Category: 66197-72-6

Etemad Moghadam, Guita published the artcileStereoselective synthesis of E or Z α-methyl α,β-ethylenic esters from phosphonates or phosphine oxides by the Wittig-Horner reaction, COA of Formula: C5H12BrO3P, the publication is Tetrahedron (1984), 40(24), 5153-66, database is CAplus.

The reaction of α-branched aldehydes with (EtO)₂P(O)CHMeCO₂Me in THF/BuLi at low temperature leads stereoselectively to Z α-Me α,β-unsaturated esters. From a linear aldehyde, the reaction is less stereoselective, while from α,β-unsaturated ones, the E isomers are predominantly formed in good yields. From Ph₂P(O)CHMeCO₂Me, E α-Me α,β-unsaturated esters are stereoselectively formed either in DMF/Me₃COK or under phase transfer conditions, regardless of the starting aldehyde. This reagent can thus advantageously replace the corresponding P-ylide.

Tetrahedron published new progress about 66197-72-6. 66197-72-6 belongs to bromides-buliding-blocks, auxiliary class Aliphatic Chain, name is Diethyl (bromomethyl)phosphonate, and the molecular formula is C5H12BrO3P, COA of Formula: C5H12BrO3P.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

McKenna, Charles E. published the artcileFunctional selectivity in phosphonate ester dealkylation with bromotrimethylsilane, Category: bromides-buliding-blocks, the publication is Journal of the Chemical Society, Chemical Communications (1979), 739, database is CAplus.

The dealkylation reaction of Me₃SiBr with mixed alkyl carboxylate-phosphonate esters RP(O)(OEt)₂ (R = EtO₂C, EtO₂CCH₂, EtO₂CCH₂CH₂, MeO₂CCH₂CH₂) at 25° is highly selective for P-O silyl dealkylation. The reaction was extended to the selective preparation of trimethylsilyl amido-, alkynyl- and iodoalkylphosphonates in high yield, giving a simple route to phosphonic acids via hydrolysis of the phosphonates with neutral H₂O.

Journal of the Chemical Society, Chemical Communications published new progress about 66197-72-6. 66197-72-6 belongs to bromides-buliding-blocks, auxiliary class Aliphatic Chain, name is Diethyl (bromomethyl)phosphonate, and the molecular formula is C5H12BrO3P, Category: bromides-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Bradley, Mildred J. published the artcileThe chemistry of Borazine. II. The synthesis of N,N’,N”-trimethyl-B,B’,B”-trialkoxyborazines and N,N’,N”-trimethyl-B,B’,B”-triphenoxyborazine, COA of Formula: C5H12BrO3P, the publication is Journal of the American Chemical Society (1959), 2635-8, database is CAplus.

cf. C.A. 53, 3240a. When alkali alkoxides or phenoxides reacted with N,N’,N”-trimethyl-B,B’,B”-trichloroborazine (I) in dry benzene, the Cl on the B were replaced by alkoxy or phenoxy groups. Thus, 0.45 mole I in 100 ml. benzene was treated during 2 hrs. with 0.15 mole Na alkoxide, the mixture refluxed 8-12 hrs., stirred over-night, concentrated in vacuo, and the residue distilled The best yields were obtained at exact stoichiometry. The products reacted immediately with either water or alcs. The following were prepared: N,N’,N”-trimethyl-B,B’,B”-trimethoxyborazine, b_0.07 62-65°, n²³_D 1.4610; N,N’,N”-trimethyl-B,B’,B”-triethoxyborazine, b_0.10 79.5-80.5%, n^22.5_D 1.4540; N,N’,N”-trimethyl-B,B’,B”-triisopropoxyborazine, b_0.10 85-87°, n²³_D 1.4460; N,N’,N”-trimethyl-B,B’,B”-tripropoxyborazine, b_0.15 101-3°, n²²_D 1.4561; N,N’,N”-trimethyl-B,B’,B”-tributoxyborazine, b_0.30 130-4°, n²³_D 1.4572; N,N’,-N”-trimethyl-B,B’,B”-tri-tert-butoxyborazine, b_0.52 120-5°, m. 84-7°; N,N’,N”-trimethyl-B,B’,B”-triphenoxyborazine, b_0.07 185-7°, m. 81-4°.

Journal of the American Chemical Society published new progress about 66197-72-6. 66197-72-6 belongs to bromides-buliding-blocks, auxiliary class Aliphatic Chain, name is Diethyl (bromomethyl)phosphonate, and the molecular formula is C5H12BrO3P, COA of Formula: C5H12BrO3P.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Maeda, Dean Y. published the artcileDiscovery of 2-[5-(4-Fluorophenylcarbamoyl)pyridin-2-ylsulfanylmethyl]phenylboronic Acid (SX-517): Noncompetitive Boronic Acid Antagonist of CXCR1 and CXCR2, Related Products of bromides-buliding-blocks, the publication is Journal of Medicinal Chemistry (2014), 57(20), 8378-8397, database is CAplus and MEDLINE.

The G protein-coupled chemokine receptors CXCR1 and CXCR2 play key roles in inflammatory diseases and carcinogenesis. In inflammation, they activate and recruit polymorphonuclear cells (PMNs) through binding of the chemokines CXCL1 (CXCR1) and CXCL8 (CXCR1 and CXCR2). Structure-activity studies that examined the effect of a novel series of S-substituted 6-mercapto-N-phenyl-nicotinamides on CXCL1-stimulated Ca²⁺ flux in whole human PMNs led to the discovery of 2-[5-(4-fluorophenylcarbamoyl)pyridin-2-ylsulfanylmethyl]phenylboronic acid (SX-517), a potent noncompetitive boronic acid CXCR1/2 antagonist. SX-517 inhibited CXCL1-induced Ca²⁺ flux (IC₅₀ = 38 nM) in human PMNs but had no effect on the Ca²⁺ flux induced by C5a, fMLF, or PAF. In recombinant HEK293 cells that stably expressed CXCR2, SX-517 antagonized CXCL8-induced [³⁵S]GTPγS binding (IC₅₀ = 60 nM) and ERK1/2 phosphorylation. Inhibition was noncompetitive, with SX-517 unable to compete the binding of [¹²⁵I]-CXCL8 to CXCR2 membranes. SX-517 (0.2 mg/kg iv) significantly inhibited inflammation in an in vivo murine model. SX-517 is the first reported boronic acid chemokine antagonist and represents a novel pharmacophore for CXCR1/2 antagonism.

Journal of Medicinal Chemistry published new progress about 66197-72-6. 66197-72-6 belongs to bromides-buliding-blocks, auxiliary class Aliphatic Chain, name is Diethyl (bromomethyl)phosphonate, and the molecular formula is C5H12BrO3P, Related Products of bromides-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Chun, Yong-Jin published the artcileSynthesis of ω-phthalimidoalkylphosphonates, Application of Diethyl (bromomethyl)phosphonate, the publication is Synthesis (1994), 909-10, database is CAplus.

Di-Et phthalimidoalkylphosphonates I (n = 1,2,3,4) were synthesized by the reaction of di-Et bromoalkylphosphonates with N-(tert-butyldimethylsilyl)phthalimide in the presence of tetrabutylammonium fluoride.

Synthesis published new progress about 66197-72-6. 66197-72-6 belongs to bromides-buliding-blocks, auxiliary class Aliphatic Chain, name is Diethyl (bromomethyl)phosphonate, and the molecular formula is C5H12BrO3P, Application of Diethyl (bromomethyl)phosphonate.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Logusch, Eugene W. published the artcileA simple preparation of S-alkyl homocysteine derivatives: S-phosphonomethyl homocysteines as inhibitors of glutamine synthetase, Name: Diethyl (bromomethyl)phosphonate, the publication is Tetrahedron Letters (1988), 29(47), 6055-8, database is CAplus.

A facile synthesis of S-alkyl homocysteines is described which features the coupling of sodium alkyl thiolates with Me 4-bromo-2-phthalimidobutyrate, followed by hydrolysis. This approach is exemplified by the synthesis of H₂O₃PCH₂SO₂CH₂CH₂CH(NH₂)CO₂H, a new inhibitor of the enzyme glutamine synthetase.

Tetrahedron Letters published new progress about 66197-72-6. 66197-72-6 belongs to bromides-buliding-blocks, auxiliary class Aliphatic Chain, name is Diethyl (bromomethyl)phosphonate, and the molecular formula is C5H12BrO3P, Name: Diethyl (bromomethyl)phosphonate.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Griffin, C. E. published the artcilePhosphoryl stretching frequency correlation for phosphonic acid derivatives, Quality Control of 66197-72-6, the publication is Chemistry & Industry (London, United Kingdom) (1960), 1058-9, database is CAplus.

A plot of Σ σ* (Taft substituent constants) vs. γ_PO (as films in CS₂ or CCl₄) for 19 phosphonates [RP(O)XY] (I) gave a linear relationship; a least squares treatment of the data gave γ_PO = 16.80 Σσ* + 1198. The following I were studied (X = Y = OEt) (R given): Me, Et, Pr, Bu, n-C₆H₁₃, CH₂:CH, CH₂:CHCH₂, PhCH₂, Ph, ClCH₂, Cl₂CH, CCl₃ (II), BrCH₂, HOCH₂, AcCH₂. Also I (R, X, and Y given): Me, OMe, OMe; Me, OEt, NMe₂; Me, NMe₂, NMe₂ (III); Ph, H, OEt. The average deviation between calculated and observed frequencies was ±4 cm.^-1; the only significant deviation occurred with II and III, and may have arisen through disturbance of the normal inductive effects of the substituents by field effects. Major deviations from the linear relationship also occurred with frequency values obtained in the presence of H-bonding solvents. The following σ* values were tentatively assigned: (CH₂)₂CO₂Et, 0.39; (CH₂)₃CO₂Et, 0.39; NEt₂, 0.68.

Chemistry & Industry (London, United Kingdom) published new progress about 66197-72-6. 66197-72-6 belongs to bromides-buliding-blocks, auxiliary class Aliphatic Chain, name is Diethyl (bromomethyl)phosphonate, and the molecular formula is C5H12BrO3P, Quality Control of 66197-72-6.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Gajda, Tadeusz published the artcilePreparation of diethyl 1-bromoalkylphosphonates, HPLC of Formula: 66197-72-6, the publication is Phosphorus, Sulfur and Silicon and the Related Elements (1990), 53(1-4), 327-31, database is CAplus.

RCHBrP(O)(OEt)₂ (R = H, Me, Et, Pr, Ph) were prepared by treating RCH(OH)P(O)(OEt)₂ with Ph₃P and CBr₄ in refluxing C₆H₆, or with Ph₃PBr₂ and pyridine in MeCN at room temperature Yields of 22-67% were obtained.

Phosphorus, Sulfur and Silicon and the Related Elements published new progress about 66197-72-6. 66197-72-6 belongs to bromides-buliding-blocks, auxiliary class Aliphatic Chain, name is Diethyl (bromomethyl)phosphonate, and the molecular formula is C5H12BrO3P, HPLC of Formula: 66197-72-6.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Cal, Dariusz published the artcileA convenient synthesis of ω-hydrazinoalkylphosphonic acids, Recommanded Product: Diethyl (bromomethyl)phosphonate, the publication is Tetrahedron Letters (2016), 57(1), 126-128, database is CAplus.

A simple, efficient, and cost effective method has been developed for the synthesis of ω-hydrazinoalkylphosphonic acids via the nucleophilic substitution reaction of di-Et ω-haloalkylphosphonates and hydrazine using mild reaction conditions, followed by hydrolysis with hydrochloric acid.

Tetrahedron Letters published new progress about 66197-72-6. 66197-72-6 belongs to bromides-buliding-blocks, auxiliary class Aliphatic Chain, name is Diethyl (bromomethyl)phosphonate, and the molecular formula is C5H12BrO3P, Recommanded Product: Diethyl (bromomethyl)phosphonate.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Cade, J. A. published the artcileMethylenediphosphonates and related compounds. I. Synthesis from methylene halides, Synthetic Route of 66197-72-6, the publication is Journal of the Chemical Society (1959), 2266-72, database is CAplus.

Two established methods for preparing Et methylenediphosphonates were extended to allyl systems, but with limited success. Only 1 method gave a product suitable for the preparation of resins for complex formation with metals. The yield of saturated alkyl esters was improved, and some new esters containing P were described. Diethyl chloromethylphosphonate (I) was prepared from the acid chloride, which was obtained from PCl₃ and paraformaldehyde. AlBr₃ (280 g.) and 272 g. PBr₃ treated portionwise with 500 cc. CH₂Br₂ with cooling, the mixture refluxed 2 hrs., the bulk of the CH₂Br₂ distilled, the residual sirup solidified, added in lumps to 1.2 l. CH₂Cl₂, at -20°, 160 cc. H₂O added dropwise, the precipitate collected, washed, the filtrate and washings distilled and degassed and the residue distilled gave pure bromomethylphosphonyl dibromide (II), b₇ 118-20°, n²⁰_D 1.512. Na (4.6 g.) in 100 cc. CH₂:CHCH₂OH treated at 0° with 32.4 g. diallyl phosphite, 26.8 g. CH₂I₂ added during 0.5 hr., the solution warmed 2 hrs. at 60°, the bulk of the alc. removed, the residual volatile matter removed at 60°/0.1 mm., the combined distillate and trap contents treated with H₂O, the insoluble material dried, and distilled gave 16 g. CH₂:CHCH₂I, b. 98-102°; S-thiuronium picrate, m. 154-6°, and 4.2 g. CH₂I₂, b₂₅ 79-82°, d²⁰ 3.32. The pasty residue (43 g.) washed with 1:1 Me₂CO-Et₂O and recrystallized gave 15 g. symmetrical di-Na diallyl methylenediphosphonate (III), m. 209-11° (MeOH-Et₂O). The washings treated with H₂O and the oil distilled gave 6.5 g. diallyl allylphosphonate (IV), b_0.5 75-8°, n²⁰_D 1.4614. Na diallyl phosphonate prepared as described above from 4.6 g. Na and 32.4 g. diallyl H phosphite in allyl alc., the dry product in 200 cc. PhMe distilled with removal of 100 cc. PhMe, the process repeated, the solution treated during 0.5 hr. at 0° with 17.5 g. CH₂Br₂ gave III. The process was unreliable. CH₂Cl₂ gave similar results, and addition of quinol also did not give reliable reactions. III (9 g.) refluxed 3 hrs. with 80 cc. constant boiling HBr, the mixture distilled 3.8 g. allyl bromide removed, the residual sirup treated with more acid and 4.9 g. NaBr removed, the filtrate evaporated, treated with 50 cc. alc., filtered, and evaporated gave 1.5 g. methylenediphosphonic acid, m. 201° (tert-BuOH). Et₃PO₄ (425 g.) and 311 g. CH₂I₂ were heated together under a column. At 148° a reaction set in and the temperature rose spontaneously to 200°; a liquid distilled and the temperature remained at 190-200° until distillation ceased. The residue on repeated distillation gave 263.6 g. diethyl ethylphosphonate (V), b_0.1 43-5°, n²⁰_D 1.4150, 56.3 g. diethyl iodomethylphosphonate (VI), b_0.2 90-100°, 81.2 g. tetraethyl methylenediphosphonate (VII), b_0.5 122-8°, n²⁰_D 1.4300, and mixed fractions and residues. The primary distillate was combined and after treatment with dilute HCl and drying gave 68.6 g. EtI, b. 70-3°, 18.9 g. mixed fraction, and 45.8 g. recovered CH₂I₂. Et₃PO₄ (183 g.) and 134 g. CH₂I₂ mixed at 185°, the rate of addition adjusted so that distillation occurred steadily and heating continued 10 min. gave products consisting of 128 g. EtI, 27.5 g. crude V, 82 g. crude VI, and 32.3 g. residue. The foregoing procedure with 83 g. Et₃PO₄ and 200 g. CH₂I₂ gave 74 g. EtI, 68 g. CH₂I₂, and 120 g. VI. The residue of 11 g. contained no iodine but pure VII was not obtained from it. Et₃PO₄ (33.2 g.) and 27.8 g. VI heated to 160° and finally to 180° (when liquid began to distil), and the temperature held 1 hr. at 195° gave a distillate containing 2 g. EtI contaminated with Et₃PO₄. The reaction mixture gave 4.6 g. forerun containing Et₃PO₄, 29.0 g. V, and 13.5 g. VI. Pure VII was not obtained from the residues. Et₃PO₄ (33.9 g.) added at 220° to 37.6 g. VI (the final temperature was 240°) gave a product containing 17.6 g. EtI and 23 g. VII; very little VI was recovered. Et₃PO₄ (40 g.) added in 1 hr. to 44 g. diethyl bromomethylphosphonate at 220-35° (as described above for VI) gave after the usual work up 14.5 g. EtBr, 19 g. V, and 263 g. VII. Et₃PO₄ (60 g.) added to 60 g. I at such a rate that the temperature never fell below 220° (14 hrs.) 4 g. crude EtCl collected in a trap, the mixture heated a further 2 hrs., and distilled afforded 36.1 g. V, and 40.8 g. of a residue which decomposed on further heating. Methylenediphosphonic acid was not obtained by hydrolysis of this residue. (CH₂:CHCH₂)₃PO₄ (VIII) (60.6 g.) and 26.8 g. CH₂I₂ heated as above with vigorous reaction beginning at 130° and the liquid distilled (after 2 hrs. heating at 170-85° distillation ceased) gave 14.2 g. CH₂:CHCH₂I, b. 98-102°, 7.5 g. CH₂I₂, 25.5 g. IV, 12 g. diallyl iodomethylphosphonate (IX), 4 g. tetraallyl methylenediphosphonate (X), various mixed fractions, and 18 g. residue. The maximum yield of X was 12%. In one experiment 8% IX was isolated. VIII (40.4 g.) and 81 g. CH₂I₂ gave 24.8 g. IX. The following compounds were prepared by the modified procedure (compound, % yield, b.p./mm., n_D, and d given): VIII, 90-2, 34°/0.06, 1.4589, 0.999; diallyl phosphite, 70-6, 40°/0.07, 1.4478, 1.087; IV, 82, 54°/0.08, 1.4622, 1.046; diallyl chloromethylphosphonate, 60, 83°/0.15, 1.4665, 1.175; diallyl bromomethylphosphonate, 72, 76°/0.1, 1.4842, 1.373; IX, 8(41), 102°/0.1, 1.5015, 1.552; X, 12, 142°/0.1, 1.4675, 1.132; diethyl bromomethylphosphonate, 82, 121°/15, 1.4595, 1.432; tetrabutyl methylenediphosphonate, 45, 150-5°/5 × 10^-4, 1.4455, 1.041; tetrabutyl ethylenediphosphonate, 51, 175-8°/5 × 10^-4, 1.4484, 1.035.

Journal of the Chemical Society published new progress about 66197-72-6. 66197-72-6 belongs to bromides-buliding-blocks, auxiliary class Aliphatic Chain, name is Diethyl (bromomethyl)phosphonate, and the molecular formula is C5H12BrO3P, Synthetic Route of 66197-72-6.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary