Ethyl 4-chloroacetoacetate supplier

Name
Ethyl 4-chloroacetoacetate
EINECS 211-317-0
CAS No. 638-07-3
Article Data21
CAS DataBase
Density 1.179 g/cm³
Solubility 47.5 g/L (20 ºC) in water
Melting Point -8 °C
Formula C₆H₉ClO₃
Boiling Point 235.5 °C at 760 mmHg
Molecular Weight 164.589
Flash Point 96.7 °C
Transport Information UN 2922 8/PG 2
Appearance Colorless to pale reddish-yellow clear liquid
Safety 26-36-45-61-36/37/39-27
Risk Codes 25-34-51/53-24/25-36
Molecular Structure
Hazard Symbols T, N, C
Synonyms Acetoaceticacid, 4-chloro-, ethyl ester (7CI,8CI);4-Chloro acetoethylacetate;4-Chloro-3-oxobutanoic acid ethyl ester;4-Chloro-3-oxobutyric acid ethylester;4-Chloroacetoacetic acid ethyl ester;Ethyl (chloroacetyl)acetate;Ethyl3-oxo-4-chlorobutanoate;Ethyl 4-chloro-3-oxobutanoate;Ethyl4-chloro-3-oxobutyrate;Ethyl g-chloroacetoacetate;Ethyl w-chloroacetoacetate;g-Chloroacetoacetic acid ethyl ester;
PSA 43.37000
LogP 0.74750

Synthetic route

: 141-97-9
ethyl acetoacetate

: 638-07-3
ethyl (2-chloroaceto)acetate

Conditions

Conditions	Yield
Stage #1: ethyl acetoacetate With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at 0℃; for 1h; Inert atmosphere; Stage #2: With methyl chlorosulfate In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere;	100%

: 141-78-6
ethyl acetate

: 105-39-5
chloroacetic acid ethyl ester

: 638-07-3
ethyl (2-chloroaceto)acetate

Conditions

Conditions	Yield
In ethanol; dimethyl sulfoxide at 128 - 152℃; under 3648.24 - 6840.46 Torr; for 22h; Temperature; Pressure; Inert atmosphere;	98.7%

: 141-78-6
ethyl acetate

: 96-34-4
methyl chloroacetate

: 638-07-3
ethyl (2-chloroaceto)acetate

Conditions

Conditions	Yield
In methanol; N,N-dimethyl-formamide at 110 - 145℃; under 2280.15 - 6080.41 Torr; for 15h; Inert atmosphere;	97.3%

: 674-82-8
4-methyleneoxetan-2-one

: 64-17-5
ethanol

: 638-07-3
ethyl (2-chloroaceto)acetate

Conditions

Conditions	Yield
Stage #1: 4-methyleneoxetan-2-one With chlorine In dichloromethane under 225.023 Torr; Flow reactor; Stage #2: ethanol at 40 - 70℃; under 712.571 Torr; for 4h;	93%
Stage #1: 4-methyleneoxetan-2-one With chlorine; sodium hydroxide; copper dichloride In dichloromethane at -40 - 10℃; Stage #2: ethanol In dichloromethane Temperature;	90%

: 591-78-6
n-hexan-2-one

: 6082-74-2
4,4-dichloro-3-oxobutyric acid ethyl ester

A: 638-07-3
ethyl (2-chloroaceto)acetate

B: (Z)-5-Methyl-3-oxo-non-4-enoic acid ethyl ester

Conditions

Conditions	Yield
With iron pentacarbonyl In benzene at 80℃; Reformatsky-type addition;	A 75 % Chromat. B n/a

...Expand

: 591-78-6
n-hexan-2-one

: 6082-74-2
4,4-dichloro-3-oxobutyric acid ethyl ester

A: 638-07-3
ethyl (2-chloroaceto)acetate

B: 141-97-9
ethyl acetoacetate

Conditions

Conditions	Yield
With iron pentacarbonyl; water; N,N-dimethyl-formamide In benzene at 80℃;	A 40 % Chromat. B 16 % Chromat.

...Expand

: 6082-74-2
4,4-dichloro-3-oxobutyric acid ethyl ester

: 638-07-3
ethyl (2-chloroaceto)acetate

Conditions

Conditions	Yield
With iron pentacarbonyl; water In benzene at 80℃;	65 % Chromat.

: 6082-74-2
4,4-dichloro-3-oxobutyric acid ethyl ester

: 100-52-7
benzaldehyde

A: 638-07-3
ethyl (2-chloroaceto)acetate

B: 1503-99-7
ethyl 3-oxo-5-phenylpent-4-enoate

Conditions

Conditions	Yield
With iron pentacarbonyl In benzene at 80℃; Reformatsky-type addition;	A 70 % Chromat. B n/a

...Expand

: 41295-64-1
4-chloroacetoacetyl chloride

: 64-17-5
ethanol

: 638-07-3
ethyl (2-chloroaceto)acetate

Conditions

Conditions	Yield
Stage #1: 4-chloroacetoacetyl chloride; ethanol Industry scale; Stage #2: With sodium hydroxide In water Product distribution / selectivity;
In dichloromethane	156.3 g

: 150-19-6
O-methylresorcine

: 638-07-3
ethyl (2-chloroaceto)acetate

: 41295-55-0
4-(chloromethyl)-7-methoxy-2H-chromen-2-one

Conditions

Conditions	Yield
With methanesulfonic acid at 20℃;	100%
With silica gel supported zirconyl chloride octahydrate at 90℃; for 0.5h; Pechmann condensation reaction;	96%
With perchloric acid; sulfuric acid at 25℃;	95.2%

: 638-07-3
ethyl (2-chloroaceto)acetate

: 2462-02-4
2-mercaptoacetophenone

: 114250-85-0
3-Oxo-4-(2-oxo-2-phenyl-ethylsulfanyl)-butyric acid ethyl ester

Conditions

Conditions	Yield
With potassium carbonate In tetrahydrofuran	100%

: 638-07-3
ethyl (2-chloroaceto)acetate

: 22179-72-2
4-fluorothiobenzamide

: 78742-98-0
ethyl 2-(2-(4-fluorophenyl)thiazol-4-yl)acetate

Conditions

Conditions	Yield
In ethanol for 4h; Heating;	100%
In ethanol for 5h; Reflux; Inert atmosphere;	89%
In ethanol for 7.5h; Reflux;	89%

: 638-07-3
ethyl (2-chloroaceto)acetate

: 89818-37-1
3-chloro-4-methoxybenzenethiol

: 89818-38-2
ethyl 4-(3'-chloro-4'-methoxyphenylthio)acetoacetate

Conditions

Conditions	Yield
In pyridine; diethyl ether for 2h; Heating;	100%

: 638-07-3
ethyl (2-chloroaceto)acetate

: 10488-69-4, 86728-85-0, 87068-18-6, 90866-33-4
ethyl (S)-4-chloro-3-hydroxybutanoate

Conditions

Conditions	Yield
With formic acid; NAD; sodium formate; formate dehydrogenase In water at 30℃; for 3.5h; pH=6.5;	100%
With Escherichia coli BL21 (fdh, adh)-cells In water for 1h; pH=6.5;	99.3%
With hydrogen; (R)-[RuCl2(BINAP)]n In ethanol at 95 - 105℃; under 67506.8 - 75007.5 Torr; for 0.5 - 8h; Conversion of starting material;	98%

: 638-07-3
ethyl (2-chloroaceto)acetate

: 108-93-0
cyclohexanol

: 126930-22-1
4-(Cyclohexyloxy)acetessigsaeure-ethylester

Conditions

Conditions	Yield
Stage #1: cyclohexanol With sodium hydride In diethyl ether at 20℃; for 1.25h; Stage #2: ethyl (2-chloroaceto)acetate In diethyl ether at 20℃;	100%
With sodium hydride 1.) ether, 2 h, RT; 2.) 20 h, RT; Yield given. Multistep reaction;

: 110-86-1
pyridine

: 638-07-3
ethyl (2-chloroaceto)acetate

: 1-(ethoxycarbonylacetonyl)pyridinium chloride

Conditions

Conditions	Yield
at 20℃; for 24h;	100%

: 108-89-4
picoline

: 638-07-3
ethyl (2-chloroaceto)acetate

: 1-ethoxycarbonylacetonyl-4-methylpyridinium chloride

Conditions

Conditions	Yield
at 20℃; for 24h;	100%

: 591-22-0
3,5-Lutidine

: 638-07-3
ethyl (2-chloroaceto)acetate

: 1-ethoxycarbonylacetonyl-3,5-dimethylpyridinium chloride

Conditions

Conditions	Yield
at 20℃; for 24h;	100%

: 638-07-3
ethyl (2-chloroaceto)acetate

: 6626-15-9
4-Bromoresorcinol

: 223420-33-5
6-bromo-4-(chloromethyl)-7-hydroxy-2H-chromen-2-one

Conditions

Conditions	Yield
In methanesulfonic acid at 25℃; for 2h;	100%
With methanesulfonic acid at 20℃; for 2h; Inert atmosphere; Darkness;	91%
With sulfuric acid Inert atmosphere;	88%

: 638-07-3
ethyl (2-chloroaceto)acetate

: 20017-67-8
3,3-diphenylpropan-1-ol

: 314776-40-4
(3,3-diphenylpropane-1-yl) 4-chloroacetoacetate

Conditions

Conditions	Yield
In toluene at 130℃;	100%
In toluene

: 638-07-3
ethyl (2-chloroaceto)acetate

: 874-42-0
2,4-dichlorobenzaldeyhde

: 915296-79-6
(Z)-ethyl 4-chloro-2-(2,4-dichlorobenzylidene)-3-oxobutanoate

Conditions

Conditions	Yield
With acetic acid; benzylamine In isopropyl alcohol at 20℃; for 96h; Knoevenagel Condensation; Inert atmosphere;	100%
With acetic acid; benzylamine In isopropyl alcohol at 20℃; for 96h;
With acetic acid; benzylamine In isopropyl alcohol at 20℃; for 96h;

: 1072-97-5
5-bromo-2-pyridylamine

: 638-07-3
ethyl (2-chloroaceto)acetate

: 59128-04-0
ethyl 2-(6-bromoimidazo[1,2-a]pyridin-2-yl)acetate

Conditions

Conditions	Yield
In ethanol for 4h; Reflux; Inert atmosphere;	100%
In toluene Reflux;	24%
In toluene at 115℃; for 18h;
In ethanol Heating / reflux;

: 14294-10-1
morpholinothiourea

: 638-07-3
ethyl (2-chloroaceto)acetate

: 329906-01-6
ethyl (2-morpholin-4-yl-1,3-thiazol-4-yl)acetate

Conditions

Conditions	Yield
With triethylamine In ethanol at 80℃; for 3h;	100%
Stage #1: morpholinothiourea; ethyl (2-chloroaceto)acetate In ethanol at 80℃; for 3h; Stage #2: With water; sodium hydrogencarbonate	100%

: 2158-02-3
morpholine-4-carboxylic acid amide

: 638-07-3
ethyl (2-chloroaceto)acetate

: 329906-01-6
ethyl (2-morpholin-4-yl-1,3-thiazol-4-yl)acetate

Conditions

Conditions	Yield
In ethanol at 80℃; for 3h;	100%

: 638-07-3
ethyl (2-chloroaceto)acetate

: 762-04-9
phosphonic acid diethyl ester

: 65043-08-5
ethyl 4-diethoxyphosphoryl-3-oxobutanoate

Conditions

Conditions	Yield
With sodium hydride	100%

: 638-07-3
ethyl (2-chloroaceto)acetate

: 40966-87-8
2-amino-5-chloro-3-hydroxypyridine

: 7-chloro-2-(chloromethyl)-9-hydroxy-4H-pyrido[1,2-a]pyrimidin-4-one

Conditions

Conditions	Yield
With phosphoric acid at 110℃; for 2.5h;	100%

: 638-07-3
ethyl (2-chloroaceto)acetate

: 22325-27-5
4,6-dimethyl-2-meraptopyrimidine

: ethyl 4-[(4,6-dimethylpyrimidin-2-yl)sulfanyl]-3-oxobutanoate

Conditions

Conditions	Yield
With triethylamine at 0℃; for 0.5h; Reagent/catalyst; Temperature;	100%

: 638-07-3
ethyl (2-chloroaceto)acetate

: 10488-69-4, 86728-85-0, 87068-18-6, 90866-33-4
ethyl (L)-4-chloro-3-hydroxybutyrate

Conditions

Conditions	Yield
With D-glucose; β-keto ester reductase L-1; tris hydrochloride; NADPH at 30℃; for 48h; relative reaction rate; other β-keto esters; var. time;	99%
With D-glucose; tris hydrochloride at 30℃; for 48h; β-keto ester reductase L-1, NADPH, GDH;	99%
With D-glucose; YOL151W reductase In aq. phosphate buffer; toluene pH=6.7; Enzymatic reaction;	98.7%

: 108-73-6
3,5-dihydroxyphenol

: 638-07-3
ethyl (2-chloroaceto)acetate

: 809234-33-1
4-chloromethyl-5,7-dihydroxy-chromen-2-one

Conditions

Conditions	Yield
With methanesulfonic acid at 20℃; for 6h;	99%
With silica gel supported zirconyl chloride octahydrate at 90℃; for 0.0833333h; Pechmann condensation reaction;	98%
With yttrium(lll) nitrate hexahydrate at 90℃; for 0.2h; Pechmann Condensation; Green chemistry;	98%

: 638-07-3
ethyl (2-chloroaceto)acetate

: 90-15-3
α-naphthol

: 4-(chloromethyl)-2H-benzo[h]chromen-2-one

Conditions

Conditions	Yield
With silica gel supported zirconyl chloride octahydrate at 90℃; for 0.75h; Pechmann condensation reaction;	99%
With sulfuric acid; silica gel at 80℃; for 1h; Pechmann condensation reaction;	96%
With ammonium cerium(IV) nitrate; silica gel for 0.05h; Pechmann reaction; microwave irradiation;	96%

: 638-07-3
ethyl (2-chloroaceto)acetate

: 15570-12-4
3-methoxybenzenethiol

: 16768-98-2
3-methoxybenzenethiol

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile at 0 - 20℃; for 2h;	99%
With potassium hydroxide In methanol at 20℃; for 6h;
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 20℃; for 2.16667h;

: 504-29-0
2-aminopyridine

: 638-07-3
ethyl (2-chloroaceto)acetate

: 16867-35-9
2-(chloromethyl)-4H-pyrido[1,2-a]pyrimidin-4-one

Conditions

Conditions	Yield
With PPA at 120℃; for 2h;	99%
With polyphosphate at 45 - 125℃; for 2h;	67%
In PPA; (2S)-N-methyl-1-phenylpropan-2-amine hydrate
In PPA; (2S)-N-methyl-1-phenylpropan-2-amine hydrate
Stage #1: 2-aminopyridine; ethyl (2-chloroaceto)acetate at 125℃; for 5h; Stage #2: With sodium hydroxide In water pH=6 - 7; Cooling with ice;

: 638-07-3
ethyl (2-chloroaceto)acetate

: 16867-35-9
2-(chloromethyl)-4H-pyrido[1,2-a]pyrimidin-4-one

Conditions

Conditions	Yield
Stage #1: 2-aminopyridine With PPA at 120℃; Stage #2: ethyl (2-chloroaceto)acetate at 120℃; for 2h;	99%

: 638-07-3
ethyl (2-chloroaceto)acetate

: 496-73-1
4-methyl resorcinol

: 1239755-10-2
4-(chloromethyl)-7-hydroxy-6-methyl-2H-chromen-2-one

Conditions

Conditions	Yield
Stage #1: ethyl (2-chloroaceto)acetate With sulfuric acid at 0℃; Stage #2: 4-methyl resorcinol at 20℃;	99%
With sulfuric acid at 0 - 20℃;	99%
With sulfuric acid at 0 - 20℃; for 24h; Pechmann Condensation;	73%

: 638-07-3
ethyl (2-chloroaceto)acetate

: 109-73-9
N-butylamine

: 5349-24-6
N-butyl-2-chloroacetamide

Conditions

Conditions	Yield
With 4-toluenesulfonyl azide In tetrahydrofuran at 20 - 25℃;	99%

: 638-07-3
ethyl (2-chloroaceto)acetate

: 28144-70-9
anthranilic acid amide

: 3817-05-8
2-(chloromethyl)quinazolin-4(3H)-one

Conditions

Conditions	Yield
With ethanolamine-phosphoric acid functionalized polyacrylonitrile fibers (PANEAPF) In water at 100℃; for 15h; Green chemistry;	99%

: 638-07-3
ethyl (2-chloroaceto)acetate

: 87-66-1
2-hydroxyresorcinol

: 19040-71-2
4-chloromethyl-7,8-dihydroxy<1>benzopyran-2(H)-one

Conditions

Conditions	Yield
zirconium(IV) chloride at 20℃; for 0.0833333h;	98%
With ammonium cerium(IV) nitrate; silica gel for 0.0333333h; Pechmann reaction; microwave irradiation;	96%
With bispyridine cobalt(II) chloride for 0.05h; Pechmann condensation; Microwave irradiation; neat (no solvent);	95%

Ethyl 4-chloroacetoacetate Chemical Properties

Product Name: Ethyl 4-chloroacetoacetate (CAS NO.638-07-3)

Molecular Formula: C₆H₉ClO₃
Molecular Weight: 164.59g/mol
Mol File: 638-07-3.mol
EINECS: 211-317-0
Appearance: Colorless to pale reddish-yellow clear liquid
Melting Point: -8 °C
Boiling point: 235.5 °C at 760 mmHg
Storage Temperature: 2-8°C
Flash Point: 96.7 °C
Density: 1.179 g/cm³
Refractive index: n20/D 1.452(lit.)
Water Solubility: 47.5 g/L (20 ºC)
Index of Refraction: 1.436
Molar Refractivity: 36.49 cm³
Molar Volume: 139.5 cm³
Surface Tension: 34.8 dyne/cm
Enthalpy of Vaporization: 47.23 kJ/mol
Vapour Pressure: 0.0498 mmHg at 25°C
XLogP3-AA: 0.9
H-Bond Donor: 0
H-Bond Acceptor: 3
Structure Descriptors of Ethyl 4-chloroacetoacetate (CAS NO.638-07-3):
IUPAC Name: ethyl 4-chloro-3-oxobutanoate
Canonical SMILES: CCOC(=O)CC(=O)CCl
InChI: InChI=1S/C6H9ClO3/c1-2-10-6(9)3-5(8)4-7/h2-4H2,1H3
InChIKey: OHLRLMWUFVDREV-UHFFFAOYSA-N
Product Categories: Pharmaceutical Intermediates; Halogen compounds; C6 to C7; Carbonyl Compounds; Esters

Ethyl 4-chloroacetoacetate Uses

Ethyl 4-chloroacetoacetate (CAS NO.638-07-3) can be used in medicine and pesticide intermediates.

Ethyl 4-chloroacetoacetate Toxicity Data With Reference

1.		ipr-rat LD50:108 mg/kg		OYYAA2 Oyo Yakuri. Pharmacometrics. 33 (1987),695.
2.		ipr-mus LD50:88 mg/kg		OYYAA2 Oyo Yakuri. Pharmacometrics. 33 (1987),695.

Ethyl 4-chloroacetoacetate Consensus Reports

Reported in EPA TSCA Inventory.

Ethyl 4-chloroacetoacetate Safety Profile

Safety Information of Ethyl 4-chloroacetoacetate (CAS NO.638-07-3):
Hazard Codes: T Toxic ,N Dangerous ,C Corrosive
Risk Statements: 25-34-51/53-24/25-36
R25 :Toxic if swallowed.
R34:Causes burns.
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
R24:Toxic in contact with skin.
R25 :Toxic if swallowed. R36:Irritating to eyes.
Safety Statements: 26-36-45-61-36/37/39-27
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
S61:Avoid release to the environment. Refer to special instructions / safety data sheets.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S27:Take off immediately all contaminated clothing.
RIDADR: UN 2922 8/PG 2
WGK Germany: 3
RTECS: AK5110000
F: 8-10-19-21
HazardClass: 8
PackingGroup: II
HS Code: 29183000

Ethyl 4-chloroacetoacetate Specification

Ethyl 4-chloroacetoacetate , its CAS NO. is 638-07-3, the synonyms are Butanoic acid, 4-chloro-3-oxo-, ethyl ester ; Ethyl 4-chloro-3-oxobutanoate ; Ethyl gamma-chloroacetoacetate ; Acetoacetic acid, 4-chloro-, ethyl ester .

Product Name

Ethyl 4-chloroacetoacetate

Synthetic route

Ethyl 4-chloroacetoacetate Chemical Properties

Ethyl 4-chloroacetoacetate Uses

Ethyl 4-chloroacetoacetate Toxicity Data With Reference

Ethyl 4-chloroacetoacetate Consensus Reports

Ethyl 4-chloroacetoacetate Safety Profile

Ethyl 4-chloroacetoacetate Specification

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