[ CAS No. 74530-56-6 ]

Name: 74530-56-6|tert-Butyl-4-chloro-3-oxobutanoate|95%
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Quality Control of [ 74530-56-6 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 74530-56-6 ]

CAS No. :	74530-56-6	MDL No. :	MFCD00052188
Formula :	C₈H₁₃ClO₃	Boiling Point :	230.5°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	192.64 g/mol	Pubchem ID :	-
Synonyms :

Safety of [ 74530-56-6 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P501-P260-P270-P264-P280-P303+P361+P353-P301+P330+P331-P363-P301+P312+P330-P304+P340+P310-P305+P351+P338+P310-P405	UN#:	3265
Hazard Statements:	H302-H314	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 74530-56-6 ]

* 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 [ 74530-56-6 ]

[ 74530-56-6 ] Synthesis Path-Downstream 1~29

1
[ 74530-56-6 ]
[ 100-51-6 ]
[ 95967-46-7 ]

Reference： [1]Tetrahedron,1984,vol. 40,p. 3667 - 3676

2
[ 674-82-8 ]
[ 75-65-0 ]
[ 74530-56-6 ]
tert-butyl 4-chloro-3-hydroxybutanoate [ No CAS ]

Reference： [1]Tetrahedron Asymmetry,1999,vol. 10,p. 1401 - 1412

3
[ 74530-56-6 ]
(+/-)-tert-butyl 3,4-epoxybutanoate [ No CAS ]
tert-butyl 4-chloro-3-hydroxybutanoate [ No CAS ]

Reference： [1]Tetrahedron Asymmetry,1999,vol. 10,p. 1401 - 1412
[2]Tetrahedron Asymmetry,1999,vol. 10,p. 1401 - 1412

4
[ 74530-56-6 ]
tert-butyl (R)-(+)-4-chloro-3-hydroxybutanoate [ No CAS ]

Reference： [1]Tetrahedron Asymmetry,1999,vol. 10,p. 1401 - 1412

5
[ 74530-56-6 ]
tert-butyl (S)-(-)-4-chloro-3-propanoyloxybutanoate [ No CAS ]

Reference： [1]Tetrahedron Asymmetry,1999,vol. 10,p. 1401 - 1412

6
[ 74530-56-6 ]
[ 87064-89-9 ]

Reference： [1]Tetrahedron,1984,vol. 40,p. 3667 - 3676

7
[ 74530-56-6 ]
[ 95967-47-8 ]

Reference： [1]Tetrahedron,1984,vol. 40,p. 3667 - 3676

8
[ 74530-56-6 ]
[ 95967-28-5 ]

Reference： [1]Tetrahedron,1984,vol. 40,p. 3667 - 3676

9
[ 74530-56-6 ]
[ 95991-81-4 ]

Reference： [1]Tetrahedron,1984,vol. 40,p. 3667 - 3676
[2]Tetrahedron,1984,vol. 40,p. 3667 - 3676

10
[ 74530-56-6 ]
[ 95967-30-9 ]

Reference： [1]Tetrahedron,1984,vol. 40,p. 3667 - 3676
[2]Tetrahedron,1984,vol. 40,p. 3667 - 3676

11
[ 74530-56-6 ]
[ 95967-31-0 ]

Reference： [1]Tetrahedron,1984,vol. 40,p. 3667 - 3676
[2]Tetrahedron,1984,vol. 40,p. 3667 - 3676

12
[ 74530-56-6 ]
[ 95967-29-6 ]

Reference： [1]Tetrahedron,1984,vol. 40,p. 3667 - 3676
[2]Tetrahedron,1984,vol. 40,p. 3667 - 3676

13
[ 74530-56-6 ]
tert-Butyl 4-chloro-3-hydroxybutyrate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen;bis[(1-isopropyl-4-methylbenzene)dichloro ruthenium]; (+)-Fluoxphos; In ethanol; at 80℃; under 3000.3 Torr; for 4.0h;	In a 150 mL autoclave under argon atmosphere [Ru2Cl4(cym)2] (7.7 mg, 0.013 mmol), (+)-Fluoxphos (17.9 mg, 0.026 mmol) and tert-butyl 4-chloro-3-oxobutyrate (assay 96.9% by GC, 1.0 g, 5.2 mmol) is dissolved in degassed ethanol (30 mL). After flushing the autoclave with argon hydrogenation is carried out during 4 hours at 80 C and at 4 bar hydrogen pressure. After cooling to room temperature the reaction solution is directly analyzed by GC for conversion (column: HP-101 25 m / 0.2 mm). Analysis for enantiomeric excess is performed by 1H-NMR using europium(III) tris[3-(trifluoromethyl-hydroxymethylene)-(+)-camphorate] as shift reagent and CDCl3 as solvent. Conversion is >99%. Yield is approx. 67% at an ee of one enantiomer of 93.2%.

Reference： [1]Patent: EP1528053,2005,A1 .Location in patent: Page/Page column 6

14
[ 110-89-4 ]
[ 74530-56-6 ]
[ 75-07-0 ]
tert.-butyl 4-chloro-2-ethylidene-3-oxobutyrate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 9 Tert.-butyl 4-chloro-2-ethylidene-3-oxobutyrate STR32 1.5 ml of piperidine are added dropwise to a stirred mixture of 212 g (1.1 mol) of tert.-butyl 4-chloro-3-oxobutyrate and 97 g (2.2 mol) of acetaldehyde at -20 C. under nitrogen.

Reference： [1]Patent: US4943568,1990,A

15
silica gel (toluene) [ No CAS ]
[ 74530-56-6 ]
[ 100-53-8 ]
tert-Butyl 4-benzylthioacetoacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; water;	EXAMPLE 27 STR60 tert.-Butyl 4-benzylthioacetoacetate 7.04 ml (60 mmols) of benzylmercaptan were slowly added dropwise to a suspension of 1.8 g (60 mmols) of sodium hydride (80% in parafin oil) in 50 ml of anhydrous tetrahydrofuran at room temperature. Thereafter, the mixture was subsequently stirred for 15 minutes and then cooled to 0 C. A solution of 10.57 g (55 mmols) of tert.-butyl 4-chloroacetoacetate in 20 ml of tetrahydrofuran was added at this temperature in the course of 1 hour. The ice-bath was removed and the mixture was stirred at room temperature for a further hour and neutralized by addition of a few drops of 10% strength HCl. The solvent was evaporated off in vacuo, ether and water were added to the residue, the mixture was extracted several times with ether and the extracts were washed with water and dried over MgSO4. Evaporation of the ether in vacuo gave an oil, which was purified by chromatography on 800 g of silica gel (toluene). 12.74 g (83%) of the title compound were obtained in the form of a colorless oil. RF: 0.13 (toluene). IR (CHCl3) 1740-1710 cm-1 (C=0, β-ketoester). 1 H-NMR (250 MHz, CDCl3) δ 1.49 (s, 9H, C(CH3)3), 3.22 (s. 2H, CH2), 3.52 (s. 2H, CH2), 3.68 (s. 2H, CH2) and 7.33 (s. 5H, Ph).
	In tetrahydrofuran; paraffin;	PREPARATION EXAMPLE 7 STR59 tert.-Butyl 4-benzylthioacetoacetate 7.04 ml (60 mmol) of benzylmercaptan were slowly added dropwise to a suspension of 1.8 g (60 mmol) of sodium hydride (80% in liquid paraffin) in 50 ml of anhydrous THF at room temperature. The mixture was then stirred for 15 min and subsequently cooled to 0 C. At this temperature, a solution of 10.57 g (55 mmol) of tert.-butyl 4-chloroacetoacetate in 23 ml of THF was added within 1 h. The icebath was removed, and the mixture was stirred for a further 1 h at room temperature and then neutralized by addition of a few drops of 10% strength HCl. The solvent was evaporated in vacuo, ether was added several times, and the extracts were washed with water and dried over MgSO4. Evaporation of the ether in vacuo produced an oil which was purified by chromatography on 800 g of silica gel (toluene). 12.74 g (83%) of the title compound were obtained in the form of a colorless oil, Rf: 0.13 (toluene). IR (CHCl3) 1740-1710 cm-1 (C=O, β-keto ester). 1 H-NMR (200 MHz, CDCl3) δ 1.49 (s, 9H, C(CH3)3), 3.22 (s, 2H, CH2), 3.52 (s, 2H, CH2), 3.68 (s, 2H, CH2), 7.33 (s, 5H, Ph).

Reference： [1]Patent: US4616084,1986,A
[2]Patent: US4841042,1989,A

16
[ 74530-56-6 ]
[ 10387-40-3 ]
tert.-butyl 4-acetylthioacetoacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethyl acetate; acetonitrile; sodium chloride;	EXAMPLE 28 STR61 tert.-Butyl 4-acetylthioacetoacetate 2.40 g (21.0 mmols) of dry potassium thioacetate were added to a solution, cooled to 0 C., of 3.85 g (20.0 mmols) of tert.-butyl 4-chloroacetoacetate in 40 ml of anhydrous acetonitrile and the mixture was stirred at this temperature for 30 minutes. Thereafter, the mixture was poured into a mixture of NaCl solution and ethyl acetate, the organic phase was separated off and extracted with 2*30 ml of ethyl acetate and the extracts were washed with water and dried over MgSO4. After the solvent had been evaporated off in vacuo and the residue had been chromatographed on 60 g of silica gel (toluene:ethyl acetate 95:5), 3.87 g (83%) of the title compound were obtained as a colorless oil, RF:0.2 (toluene:ethyl acetate 95:5). IR (CHCl3) 1740-1710 cm-1 (C=0). 1 H-NMR (250 MHz, CDCl3) 1.50 (s. 9H, C(CH3)3), 2.42 (s. 3H, CH3 CO3), 3.53 (s. 2H, CH2) and 3.90 (s, 2H, CH2).
	In ethyl acetate; acetonitrile; sodium chloride;	PREPARATION EXAMPLE 6 STR58 tert.-Butyl 4-acetylthioacetoacetate 2.40 g (21.0 mmol) of dry potassium thioacetate were added to a solution, which had been cooled to 0 C., of 3.85 g (20.0 mmol) of tert.-butyl 4-chloroacetoacetate in 40 ml of anhydrous acetonitrile, and the mixture was stirred at this temperature for 30 min. It was then poured into a mixture of NaCl solution and ethyl acetate, the organic phase was separated off, extraction with 2*30 ml of ethyl acetate was carried out, and the extract was washed with water and dried over MgSO4. After evaporation of the solvent in vacuo and chromatography of the residue on 60 g of silica gel (toluene:ethyl acetate 95:5), 3.87 g (83%) of the title compound were obtained as a colorless oil, Rf: 0.24 (toluene:ethyl acetate 95:5). IR (CHCl3) 1740-1710 cm-1 (C=O). 1 H-NMR (250 MHz, CDCl3) δ 1.50 (s, 9H, C(CH3)3), 2.42 (s, 3H, CH3 CO), 3.53 (s, 2H, CH2), 3.90 (s, 2H, CH2).

Reference： [1]Patent: US4616084,1986,A
[2]Patent: US4841042,1989,A

17
[ 74530-56-6 ]
[ 95967-46-7 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; benzyl alcohol; In tetrahydrofuran;	EXAMPLE 1 STR34 tert.-Butyl 4-benzyloxyacetoacetate A solution of 64.9 g=62.1 ml (0.6 mol) of benzyl alcohol in 50 ml of tetrahydrofuran was added dropwise to an ice-cooled suspension of 18.0 g (0.6 mol) of sodium hydride (80% strength in parafin oil) in 150 ml of anhydrous tetrahydrofuran in the course of 1 hour with ice-cooling. Thereafter, the mixture was subsequently stirred at room temperature for 0.5 hour. A solution of 57.8 g (0.3 mol) of tert.-butyl 4-chloroacetoacetate in 50 ml of tetra-hydrofuran was added dropwise at 0 C. in the course of 1 hour. The ice-bath was removed and the reaction mixture was stirred at room temperature for a further hour and neutralized by careful addition of 0.5N HCl, with cooling (pH control). The mixture was extracted several times with ether and the combined ether extracts were washed with water and dried over MgSO4. Evaporation of the ether in vacuo gave an oil, which was purified by chromatography on 1.7 kg of silica gel (toluene:ethyl acetate 95:5). 41.7 g (53%) of tert.-butyl 4-benzyloxyacetoacetate were obtained, RF: 0.47 (toluene:ethyl acetate 9:1). 1 H-NMR (200 MHz, CDCl3) δ 1.50 (s, 9H, C(CH3)3), 3.48 (s, 2H, CH2), 4.18 (s, 2H, CH2), 4.63 (s, 2H, CH2) and 7.40 (s, 5H, Ph). IR (CHCl3) 1740-1710 (c=0, β-keto ester) and 1656 cm-1 (C=C, enol form). C15 H20 O4 (264.3) calculated: C 68.2, H 7.6; found: C 68.2, H 7.6.

Reference： [1]Patent: US4616084,1986,A

18
silica gel (toluene) [ No CAS ]
[ 74530-56-6 ]
[ 105940-01-0 ]

Yield	Reaction Conditions	Operation in experiment
		PREPARATION EXAMPLE 8 STR60 tert.-Butyl 4-chloro-2-diazo-3-oxobutanoate As described for Preparation Example 1, 2.67 g (84%) of the title compound were obtained as crystals, Rf: 0.29 (toluene), melting point: 40-41 C., from 2.79 g (14.5 mmol) of tert.-butyl 4-chloroacetoacetate and filtration of the crude product on 30 g of silica gel (toluene). IR (CHCl3): 2140 (N2), 1708 (C=O), 1662 cm-1. 1 H-NMR (300 MHz, CDCl3) δ 1.54 (s, 9H, C(CH3)3), 4.60 (s, 2H, CH2).

Reference： [1]Patent: US4841042,1989,A

19
[ 74530-56-6 ]
[ 2353-44-8 ]
3-(2,4-dioxopyrrolidin-1-yl)piperidine-2,6-dione [ No CAS ]