78-75-1

Usage

Uses

Used in Organic Synthesis:
1,2-Dibromopropane is used as a reagent in organic synthesis for the production of various chemical compounds.
Used in Solvent Applications:
1,2-Dibromopropane is used as a solvent in various chemical processes due to its properties.
Used in Environmental Research:
1,2-Dibromopropane is used to study the effect of reductant concentration, reductant contact time, and suspension pH on reductive dechlorination of carbon tetrachloride by soil manipulated with Fe(II) and HS-.
Used in Analytical Chemistry:
1,2-Dibromopropane is used as an internal standard during the determination of nitrogenous disinfection byproduct trichloronitromethane by gas chromatography mass spectrometry.
Used in Photodissociation Dynamics Research:
1,2-Dibromopropane has been investigated for its photodissociation dynamics at 234 and 265 nm using the velocity map ion imaging method.

Preparation

1,2-Dibromopropane is synthesized from bromopropane by bromination. First mix bromopropane and iron powder, heat to 40-50°C, slowly add bromine, and continue to reflux for 2h after adding. Then, the iron slag was filtered off, and the filtrate was washed several times with water, once with 5% sodium carbonate solution, and then with 5% sodium thiosulfate solution to remove free bromine. Dry with anhydrous calcium chloride. Fractional distillation, collecting 139-142 ℃ fraction is the finished product of 1,2-dibromopropane.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Halogenated aliphatic compounds, such as 1,2-Dibromopropane, are moderately or very reactive. Reactivity generally decreases with increased degree of substitution of halogen for hydrogen atoms. Materials in this group may be incompatible with strong oxidizing and reducing agents. Also, they may be incompatible with many amines, nitrides, azo/diazo compounds, alkali metals, and epoxides. 1,2-Dibromopropane is considered nonflammable.

Fire Hazard

1,2-Dibromopropane is considered non-flammable.

Biochem/physiol Actions

1,2-Dibromopropane induces hepatotoxicity and immunotoxicity in female BALB/c mice.

InChI:InChI=1/C3H6Br2/c1-3(5)2-4/h3H,2H2,1H3/t3-/m0/s1

Upstream product

• 71-23-8 propan-1-ol 
• 57-55-6 propylene glycol 
• 627-27-0 homoalylic alcohol 
• 590-14-7 1-bromo-1-propene 
• 74-98-6 propane 
• 540-54-5 1-Chloropropane 
• 75-29-6 isopropyl chloride 
• 594-16-1 2,2-dibromopropane 
• 2919-23-5 cyclobutanol 
• 106-94-5 propyl bromide 
• 106-95-6 allyl bromide 
• 109-64-8 1,3-dibromo-propane 
• 74-99-7 prop-1-yne 
• 109-61-5 propoxycarbonyl chloride 

Downstream Products

• 54576-13-5 dimethyl 3-methylhexanedioate 
• 123265-55-4 5-methyl-3-phenyl-2-phenylimino-1,3-thiazolidine 
• 875249-17-5 1,2-dimethyl-4-phenyl-piperidine-4-carbonitrile 
• 66623-35-6 1,2-Bis(4-methylphenylsulfonyl)propane 
• 623-84-7 1,2-diacetoxypropane 
• 590-14-7 1-bromo-1-propene 
• 557-93-7 2-bromoprop-1-ene 
• 4696-23-5 (prop-1-enyloxy)benzene 
• 698-91-9 2-phenoxypropene 
• 69813-63-4 1,2-diphenoxy-propane 
• 38377-19-4 1,2-bis-benzenesulfonyl-propane 
• 93722-56-6 1,2-bis-benzylsulfanyl-propane 
• 19224-26-1 1,2-bis-benzoyloxy-propane 
• 90904-35-1 ethyl 2,6-dihydroxy-4-methylbenzoate 

Relevant academic research and scientific papers

Induced Fitting and Polarization of a Bromine Molecule in an Electrophilic Inorganic Molecular Cavity and Its Bromination Reactivity

Dodecavanadate, [V12O32]4? (V12), possesses a 4.4 ? cavity entrance, and the cavity shows unique electrophilicity. Owing to the high polarizability, Br2 was inserted into V12, inducing the inversion of one of the VO5 square pyramids to form [V12O32(Br2)]4? (V12(Br2)). The inserted Br2 molecule was polarized and showed a peak at 185 cm?1 in the IR spectrum. The reaction of V12(Br2) and toluene yielded bromination of toluene at the ring, showing the electrophilicity of the inserted Br2 molecule. Compound V12(Br2) also reacted with propane, n-butane, and n-pentane to give brominated alkanes. Bromination with V12(Br2) showed high selectivity for 3-bromopentane (64 %) among the monobromopentane products and preferred threo isomer among 2-,3-dibromobutane and 2,3-dibromopenane. The unique inorganic cavity traps Br2 leading the polarization of the diatomic molecule. Owing to its new reaction field, the trapped Br2 shows selective functionalization of alkanes.

Oxidative bromination of alkenes mediated with nitrite in ionic liquids

The oxidative bromination of C2-C8 alkenes with HBr-NaNO2-O2 in solutions of BMImBr, HMImBr or BMImBF 4 containing 16-28 wt% H2O was studied using volumetric method, GC-MS analysis, 14N NMR and UV-VIS spectroscopy. The optimal conditions to conduct the reaction at high selectivity for 1,2-dibromoalkanes in BMImBr were determined. The composition of ionic liquid affects the catalytic performance. Although in BMImBF4 the reaction runs with equal rate as in bromide ionic liquid, the fraction of bromohydrin in the reaction products increases to 20 %. Generated from NaNO2, NOx operated as a catalyst in the oxidation of Br- and was oxidized to catalytically inert NO3 - anions when complete conversion of HBr was attained. Graphical Abstract: Oxidative bromination of alkenes [Figure not available: see fulltext.]

Synthesis of propylene from renewable allyl alcohol by photocatalytic transfer hydrogenolysis

Photochemical transformation of biomass-derived or renewable substances with promising scalability is an important challenge for promoting green and sustainable chemistry. We report here that photocatalytic transfer hydrogenolysis of allyl alcohol (obtained from glycerol) gives potentially sustainable propylene with high chemo- and redox selectivity, promoted by powdered Pd/TiO2 in CH3OH (obtained from CO2) under near-ultraviolet-visible light irradiation (λ > 365 nm) at ambient temperature.

Rhodium-catalyzed reductive allylation of conjugated aldehydes with allyl acetate

Reductive allylation of aryl and alkenyl aldehydes with allyl acetate catalyzed by the ionic diamine carbonyl rhodium complex, [Rh(TMEDA)(CO) 2][RhCl2(CO)2], under a carbon monoxide atmosphere afforded the corresponding homoallylic alcohols in good isolated yields.

An economical and convenient synthesis of vinyl sulfones

A general process for the efficient synthesis of vinyl sulfones has been developed using commercially available sulfinic acid sodium salts and dibromides. A variety of phenyl and methyl vinyl sulfones have been formed in good yields, in the absence of any catalyst. Georg Thieme Verlag Stuttgart.

Synthesis of hydroxylated hydrocarbons

Ethylene glycol, other diols, triols, and polyols are made in an efficient manner by reacting dibromides with water in the presence of a metal oxide. An integrated process of dibromide formation, alcohol synthesis, metal oxide regeneration, and bromine recycling is also provided.

REACTION OF ORGANIC COMPOUNDS WITH SF4-HF-HALOGENATING SYSTEM VII. REACTIONS OF OLEFINS WITH THE SF4-HF-Cl2(Br2) SYSTEM

Under the influence of the SF4-HF-Cl2(Br2) system halogen-containing olefins undergo conjugate halogenofluorination.It was shown for the case of (Z)- and (E)- 1,2-dichloroethenes that these reactions take place anti-stereospecifically through the formation of the bromonium ions.The accumulation of chlorine atoms in the olefin molecule hinders electrophilic addition of stoichiometric equivalents of ClF and BrF at the double bond.The SF4-HF-Br2 system is an effective agent for substitutive fluorination of organic compounds containing bromine.Only the bromine atoms situated at the secondary carbon atom are substituted by fluorine.

Gas-Phase Pyrolysis of Phenylcyclopropane

The gas-phase pyrolysis of phenylcyclopropane (5) has been ivestigated in a quartz tubular reactor between 560 and 680 deg C and a contact time of about 1 s.Main reaction is the thermal isomerization to allylbenzene (4) as well as to cis-(1b) and trans--β-methylstyrene (3b).Besides 1, 3, and 4, indene (8) is formed, which is characterized by a statistical distribution of the H atom over the three positions of the five-membered ring.To distinguish between the two possible mechanisms of the isomerization (opening of the cyclopropane ring C-C bond dissociation/ 1,3-diyl formation and 1,2-C,H retro-insertion/ethylcarbene formation), the D distribution in 1 and 3 was carefully determined by 1H-NMR spectroscopy.The results show that the isomerization is initiated by generation of a 1,3-diradical. - Keywords: Isotopic labeling/ Isomerization/ Phenylcyclopropane/ Pyrolysis

Efficient Conversion of Alkyl Chlorides into Bromides

The convenient and selective catalytic conversion of secondary and tertiary alkyl chlorides into bromides with hydrogen bromide in the presence of small amounts of anhydrous iron(III) bromide is described.