56718-04-8

Basic information

• Product Name: 1,4-Pentanediol, (R)-
• Synonyms: (R)-(-)-pentane-1,4-diol;(R)-(-)-1,4-pentanediol;(4R)-pentane-1,4-diol;(4R)-(-)-1,4-pentanediol;(4R)-1,4-Pentandiol;(R)-pentane-1,4-diol
• CAS NO: 56718-04-8
• Molecular Formula: C5H12O2
• Molecular Weight: 104.149
• Mol File: 56718-04-8.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 103-112 °C(Press: 4 Torr)
• Density: 0.978±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 1,4-Pentanediol, (R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Pentanediol, (R)-(56718-04-8)
• EPA Substance Registry System: 1,4-Pentanediol, (R)-(56718-04-8)

Safety Data

• Hazardous Substances Data: 56718-04-8(Hazardous Substances Data)

Usage

Chemical classification

Diol A compound with two hydroxyl (OH) groups.

Primary uses

Solvent and precursor Used in the production of various polymers and plastics.

Common applications

Adhesives, coatings, and cosmetics Found in these types of products.

Enantiomer

(R)-1,4-Pentanediol The specific spatial arrangement of atoms that gives it distinct properties and reactivity.

Safety profile

Relatively safe compound Low toxicity, making it suitable for a wide range of industrial and commercial applications.

Upstream product

• 10229-10-4 pent-3-yn-1-ol 
• 52813-63-5 (5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone 
• 29264-40-2 5-pentenylbenzoate 
• 144762-81-2 C₂₁H₃₈N₂O₆ 
• 58879-34-8 (S)-5-tosyloxypentan-4-olide 
• 625-31-0 (S)-4-penten-2-ol 
• 112789-84-1 (+)-(S)-ethyl 4-hydroxypentanoate 
• 52813-64-6 (R)-5-(chloromethyl)tetrahydro-2-furanone 
• 58879-33-7 (R)-(-)-γ-<(tosyloxy)methyl>-γ-butyrolactone 
• 32780-06-6 (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran 

Downstream Products

• 126386-37-6 (R)-1,4-bis(4-toluenesulfonyloxy)pentane 
• 104784-02-3 (R)-1-<(triphenylmethyl)oxy>pentan-4-ol 
• 74500-57-5 (S)-4-t-butyldimethylsilyloxy-1-trityloxypentane 
• 31087-44-2 (R)-2-pentanol 
• 140460-53-3 nonenolide 
• 93929-68-1 (1R,2S,4S)-2-<(6S)-t-butyldimethylsilyloxy-1-heptynyl>-4-(2-methoxyethoxymethoxy)-1-cyclopentylmethyl benzyl ether 
• 20350-15-6 (+)-brefeldin A 
• 104784-03-4 (R)-4-t-Butyldimethylsilyloxy-1-trityloxypentane 
• 104784-05-6 (R)-4-t-Butyldimethylsilyloxy-1-tosyloxypentane 
• 155853-18-2 {(S)-6-[(1R,2R,4S)-2-[(S)-2-Benzyloxy-1-(2-methoxy-ethoxymethoxy)-ethyl]-4-(2-methoxy-ethoxymethoxy)-cyclopentyl]-1-methyl-hex-5-ynyloxy}-tert-butyl-dimethyl-silane 
• 74500-59-7 (4S)-4-[tert-butyl(dimethyl)silyl]oxypentyl 4-methylbenzenesulfonate 
• 765-38-8 (S)-2-methylpyrrolidine 
• 774-91-4 (S)-1-benzyl-2-methylpyrrolidine 
• 1025896-96-1 tert-Butyl-((E)-(1R,9R)-9-methoxy-1-methyl-11-trityloxy-undec-5-enyloxy)-diphenyl-silane 

Relevant articles and documents

Combination of Metal-Catalyzed Cycloisomerizations and Biocatalysis in Aqueous Media: Asymmetric Construction of Chiral Alcohols, Lactones, and γ-Hydroxy-Carbonyl Compounds

The combination of the metal-catalyzed cycloisomerization of alkynes containing a tethered nucleophile as substituent in aqueous media (followed by the spontaneous hydrolysis, hydroalkoxylation, or aminolysis of the transiently formed five-membered heterocycles) with the subsequent enantioselective ketone bioreduction (mediated by KREDs) has been achieved. The overall transformations, which formally involve a three-step one-pot reaction, provide a variety of enantiopure valuable molecules (e.g., 1,4-diols, lactones, and γ-hydroxy-carbonyl compounds (carboxylic acids, esters, and amides)) with high conversions and enantioselectivities and under mild reaction conditions, disclosing the concept of integrated metal-catalyzed cycloisomerizations of alkynes and enzymatic catalysis in water.

Asymmetric synthesis of 2-substituted butane-1,4-diols by hydrogenation of homochiral fumaramide derivatives

Diastereoselective hydrogenation of homochiral fumaramides 1 derived from (2R)-Oppolzer's sultam was observed by analysis of the 1H NMR spectra of the succinamide mixtures with de's of 77-88%. Reduction of these succinamides using LiAlH4 gave the corresponding (2S)-butane-1,4- diols and established that addition of hydrogen takes place selectively on the re-face of fumaramides 1. The stereoselectivity was confirmed by estimating the ee's from the 19F NMR spectra of the Mosher's diesters of the diols. This methodology was applied to the synthesis of selected pyrrolidine natural products in homochiral form.

Asymmetric Hydrosilylation of 1-Alkenes Catalyzed by Palladium-MOP

Asymmetric hydrosilylation of simple terminal alkenes (RCH=CH2) with trichlorosilane at 40 deg C in the presence of 1*10-3 or 1*10-4 molar amounts of palladium catalyst prepared in situ from 3-C3H5)>2 and (S)-2-diphenylphosphino-2'-methoxy-1,1'-binaphthyl ((S)-MeO-MOP) proceeded with unusual regioselectivity and with high enantioselectivity to give high yields of 2-(trichlorosilyl)alkanes together with a minor amount of 1-(trichlorosilyl)alkanes.Optically active alcohols, RCH(OH)CH3, were obtained by oxidation of the carbon-silicon bond.Regioselectivities for forming 2-silylalkanes over 1-silylalkanes and enantiomeric purities of alcohols are as follows: R=n-C4H9: 89/11, 94percent ee (R).R=n-C6H13: 93/7, 95percent ee (R).R=n-C10H21: 94/6, 95percentee (R).R=PhCH2CH2: 81/19, 97percentee (S).R=PhCH2CH2CH2: 80/20, 92percent ee (R).R=cyclo-C6H11: 66/34, 96percent ee (R).A similar hydrosilylation of 1-alkenes, 4-pentenyl benzoate and 1,5-heptadiene gave corresponding 2-alkanols of 90percent ee and 87percent ee, respectively, the ester carbonyl and the internal double bond remaining intact.