonen-3-yn-1-ol [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 1831 - 1836

12
[ 95924-34-8 ]
(E)-9-(1-naphthalenyl)-2,2,8-trimethyl-5-nonen-3-ynoic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 1831 - 1836

13
[ 95924-34-8 ]
(E)-2,2,8-Trimethyl-9-naphthalen-1-yl-non-5-en-3-ynoic acid methylamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 1831 - 1836

14
[ 42016-93-3 ]
[ 95924-34-8 ]
[ 871476-68-5 ]

Yield	Reaction Conditions	Operation in experiment
86%		EXAMPLE 4; (ENTRY 4067); a) Compound 4.3; To a solution of aniline 4.1 (706.2 mg, 2.78 mmol) in THF (27 mL) was added cuprous iodide (55.8 mg, 0.29 mmol), Et2NH (2.37 mL, 22.9 mmol) and compound 4.2 (370 mg, 2.93 mmol). The mixture was degassed for 15 min by bubbling argon through the solution. Pd (PPh3)4 mg, 0.29 mmol) was added and the reaction mixture was heated at reflux until total disappearance of the starting material as indicated by TLC. The black solution was cooled to room temperature,, silica gel was added and all volatiles were removed under reduced pressure to give a dry powder which was applied at the top of a column. The crude compound was purified by flash chromatography (hexane/EtOAc, 75/25) to afford compound 4.3 (600 mg, 86% yield) as a brown oil.

Reference： [1]Patent: WO2005/118575,2005,A1 .Location in patent: Page/Page column 84-85

15
[ 2499-77-6 ]
[ 95924-34-8 ]
C₁₉H₁₇NO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94.9%	With triethylamine;bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; at 29℃;	Intermediate (A):; Under nitrogen 7.9g 2-Nitro-4'iodo-biphenyl are suspended in 50 ml triethylamine and46 mg CuI and 170 mg PdCl2(Ph3P)2 (Ph is C6H5) are added sequentially. 3.7 g Methyl2,2 -dimethyl-but-3-ynoate is added dropwise while the temperature rose slowly to 290C. The mixture is stirred overnight and the crude reaction mixture is pufied by chromatography with silica gel (eluent: hexane:ethyl acetate 4:1). 7.5 g intermediate (A) were obtained (94.9 % of theory, m.p. 83.5-84.5C).

Reference： [1]Patent: WO2007/65661,2007,A1 .Location in patent: Page/Page column 29

16
[ 13296-94-1 ]
[ 95924-34-8 ]
[ 952665-08-6 ]

Yield	Reaction Conditions	Operation in experiment
9%	With triethylamine;copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); In water; toluene; at 70℃; for 24.0h;	To a deoxygenated solution of compound 2-bromo-4-nitroaniline (9.43 g, 43.7 mmol), <strong>[95924-34-8]methyl 2,2-dimethylbut-3-ynoate</strong> (5.00 g, 39.7 mmol), CuI (754 mg, 3.97 mmol) and triethylamine (8.03 g, 79.4 mmol) in toluene/H2O (100/30 mL) was added Pd(PPh3)4 (6.17 g, 3.97 mmol) under N2. The mixture was heated at 70 C. and stirred for 24 h. After cooling, the solid was filtered off and washed with EtOAc (50 mL×3). The organic layer was separated and the aqueous phase washed with EtOAc (50 mL×3). The combined organic layers were dried and evaporated under reduced pressure to give a residue, which was purified by column chromatography on silica gel (petroleum ether/ethyl acetate=10/1) to obtain methyl 4-(2-amino-5-nitrophenyl)-2,2-dimethylbut-3-ynoate (900 mg, 9%). 1H NMR (400 MHz, CDCl3) delta 8.17 (d, J=2.8 Hz, 1H), 8.01 (dd, J=2.8, 9.2 Hz, 1H), 6.65 (d, J=9.2 Hz, 1H), 5.10 (brs, 2H), 3.80 (s, 3H), 1.60 (s, 6H).
9%	With CuI; triethylamine;Pd(PPh3)4; In water; toluene;	Methyl 4-(2-amino-5-nitrophenyl)-2,2-dimethylbut-3-ynoate To a deoxygenated solution of compound 2-bromo-4-nitroaniline (9.43 g, 43.7 mmol), <strong>[95924-34-8]methyl 2,2-dimethylbut-3-ynoate</strong> (5.00 g, 39.7 mmol), CuI (754 mg, 3.97 mmol) and triethylamine (8.03 g, 79.4 mmol) in toluene/H2O (100/30 mL) was added Pd(PPh3)4 (6.17 g, 3.97 mmol) under N2. The mixture was heated at 70 C. and stirred for 24 h. After cooling, the solid was filtered off and washed with EtOAc (50 mL3). The organic layer was separated and the aqueous phase was washed with EtOAc (50 mL3). The combined organic layers were dried and evaporated under reduced pressure to give a residue, which was purified by column chromatography on silica gel (petroleum ether/ethyl acetate=10/1) to obtain methyl 4-(2-amino-5-nitrophenyl)-2,2-dimethylbut-3-ynoate (900 mg, 9%). 1H NMR (400 MHz, CDCl3) delta 8.17 (d, J=2.8 Hz, 1H), 8.01 (dd, J=2.8, 9.2 Hz, 1H), 6.65 (d, J=9.2 Hz, 1H), 5.10 (brs, 2H), 3.80 (s, 3H), 1.60 (s, 6H).
9%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine; In water; toluene; at 70℃; for 24.0h;Inert atmosphere;	To a deoxygenated solution of compound 2-bromo-4-nitroaniline (9.43 g, 43.7 mmol), <strong>[95924-34-8]methyl 2,2-dimethylbut-3-ynoate</strong> (5.00 g, 39.7 mmol), CuI (754 mg, 3.97 mmol) and triethylamine (8.03 g, 79.4 mmol) in toluene/H2O (100/30 mL) was added Pd(PPh3)4 (6.17 g, 3.97 mmol) under N2. The mixture was heated at 70 C. and stirred for 24 h. After cooling, the solid was filtered off and washed with EtOAc (50 mL3). The organic layer was separated and the aqueous phase was washed with EtOAc (50 mL3). The combined organic layers were dried and evaporated under reduced pressure to give a residue, which was purified by column chromatography on silica gel (petroleum ether/ethyl acetate=10/1) to obtain methyl 4-(2-amino-5-nitrophenyl)-2,2-dimethylbut-3-ynoate (900 mg, 9%). 1H NMR (400 MHz, CDCl3) delta 8.17 (d, J=2.8 Hz, 1H), 8.01 (dd, J=2.8, 9.2 Hz, 1H), 6.65 (d, J=9.2 Hz, 1H), 5.10 (brs, 2H), 3.80 (s, 3H), 1.60 (s, 6H).

Reference： [1]Patent: US2007/244159,2007,A1 .Location in patent: Page/Page column 130
[2]Patent: US2011/98311,2011,A1
[3]Patent: US2015/231142,2015,A1 .Location in patent: Paragraph 1713

17
[ 38923-57-8 ]
[ 95924-34-8 ]

Reference： [1]Patent: US2011/98311,2011,A1
[2]Patent: WO2013/185103,2013,A1
[3]Patent: US2015/231142,2015,A1
[4]Patent: US2017/190737,2017,A1

18
[ 95924-34-8 ]
[ 952665-10-0 ]

Reference： [1]Patent: US2011/98311,2011,A1
[2]Patent: US2015/231142,2015,A1

19
[ 95924-34-8 ]
[ 174274-84-1 ]

Reference： [1]Patent: US2011/98311,2011,A1
[2]Patent: US2015/231142,2015,A1

20
[ 95924-34-8 ]
[ 952665-09-7 ]

Reference： [1]Patent: US2011/98311,2011,A1
[2]Patent: US2015/231142,2015,A1

21
[ 56663-74-2 ]
[ 95924-34-8 ]

Reference： [1]Patent: US2011/98311,2011,A1
[2]Patent: US2015/231142,2015,A1

22
[ 143225-17-6 ]
[ 95924-34-8 ]

Yield	Reaction Conditions	Operation in experiment
97%	With pyridine; at 70 - 90℃; for 90.5h;	A solution of 17a (6.2 g, 22 mmol) in anhydrous pyridine (1 1 mL, 140 mmol) was heated to 70C. After 18.5 h, the temperature was increased to 90C. After stirring for a total of 72 h, the reaction mixture was partitioned between a stirred mixture of diethyl ether (100 mL) and 3 M aqueous hydrochloric acid (100 mL). The phases were separated, and the organic layer was washed with saturated aqueous sodium bicarbonate (75 mL), dried over magnesium sulfate, filtered, and concentrated to afford the title compound (2.7 g, 97%) as a slightly brown liquid that was used without further purification.
	With pyridine; at 70 - 90℃; for 72.0h;	A solution of 17a (6.2 g, 22 mmol) in anhydrous pyridine (11 mL, 140 mmol) was heated to 70 C. After 18.5 h, the temperature was increased to 90 C. After stirring for a total of 72 h, the reaction mixture was partitioned between a stirred mixture of diethyl ether (100 mL) and 3 M aqueous hydrochloric acid (100 mL). The phases were separated, and the organic layer was washed with saturated aqueous sodium bicarbonate (75 mL), dried over magnesium sulfate, filtered, and concentrated to afford the title compound (2.7 g, 97%) as a slightly brown liquid that was used without further purification.

Reference： [1]Patent: WO2013/185103,2013,A1 .Location in patent: Page/Page column 101
[2]Patent: US2017/190737,2017,A1 .Location in patent: Paragraph 0295

23
[ 95924-34-8 ]
[ 73183-34-3 ]
C₁₃H₂₃BO₄ [ No CAS ]