Category: 4543-95-7

Wang, Yu-Huang published the artcileReductive hydroxyalkylation/alkylation of amines with lactones/esters, COA of Formula: C8H19NO, the publication is Organic & Biomolecular Chemistry (2012), 10(32), 6504-6511, database is CAplus and MEDLINE.

We have developed a one-pot method for the direct intermol. reductive hydroxyalkylation or alkylation of amines using lactones or esters as the hydroxyalkylating/alkylating reagents. The method is based on the in situ amidation of lactones/esters with DIBAL-H-amine complex (for primary amines) or DIBAL-H-amine hydrochloride salt complex (for secondary amines), followed by reduction of the amides with an excess of DIBAL-H. Different from the reduction of Weinreb amides with DIBAL-H where aldehydes are formed, the reduction of the in situ formed Weinreb amides yielded amines. Moreover, this method is not limited to Weinreb amides, instead, it also works for other amides in general. A plausible mechanism is suggested to account for the outcome of the reactions.

Organic & Biomolecular Chemistry published new progress about 4543-95-7. 4543-95-7 belongs to alcohols-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Alcohol, name is 4-(Butylamino)butan-1-ol, and the molecular formula is C6H5F4NO3S, COA of Formula: C8H19NO.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Hsin, Ling-Wei published the artcileSynthesis and biological activity of fluoro-substituted pyrrolo[2,3-d]pyrimidines: the development of potential positron emission tomography imaging agents for the corticotropin-releasing hormone type 1 receptor, COA of Formula: C8H19NO, the publication is Bioorganic & Medicinal Chemistry Letters (2000), 10(8), 707-710, database is CAplus and MEDLINE.

A series of fluoro-substituted 4-(dialkylamino)pyrrolo[2,3-d]pyrimidines was synthesized and their binding affinity for corticotropin-releasing hormone type 1 receptor (CRHR₁) was investigated. Thus, N-ethyl-N-(4-fluorobutyl)-2,5,6-trimethyl-7-(2,4,6-trimethylphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine and N-(4-fluorobutyl)-2,5,6-trimethyl-N-propyl-7-(2,4,6-trimethylphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine possessed very high CRHR₁ affinity (K_i=3.5, 0.91 nM, resp.). They are promising candidates for the development of ¹⁸F-containing non-peptide PET radioligands for CRHR₁.

Bioorganic & Medicinal Chemistry Letters published new progress about 4543-95-7. 4543-95-7 belongs to alcohols-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Alcohol, name is 4-(Butylamino)butan-1-ol, and the molecular formula is C8H19NO, COA of Formula: C8H19NO.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Ishidate, Motoi Jr. published the artcileChromosome tests with 134 compounds on Chinese hamster cells in vitro – a screening for chemical carcinogens, Formula: C8H19NO, the publication is Mutation Research, Genetic Toxicology Testing (1977), 48(3-4), 337-53, database is CAplus.

Chromosomal aberration tests in vitro were carried out on Chinese hamster cells grown in culture with various chems., including carcinogenic N-nitroso compounds and their related derivatives, food additives, medical drugs, pesticides and other chems. commonly used in laboratories or industries. Of the 134 chems. tested, 63 gave neg. results in the test system even with doses at which the cell growth was markedly inhibited. Nearly all compounds known to be mutagenic in bacteria were also pos. in this system. Both urethane [51-79-6] and diethylstilbestrol [56-53-1] were pos., even though they are known to be carcinoenic but not mutagenic in bacteria. Compounds such as N-alkyl-N’-nitrogunidines, barbital [57-44-3], Na benzoate [532-32-1], saccharin sodium [128-44-9], NaNO2, NaNO3, and 4-aminoquinoline-1-oxide [2508-86-3] were pos. in the chromosome tests, but they have not been conclusively tested for their carcinogenicity.

Mutation Research, Genetic Toxicology Testing published new progress about 4543-95-7. 4543-95-7 belongs to alcohols-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Alcohol, name is 4-(Butylamino)butan-1-ol, and the molecular formula is C8H19NO, Formula: C8H19NO.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Lunsford, Carl D. published the artcilePreparation of 4-amino-1-butanols and some derivatives of pharmacological interest, Synthetic Route of 4543-95-7, the publication is Journal of Organic Chemistry (1957), 1225-8, database is CAplus.

The 4-alkylamino (I) and 4-dialkylamino-1-butanols (II) were prepared by LiAlH₄ reduction of the product from equimolar amounts of butyrolactone (III) and a primary or secondary amine. Use of 2 moles amine resulted in N,N’-symmetrically substituted putrescines. The 3-aminopropanols were prepared similarly by the substitution of propiolactone (IV) for III. The 3,4,5-trimethoxybenzoates, the diphenylacetates, and the benzhydryl ethers of some of the II and of N-3-hydroxypropylpiperidine (V) and their quaternary salts were prepared and their pharmacol. activity examined III (68.8 g.) and 104 g. NHBu₂ heated 4 hrs. at 150°, the mixture in Et₂O added dropwise to 25.1 g. LiAlH₄ in 300 ml. Et₂O, refluxed 1 hr., the excess hydride decomposed with H₂O, the mixture filtered, the filtrate concentrated, and the residue fractionated gave 97.4 g. II (di-Bu derivative), b₄₀ 172-5°. When the starting amine refluxed below 150°, the reaction with III was carried out at reflux until the pot temperature reached 150° where it was kept 4 hrs.; when the starting amine was NHMe₂ or NHEt₂ the reaction was run in a sealed tube at 150°. The following results were obtained in preparing I and II, RR’N(CH₂)₄OH (RR’N, b.p./mm., % yield, n²⁵_D, and d. given): BuNH, 80-0.5°/0.2, 44, 1.4503, 0.8900; PhCH₂NH, 137-40°/0.8, 56, 1.5288, -; Me₂N, 98°/22, 56, 1.4390, 0.8798; Et₂N, 83-5°/0.8, 80, 1.4460, 0.8653; Pr₂N, 114°/4.3, 77, 1.4472, 0.8723; Bu₂N, 135°/0.3, 62, 1.4502, 0.8616; (CH₂)₅N, 75°/0.2, 71, 1.4733, 0.9471. III (172 g.) and 180 g. NHMe₂ heated 4 hrs. at 200° in 2 sealed tubes, the mixture heated to 125° in vacuo, and reduced with 125 g. LiAlH₄ gave 86 g. N,N,N’,N’-tetramethylputrescine, b₂₈ 78-80°, n²⁵_D 1.4261, d₂₇ 0.7864; dipicrate, m. 203-5°. There was also a higher-boiling fraction which proved to be II (di-Me derivative). Similarly, 17.2 g. III, 34 g. piperidine, and 11.4 g. LiAlH₄ gave 25 g. 1,4-piperidinobutane, b_0.3 117-18°; HCl salt, m. above 300°. IV (28.4 g.) added dropwise to 34 g. piperidine at 5-10° and towards the end of the addition the temperature allowed to rise to 20°, the sirup dissolved in 100 ml. tetrahydrofuran and reduced as above with 11.4 g. LiAlH₄, and the product fractionally distilled gave 31 g. V, b₂₅ 117-22°, n²⁵_D 1.4750, d²⁹₂₅ 0.9585; 3,4,5-trimethoxybenzoate hydrochloride, 51% yield, m. 169-71°; diphenylacetate nitrate, 90% yield, m. 115-16°(H₂O); diphenylacetate-MeI, m. 144.5-46° (alc.); diphenylacetate-MeBr, m. 165-6° (iso-PrOH). The 3,4,5-trimethoxybenzoic acid and diphenylacetic acid esters of I and II were prepared from the acid chloride with I or II. 3,4,5-Trimethoxybenzoyl chloride (23 g.) in 50 ml. CHCl₃ refluxed 2 hrs. with 11.7 g. II (di-Me derivative), the residue partitioned between dilute HCl and Et₂O, the acid extract made alk. and extracted with Et₂O, dried, and separated gave 26 g. II 3,4,5-trimethoxybenzoate-HCl, m. 122-4°. The quaternary salts of both the esters and the ethers were prepared by addition of MeI or MeBr to the base in Et₂O. When crystallization did not occur spontaneously the Et₂O was decanted and the oil crystallized from a suitable solvent. The following RCO₂(CH₂)NR”R’₂X were thus formed (R, R’, R”, X, m.p., and % yield given): 3,4,5-(MeO)₃C₆H₂, Me, H, Cl, 122-4°, 75; 3,4,5-(MeO)₃C₆H₂, Et, H, Cl, 140-1°, 97; 3,4,5-(MeO)₃C₆H₂, Et, Me, I, 142.5-44°, 78; 3,4,5-(MeO)₃C₆H₂, Pr, H, Cl, 118-19°, 35; 3,4,5-(MeO)₃C₆H₂, Pr, Me, I, 115-17°, 37; 3,4,5-(MeO)₃C₆H₂, [R’₂ = (CH₂)₅], H, Cl, 156.5-57°, 83; 3,4,5-(MeO)₃C₆H₂, [R’₂ = = (CH₂)₅], Me, I, 171-3°, 35; Ph₂CH, [R’₂ = (CH₂)₅], H, Cl, 148-50°, 53; Ph₂CH, [R’₂ = (CH₂)₅], Me, I, 69-72°, 34; Ph₂CH, [R’₂ = (CH₂)₅], Me, Br, 144-6°, 61. Benzhydryl bromide (49.3 g.) and 69.2 g. 4-dipropylamino-1-butanol in 200 ml. PhMe refluxed 15 hrs., concentrated in vacuo, partitioned between 5% NaOH and Et₂O, the extract then extracted with 5% HCl, this made alk. with 20% NaOH, and extracted with Et₂O gave 39 g. unchanged II (alkyl = Pr) and 26 g. N-(4-benzhydryloxybutyl)-N,N-dipropylamine, b_1.5 175-7°. The following PhRCHO(CH₂)₄NR’R’ were similarly prepared (R, R’R’N, salt, b.p./mm., or m.p., and % yield given): Ph, Et₂N, -, 202-5°/1.4, 68; Ph, Et₂N, HBr, 109-11.5°, -; Ph, Et₂N, MeBr, 120-1°, 81; Ph, Bu₂N, -, 192-4°/1.5, 38; Ph, (CH₂)₅N, -, 217-20°/2.0, 46; Ph, (CH₂)₅N, HCl, 135.5-37°, -; Ph, (CH₂)₅N, MeI, 126-6.5°, 73; p-ClC₆H₄, Et₂N, citrate, 123-4°, 62.

Journal of Organic Chemistry published new progress about 4543-95-7. 4543-95-7 belongs to alcohols-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Alcohol, name is 4-(Butylamino)butan-1-ol, and the molecular formula is C8H19NO, Synthetic Route of 4543-95-7.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Estrada, Ernesto published the artcileAutomatic extraction of structural alerts for predicting chromosome aberrations of organic compounds, COA of Formula: C8H19NO, the publication is Journal of Molecular Graphics & Modelling (2006), 25(3), 275-288, database is CAplus and MEDLINE.

We use the topol. sub-structural mol. design (TOPS-MODE) approach to formulate structural alert rules for chromosome aberration (CA) of organic compounds First, a classification model was developed to group chems. as active/inactive respect to CA. A procedure for extracting structural information from orthogonalized TOPS-MODE descriptors was then implemented. The contributions of bonds to CA in all the mols. studied were then generated using the orthogonalized classification model. Using this information we propose 22 structural alert rules which are ready to be implemented in expert systems for the automatic prediction of CA. They include, among others, structural alerts for N-nitroso compounds (ureas, urethanes, guanidines, triazines), nitro compounds (aromatic and heteroaromatic), alkyl esters or phosphoric acids, alkyl methanesulfonates, sulfonic acids and sulfonamides, epoxides, aromatic amines, azaphenanthrene hydrocarbons, etc. The chemico-biol. anal. of some of the structural alerts found is also carried out showing the potential of TOPS-MODE as a knowledge generator.

Journal of Molecular Graphics & Modelling published new progress about 4543-95-7. 4543-95-7 belongs to alcohols-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Alcohol, name is 4-(Butylamino)butan-1-ol, and the molecular formula is C8H19NO, COA of Formula: C8H19NO.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Grigg, R. published the artcileTransition metal-catalyzed N-alkylation of amines by alcohols, SDS of cas: 4543-95-7, the publication is Journal of the Chemical Society, Chemical Communications (1981), 611-12, database is CAplus.

Primary and secondary alcs. alkylate primary and secondary alkyl and heterocyclic amines in the presence of Rh, Ir and Ru compounds at ≤100° to give monoalkylated products. Thus, BuNH₂ was refluxed 8 h in MeOH with RhH(PPh₃)₄ (I) to give 98% BuNHMe. Heterocyclic rings were prepared by inter- or intramol. alkylation. E.g., BuN(CH₂)₄OH was refluxed in dioxane with I to give 56% N-butyltetrahydropyrrole.

Journal of the Chemical Society, Chemical Communications published new progress about 4543-95-7. 4543-95-7 belongs to alcohols-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Alcohol, name is 4-(Butylamino)butan-1-ol, and the molecular formula is C8H19NO, SDS of cas: 4543-95-7.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Corey, E. J. published the artcileA study of the formation of halo amines and cyclic amines by the free radical chain decomposition of N-haloammonium ions (Hofmann-Löffler reaction), Recommanded Product: 4-(Butylamino)butan-1-ol, the publication is Journal of the American Chemical Society (1960), 1657-68, database is CAplus.

cf. Wawzonek and Thelen, CA 44, 9444g; W., et al., CA 46, 2058a. Cyclization of N-halo amines to pyrrolidines by heating in H₂SO₄ was a free-radical chain reaction which was initiated by ultraviolet light or by persulfate and (or) ferrous ions and was inhibited by O. The reaction was acid-catalyzed; the acid most likely accelerated chain-propagation or retarded chain-termination. Five-membered rings were formed almost exclusively. The ease of removal of H from the δ-C involved was tertiary > secondary > primary; there was virtually no competition when different types were present. No pyrrolidines were obtained when the δ-H was tertiary; solvolysis of the intermediate δ-Cl amine apparently predominated. Irradiation of dibutylchloramine in H₂SO₄ did not liberate Cl ion, indicating that a δ-Cl amine was an intermediate. The exptl. data support the Wawzonek mechanism (loc. cit.). For isotope effect and stereochem. studies, some deuteriated amines were synthesized. Valerolactone [66.2% L-(-)isomer, 33.8% D(+)-isomer] (26 g.) and liquid MeNH₂ under N for 7 days in a sealed tube gave 100% crude N-methyl-4-hydroxyvaleramide (I), which with LiAlH₄ gave 39% N-methyl-4-hydroxyamylamine (II), b₈ 97-8°, n²⁵_D 1.4460, [α]²²_D 4.23° (c 10, EtOH). II and p-MeC₆H₄SO₂Cl in pyridine gave 82% (-)-N-methyl-N-(4-p-toluenesulfonoxyamyl)-p-toluenesulfonamide (III), [α]²⁰_D -2.73° (c 10, CHCl₃). Reduction of III with LiAlD₄ gave 73% (-)-methylamylamine-4-d (IV), n²⁵_D 1.4068, α²⁰_D -0.135 ± 0.03° (1 dm.). Cyclization of IV (Coleman, et al., Organic Syntheses Collective volume III, 159(1955)) gave 43% optically inactive 1,2-dimethylpyrrolidine; analysis of the picrate showed 4.88 atom-% D, corresponding to an isotope effect (k_H/k_D) of 3.54 ± 0.5. As a check on the anal. data, 1,2-dimethylpyrrolidine-2-d (V) was synthesized and the isotope effect determined from infrared absorption. 1,2-Dimethyl-2-pyrroline (30 g.), neutralized with 3N HCl and treated with aqueous KCN gave 79% 1,2-dimethyl-2-cyanopyrrolidine (VI), b₃₆ 83-4°, n^22.5_D 1.4447; picrate m. 154.5-6.5° (C₆H₆EtOH). Reduction of VI with LiAlD₄ gave 72% V, b. 94-5°, n²⁵_D 1.4203. From the absorption band at 2040 cm.^-1, the amount of V present in the product from cyclization of IV was determined, giving an isotope effect of 3.42 ± 0.5. N-Butyl-2-pyrrolidone was hydrolyzed with Ba(OH)₂ to 4-butylaminobutyric acid, m. 145-6° (MeOH-Et₂O), which on reduction with LiAlD₄ gave 36% 4-butylaminobutanol-1,1-d₂ (VII), b₁₆ 131-2°, n^24.5_D 1.4508. VII was converted to N-butyl-N-(4-p-toluenesulfonoxybutyl)-p-toluenesulfonamide-4,4-d₂ (oil), which on reduction with LiAlD₄ gave 66% dibutylamine-4,4-d₃ (VIII), b₄₆ 76-7°; HCl salt m. 292-6° (decomposition). Cyclization of VIII after chlorination gave N-butylpyrrolidine, b₅₅ 75°; the infrared absorption showed bands corresponding to N-CD₂– and C-CD₃ groups. The isotope effect for this cyclization, calculated from infrared absorption, was approx. 2.6. Other amine derivatives synthesized for study were as follows. Isocaproyl chloride and amylamine gave 78% N-amylisocaproamide, b_0.35 103-5°, n²²_D 1.4481, which on reduction with LiAlH₄ gave amylisohexylamine, b₁₆ 99-102°, n²²_D 1.4295, yield 81%; HBr salt m. 291-2.5° (decomposition) (dioxane-EtOH). Attempted cyclization of the N-Cl derivative gave no tertiary amines. Similar failure was experienced with butyl-sohexylamine, although HCl was evolved during heating. The product amounted to 0.147 g., b₁₄ about 75°, n^21.8_D 1.4378; HBr salt (IX) m. 162-4° (dioxane). IX was not identical with N-butyl-2,2-dimethylpyrrolidine-HBr nor with N-isohexylpyrrolidine-HBr, which was prepared for comparison by LiAlH₄ reduction of N-isocaproylpyrrolidine [N-isohexylpyrrolidine b₁₅ 79-82°, n²⁵_D 1.4428; HBr salt m. 179-80° (dioxane)].

Journal of the American Chemical Society published new progress about 4543-95-7. 4543-95-7 belongs to alcohols-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Alcohol, name is 4-(Butylamino)butan-1-ol, and the molecular formula is C8H19NO, Recommanded Product: 4-(Butylamino)butan-1-ol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Asahara, Teruzo published the artcileTelomerization of ethylene and carbon tetrachloride initiated by amines, Quality Control of 4543-95-7, the publication is Bulletin of the Japan Petroleum Institute (1965), 35-40, database is CAplus.

cf. CA 62, 1554a. In this reaction, strongly basic amines are excellent initiators. Primary amines are more effective than secondary or tertiary structures, and branched amines are inferior to n-amines. Alkanolamines are also excellent initiators. The experiments were carried out in a stainless steel autoclave in the absence of metallic salts. tert-Butanol is a preferred solvent for this reaction. Generally, the higher the dielec. constant of the hydroxylic solvent, the greater the yield of telomer. Aprotic solvents show no such regular influence. 13 references.

Bulletin of the Japan Petroleum Institute published new progress about 4543-95-7. 4543-95-7 belongs to alcohols-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Alcohol, name is 4-(Butylamino)butan-1-ol, and the molecular formula is C8H19NO, Quality Control of 4543-95-7.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Oliveira, Marilene Silva published the artcileMechanism of Photochemical O-Atom Exchange in Nitrosamines with Molecular Oxygen, SDS of cas: 4543-95-7, the publication is Journal of Organic Chemistry (2015), 80(12), 6119-6127, database is CAplus and MEDLINE.

The detection of an oxygen-atom photoexchange process of N-nitrosamines is reported. The photolysis of four nitrosamines (N-nitrosodiphenylamine 1, N-nitroso-N-methylaniline 2, N-butyl-N-(4-hydroxybutyl)nitrosamine 3, and N-nitrosodiethylamine 4) with UV light was examined in an ¹⁸O₂-enriched atm. in solution HPLC/MS and HPLC-MS/MS data show that ¹⁸O-labeled nitrosamines were generated for 1 and 2. But nitrosamines 3 and 4 do not exchange the ¹⁸O label and instead decomposed to amines and/or imines under the conditions. For 1 and 2, the ¹⁸O atom was found not to be introduced by moisture or by singlet oxygen [¹⁸(¹O₂¹Δ_g)] produced thermally by ¹⁸O-¹⁸O labeled endoperoxide of N,N’-di(2,3-hydroxypropyl)-1,4-naphthalene dipropanamide (DHPN¹⁸O₂) or by visible-light sensitization. A d. functional theory study of the structures and energetics of peroxy intermediates arising from reaction of nitrosamines with O₂ is also presented. A reversible head-to-tail dimerization of the O-nitrooxide to the 1,2,3,5,6,7-hexaoxadiazocane (30 kcal/mol barrier) with extrusion of O=¹⁸O accounts for exchange of the oxygen atom label. The unimol. cyclization of O-nitrooxide to 1,2,3,4-trioxazetidine (46 kcal/mol barrier) followed by a retro [2 + 2] reaction is an alternative, but higher energy process. Both pathways would require the photoexcitation of the nitrooxide.

Journal of Organic Chemistry published new progress about 4543-95-7. 4543-95-7 belongs to alcohols-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Alcohol, name is 4-(Butylamino)butan-1-ol, and the molecular formula is C8H19NO, SDS of cas: 4543-95-7.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

De Crozals, Gabriel published the artcileMethylene blue phosphoramidite for DNA labelling, Recommanded Product: 4-(Butylamino)butan-1-ol, the publication is Chemical Communications (Cambridge, United Kingdom) (2015), 51(21), 4458-4461, database is CAplus and MEDLINE.

We report the first synthesis of a methylene blue (MB) phosphoramidite derivative suitable for DNA solid-phase synthesis. The electrochem. and optical properties of the resulting MB modified oligonucleotides were confirmed. This new mol. is an important breakthrough in the design of new probes labeled with MB.

Chemical Communications (Cambridge, United Kingdom) published new progress about 4543-95-7. 4543-95-7 belongs to alcohols-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Alcohol, name is 4-(Butylamino)butan-1-ol, and the molecular formula is C8H19NO, Recommanded Product: 4-(Butylamino)butan-1-ol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts