Ethyl dibromoacetate

Ethyl dibromoacetate structural formula

Structural formula

Business number 06HX
Molecular formula C4H6Br2O2
Molecular weight 245.90
label

None yet

Numbering system

CAS number:617-33-4

MDL number:MFCD00041718

EINECS number:210-510-7

RTECS number:None

BRN number:None

PubChem ID:None

Physical property data

1. Properties: colorless or light yellow liquid

2. Boiling point (℃, 1.0 mmHg): 194

3. Boiling point (℃, 12 mmHg): 77

4. Density: d 1.9025 g/cm3

5. Solubility: Insoluble in water, slightly soluble in hexane, ether, methylene chloride, acetone, ethyl acetate, ethanol.

6. Relative density (20℃, 4℃): 1.8991

7. Refractive index at room temperature (n20): 1.4633

Toxicological data

None yet

Ecological data

1. Other harmful effects: This substance may be harmful to the environment, and special attention should be paid to water bodies.

Molecular structure data

1. Molar refractive index: 37.77

2. Molar volume (cm3/mol): 124.7

3. Isotonic specific volume (90.2K ): 317.6

4. Surface tension (dyne/cm): 42.0

5. Polarizability (10-24cm3): 14.97

Compute chemical data

1. Reference value for hydrophobic parameter calculation (XlogP): 2.2

2. Number of hydrogen bond donors: 0

3. Number of hydrogen bond acceptors: 2

4. Number of rotatable chemical bonds: 3

5. Number of tautomers: none

6. Topological molecule polar surface area 26.3

7. Number of heavy atoms: 8

8. Surface charge: 0

9. Complexity: 82.1

10. Number of isotope atoms: 0

11. Determine the number of atomic stereocenters: 0

12. Uncertain number of atomic stereocenters: 0

13. Determine the number of chemical bond stereocenters: 0

14. Number of uncertain chemical bond stereocenters: 0

15. Number of covalent bond units: 1

Properties and stability

It has tear-inducing effect. Avoid inhalation and operate in a fume hood.

Storage method

Seal the secret container and store it in a sealed main container in a cool, dry place.

Synthesis method

It is derived from the interaction between ethyl acetate and bromine in the presence of red phosphorus.

Purpose

Under the action of potassium tert-butoxide or highly hindered phenoxide, ethyl dibromoacetate and organoborane undergo an alkylation reaction. α-bromo ester or α,α-dialkyl substituted ester (formula 1)[1]. The use of phenoxy groups (pK 11.7) can reduce self-condensation reactions of starting materials or products. This is an alternative to traditional malonate synthesis methods.

Under low temperature conditions, under the action of zinc/silver-graphite, the Reformatsky reaction of ethyl dibromoacetate occurs to generate α -Bromo-β-hydroxyester (formula 2)[2], then treat α-bromo- with the appropriate group β-Hydroxyesters can give a variety of products. Zinc/silver-carbon reagents can also be used on aldose [3]. Adding diethyl to the Organozinc Reagent in the Reformatsky Reaction Aluminum chloride can improve the reaction to obtainα,β-unsaturated ester, which is an alternative to the Wadsworth-Emmons reaction. Samarium chloride or chromium chloride It can also be used for this reaction (Equation 3)[4].

Underthecatalysisoftriethylborane,theadditionreactionofethyldibromoacetatetoketeneacetalyields1,4-diester(formula4)[5].

Controlling the reaction conditions, benzenethiol can react with ethyl dibromoacetate to generate the corresponding thioacetal (formula 5)[6]. Further alkylation can give pyruvic acid derivatives Object.

In copper or zinc powder Under the action of ethyl dibromoacetate, monoolefins can undergo ethoxycarbonylcyclopropanation reaction with ethyl dibromoacetate (Formula 6)[7].

Resource:allhdi.com

BDMAEE:Bis (2-Dimethylaminoethyl) Ether

CAS NO:3033-62-3

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