50468-22-9

Usage

Uses

Used in Personal Care Industry:
3-methylbutane-1,2-diol is used as a humectant and solvent in personal care products such as cosmetics, lotions, and creams. Its hygroscopic properties help to retain moisture in the skin, providing hydration and improving skin texture.
Used in Pharmaceutical Industry:
3-methylbutane-1,2-diol is used as a pharmaceutical excipient and solvent in the formulation of liquid medications. Its ability to dissolve a wide range of active ingredients makes it a versatile component in drug delivery systems.
Used in Food and Beverage Industry:
3-methylbutane-1,2-diol is used as a humectant and flavoring agent in the food and beverage industry. It helps to maintain the moisture content in food products, enhancing their texture and shelf life, while also providing a sweet taste in certain applications.
Used in Chemical Synthesis:
3-methylbutane-1,2-diol is used as a starting material or intermediate in the synthesis of various organic compounds, including polymers, surfactants, and pharmaceuticals. Its reactive hydroxy groups make it a valuable building block in organic chemistry.

InChI:InChI=1/C5H12O2/c1-4(2)5(7)3-6/h4-7H,3H2,1-2H3

Upstream product

• 10288-13-8 1,2-dibromo-3-methylbutane 
• 2441-06-7 ethyl 2-hydroxy-3-methylbutanoate 
• 563-45-1 3-Methyl-1-butene 
• 759-65-9 diethyl oxalpropionate 
• 80325-76-4 1-(benzyloxy)-3-methylbutan-2-ol 
• 1438-14-8 2-isopropyloxirane 
• 7732-18-5 water 
• 600-10-2 1,2-dichloro-3-methylbutane 
• 38585-87-4 (±)-3-methylbut-3-ene-1,2-diol 
• 78-79-5 isoprene 
• 4026-18-0 2-hydroxy-3-methylbutanoic acid 
• 20201-24-5 ethyl 3-methyl-2-oxobutanoate 
• 3952-67-8 methyl 3-methyl-2-ketobutanoate 

Downstream Products

• 4141-35-9 (2R,4R)-4-Isopropyl-2-phenyl-[1,3]dioxolane 
• 4141-35-9 2-phenyl-4-(propan-2-yl)-1,3-dioxolane 
• 1258048-31-5 2-hydroxy-3-methylbutyl-p-toluenesulfonate 
• 4026-18-0 2-hydroxy-3-methylbutanoic acid 
• 79-31-2 isobutyric Acid 
• 563-80-4 3-methyl-butan-2-one 
• 590-86-3 isovaleraldehyde 
• 2026-48-4 (S)-valinol 
• 176094-53-4 4-(1-methylethyl)-1,3,2-dioxathiolane 2,2-dioxide 

Relevant academic research and scientific papers

Asymmetric ring opening of racemic epoxides for enantioselective synthesis of (S)-β-amino alcohols by a cofactor self-sufficient cascade biocatalysis system

A novel one-pot epoxide hydrolase/alcohol dehydrogenase/transaminase cascade process for the asymmetric ring opening of racemic epoxides to enantiopure β-amino alcohols is reported. The product (S)-β-amino alcohols were obtained in 97-99% ee and 79-99% conversion from readily available racemic epoxides.

Ru-MACHO-Catalyzed Highly Chemoselective Hydrogenation of α-Keto Esters to 1,2-Diols or α-Hydroxy Esters

A ruthenium pincer catalyst has been shown to be highly effective for the hydrogenation of a wide range of α-keto esters, affording either diols or hydroxy esters depending on the choice of reaction conditions. Strong base, high temperature, and pressure favor the formation of diols whilst the opposite is true for the hydroxy esters.

Reduction of aromatic and aliphatic keto esters using sodium borohydride/MeOH at room temperature: a thorough investigation

Reduction of keto esters is a valuable alternative to produce diols. Sodium borohydride/MeOH system at room temperature and short reaction time efficiently reduced α, β, γ, and δ-keto esters having α-keto esters as the most reactive. The ester functionality was reduced effectively due to the presence of oxo group that somehow facilitates the formation of ring intermediate. As expected, the chemoselective experiments showed that ester functionality was not reduced using this system. This study presents a simple, easy, and benign reduction process of various keto esters to its corresponding diols.

Reactivity of the lithium anion of the (S,S)-bis-p-tolylsulfinyl methane. A versatile synthesis of enantiopure alkylidene 1,1-bis-tolysulfoxides

We describe herein a new synthesis of enantiopure alkylidene 1,1-bis-p-tolyl-sulfoxides (5), based on a two-steps sequence. The first one involves the alkylation of the lithium anion of the (S,S)-bis-p-tolylsulfinylmethane (1) with aldehydes. The second one consists in a mild dehydration of the sulfinyl alcohols 3 and 4 with the morpho CDI reagent. Some features (reactivity, diastereoselectivity) of the alkylation reaction are discussed.

Bacterial biotransformation of isoprene and related dienes

The bacterium Pseudomonas putida ML 2 was used in the oxidative biodegradation of the acyclic dienes isoprene, trans-piperylene, cis-piperylene, and 1,3-butadiene. Regioselective dioxygenase-catalyzed dihydroxylation of alkenes yielded vicinal diols in the preferred sequence monosubstituted 〉 cis-disubstituted 〉 gem-disubstituted 〉 trans-disubstituted. The isolated diol metabolites had an excess of the R configuration (9-97% ee), and further diol oxidation was controlled by addition of propylene glycol as an inhibitor. Stereoselectivity using the ML2 strain resulted from both enzymatic asymmetric alkene dihydroxylation and kinetic resolution of diols. Enantioselective oxidation of the allylic secondary alcohol group of R configuration yielded the corresponding unsaturated ketoalcohol; the residual diol was recovered with a large excess (≥ 93% ee) of the S configuration. In addition to the enzymatic diene oxidation steps yielding unsaturated diols and ketoalcohols, evidence was also found of enzymatic alkene hydrogenation to yield saturated ketoalcohols and diols.

Product distributions from the OH radical-induced oxidation of but-1-ene, methyl-substituted but-1-enes and isoprene in NO(x)-free air

Product distributions resulting from the OH-induced oxidation of but-1-ene, 2-methylbut-1-ene, 3-methylbut-1-ene and isoprene in air were measured in the absence of nitrogen oxides and compared with predictions based on currently accepted oxidation mechanisms. In the case of butenes, the observed distributions of carbonyl compounds, hydroxyketones, hydroxyalkanals and diols were evaluated to obtain probabilities for the initial attack of OH radical on the outer position of the double bond (y = 0.90 ± 0.03 for 2-Me-but-1-ene and y = 0.76 ± 0.05 for both but-1-ene and 3-Me-but-1-ene), for the probability of formation of stable products in the self-reaction of secondary β-hydroxyperoxyl radicals (k(ssb)/k(ss) = 0.29 ± 0.07 for but-1-ene and k(ssb)/k(ss) = 0.19 ± 0.06 for 3-Me-but-1-ene), and for the ratio of the reaction with oxygen vs. decomposition of β-hydroxyalkoxyl radicals, k3[O2]/(k4 + k3[O2]) = 0.25 ± 0.04 for but-1-ene and = 0.38 ± 0.04 for 3-Me-but-1-ene. The last two values disagree with other published data, which suggest a smaller effect of oxygen. The oxidation of isoprene produced methacrolein and methyl vinyl ketone with a ratio 0.93 ± 0.10, the ratio of methyl vinyl ketone and 3-methylfuran was 7.3 ± 1.0. Other products were 1-hydroxy-3-methylbut-3-en-2-one (identified by mass spectrometry) and 3-methyl-3-oxo-butane (tentatively identified). The overall product distribution was complex and could not be fully elucidated. Computer simulations based on several mechanisms applied the relative probabilities for OH addition found for the but-1-enes. Comparison with the experimental data suggests probabilities for OH addition to the methylated double bond of 0.504 ± 0.027 (outer position) and 0.056 ± 0.003 (inner position), and to the non-methylated double bond of 0.335 ± 0.023 (outer position) and 0.105 ± 0.008 (inner position).

EPOXIDATION AND/OR HYDROXYLATION OF 3-METHYLBUT-1-ENE BY ORGANIC HYDROPEROXIDES AND HYDROGEN PEROXIDE

An examination has been made of the hydroperoxide and peroxide epoxidation of 3-methylbut-1-ene.The indices of hydroperoxide epoxidation are given.A mathematical model of the production of tert-amyl hydroperoxide by the liquid-phase oxidation of isopentane has been developed.The optimum conditions have been selected for the epoxidation of 3-methylbut-1-ene to the corresponding oxide and diol under interphase catalysis conditions.

SYNTHESIS OF SOME 2'-C-ALKYL DERIVATIVES OF 9-(2-PHOSPHONOMETHOXYETHYL)ADENINE AND RELATED COMPOUNDS

To study the effect of β-substitution in 2'-alkyl derivatives of 9-(2-phosphonomethoxyethyl)adenine (Ia) on the antiviral activity or group specificity, these derivatives were synthesized. 9-(2-Hydroxyalkyl)adenines VIII were prepared by alkylation of adenine with suitably substituted oxiranes XIII or 2-hydroxyalkyl p-toluenesulfonates IV and VI.After protection of the adenine amino group by benzylation (compounds IX) or amidine formation (compounds X), the intermediates were alkylated with bis(2-propyl) p-toluenesulfonyloxymethanephosphonate (XI) in the presence of sodium hydride.After deprotection, the obtained phosphonate diesters XII were converted into phosphoniuc acids I by transsilylation and hydrolysis.This synthetic scheme was used for the preparation of ethyl (Ie), propyl (If), 2-propyl (Ig), 2-methylpropyl (Ih), cyclopropyl (Ii), cyclohexyl (Ij), benzyl (Ik) and phenyl (Il) derivatives.The 2'-trifluoromethyl derivative XXIIa was prepared analogously from 9-(2-hydroxy-3,3,3-trifluoropropyl)adenine (XXa), obtained by alkylation of adenine sodium salt with 2-hydroxy-3,3,3-trifluoropropyl bromide. 2,6-Diaminopurine derivative XXIIb was obtained analogously. 2'-Trimethylsilyl derivative XIXa was obtained by alkylation of adenine with 2-phosphonylmethoxy-3-(4-toluenesulfonyloxy)propyltrimethylsilane (XVII) followed by transsilylation and hydrolysis of diester XVIIIa. 9-(3-Phosphonomethoxybutyl)adenine (XXVIII) and 9-(2-methyl-2-phosphonomethoxypropyl)adenine (XXXV) were prepared from the corresponding hydroxy derivatives XXVIb and XXXII, respectively, by the same reaction pathway as derivatives I.