108340-61-0

Basic information

• Product Name: (R)-(+)-1,2-PENTANEDIOL
• Synonyms: (R)-(+)-1,2-PENTANEDIOL;(2R)-1,2-Pentanediol;(2R)-Pentane-1,2-diol;(R)-Pentane-1,2-diol
• CAS NO: 108340-61-0
• Molecular Formula: C₅H₁₂O₂
• Molecular Weight: 104.14758
• Mol File: 108340-61-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (R)-(+)-1,2-PENTANEDIOL(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-1,2-PENTANEDIOL(108340-61-0)
• EPA Substance Registry System: (R)-(+)-1,2-PENTANEDIOL(108340-61-0)

Safety Data

• Hazardous Substances Data: 108340-61-0(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
(R)-(+)-1,2-Pentanediol is used as a precursor in the synthesis of various chemicals for its ability to serve as a building block in the creation of more complex molecules.
Used in Asymmetric Synthesis:
(R)-(+)-1,2-Pentanediol is used as a chiral resolving agent in asymmetric synthesis, which is crucial for producing enantiomerically pure compounds, often important in pharmaceutical development.
Used in the Pharmaceutical Industry:
(R)-(+)-1,2-Pentanediol is used as a component in the manufacturing of pharmaceuticals, leveraging its chiral nature and solubility properties to enhance drug formulations.
Used in the Agricultural Industry:
(R)-(+)-1,2-Pentanediol is used in the production of agricultural products, potentially as a component in the formulation of pesticides or other agrochemicals.
Used in the Cosmetics Industry:
(R)-(+)-1,2-Pentanediol is used as a humectant in cosmetic formulations, helping to retain moisture and maintain the product's effectiveness.
Used in the Plastics Industry:
(R)-(+)-1,2-Pentanediol is used in the production of plasticizers, which are additives that increase the flexibility and workability of plastics.
Used in Personal Care Products:
(R)-(+)-1,2-Pentanediol is used in personal care products due to its antimicrobial properties, making it suitable for inclusion in products that require preservation and hygiene.
Used in Disinfectants:
(R)-(+)-1,2-Pentanediol is used in disinfectants for its antimicrobial properties, contributing to the sanitization and cleanliness of various surfaces and products.

Upstream product

• 139164-92-4 (3R)-1-hexen-3-ol 
• 64502-89-2 1-hydroxypentan-2-one 
• 41014-93-1 2-(S)-hydroxyvaleric acid 
• 109-67-1 1-penten 
• 5343-92-0 1,2-pentanediol 
• 81947-72-0 1,2-diacetoxypentane 
• 853784-89-1 (R)-2-(benzyloxy)pentan-1-ol 
• 1003-14-1 2-pentyloxirane 
• 61574-63-8 butyl 2-oxopentanoate 
• 78935-60-1 tert-butyl-(R)-2-hydroxypentanoate 
• 152885-90-0 (2R)-2-hydroxypentanoic acid benzyl ester 
• 240128-93-2 butyl (R)-2-hydroxypentanoate 
• 732279-39-9 isopropyl (R)-2-hydroxypent-4-enoate 
• 732279-40-2 (R)-2-hydroxy-4-pentenoic acid tert-butyl ester 

Downstream Products

• 529510-44-9 (R)-(+)-2-hydroxypentyl tosylate 
• 63095-51-2 (+)-(R)-4-propyl-4,5-dihydrofuran-2(3H)-one 

Relevant articles and documents

A novel generation of optically active 1,2-diols from the racemates by using halohydrin dehydro-dehalogenase

A novel enzyme dehalogenating halohydrins, designated as halohydrin dehydo-dehalogenase (HDDase), was purified from Alcaligenes sp. DS-S-7G. The enzyme catalyzed oxidative dehalogenation of (R)-3-chloro-1,2-propanediol [monochlorohydrin (MCH)] to acetic acid and formaldehyde via hydroxyacetone stereoselectively by the addition of artificial electron acceptors. The dehalogenating activity was much higher in the presence of 2,6- dichlorophenolindophenol (DCIP) and phenazine methosulfate (PMS). The resulting stereoselective dehydro-dehalogenation was applicable to preparation of various optically active halohydrins and 1,2-diols so that the respective residual isomers had excellent enantiomeric excesses (ee) (60-99% ee).

Industrialization of the Microbial Resolution of Chiral C3 and C4 Synthetic Units: From a Small Beginning to a Major Operation, a Personal Account

This account describes the research and development of the microbial resolution of chiral C3 and C4 synthetic units through to the production stage. These chiral C3 and C4 synthetic units are mainly used for the production of various pharmaceuticals, new materials such as liquid crystals, chiral polymers, and natural compounds as well as in basic chemical research. The research started in 1983 and the industrial plant was built in 1994. The development is still ongoing and is being broadened to include C4 chiral units, chiral propylene glycol, and so on. This project started as simple research on the activated sludge from an epichlorohydrin plant and evolved through many events and much research to an industrial production. We describe the various implications and the flow of events in the research and development through to the production of these chiral C3 and C4 synthetic units.

The stereoselective conversion of 2-alkenyl alcohols to (R)- or (S)- alkane-1, 2-diols using D-glucose as a chiral auxiliary

The stereoselective addition of the 2-hydroxyl group of glucose to the mercurated vinyl group of 2-alkenyl glycosides followed by hydride reduction and removal of the saccharide fragment was used to prepare enantiomerically pure 1,2-dihydroxy alkanes. Diols of (R) or (S) configuration can be synthesized from (α)-glycosides or the (β) form respectively. Demercuration with chloride ion led to the insertion of a halo group adjacent to the new chiral center thus allowing for the possibility of further functionalization.

Highly Enantioselective Dihydroxylation of Trans-Disubstituted and Monosubstituted Olefins

Extremely high levels of asymmetric induction have been achieved in osmium tetraoxide oxidation of trans-disubstituted and monosubstituted olefins by using chiral N,N'-dineohexyl-2,2'-bipyrrolidine ligand.

Total Synthesis of the Antitumor Depsipeptide FE399 and Its S-Benzyl Derivative: A Macrolactamization Approach

An efficient and practical method for the synthesis of (9R,14R,17R)-FE399, a novel antitumor bicyclic depsipeptide, was developed. A 2-methyl-6-nitrobenzoic anhydride (MNBA)-mediated dehydration condensation reaction was effectively employed for the formation of the 16-membered macrocyclic depsipeptide moiety of FE399. FE399 was found to exist as an inseparable equilibrium mixture of conformational isomers; the mixture was quantitatively transformed into the corresponding S-benzyl product and isolated as a single isomer. Thus, we could confirm that the molecular structure of FE399 obtained by this method is identical to that of the natural product.

Kinetic Resolution of 1,2-Diols via NHC-Catalyzed Site-Selective Esterification

A kinetic resolution of 1,2-diols bearing both a secondary and a primary alcohol motif through an N-heterocyclic carbene-catalyzed oxidative acylation reaction has been developed. A site- and enantioselective esterification reaction is involved for this process. Both the monoacylated diols obtained and the remaining enantioenriched 1,2-diols are versatile building blocks for the preparation of functional molecules with proven biological activities.

3-CARBOXY- 2-OXO-1 -PYRROLIDINE DERIVATIVES AND THEIR USES

The present invention relates to 3-carboxy-2-oxo-l -pyrrolidine derivatives of formula (I), geometrical isomers, enantiomers, diastereoisomers, pharmaceutically acceptable salts and all possible mixtures thereof, and processes using them.

Catalytic asymmetric allylation of aldehydes using the chiral (salen)chromium(III) complexes

The enantioselective addition of allylstannanes to glyoxylates and glyoxals, as well as simple aromatic and aliphatic aldehydes, catalyzed by chiral (salen)Cr(III) complexes, has been studied. The reaction proceeded smoothly for the reactive 2-oxoaldehydes and allyltributyltin in the presence of small amounts (1-2 mol %) of (salen)Cr(III)BF4 (1b) under mild, undemanding conditions. However, in the case of other simple aldehydes, the use of high-pressure conditions is required to obtain good yields. Classic chromium catalyst 1b, easily prepared from the commercially available chloride complex 1a, affords homoallylic alcohols usually in good yield and with enantiomeric purity of 50-79% ee. The stereochemical results are rationalized on the basis of the proposed model.

A highly diastereoselective synthesis of (1R)-(+)-camphor-based chiral allenes and their asymmetric hydroboration-oxidation reactions

Synthesis of camphor derived chiral allenes and their hydroboration-oxidation reactions are described. Reaction of (1R)-(+)-camphor with alkynyllithium followed by the reduction of the resulted propargyl alcohol derivatives using AlH3 furnished chiral allenes 2a-g in excellent yields with high diastereoselectivity. Reduction of the propargyl alcohols with aluminum hydride proceeded through selective intermolecular anti-addition of hydride ion. The stereochemistry of the chiral allenes 2 was assigned based on lanthanide shift studies and chemical correlations. Diastereoselectivity was observed in the hydroboration-oxidation of 2 which produced a mixture of (E,R) and (E,S) stereoisomers in a ratio of 6:1 to 18:1.

The bakers' yeast reductions of α- and β-keto ester derivatives in the presence of a sulfur compound

Improvement of the enantioselectivity and enhancement of the reactivity were achieved in the bakers' yeast reduction of the α- and β-keto ester derivatives by the addition of a sulfur compound. High enantioselectivity in the bakers' yeast reduction of keto esters was accomplished by using combination of an addition of a sulfur compound with an appropriate selection of the alcohol part of the ester.