109-64-8 Usage
Description
1,3-Dibromopropane is a dihalogenated propane, which is a colorless to slightly yellow liquid with a sweet odor. It is soluble in ether, acetone, and chloroform, but insoluble in water. 1,3-Dibromopropane undergoes reduction catalyzed by electrogenerated solution-phase nickel(I) salen and nickel(I) salen confined in a polymer film on the surface of a carbon electrode, resulting in the formation of cyclopropane and propylene. Additionally, 1,3-dibromopropane decomposes when exposed to heat for an extended period and is partially converted to 1,2-dibromopropane. Boiling with water leads to the production of propylene glycol, and it is also used to study the substrate specificity of haloalkane dehalogenases.
Uses
1. Used in Chemical Synthesis:
1,3-Dibromopropane is used as a chemical intermediate for the preparation of C3-bridged compounds through C-N coupling reactions. It serves as a reactant in the synthesis of 2,3,4,5-tetrahydro-7,7-diphenylimidazo-[2,1-b]-thiazine-6(7H)-one by reacting with the potassium salt of 5,5-diphenyl-2-thiohydantoin.
2. Used in Electrochemical Reduction Studies:
1,3-Dibromopropane is utilized in the study of electrochemical reduction processes, specifically in the investigation of the catalytic activity of electrogenerated solution-phase nickel(I) salen and nickel(I) salen confined in a polymer film on the surface of a carbon electrode. This application aids in understanding the reduction pathways and the formation of cyclopropane and propylene.
3. Used in Haloalkane Dehalogenase Research:
1,3-Dibromopropane is also used as a substrate in the study of haloalkane dehalogenases, which are enzymes that catalyze the dehalogenation of haloalkanes. The use of 1,3-dibromopropane in these studies helps to elucidate the substrate specificity and reaction mechanisms of these enzymes.
4. Used in the Production of Propylene Glycol:
1,3-Dibromopropane can be boiled with water to produce propylene glycol, which is a versatile chemical used in various industries, including pharmaceuticals, cosmetics, and the food industry, as a humectant, solvent, and preservative.
Hazard
Colorless liquid; sweet odor. Insoluble in water;
soluble in organic solvents. Combustible.
Synthesis
1,3-Dibromopropane can be prepared via the free radical addition between allyl bromide and hydrogen bromide. It can derived from the reaction of propylene glycol with brominated hydrochloric acid.
Purification Methods
1,3-Dibromopropane [109-64-8] M 201.9, f -34.4o, b 63 -63.5o/26mm, 76 -77o/40mm, 9 0o/80mm, 165o/atm, d 4 1.977, n 1.522. Wash the dibromide with dilute aqueous Na2CO3, then water. Dry and fractionally distil it under reduced pressure. [Beilstein 1 IV 216.]
Check Digit Verification of cas no
The CAS Registry Mumber 109-64-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 9 respectively; the second part has 2 digits, 6 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 109-64:
(5*1)+(4*0)+(3*9)+(2*6)+(1*4)=48
48 % 10 = 8
So 109-64-8 is a valid CAS Registry Number.
InChI:InChI=1/C3H6Br2/c1-3-5-11-19-15(17)13-9-7-8-10-14(13)16(18)20-12-6-4-2/h7-10H,3-6,11-12H2,1-2H3
109-64-8Relevant articles and documents
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Freund
, p. 638 (1881)
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Urushibara,Simamura
, p. 323,330 (1939)
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ANALYSE STRUCTURALE EN SERIE CYCLOBUTANIQUE. Partie 1. Derives monosubstitues et gem disubstitues du cyclobutane
Karimine, Mohamed,Galsomias, Jacqueline,Lere-Porte, Jean-Pierre,Petrissans, Jean
, p. 321 - 332 (1987)
Methylene bending mode analysis of some cyclobutane-d2 molecules reveals that in the dissolved state (solvent CCl4), bromocyclobutane occurs exclusively in a pseudo-equatorial form, whereas, under the same conditions, cyclobutanol and 1-bromocyclobutane carbonitrile exist both in pseudo-axial and pseudo-equatorial conformations.NMR spectroscopy confirms the results obtained for bromocyclobutane and leads to the conclusion that the pseudo-equatorial conformer is predominant in the case of cyclobutanol as well as in that of cyclobutane carbonitrile.A theoretical study of cyclobutanol in the gaseous state by the P.C.I.L.O. method gives results which are consistent with a pseudo-equatorial conformer.
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Silbert,Tomlinson
, p. 706,709 (1961)
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Synthesis of 1,3-dibromopropane
Fel'dman, D. P.,Stonkus, V. V.,Shimanskaya, M. V.,Avot-s, A. A.
, p. 250 - 253 (2007/10/03)
A method for preparation of 1,3-dibromopropane from akrolein is proposed; it consists of alkylation of the starting compound, followed by catalytic reduction of the carbonyl group and bromination.