Category: 1001-26-9

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Purines, pyrimidines, and glyoxalines. VII. New syntheses of 2-thiouracils and 2-thiothymines》. Authors are Shaw, G.; Warrener, R. N..The article about the compound:Ethyl 3-Ethoxy-2-Propenoatecas:1001-26-9,SMILESS:O=C(OCC)/C=C/OCC).Synthetic Route of C7H12O3. Through the article, more information about this compound (cas:1001-26-9) is conveyed.

cf. C.A. 51, 17939f. β-Ethoxy-acryloyl (I) and β-methoxy-α-methylacryloyl isothiocyanate (II) were prepared by reaction of the corresponding acid chlorides (III) (IV) with KSCN. I and II with NH3 or primary amines gave linear acylthioureas which when treated with dilute aqueous alkali afforded 1-substituted 2-thiouracils and 2-thiothymines. Reaction of the acyl isothiocyanates with PhNHNH2 (V) similarly gave acylthiosemicarbazides which with alkali afforded thiotriazoles. BrCH2CO2Et (334 g.), 400 mg. CH(OEt)3, and 1 kg. Zn shavings gave 104 g. Et β-ethoxyacrylate (VI), b. 189-91°. VI (48 g.) stirred 2 hrs. on an H2O bath with 180 ml. 2N NaOH, cooled, and acidified gave 35 g. β-ethoxyacrylic acid (VII), m. 109°. Na salt of VII (15 g.) refluxed 4 hrs. in 200 ml. Et2O containing 10 ml. SOCl2, kept overnight, and filtered through asbestos gave 11.5 g. III, b35104°. III (9.33 g.) in 50 ml. dry MeCN shaken 3 hrs. with 6.8 g. KSCN gave 6.2 g. I, b1.5 90°. I (1.35 g.) reacted vigorously with 3 ml. 3.34N MeOH-NH3 to give 0.74 g. N-(β-ethoxyacryloyl)thiourea (VIII), prisms, m. 165° (alc.). VIII (0.5 g.) heated 45 min. with 5 ml. 2N NaOH, cooled, acidified, and the solids triturated with a little alc. gave 0.05 g. 2-thiouracil, needles, m. 304° (decomposition). I (0.84 g.) in 15 ml. Et2O treated with 0.5 ml. 33% MeOH-MeNH2 gave 0.45 g. N-(β-ethoxyacryloyl)-N’-methylthiourea (IX), needles, m. 124° (alc.). IX (0.35 g.) warmed with 4 ml. 2N NaOH gave 0.23 g. 1-methyl-2-thiouracil, m. 228° (alc.). Similarly, 1.15 g. I and 0.7 g. PhNH2 mixed in Et2O gave 1.25 g. N-(β-ethoxyacryloyl)-N’-phenylthiourea (X), plates, m. 152°. X (0.85 g.) similarly heated 15 min. with alkali gave 0.68 g. 1-phenyl-2-thiouracil, laths, m. 236° (alc.). I (0.87 g.), 0.6 g. V, and 5 ml. alc. gave 0.87 g. N1-(β-ethoxyacryloyl)-N3-phenylthiosemicarbazide (XI), plates, m. 161° (alc.). XI (0.4 g.) heated 5 min. with 5 ml. 2N NaOH and the cooled solution acidified gave 0.37 g. 5-β-ethoxyvinyl-2,3-dihydro-1-phenyl-3-thio-1,2,4-triazole, prisms, m. 161°. The following method was found suitable for the preparation of β-methoxy-α-methylacrylic acid (XII). Me α,β-dibromo-α-methylpropionate (467 g.) in 500 ml. MeOH refluxed with 82.6 g. Na in 1 l. MeOH, next morning the mixture filtered, the filtrate and washings evaporated to half volume, NaBr again removed, most of the solvent removed, the residue treated with 250 ml. H2O, the precipitated oil extracted with Et2O, and the residue from the Et2O evaporation heated with 1.5 g. fused NaHSO4 at 170° until the evolution of alc. was complete, and the residue distilled gave 159 g. Me β-methoxy-α-methylacrylate (XIII), b10 66-7°, n23D 1.455. XIII (39 g.) heated with alkali 3 hrs. gave 35.5 g. XII, plates, m. 106° (ligroine). XII Na salt was prepared by neutralizing a suspension of XII in H2O with 2N NaOH, evaporating to dryness, and drying the salt at 100°/0.5 mm. for 4.5 hrs. before using. This salt (25.72 g.) suspended in 100 ml. Et2O treated with 16 ml. SOCl2 in 100 ml. Et2O and finally refluxed 3 hrs. gave 20 g. IV, b35 102°. IV with a little H2O gave XII. IV (8.6 g.) in 50 ml. MeCN treated with 6.2 g. KSCN gave 7.2 g. II, b2 102°, plates, melting a little above room temperature II (0.86 g.) in 5 ml. MeOH treated with 0.6 ml. 25% alc. MeNH2 gave 0.55 g. N-(β-methoxy-α-methylacryloyl)-N’-methylthiourea (XIV), needles, m. 140° (alc.). XIV (0.28 g.) warmed with 2N NaOH gave 0.19 g. 1-methyl-2-thiothymine, needles, m. 226-7° (alc.). Similarly, 0.5 g. II with 0.5 g. PhNH2 in alc. gave 0.6 g. N-(β-methoxy-α-methylacryloyl)-N’-phenylthiourea (XV), m. 110-12° (alc.). XV (0.2 g.) treated with alkali and acidified gave 0.15 g. 1-phenyl-2-thiothymine, needles, m. 202-3°. II (1.12 g.) shaken with 0.54 g. glycine in alkali until a clear solution resulted and then 10-15 min., cooled, acidified, and kept overnight at 0° gave 0.7 g. 1-carboxymethyl-2-thiothymine, needles, m. 246-7° (decomposition) (H2O). V (0.5 g.) in 5 ml. alc. added to 0.68 g. II gave 0.75 g. N1-(β-methoxy-α-methylacryloyl)-N3-phenylthiosemicarbazide (XVI), plates, m. 180-1° (decomposition). XVI (0.31 g.) warmed with 2N NaOH gave 0.28 g. 2,3-didihydro-5-(β-methoxy-α-methylvinyl)-1-phenyl-3-thio-1,2,4-triazole, m. 195-6° (alc.). II (0.935 g.) similarly added to 1.5 ml. MeOH-NH3 gave 0.85 g. N-(β-methoxy-α-methylacryloyl)thiourea (XVII), prisms, m. 163°. XVII was recovered unchanged from its solution in 2N NaOH; longer heating gave H2S and no evidence of pyrimidine formation.

《Purines, pyrimidines, and glyoxalines. VII. New syntheses of 2-thiouracils and 2-thiothymines》 provides a strategy for the preparation of materials with excellent comprehensive properties, which is conducive to broaden the application field of this compound(Ethyl 3-Ethoxy-2-Propenoate)Synthetic Route of C7H12O3.

Reference:
Bromide – Wikipedia,
bromide – Wiktionary

In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Spectrochemistry of Enols and of Enolic Derivatives, published in 1912, which mentions a compound: 1001-26-9, mainly applied to , Electric Literature of C7H12O3.

The following physical constants have been determined: β-Methoxystyrene, PhCH : CHOMe, b13 99°; d423.3 0.9894; d424.3 0.9886; d420 0.992; nα 1.55467; nβ 1.56197; nβ 1.58139; nβ 1.59962 at 24.3°; nD20 1.5639; Mα 43.52; MD 43.99; Mβ-Mα 1.71; Mτ-Mα 2.86; EM 2.50, 2.65, 0.69 and 1.24, resp. β-Ethoxystyrene, PhCH : CHOEt, b14 105°; d421.4 0.9714; d421.2 0.9716; d420 0.973; nα 1.54346; nD 1.55023; nβ 1.56838; nτ 1.58530 at 21.2°; nD20 1.5508; Mα 48.08; MD 48.57; Mβ-Mα 1.81; Mr-Mα 3.03; EM 2.46, 2.63, 0.72 and 1.30, resp. α-Methoxystyrene, MeOCPh:CH2 b18 90.5°; b. 197°; d425.1 0.9935; d425.0 0.9936; d420 0.998; nα 1.53402; nD 1.53997; nβ 1.55521; nτ 1.56918 at 25.0°; nD20 1.5422; Mα 41.95; MD 42.34; Mβ-Mα 1.38; Mr-Mα 2.28; EM 0.93, 1.00, 0.36 and 0.66, resp. α-Ethoxystyrene, EtOCPh : CH2, b18 99.6; d423.0 0.9675; d423.2 0.9673; d420 0.970; nα 1.52233; nD 1.52775; nβ 1.54198: nτ 1.55480, at 23.2°; nD20 1.5292; Mα 46.72; MD 47.13; Mβ-Mα 1.46; Mr-Mα 2.41; EM 1.10, 1.18, 0.37 and 0.68, resp. Et β-ethoxyacrylate, EtOCH : CHCO2Et, b11 83.5-4.0°; d417.8 0.9957; d418.1 0.9953; d420 0.994; nα 1.44442; nD 1.44802; nβ 1.45706; nr 1.46504, at 18.1°; nD20 1.4472; Mα 38.49; MD 38.76; Mβ-Mα 0.94; Mr-Mα 1.54. Another specimen, b10 78.5-9.0°; d417.8 0.9956; d416.7 0.9965; d420 0.994; nα 1.44497; nD 1.44852; nβ 1.45765; nτ 1.46574 16.7°; nD20 1.4470; Mα 38.48; MD 38.75; Mβ-Mα 0.95; Mr-Mα 1.55; EM (mean) 1.34, 1.41, 0.28, 0.49, resp. Et β-ethoxy-α-methylacrylate, EtOCH : CMeCO2Et, b. 195.6°; d418.4 0.9806; d421.0 0.9788; d420 0.980; nα 1.44649; nD 1.45009; nβ 1.45931; nτ 1.46760 at 21.6°; nD30 1.4508; Mα 43.10; MD 43.42; Mβ-Mα 1.08; Mr-Mα 1.70; EM 1.35, 1.45, 0.34 and 0.53, resp. Me α,α-dimethoxypropionate, (MeO)2CMeCO8Me, d419.2 1.0675; d419.35 1.0674; d420 1.067; nα 1.40915; nD 1.41127; nβ 1.41611; nτ 1.42017, at 19.35°; nD20 1.4110; Mα 34.31; MD 34.17; Mβ-Mα 0.52; Mr-Mα 0.82. Another specimen, b18 66.0-66.5°; d419.8 1.0678; d420 1.066; nα 1.41035; nD 1.41221; nβ 1.41721: nr 1.42130, at 17.6°; nD20 1.4111; Mα 34.39; MD 34.53; Mτ-Mα 0.50; Mr-Mα 0.08; EM (mean) -0.35,-0.35, -0.01 and -0.01, resp.: EM (mean) -0-24, -0.24, -1% and -1%, resp. Meα-methoxyacrylate, CH2:C(OMe)CO2Me, b1353-4°; d419 1.0701; d418.95 1.0702; 420 1.069; na1.42911; nD 1.43207; nβ 1.43960; nτ 1.44614, at 18.95°; nD20 1.4316; Ma 27.97; MD 28.14;Mβ-Mα 0.60; Mτ-Mα 0.97. Another specimen, b13 55-6°; d420.7 1.0674; d420.35 1.0677;d420 1.068; na 1.42886; nD 1.43177; nβ 1.43935; nτ 1.44585, at 20.35°; nD20 1.4316; Ma28.03; MD 28.19; Mβ-Mα, 0.59; Mτ-Mα 0.96; EM (mean) 0.04, 0.05, 0.07 and 0.14, resp. Et α,α-diethoxypropionate, (EtO)2CMeCO2Et, d417.6 0.9795; d418.2 0.9790; d420 0.978;na 1.41255; nD 1.41449; nβ 1.41949; nβ 1.42358, at 18.2°; nD20 1.4104; Mα 48.37; MD48.57; Mβ-Mα 0.72; Mτ-Mα 1.14. Another specimen, b11 81.5-2.5°; d418.2 0.97°3 d417.1 0.9792; d420 0.977; na 1.41314; nD 1.41508; nβ 1.42001; nτ 1.42419, at 17.1°; nD20 1.4101;Ma 48.42; MD 48.62; Mβ-Mα 0.71; Mτ-Mα 1.14; EM (mean) -0.09, -0.10 -0.01 and 0.02, resp.; E∑ (mean) -0.05, -0.05, -1% and -2%, resp. Et α-ethoxyacrylate,CH2: C(OEt)CO3 Et, b700 178-80°; d418.2 0.9937: d417.8 0.9940; d420 0.992; na 1.42941;0.75; Mβ-Mα 1.20. Another specimen, b13 72.5-4.5°; d417.2 0.9956; d420 0.993; na 1.42941;nD 1.43241; nβ 1.43925; nτ 1.44536, at 17.2°; nD20 1.4312; Ma 37.35; MD 37.57; Mβ-Mα 0.74; Mτ-Mα 1.20; EM (mean) 0.23, 0.24, 0.08 and 0.14, resp. The above results show that the exaltation due to a C-C conjugated linkage is increased considerably by the presence of substituents containing O if they are linked to an end (side) C at., whereas their attachment to a middle C at. produces only a slight and variable effect on the exaltation.

《Spectrochemistry of Enols and of Enolic Derivatives》 provides a strategy for the preparation of materials with excellent comprehensive properties, which is conducive to broaden the application field of this compound(Ethyl 3-Ethoxy-2-Propenoate)Electric Literature of C7H12O3.

Reference:
Bromide – Wikipedia,
bromide – Wiktionary

COA of Formula: C7H12O3. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: Ethyl 3-Ethoxy-2-Propenoate, is researched, Molecular C7H12O3, CAS is 1001-26-9, about Elimination versus diastereoselective alkylation in homochiral 2-(β-ethoxycarbonyl) acetals. Author is Caballero, Mercedes; Garcia-Valverde, Maria; Pedrosa, Rafael; Vicente, Martina.

The reaction of the homochiral 2-(β-ethoxycarbonyl)dioxolane I derived from (-)-exo-camphanediol with Me iodide in the presence of one equivalent of LDA lead to the alkylated product in very good chem. yield and poor diastereomeric excess. 2-(β-Ethoxycarbonyl)-1,3-dioxanes II derived from 2,4-pentanediol behave in a different way, whereas the diequatorial form is alkylated in excellent chem. yield, the equatorial-axial diastereoisomer III yields a mixture of alkylation and elimination products.

Different reactions of this compound(Ethyl 3-Ethoxy-2-Propenoate)COA of Formula: C7H12O3 require different conditions, so the reaction conditions are very important.

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The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: Ethyl 3-Ethoxy-2-Propenoate(SMILESS: O=C(OCC)/C=C/OCC,cas:1001-26-9) is researched.COA of Formula: C13H14ClN3. The article 《Syntheses with heterocyclic amines. XI. Reaction of 2-aminobenzothiazole with α,β-unsaturated esters. Synthesis of oxopyrimido[2,1-b]benzothiazoles》 in relation to this compound, is published in Chemische Berichte. Let’s take a look at the latest research on this compound (cas:1001-26-9).

2-Aminobenzothiazole (I) reacted with HCCCO2Me to give pyrimidobenzothiazoles II (R2 = H) and acrylate III. I and EtOCH:CHCO2Et gave only the 1:1 adduct IV. MeO2CCCCO2Me reacted with I at room temperature in 7 days to give II (R2 = CO2Me), V, and a 1:1 adduct, either VI or VII. In boiling THF, II (R2 = CO2Me), V, a compound C18H10N4O2S, and undefined products were obtained. The same reaction in boiling EtOH gave II (R2 = CO2Me).

Different reactions of this compound(Ethyl 3-Ethoxy-2-Propenoate)Name: Ethyl 3-Ethoxy-2-Propenoate require different conditions, so the reaction conditions are very important.

Reference:
Bromide – Wikipedia,
bromide – Wiktionary

Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Tetrahedron Letters called α-Alkylation of lithium dienolates derived from 3(2H)-furanones and related α,β-unsaturated carbonyl compounds, Author is Smith, Amos B. III; Scarborough, Robert M. Jr., which mentions a compound: 1001-26-9, SMILESS is O=C(OCC)/C=C/OCC, Molecular C7H12O3, Recommanded Product: 1001-26-9.

The regioselectivity was studied of the alkylation of the Li dienolates derived from 3(2H)-furanones and β-alkoxy-α,β-unsaturated carbonyl compounds by treatment with (Me2CH)2NLi in THF. Exclusive γ-alkylation was observed when the resulting dienolate contained a double bond exocyclic to the ring whereas no γ-alkylation occurred for substrates whose dienolate possessed an endocyclic or acyclic olefin. E.g., the dienolate I, derived from 2,2-dimethyl-5-isopropyl-3(2H)-furanone, reacted with MeI, CH2:CHCH2Br, Me(CH2)4I, or PhSeBr gave 75-93% γ-alkylated product whereas the dienolate derived from EtOCMe:CHCO2Et reacted with Me(CH2)4I to give 88% α-alkylated product.

Different reactions of this compound(Ethyl 3-Ethoxy-2-Propenoate)Recommanded Product: 1001-26-9 require different conditions, so the reaction conditions are very important.

Reference:
Bromide – Wikipedia,
bromide – Wiktionary

Li, Shi-ying; Zhu, Xie-fei; Zhang, Li-qiang; Zhu, Xi-feng published the article 《Atmospheric distillation of bio-oil based on different extractants》. Keywords: biomass pyrolytic fuel oil distillation extractive.They researched the compound: Ethyl 3-Ethoxy-2-Propenoate( cas:1001-26-9 ).Name: Ethyl 3-Ethoxy-2-Propenoate. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:1001-26-9) here.

In order to sep. and enrich the high value-added chems. in bio-oil, solvent extraction and distillation methods were combined to sep. and purify bio-oil. Ethyl-acetate, dichloromethane, di-Et ether and toluene were elected as extracting agents, which were mixed with bio-oil in a certain mass ratio. The 4 oil phases distilled from four extract phases were compared with bio-oil to study effects of different solvents on the yield, moisture and high value-added components of distillate. The results show that the distillate had higher yield and lower moisture content compared with that of bio-oil after the extraction and distillation Among the 4 solvents, toluene had the poorest ability to extract high value-added components of bio-oil, achieving the lowest yield of phenols of distillate. The extraction efficiency of ethyl-acetate and di-Et ether was higher than that of toluene, but the contents of high value-added components in their oil phases were lower than those of others. The relative content of guaiacol and its derivatives was 34.11% in the oil phases of dichloromethane, which was 15.52% higher than that of bio-oil, and conducive to further extract for high value-added chems. such as guaiacol and its derivatives

The article 《Atmospheric distillation of bio-oil based on different extractants》 also mentions many details about this compound(1001-26-9)Name: Ethyl 3-Ethoxy-2-Propenoate, you can pay attention to it, because details determine success or failure

Reference:
Bromide – Wikipedia,
bromide – Wiktionary

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Condensation of carboxylic acid esters with ethoxyacetylene》. Authors are Krasnaya, Zh. A.; Kucherov, V. F..The article about the compound:Ethyl 3-Ethoxy-2-Propenoatecas:1001-26-9,SMILESS:O=C(OCC)/C=C/OCC).Recommanded Product: Ethyl 3-Ethoxy-2-Propenoate. Through the article, more information about this compound (cas:1001-26-9) is conveyed.

To 7.4 g. HCO2Et was added with ice-cooling 6.4 ml. BF3.Et2O, followed by 3.5 g. EtOC:CH and, after 15 min., aqueous NaOAc to yield 31% EtOCH:CHCO2Et, b13 80-2°, n20D 1.4400. Similar reaction of EtOAc gave 29% EtOCMe:CHCO2Et (I), b7 70-2°, n20D 1.4460, m. 30-1°. Iso-BuCO2Et gave a mixture of products from which was isolated, with difficulty, some pure iso-BuC(OEt):CHCO2Et, b4 83-5°, n20D 1.4510. EtOCCH and BF3.Et2O in Et2O with ice-cooling gave in 15 mill. some EtOAc, AcCH2CO2Et, and I. Treatment of BzOMe with BF3 and EtOCCH as above gave 6% Et β-methoxycinnamate, b0.1 78-82°, n20D 1.5210. AcCH2CO2Et in this reaction gave 24% EtO2CCH:CMeCH2CO2Et, b13 124-6°; saponification with aqueous alc. KOH gave mixed cis- and trans-β-methylglutaconic acid, m. 90-107°, from which the trans form, m. 136-8°, was isolated by recrystallization from C6H6.

The article 《Condensation of carboxylic acid esters with ethoxyacetylene》 also mentions many details about this compound(1001-26-9)Recommanded Product: Ethyl 3-Ethoxy-2-Propenoate, you can pay attention to it, because details determine success or failure

Reference:
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of C7H12O3. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: Ethyl 3-Ethoxy-2-Propenoate, is researched, Molecular C7H12O3, CAS is 1001-26-9, about Anticoccidial activity of 1-phenyluracils. Author is Miller, Max W.; Chappel, Larry R..

The title compounds I (R = H, 4-ClC6H4O, 4-ClC6H4S, or 4-ClC6H4SO2; R1 = Cl or Me; R2 = H, Cl, or Me) were prepared from Et 3,3-diethoxypropionate  [10601-80-6] by known methods via 3-ethoxy-2-propenoyl isocyanate  [57796-78-8] and its reaction products (ureas) with substituted anilines, and tested against Eimeria tenella in Leghorn cockerels. 1-[3-Chloro-5-methyl-4-[(4-chlorophenyl)thio]phenyl]uracil (I; R = 4-ClC6H4S; R1 = Cl; R2 = Me) [76993-09-4] was effective at 60 ppm. I were less active than the corresponding 1-phenyl-6-azauracils, and less acidic.

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Reference:
Bromide – Wikipedia,
bromide – Wiktionary

Jaeger, Ernst G.; Seidel, Dietrich; Schade, Wolfgang published the article 《Side-results in macrocyclic synthesis: template reaction of metal ions with N-(2-aminophenyl)azomethines of β-ketoaldehydes》. Keywords: copper ketoaldehyde aminophenylazomethine; nickel ketoaldehyde aminophenylazomethine; cobalt ketoaldehyde aminophenylazomethine; azomethine aminophenyl ketoaldehyde metal complex.They researched the compound: Ethyl 3-Ethoxy-2-Propenoate( cas:1001-26-9 ).HPLC of Formula: 1001-26-9. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:1001-26-9) here.

o-NH2C6H4NHCH:C(CO2Et)C(O)Me (I) underwent a template reaction in the presence of M(OAc)2 (M-Ni,Cu,Co) in MeOH to form II which were characterized by IR, UV, and mass spectra. I was prepared from o-phenylenediamine and ethyl ethoxymethylideneacetate.

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Reference:
Bromide – Wikipedia,
bromide – Wiktionary

Asahara, Teruzo; Seno, Manabu; Tsuchiya, Mitsuru published an article about the compound: Ethyl 3-Ethoxy-2-Propenoate( cas:1001-26-9,SMILESS:O=C(OCC)/C=C/OCC ).SDS of cas: 1001-26-9. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:1001-26-9) through the article.

The Hueckel M.O. method was used to calculate energy levels of vinyl compounds; CH2:CHCN, CH2:CMeCN, Me2C:CHCN, MeCH:CHCN, EtCH:CHCN, CH2:CHCO2Et, Me2C:CHCO2Et, EtOCH:CHCO2Et, trans-BuEtCHCH2O2CCH:CHCO2CH2CHEtBu, MeCH:C(CO2Et)2, PhCH:CHCO2Et, PhCH:CHCN, PhCH:C(CO2Et)2. It is shown that the lower the energies of lowest vacant M.O. (or the higher the electron affinities) the higher the yields of dimers of the vinyl compounds from electrode reactions. Also the higher the π-bond order the lower the yields of dimers.

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Reference:
Bromide – Wikipedia,
bromide – Wiktionary