2 bromopropionyl bromide

Manufactured by Merck Group

Sourced in United States, New Zealand

2-bromopropionyl bromide is a chemical compound used as a laboratory reagent. It is a colorless liquid with a boiling point of approximately 190°C. The compound is primarily used in organic synthesis reactions, particularly in the preparation of other chemical intermediates.

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5 protocols using 2 bromopropionyl bromide

Synthesis of Functional Polymer Particles with Controlled Properties

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Iron (III) chloride hexahydrate FeCl₃·6H₂O and iron (II) chloride tetrahydrate FeCl₂·6H₂O (Sigma-Aldrich, St. Louis, MO, USA), 3-aminoproplotrimethoxysilane (APTMS, 97%, Sigma-Aldrich, St. Louis, MO, USA), 2-bromopropionyl bromide (97%, Sigma-Aldrich, St. Louis, MO, USA), carbon disulfide (CS₂, ≥ 99.9%, Sigma-Aldrich, St. Louis, MO, USA), potassium hydroxide (KOH, pure, Avantor Performance Materials Poland S.A., Gliwice, Poland), triethylamine (Et₃N, Avantor Performance Materials Poland S.A., Gliwice, Poland), acryloyl chloride (96%, Alfa Aesar, Ward Hill, MA, USA) were used as received. The initiator, 2,2′-azobis(2-methylpropionitrile) (AIBN, ≥ 98%, Sigma-Aldrich, St. Louis, MO, USA), was recrystallized from methanol. N-vinylcaprolactam (NVCL, > 98%, TCI, Tokyo, Japan) was recrystallized from hexane prior to use and stored in a freezer. N-isopropylacrylamide (NIPAAm, 99 %, Acros Organics, Geel, Belgium) was recrystallized from toluene–hexane (60:40, v/v) prior to use. Potassium O-ethyl carbonodithioate (KSCSOEt) was synthesized according to the well-known procedure [11 (link)]. All organic solvents were purchased from Avantor Performance Materials Poland S.A. (Gliwice, Poland) and were distilled before use.

Markiewicz K.H., Niemirowicz-Laskowska K., Szymczuk D., Makarewicz K., Misztalewska-Turkowicz I., Wielgat P., Majcher-Fitas A.M., Milewska S., Car H, & Wilczewska A.Z. (2021). Magnetic Particles with Polymeric Shells Bearing Cholesterol Moieties Sensitize Breast Cancer Cells to Low Doses of Doxorubicin. International Journal of Molecular Sciences, 22(9), 4898.

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Synthesis and Characterization of PEDOT-Based Polymer

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3,4-Ethylenedioxythiophene (EDOT) and (2,3-dihydrothieno [3,4-b][1,4]dioxin-2-yl)methanol were obtained from AK scientific, oligoethylene glycol methyl ether methacrylate (OEGMA), 2-bromopropionyl bromide, copper bromide, 2,2′-bipyridine and lithium perchlorate were purchased from Sigma-Aldrich (Auckland, New Zealand). Dichloromethane, acetonitrile, sodium bicarbonate, magnesium sulphate, ethanol and methanol were provided by ECP Ltd. (Auckland, New Zealand). Triethylamine (TEA) was purchased from BDH (Poole, UK). Bovine serum albumin (BSA) was acquired from pH Scientific (Auckland, New Zealand). Pierce^TM Bicinchoninic acid (BCA) Protein Assay Kit was purchased from ThermoFisher Scientific (Auckland, New Zealand). Iron (III) chloride was obtained from ECP Ltd. and all the deionised water was obtained from MilliQ (18.2 MΩ cm) system (Arium Pro Ultrapure Water Systems, Sartorius, Germany).

Ashraf J., Lau S., Akbarinejad A., Evans C.W., Williams D.E., Barker D, & Travas-Sejdic J. (2022). Conducting Polymer-Infused Electrospun Fibre Mat Modified by POEGMA Brushes as Antifouling Biointerface. Biosensors, 12(12), 1143.

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Synthesis of Phenylalanine-Based Compounds

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L-Phenylalanine methyl ester hydrochloride
(HCl·H₂N-F-OMe, 98%) was purchased from Carbolution
Chemicals. Boc-L-phenylalanine monohydrate (Boc-F-OH·H₂O, 99%) was received from TCI chemicals. Tris(2-carboxyethyl)phosphine
hydrochloride (TCEP, 98%), 1-hydroxybenzotriazole hydrate (HOBt, 97%),
trifluoroacetic acid (TFA, 99%), poly(ethylene glycol) (HO-PEG-OH,
average M_w = 1500 g/mol), potassium thioacetate
(KSOAc, 98%), triethylamine (Et₃N, 99%), sodium methoxide
solution (NaOMe, 25 wt % in methanol), and 2-bromopropionyl bromide
(97%) were purchased from Sigma-Aldrich and used as received. Mesylchloride
(MsCl, 99%) and N,N-dicyclohexylcarbodiimide
(DCC, 99%) were received from Merck and Alfa Aesar, respectively.
Br-FFFF-OMe was adopted from our recent work published elsewhere.^{32 (link)} Reaction solvents were dried and distilled according
to the standard procedures.

Kumar S., Hause G, & Binder W.H. (2020). Bifunctional Peptide–Polymer Conjugate-Based Fibers via a One-Pot Tandem Disulfide Reduction Coupled to a Thio-Bromo “Click” Reaction. ACS Omega, 5(30), 19020-19028.

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Synthesis of Functional Polymer Materials

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tert-Butyl methacrylate (tBMA, Aldrich, 99%) was distilled with CaH₂ under reduced pressure prior to use. Copper(I) bromide (CuBr, Aldrich, 98%) was purified by stirring overnight over CH₃COOH at room temperature, followed by washing with ethanol, diethyl ether, and acetone prior to drying at 40 °C in vacuo for one day. N-Phenyl-1-naphthylamine (PNA, Alfa Aesar, 97%) was purified by recrystallization in ethanol three times. 2-Butanone (Aldrich, 99%) was dried with CaCl₂ and then distilled under vacuum. Dichloromethane (CH₂Cl₂, Aldrich, 99.5%) was dried over KOH and distilled from CaH₂ under N₂ prior to use. Poly(ethylene glycol) methyl ether (PEG-OH, M_n = 2,000 and 5,000 g/mol, Aldrich), 2-bromopropionyl bromide (Alfa Aesar, 97%), N,N,N′,N′,N″-pentamethyl diethylenetriamine (PMDETA, Aldrich, 99%), 4-(dimethylamino)pyridine (DMAP, Aldrich, 99%), triethylamine (TEA), trifluoroacetic acid (TFA, Aldrich, 99%), and pyrene (Aldrich, 99%), rhodamine 6 G (R6G, Aldrich, 99%) were used as received. Other solvents were obtained from commercial sources and used as received. p-(2-(4-Biphenyl)perfluorocyclobutoxy)phenyl methacrylate (BPFCBPMA)23 and PEG₁₁₃-b-PS₁₀₀ diblock copolymer66 (link) was synthesized according to previous report.

Xu B., Yao W., Li Y., Zhang S, & Huang X. (2016). Perfluorocyclobutyl Aryl Ether-Based ABC Amphiphilic Triblock Copolymer. Scientific Reports, 6, 39504.

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Synthesis of Thermoresponsive Polymers

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The initiator, 2,2′-azobis(2-methylpropionitrile) (AIBN, MERCK) was recrystallized from chloroform. Monomer, N-isopropylacrylamide (NIPAAm, 99%, ACROS) was recrystallized from toluene-hexane (60:40, v/v), prior to use. 2-Bromopropionylbromide (97%, ALDRICH), carbon disulfide (CS₂, ≥99.9%, SIGMA-ALDRICH), potassium hydroxide (KOH, Pure, AVANTOR), triethylamine (Et₃N, AVANTOR), n-propylamine (99%, Riedel-de Haen AG), tributylphosphine (TBP, >90% GC, FLUKA), Phosphate Buffer Solution (PBS, pH=7.4, GIBCO) and Dulbecco’s Modified Eagle Medium (DMEM, GIBCO) were used as received. All organic solvents were purchased from Avantor Performance Materials, Poland S.A., and were distilled prior to use.

Misiak P., Niemirowicz-Laskowska K., Markiewicz K.H., Misztalewska-Turkowicz I., Wielgat P., Kurowska I., Siemiaszko G., Destarac M., Car H, & Wilczewska A.Z. (2020). Evaluation of Cytotoxic Effect of Cholesterol End-Capped Poly(N-Isopropylacrylamide)s on Selected Normal and Neoplastic Cells. International Journal of Nanomedicine, 15, 7263-7278.

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