Category: 115-84-4

O-Alkyl substituted hydroxycarbamates was written by Major, Randolph T.;Dursch, Friedrich;Hess, Hans Jurgen. And the article was included in Journal of Organic Chemistry in 1959.Computed Properties of C9H20O2 The following contents are mentioned in the article:

Some O-alkyl substituted hydroxylamine derivatives possess pharmacol. properties similar to those of related amines. HONHCO₂Et (I), the related compound MeONHCSOEt (II) and various 2,2-dialkyl-1,3-propanediol bis(alkoxyalkylcarbamates), RR¹C(CHOCONR²OR³)₂ (III) were prepared Finely powd. HONH₂.HCl(195 g.) and anhydrous K₂CO₃ (380 g.) stirred in 1500 mL. Et₂O with addition of 20 mL. H₂O, the cooled (ice bath) mixture stirred 1 h. with gradual addition of 300 g. ClCO₂Et (immediate evolution of CO₂) and then overnight at room temperature, the filtered solution evaporated in a slight vacuum and the residue distilled through a 15-cm. Vigreux column in vacuo yielded 66% I, b₃ 113-16°, giving a deep purple color with aqueous FeCl₃. ClCH₂CO₂H (39 g.) slowly neutralized with 17 g. NaOH in 180 mL. ice-cold H₂O and the solution added to 0.30 mol aqueous EtOCS₂Na, the mixture kept overnight and concentrated to 150 mL. in vacuo on a steam bath, the cooled concentrate treated with 21 g. MeONH₂ and the mixture kept overnight, neutralized with AcOH and extracted with Et₂O, the dried (Na₂SO₄) extract evaporated at room temperature and the residual solid (37 g.) recrystallized (petr. ether, b. 30-60°) yielded 66% II, m. 33-6°. Freshly distilled COCl₂ (16.0 g.) in 400 mL. dry PhMe slowly added to 220 g. 1,5-dimethyl-2-phenyl-3-pyrazolone and 70 g. Me₂C(CH₂OH)₂ in 50 mL. CHCl₃ at – 10 to 0° (ice-NaCl bath) and the mixture stirred overnight at room temperature, filtered from antipyrine-HCl (almost quant. yield) and the salt washed with Et₂O, the combined filtrates evaporated in vacuo and the yellow oily residue distilled yielded 2,2-dimethyl-1,3-propanediol bis(chloroformate), RR¹C(CH₂OCOCl)₂ (IV, R = R¹ = Me) (V). Similarly were prepared the analogous IV (R, R¹, b.p./mm., and % yield given): Me, Me, 122-5°/17, 56; Et, Et (VI), 153-5°/24, 64; Et, Bu, 165-8°/20, 60. MeONHMe (3.0 g.) and 5.0 g. powd. anhydrous K₂CO₃ stirred in 30 mL. absolute Et₂O (ice-cooling) with gradual addition of 5.0 g. V (slow evolution of CO₂), and the mixture stirred 24 h. at room temperature, the Et₂O evaporated and the residue taken up in 25 mL. H₂O, extracted with Et₂O and the oily product distilled yielded 86% III (R = R¹ = R² = R³ = Me) (method A). VI (25.7 g.) in 150 mL. absolute Et₂O treated dropwise with 30.5 g. MeON HMe with shaking and cooling, the mixture kept overnight at room temperature and filtered from MeONHMe.HCl, the washed (25 mL. H₂O) and dried (Na₂SO₄) filtrate evaporated and the oily residue distilled yielded 60% III (R = R¹ = Et, R² = R³ = Me) (method B). Similarly were prepared the carbamates III (R, R¹, R², R³, method and b.p./mm. given): Me, Me, Me, Me (VII), A, 183-4°/20; Me, Me, H, Me (VIII), A, 194-5°/1.0; Me, Me, Et, Et (IX), B, 136-8°/0.15; Me, Me, H, Et (X), B, 175-80°/0.5; Et, Et, Me, Me (XI), B, 163-5°/0.3; Et, Et, Et, Et, B, 133.8°/0.1; Et, Bu, Me, Me (XII), B, 166-9°/0.3; Et, Bu, Et, Et, B, 142.8°/0.2. None of the compounds I, MeONHCO₂Et, EtONHCO₂Et (XIII), II, VIII, X, and XII inhibited Sarcoma 180 in vivo at non-toxic doses. XIII showed little effect in mice (i.p. in Mazola oil) in doses below the toxic level of 441 mg./kg. but EtONEtCO₂Et (XIV) produced depression at or near the lethal level of 1069 mg./kg. XIV (1% suspension in tragacanth) abolished the corneal reflex 18 min. on instillation into the rabbit eye. VIII-XII were inactive in tests designed to test their activity in mice similar to that produced by meprobamate. This study involved multiple reactions and reactants, such as 2-Butyl-2-ethylpropane-1,3-diol (cas: 115-84-4Computed Properties of C9H20O2).

2-Butyl-2-ethylpropane-1,3-diol (cas: 115-84-4) belongs to alcohols. Alcohols are among the most common organic compounds. They are used as sweeteners and in making perfumes, are valuable intermediates in the synthesis of other compounds, and are among the most abundantly produced organic chemicals in industry. Secondary alcohols are easily oxidized without breaking carbon-carbon bonds only as far as the ketone stage. No further oxidation is seen except under very stringent conditions.Computed Properties of C9H20O2

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

The preparation of N-substituted 1,3-propanediol dicarbamates was written by Schneider, G.;Halmos, M.;Meszaros, P.;Kovaes, O.. And the article was included in Monatshefte fuer Chemie in 1963.SDS of cas: 115-84-4 The following contents are mentioned in the article:

As part of a study of 1,3-diols, a number of substituted 1,3-propanediol dicarbamates was prepared The 2,2-dialkyl-1,3-propanediol dicarbamates rand the sym. N,N’-di- (I) or N,N,N’,N’-tetrasubstituted (II) derivatives were obtained by treating the corresponding dichlorides with aqueous NH₃ or dry alkylamine. A typical preparation of I involved treatment of a solution of 1 mole of diol in 500 cc. absolute C₆H₆ with COCl₂ at 0-5°, followed by reaction with concentrated NH₃. After separation of the aqueous phase, the C₆H₆ solution was washed with H₂O, dried (Na₂SO₄), and concentrated to yield a solid product. By this method were prepared the following I, RR¹C(CH₂O₂CNH₂)₂ (R,R¹,and m.p. given): Me, Me, 152°; Et, Et, 158°; Me, Pr, 99-100°; Et, Bu, 118°. The preparation of II was carried out in a manner analogous to that of I, except that the reaction with COCl₂ was carried out in the presence of R₂NH. The mixture was kept 1 day at room temperature, the amine hydrochloride was removed, and gaseous alkylamine passed into the dichloride solution at 5°. After removal of the amine hydrochloride, II was isolated as described above. In this manner were prepared the following II, RR¹C(CH₂O₂CNR²R³)₂ (R, R¹, R², R³, and m.p. or n²⁵_D given): Me, Me, Me, H, 39-40°; Et, Et, Me, H, 85-6°; Me, Pr, Me, H, 1.4872; Et, Bu, Me, H, 1.4686; Me, Me, Me, Me, 14562; Et, Et, Me, Me, 30-2°; Me, Pr, Me, Me, 1.4596; Et, Bu, Me, Me, 1.4661; Me, Me, iso-Pr, H, 92-3°; Et, Et, iso-Pr, H, 44-5°, Me, Pr, iso-Pr, H, 68-9°; Et, Bu, iso-Pr, H, 1.4627. N-Monoalkyl and mixed N,N’-dialkyl-1,3-propanediol dicarbamates (III) were obtained from the appropriate monocarbamates (IV). The latter were frequently prepared by reaction of 1.5 moles of the corresponding cyclic carbonate with 2 moles of liquid alkylamine for 6 hrs. at 80° in an autoclave. The cooled reaction mixture was dissolved in C₆H₆, the C₆H₆ and excess amine removed, and IV isolated. By this method were prepared the following IV, RR¹C(CH₂OH)CH₂O₂CNR²R³ (R, R¹, R², R³, and m.p. or n²⁵_D given): Me, Me, iso-Pr, H, 58-60°, Et, Et, iso-Pr, H, 53°; Me, Pr, iso-Pr, H, 1.4594; Et, Bu, iso-Pr, H, 1.4540; Me, Pr, Bu, H, 1.4547. V, n²⁵5_D 1.4480, was prepared in 95% yield by reaction of the corresponding diol with diethyl carbonate and Na at 90°; use of a large amount of Na avoided formation of polymers. The N-monoalkyl-2,2-dialkyl-1-3-propanediol dicarbamates were prepared by treatment of a C₆H₆ solution of 1 mole IV with 1 mole COCl₂, followed by reaction with aqueous NH₃. The mixed N,N-dialkyl derivatives of III were prepared similarly, except that the reaction with COCl₂ was carried out in the presence of 1 mole R₂NH. The remainder of this procedure was similar to that described for the preparation of II. By this method were prepared the following RR¹C(CH₂O₂CNR²Ra³CH₂O₂CNR⁴Rp5 (R, R1, R², R³, R⁴, R⁵,and m.p. or n²⁵_D given): Me, Me, iso-Pr, H, H, H, 118-20°; Et, Et, iso-Pr, H, H, H, 88-90°; Me, Pr, iso-Pr, H, H, H, 91-3°; Et, Bu, iso-Pr, H, H, H, 74-6°; Me, Me, iso-Pr, H, Me, H, 75°; Et, Et, iso-Pr, H, Me, H, 63-5°; Me, Pr, iso-Pr, H, Me, H, 76-8°; Et, Bu, iso-Pr, H, Me, H, 34-5°; Me, Me, iso-Pr, H, Me, Me, 43°; Et, Et, iso-Pr, H, Me, Me, 48-50°; Me, Pr, iso-Pr, H, Me, Me, 1.4560; Et, Bu, iso-Pr, H, Me, Me, 1.4587; Me, Pr, Bu, H, H, H, 1.4603; Me, Pr, Bu, H, Me, H, 1.4594; Me, Pr, Bu, H, Me, Me, 1.4612. This study involved multiple reactions and reactants, such as 2-Butyl-2-ethylpropane-1,3-diol (cas: 115-84-4SDS of cas: 115-84-4).

2-Butyl-2-ethylpropane-1,3-diol (cas: 115-84-4) belongs to alcohols. A strong base can deprotonate an alcohol to yield an alkoxide ion (R―O−). For example, sodamide (NaNH2), a very strong base, abstracts the hydrogen atom of an alcohol. Converting an alcohol to an alkene requires removal of the hydroxyl group and a hydrogen atom on the neighbouring carbon atom. Dehydrations are most commonly carried out by warming the alcohol in the presence of a strong dehydrating acid, such as concentrated sulfuric acid.SDS of cas: 115-84-4

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Synthesis of some cyclopropane and spiran hydrocarbons was written by Shortridge, R. W.;Craig, R. A.;Greenlee, K. W.;Derfer, J. M.;Boord, C. E.. And the article was included in Journal of the American Chemical Society in 1948.Application In Synthesis of 2-Butyl-2-ethylpropane-1,3-diol The following contents are mentioned in the article:

Details are given of the preparation from Me₂CHCHO and HCHO of 76% Me₂C(CH₂OH)₂ which with PBr₃ yields 46% Me₂C(CH₂Br)₂, b₉ 68°, n²_D 1.5050, d²⁰₄ 1.6934 (all n and d. are at 20°). A mixture 1900 ml. 95% EtOH, 90 ml. H₂O, and 628 g. Zn dust, brought to gentle reflux and treated dropwise with 562 g. Me₂C(CH₂Br)₂, with heating and stirring 24 hrs., gives 162 g. 1,1-dimethylcyclopropane, b₇₆₀ 19.9°, f.p. -108.4 to -107.3°. MeEtCHCH₂CHO gives 91% 2,2-diethyl-1,3-propanediol, b₁₃ 131°, m. 61-1.6°; PBr₃ yields 40% 1,3-dibromo-2,2-diethylpropane, b₁₀ 97°, m. 39.2-40.6°; this gives 92% 1,1-diethylcyclopropane (I), b₇₆₀ 88.67°, f.p. -105.91°, n 0.7318, d. 1.4042. EtPrCHCH₂CHO yields 70% 2-ethyl-2-butyl-1,3-propanediol, b₁₀ 152°, m. 41.4-1.9°; PBr₃ gives about 47% 1,3-dibromo-2-ethyl-2-butylpropane, b₁₆ 133°, d. 1.4400, n 1.5018; this yields 94% 1-ethyl-1-butylcyclopropane, b₇₆₀ 140.41°, f.p. -102.68°, d. 0.7559, n 1.4183. Five mols. each of (CH:CH₂)₂ and CH₂:CHCHO and 5 g. hydroquinone, heated to 130° (temperature rise to 185°), give 74% 3-cyclohexene-1-carboxaldehyde, b₇₆₀ 164°, f.p. -96.1°, d. 0.9709, n 1.4725; this yields 84% 4,4-bis(hydroxymethyl)cyclohexene, b₃ 128°, m. 92°, giving on catalytic reduction in MeOH over Raney Ni at 45° and 1000 lb./sq. in. 1,1-bis(hydroxymethyl)cyclohexane, which yields 27% 1,1-bis(bromomethyl)cyclohexane, b₆ 117°, d. 1.6302, n 1.5390; cyclization yields 91% spiro[2.5]octane (II), b₇₆₀ 125.5°, f.p. -86.2°, d. 0.8282, n 1.4476. (CH:CH₂)₂ and MeCH:CHCHO give 46% 6-methyl-3-cyclohexene-1-carboxaldehyde, b₆₄ 99°, b₇₆₀ 117.8°, d. 0.9500, n 1.4680; this yields 4,4-bis(hydroxymethyl)-5-methylcyclohexene, b₆ 134°, m. 45°. 1,1-Bis(hydroxymethyl)-2-methylcyclohexane (m. 77°, 51%) yields 28% 1,1-bis(bromomethyl)-2-methylcyclohexane, b₄ 115°, n 1.5380; cyclization yields 89% 4-methylspiro[2.5]octane (III), b₇₆₀ 149°, f.p. -53.6°, d. 0.8386, n 1.4529. I, hydrogenated over Raney Ni at 180° and 2000 lb./sq. in., gives 80% Me₂CEt₂; at 155° and 1900 lb./sq. in., II over Raney Ni gives 91% 1,1-dimethylcyclohexane; III gives 1,1,2-trimethylcyclohexane, b₇₆₀ 145.2°, f.p. -29.2°, d. 0.7986, n 1.4385. When a gem-dialkylcyclopropane or a spirane containing a cyclopropane ring is hydrogenated under the above conditions, rupture of the cyclopropane ring occurs almost exclusively at the bond opposite the gem-disubstituted C atom. Thus, hydrogenation under controlled conditions can provide an easy, reliable method for proving the structure of these types of compounds and in some cases it may prove to be a good preparative reaction for synthesizing gem-dimethylcycloalkanes with rings containing more than 3 C atoms. This study involved multiple reactions and reactants, such as 2-Butyl-2-ethylpropane-1,3-diol (cas: 115-84-4Application In Synthesis of 2-Butyl-2-ethylpropane-1,3-diol).

2-Butyl-2-ethylpropane-1,3-diol (cas: 115-84-4) belongs to alcohols. Alcohols are weak acids. The most acidic simple alcohols (methanol and ethanol) are about as acidic as water, and most other alcohols are somewhat less acidic. Tertiary alcohols cannot be oxidized at all without breaking carbon-carbon bonds, whereas primary alcohols can be oxidized to aldehydes or further oxidized to carboxylic acids.Application In Synthesis of 2-Butyl-2-ethylpropane-1,3-diol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Some anticonvulsant agents derived from 1,3-propanediols was written by Ludwig, B. J.;Piech, E. C.. And the article was included in Journal of the American Chemical Society in 1951.Quality Control of 2-Butyl-2-ethylpropane-1,3-diol The following contents are mentioned in the article:

Mono- and dicarbamate esters of 2,2-disubstituted-1,3-propanediols were prepared for evaluation as anticonvulsants. Preparation of 2,2-disubstituted-1,3-propanediol dicarbamates. General method: COCl₂ (20 g.) in 200 cc. PhMe at -10° treated with a cooled solution of 13.2 g. (HOCH₂)₂CEt₂ and 38 g. antipyrine in 100 cc. CHCl₃ (temperature kept at -5 to 0°), the mixture let stand overnight at room temperature, filtered, the filtrate treated with NH₃ (moderate cooling), the amide filtered off, extracted with 250 cc. cold water, and recrystallized from water yielded 17.5 g. di-Et compound (I). The PhMe-CHCl₃ filtrate concentrated and the residue distilled in vacuo yielded 75% 2,2-diethyl-1,3-propanediol bis(chlorocarbonate), b_4.5 108°, n_D²⁵ 1.4628. For the compounds RR’C(CH₂OCONH₂)₂, R, R’, yield (%), and m.p. (all m.ps. uncorrected) are: Me, Me, 82, 151.5-2.5°; Et, Me, 65, 135-6°; Me, Pr, 90, 105-6°; Me, iso-Pr, 61, 99-100°; Et, Et, 80, 149-50°; Et, Bu, 63, 117-18°; Et, Ph, 70, 119-20°; Pr, Pr, 87, 152-3°; RR’ = (CH₂)₅, 60, 112-13°. N-Substituted-2,2-diethyl-1,3-propanediol dicarbamates were prepared by the same procedure (R, yield (%), and m.p. given): Me, 56, 85-6°; Ph, 67, 135.5-6.5°; Ac, 65, 123-4°; PhCH₂CO₂, 20, 204-5°; Et, 50,-[bis(diethylamino) derivative b₅ 130-2°, n_D²⁵ 1.4569]. The following method yielded cyclic carbonate derivatives: a cooled 10% solution of 0.1 mole of COCl₂ in PhMe added to 13.2 g. I and 0.2 mole antipyrine in a min. of CHCl₃ (temperature held at 25°), the mixture held at 25° overnight, filtered, the filtrate concentrated, the residue dissolved in Et₂O, the Et₂O solution extracted with water, and the Et₂O evaporated yielded 10.5 g. 5,5-diethyl-2-m-dioxanone, b₂ 131-2°, m. 45-6° (from C₆H₆-petr. ether). For other 5,5-disubstituted-2-m-dioxanones, R, R’, yield (%), and m.p. are: Me, Me, 60, 110-11°; Me, Pr, 74, b_0.25 95-104°, n_D²⁵ 1.4550; Et, Et, 66, 45-6°; Et, Bu, 80, b₁ 125-30°, n_D²⁵ 1.4638; Et, Ph, 85, 99.5-100.5°. A 5,5-disubstituted-2-m-dioxanone (5 g.) in a stainless-steel pressure bomb cooled in Dry Ice, 7.5 cc. NH₃ added, the vessel closed and shaken 48 hrs. at room temperature, and the NH₃ evaporated yielded 2,2-disubstituted-3-hydroxypropyl carbamates, HOCH₂CRR’CH₂OCONH₂ (R, R’, yield (%), and m.p. given): Me, Me, 53, 60-1°; Me, Pr, 60, 61.5-2.5°; Et, Et, 75, 75-6°; (N-Me derivative, n_D²⁵ 1.4640, b_0.5 110-16°; N,N-di-Et derivative, n_D²⁵ 1.4587, b_0.5 104-8°); Et, Bu, 73, 66.5-7.5°; Et, Ph, 69, 89-90°. This study involved multiple reactions and reactants, such as 2-Butyl-2-ethylpropane-1,3-diol (cas: 115-84-4Quality Control of 2-Butyl-2-ethylpropane-1,3-diol).

2-Butyl-2-ethylpropane-1,3-diol (cas: 115-84-4) belongs to alcohols. Similar to water, an alcohol can be pictured as having an sp3 hybridized tetrahedral oxygen atom with nonbonding pairs of electrons occupying two of the four sp3 hybrid orbitals. Tertiary alcohols cannot be oxidized at all without breaking carbon-carbon bonds, whereas primary alcohols can be oxidized to aldehydes or further oxidized to carboxylic acids.Quality Control of 2-Butyl-2-ethylpropane-1,3-diol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Determining the repellency of solid chemicals to mosquitoes was written by Linduska, J. P.;Morton, F. A.. And the article was included in Journal of Economic Entomology in 1947.Safety of 2-Butyl-2-ethylpropane-1,3-diol The following contents are mentioned in the article:

Although difficult to apply and retain on the skin, most solid substances have lower vapor pressure and lower rate of absorption by the skin than liquids. These characteristics appear to make solids a fertile field for study as repellents for mosquitoes and other blood-sucking insects. Solids were tested against adult mosquitoes by impregnating mercerized cotton stocking fabric with 3.3 g. solid per sq. ft. of fabric, slipping the impregnated fabric over the arm, and exposing the covered arm to caged mosquitoes for 2 min. daily until a total of 5 bites was recorded. The primary test mosquito was A edes aegypti; a less sensitive species to repellents, Anopheles quadrimaculatus, was also used. Dimethyl phthalate, which gives 30 days’ protection against A. aegypti at 3.3 g. per sq. ft., was used as a standard for comparison. Chemicals allowing fewer than 5 bites in 10 days were considered worthy of further study. Of 1339 solids tested, 9% were selected on the basis of this test for addnl. study. They were then considered from the viewpoints of toxicity (to human subjects), skin irritation, pronounced odor, and staining properties. Materials that passed these tests were subjected to more definite examination with respect to suitability for skin application, resistance to removal from cloth by cool-water rinsing, efficiency at reduced rates of impregnation in cloth, and irritation to human subjects. Solids that were repellent when impregnated in cloth were tested as repellents on the human skin as solutions in dimethyl phthalate, as aqueous suspensions, or both. The testing procedure of Granett (C.A. 34, 7035.1) was used. Solids that were highly effective skin repellents (protected longer than dimethylphthalate) were: n-butyl sulfone; p-methoxyacetophenone; 8-hydroxyquinoline; piperonal; α,α-β-trichloropropionamide; 2-ethyl-2-butyl-1,3-propanediol; N,n-propylacetanilide; propiophenone oxime. Solids impregnated in cloth that were repellent after rinsing in tap water at 28.9-29.4° for 30 min. were: o-phenylphenol; p-tert-butylphenol; hexachlorophenol; 4,6-dinitro-o-cresol (I); a mixture of chlorinated phenols; dinitro-o-sec-butylphenol (II); phenylcyclohexanol. II and I were best in the order given. Materials that provided more than 10 days’ protection when impregnated in cloth at 3.3 g. per sq. ft. were tested at half this dosage against A. aegyptii. The materials that passed this test were: o-phenylphenol; 2,4,6-trichlorophenol; 2,4-dinitro-o-cresol; p-nitroanisole; 2-isovaleryl-1,3-indandione (Valone); dinitro-o-sec-butylphenol; piperonal; 2-ethyl-2-butyl-1,3-propanediol; N-ethylacetanilide; N,n-propylacetanilide; 1-benzylcyclohexanol; 1-(p-chlorophenyl)-3-methyl-2-butanol; N-methylpropionanilide; 2,4,7,9-tetramethyl-5-decane-4,7-diol. 2-Ethylhexane-1,3-diol (Rutgers 612) and dimethyl phthalate, used as standards, also passed these tests. This study involved multiple reactions and reactants, such as 2-Butyl-2-ethylpropane-1,3-diol (cas: 115-84-4Safety of 2-Butyl-2-ethylpropane-1,3-diol).

2-Butyl-2-ethylpropane-1,3-diol (cas: 115-84-4) belongs to alcohols. Alcohols are among the most common organic compounds. They are used as sweeteners and in making perfumes, are valuable intermediates in the synthesis of other compounds, and are among the most abundantly produced organic chemicals in industry. Secondary alcohols are easily oxidized without breaking carbon-carbon bonds only as far as the ketone stage. No further oxidation is seen except under very stringent conditions.Safety of 2-Butyl-2-ethylpropane-1,3-diol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts