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DL-Ethyl 2-bromobutyrate

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Name

DL-Ethyl 2-bromobutyrate

EINECS 208-574-6
CAS No. 533-68-6 Density 1.348 g/cm3
PSA 26.30000 LogP 1.72300
Solubility Insoluble in water. Miscible with alcohol and ether Melting Point -4°C
Formula C6H11BrO2 Boiling Point 179.4 °C at 760 mmHg
Molecular Weight 195.056 Flash Point 69.5 °C
Transport Information UN 1993 3/PG 3 Appearance clear colorless to yellow liquid
Safety 26-39-24/25-23 Risk Codes 22-37/38-41-36/37/38
Molecular Structure Molecular Structure of 533-68-6 (DL-Ethyl 2-bromobutyrate) Hazard Symbols HarmfulXn, IrritantXi
Synonyms

Ethyl 2-bromobutyrate;Butanoic acid, 2-bromo-, ethyl ester;2-ethyl bromobutyrate;Ethyl 2-bromobutanoate;Butyric acid, 2-bromo-, ethyl ester;2-Bromobutanoic acid ethyl ester;Ethyl 2-Bromo butyrate;α-bromo-butanoic acid ethyl ester;Ethyl-2-Bromo butyrate;

Article Data 19

DL-Ethyl 2-bromobutyrate Synthetic route

64-17-5

ethanol

80-58-0

2-Bromobutyric acid

533-68-6

2-bromobutyric acid ethyl ester

Conditions
ConditionsYield
With potassium hydrogensulfate at 70 - 90℃; for 2h; Reagent/catalyst; Large scale;98.5%
With dmap; dicyclohexyl-carbodiimide In diethyl ether at 25℃; for 3h; Inert atmosphere;70%
With hydrogenchloride
With sulfuric acid
64-17-5

ethanol

104165-34-6

ethoxymethylenemalonodinitrile

533-68-6

2-bromobutyric acid ethyl ester

Conditions
ConditionsYield
With hydrogen bromide for 3h; Heating;70%
141-75-3

butyryl chloride

533-68-6

2-bromobutyric acid ethyl ester

Conditions
ConditionsYield
With carbon disulfide; bromine Eintragen des Reaktionsprodukts in abs.Alkohol,mit Wasser faellen und fraktionieren;
64-17-5

ethanol

107-92-6

butyric acid

533-68-6

2-bromobutyric acid ethyl ester

Conditions
ConditionsYield
aus dem Rohprodukt der Bromierung der Buttersaeure;
(i) SOCl2, (ii) Br2, I2, (iii) /BRN= 1718733/; Multistep reaction;
(i) SOCl2, (ii) Br2, (iii) /BRN= 1718733/; Multistep reaction;
623-73-4

diazoacetic acid ethyl ester

97-94-9

triethyl borane

533-68-6

2-bromobutyric acid ethyl ester

Conditions
ConditionsYield
(i) O2, THF, (ii) Br2, CCl4, (iii) EtOH; Multistep reaction;
141-97-9

ethyl acetoacetate

75-03-6

ethyl iodide

533-68-6

2-bromobutyric acid ethyl ester

Conditions
ConditionsYield
Multistep reaction;
80-58-0

2-Bromobutyric acid

541-41-3

chloroformic acid ethyl ester

533-68-6

2-bromobutyric acid ethyl ester

Conditions
ConditionsYield
With dmap; triethylamine 1.) CH2Cl2, 0 deg C, 5 min, 2.) 0 deg C, 0.25 h; Yield given. Multistep reaction;
7726-95-6

bromine

141-75-3

butyryl chloride

A

533-68-6

2-bromobutyric acid ethyl ester

B

β-bromo-butyric acid ethyl ester

β-bromo-butyric acid ethyl ester

Conditions
ConditionsYield
im Sonnenlicht und nachfolgender Behandlung mit Alkohol;
potassium salt of ethylmalonic acid monoethyl ester

potassium salt of ethylmalonic acid monoethyl ester

533-68-6

2-bromobutyric acid ethyl ester

Conditions
ConditionsYield
With tetrachloromethane; bromine
64-17-5

ethanol

26074-52-2

2-bromo-butyryl bromide

533-68-6

2-bromobutyric acid ethyl ester

Conditions
ConditionsYield
With pyridine In chloroform at 0℃; for 1h;
In ethyl acetate at 20℃;

DL-Ethyl 2-bromobutyrate Specification

The IUPAC name of DL-Ethyl 2-bromobutyrate is ethyl 2-bromobutanoate. With the CAS registry number 533-68-6, it is also named as Butanoic acid, 2-bromo-, ethyl ester. The product's categories are aromatic halides (substituted); acid based bromo compounds; carbonyl compounds; esters. It is clear colorless to yellow liquid which is sensitive to light. In addition, it is stable under normal temperatures and pressures. And it is incompatibilities with strong oxidizing agents, strong oxidizing agents, reducing agents, acids, bases.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 2.25; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.25; (4)ACD/LogD (pH 7.4): 2.25; (5)ACD/BCF (pH 5.5): 30.11; (6)ACD/BCF (pH 7.4): 30.11; (7)ACD/KOC (pH 5.5): 398.19; (8)ACD/KOC (pH 7.4): 398.19; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 4; (12)Index of Refraction: 1.455; (13)Molar Refractivity: 39.31 cm3; (14)Molar Volume: 144.6 cm3; (15)Polarizability: 15.58×10-24 cm3; (16)Surface Tension: 32.4 dyne/cm; (17)Enthalpy of Vaporization: 41.57 kJ/mol; (18)Vapour Pressure: 0.944 mmHg at 25°C; (19)Rotatable Bond Count: 4; (20)Exact Mass: 193.994242; (21)MonoIsotopic Mass: 193.994242; (22)Topological Polar Surface Area: 26.3; (23)Heavy Atom Count: 9.

Uses of DL-Ethyl 2-bromobutyrate: It can be used as intermediates of pesticide and pharmaceutical. And it reacts with cyclohexanone to get 2-(1-hydroxy-cyclohexyl)-butyric acid ethyl ester. This reaction which is Reformatzky reaction needs reagent Zn and I2 and solvent 1,2-dimethoxy-ethane at temperature of 100 - 105 °C. The reaction time is 1 hours. The yield is 44.8%.

When you are using this chemical, please be cautious about it as the following:
It is harmful if swallowed. And it is irritating to eyes, respiratory system and skin, so people should not breathe vapour. In addition, people should avoid contact with skin and eyes due to it may cause serious damage to the eyes. If you want to contact this product, you must wear eye / face protection.

People can use the following data to convert to the molecule structure.
1. SMILES: BrC(C(=O)OCC)CC;
2. InChI: InChI=1/C6H11BrO2/c1-3-5(7)6(8)9-4-2/h5H,3-4H2,1-2H3

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