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3153-36-4

Basic Information
CAS No.: 3153-36-4
Name: ETHYL 4-CHLOROBUTYRATE
Article Data: 33
Molecular Structure:
Molecular Structure of 3153-36-4 (ETHYL 4-CHLOROBUTYRATE)
Formula: C6H11ClO2
Molecular Weight: 150.605
Synonyms: Butyricacid, 4-chloro-, ethyl ester (6CI,7CI,8CI);4-Chlorobutyric acid ethyl ester;Ethyl 4-chlorobutanoate;Ethyl 4-chlorobutyrate;Ethyl g-chlorobutyrate;Ethyl w-chlorobutyrate;NSC 81215;Ethyl gamma-chlorobutyrate;
EINECS: 221-591-3
Density: 1.057 g/cm3
Melting Point: -70oC
Boiling Point: 186 °C at 760 mmHg
Flash Point: 51.7 °C
Solubility: insoluble in water
Appearance: clear yellow to brownish liquid
Hazard Symbols: IrritantXi, HarmfulXn
Risk Codes: 36/37/38-22-10
Safety: 26-36-37/39-16
Transport Information: UN 1993
PSA: 26.30000
LogP: 1.56850
Synthetic route
96-48-0

4-butanolide

64-17-5

ethanol

3153-36-4

4-chloro-butyric acid ethyl ester

Conditions
ConditionsYield
With thionyl chloride for 16h; Heating;80%
With hydrogenchloride
With hydrogenchloride
1191-95-3

cyclobutanone

1801-77-0

oxovanadium(V) ethoxydichloride

3153-36-4

4-chloro-butyric acid ethyl ester

Conditions
ConditionsYield
With lithium chloride In diethyl ether for 13h; Ambient temperature;43%

ethyl 4-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butanoate

3153-36-4

4-chloro-butyric acid ethyl ester

Conditions
ConditionsYield
With trimethylsilyl trifluoromethanesulfonate; 4-tert-Butylcatechol; 2-methoxybenzo[d][1,3,2]dioxaborole; trans-di-O-tert-butyl hyponitrite In methanol; dichloromethane; benzene at 70℃; for 16h; Inert atmosphere;30%
123-91-1

1,4-dioxane

14077-66-8

4-ethoxy-butyryl chloride

3153-36-4

4-chloro-butyric acid ethyl ester

Conditions
ConditionsYield
at 70℃; Geschwindigkeit der Umlagerung verschiedener Konz.;
at 100℃; Geschwindigkeit der Umlagerung verschiedener Konz.;
96-48-0

4-butanolide

64-17-5

ethanol

A

3153-36-4

4-chloro-butyric acid ethyl ester

B

4-(4-chloro-butyryloxy)-butyric acid ethyl ester

Conditions
ConditionsYield
With hydrogenchloride
628-20-6

4-Chlorobutyronitrile

64-17-5

ethanol

3153-36-4

4-chloro-butyric acid ethyl ester

Conditions
ConditionsYield
With hydrogenchloride
With sulfuric acid
With hydrogenchloride
With hydrogenchloride In dichloromethane at 8℃;
64-17-5

ethanol

28341-54-0

4-(4-nitrophenoxy)butanoic acid

3153-36-4

4-chloro-butyric acid ethyl ester

Conditions
ConditionsYield
With hydrogenchloride zuletzt bei Siedetemperatur;
14077-66-8

4-ethoxy-butyryl chloride

3153-36-4

4-chloro-butyric acid ethyl ester

Conditions
ConditionsYield
at 100℃;
at 100℃;
at 50℃; Geschwindigkeit der Umlagerung;
at 100℃; Geschwindigkeit der Umlagerung;
10374-37-5

4-ethoxybutanoic acid

3153-36-4

4-chloro-butyric acid ethyl ester

Conditions
ConditionsYield
With thionyl chloride
Multi-step reaction with 2 steps
1: hydrogen; SOCl2
2: 100 °C / Geschwindigkeit der Umlagerung
View Scheme
Multi-step reaction with 2 steps
1: hydrogen; SOCl2
2: 100 °C
View Scheme
105-54-4

butanoic acid ethyl ester

3153-36-4

4-chloro-butyric acid ethyl ester

Conditions
ConditionsYield
With tetrachloromethane; sulfuryl dichloride; dibenzoyl peroxide
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Specification

The IUPAC name of Ethyl 4-chlorobutyrate is Ethyl 4-chlorobutanoate. With the CAS registry number 3153-36-4, it is also named as Ethyl gamma-chlorobutyrate. The product's categories are Aromatic Esters; C6 to C7; Carbonyl Compounds; Esters. Besides, it is clear yellow to brownish liquid, which should be stored in a closed, cool and dry place. In addition, its molecular formula is C6H11ClO2 and molecular weight is 150.60. This chemical is also insoluble in water.

The other characteristics of this product can be summarized as: (1)EINECS: 221-591-3; (2)ACD/LogP: 1.70; (3)# of Rule of 5 Violations: 0; (4)ACD/LogD (pH 5.5): 1.7; (5)ACD/LogD (pH 7.4): 1.7; (6)ACD/BCF (pH 5.5): 11.44; (7)ACD/BCF (pH 7.4): 11.44; (8)ACD/KOC (pH 5.5): 199.2; (9)ACD/KOC (pH 7.4): 199.2; (10)H bond acceptors: 2; (11)H bond donors: 0; (12)Freely Rotating Bonds: 5; (13)Polar Surface Area: 26.3 Å2; (14)Index of Refraction: 1.425; (15)Molar Refractivity: 36.47 cm3; (16)Molar Volume: 142.4 cm3; (17)Polarizability: 14.45×10-24cm3; (18)Surface Tension: 30.2 dyne/cm; (19)Density: 1.057 g/cm3; (20)Flash Point: 51.7 °C; (21)Enthalpy of Vaporization: 42.22 kJ/mol; (22)Boiling Point: 186 °C at 760 mmHg; (23)Vapour Pressure: 0.678 mmHg at 25 °C.

Preparation of Ethyl 4-chlorobutyrate: this chemical can be prepared by Dihydro-furan-2-one and Ethanol.



This reaction needs SOCl2 by heating. The reaction time is 16 hours. The yield is 80 %.

Uses of Ethyl 4-chlorobutyrate: this chemical is used in organic synthesis. Moreover, it can be used for producting 4-Iodo-butyric acid ethyl ester.



This reaction needs NaI and Butan-2-one by heating. The reaction time is 18 hours.

When you are using this chemical, please be cautious about it as the following: Ethyl 4-chlorobutyrate is flammable and harmful if swallowed. Please keep away from sources of ignition. Furthermore, this product is irritating to eyes, respiratory system and skin. You should wear suitable protective clothing, gloves and eye/face protection. And in case of contact with eyes, please rinse immediately with plenty of water and seek medical advice.

People can use the following data to convert to the molecule structure.
(1)SMILES:ClCCCC(=O)OCC
(2)InChI:InChI=1/C6H11ClO2/c1-2-9-6(8)4-3-5-7/h2-5H2,1H3
(3)InChIKey:OPXNFHAILOHHFO-UHFFFAOYAU
(4)Std. InChI:InChI=1S/C6H11ClO2/c1-2-9-6(8)4-3-5-7/h2-5H2,1H3
(5)Std. InChIKey:OPXNFHAILOHHFO-UHFFFAOYSA-N