136030-28-9

Basic information

• Product Name: (2R,4R)-1,5-dichloropentane-2,4-diol
• Synonyms: (2R,4R)-1,5-dichloropentane-2,4-diol
• CAS NO: 136030-28-9
• Molecular Weight: 173.039
• Mol File: 136030-28-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2R,4R)-1,5-dichloropentane-2,4-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,4R)-1,5-dichloropentane-2,4-diol(136030-28-9)
• EPA Substance Registry System: (2R,4R)-1,5-dichloropentane-2,4-diol(136030-28-9)

Safety Data

• Hazardous Substances Data: 136030-28-9(Hazardous Substances Data)

Usage

Description

(2R,4R)-1,5-dichloropentane-2,4-diol is a chiral diol compound with the molecular formula C5H10Cl2O2. It features two hydroxyl (-OH) groups and two chiral centers, each with the R configuration. This colorless liquid is slightly soluble in water and serves as a versatile building block in organic synthesis.

Uses

Used in Pharmaceutical Industry:
(2R,4R)-1,5-dichloropentane-2,4-diol is used as a key intermediate in the synthesis of various pharmaceuticals. Its unique stereochemistry and functional groups enable the development of chiral drugs with specific therapeutic effects.
Used in Agrochemical Industry:
In the agrochemical sector, (2R,4R)-1,5-dichloropentane-2,4-diol is utilized as a precursor for the production of chiral pesticides and other agrochemicals. Its selective synthesis allows for the creation of targeted and environmentally friendly products.
Used in Fine Chemicals Industry:
(2R,4R)-1,5-dichloropentane-2,4-diol is employed as a building block for the preparation of various fine chemicals, including specialty chemicals and chiral compounds used in research and development. Its versatility in chemical reactions contributes to the synthesis of high-value products.

Upstream product

• 591-51-5 phenyllithium 
• 209119-58-4 (4R,6R)-4,6-Bis-chloromethyl-[1,3]dioxan-2-one 

Downstream Products

• 1426140-07-9 (R)-2-[(S)-2-hydroxypent-4-en-1-yl]-6-[(E)-styryl]-2H-pyran-4(3H)-one 
• 1426140-00-2 (S)-6-{[(R)-4-oxo-6-[(E)-styryl]-3,4-dihydro-2H-pyran-2-yl]methyl}-5,6-dihydro-2H-pyran-2-one 
• 1426140-05-7 (E)-1-[(4R,6S)-6-allyl-2,2-dimethyl-1,3-dioxan-4-yl]-4-hydroxy-6-phenylhex-5-en-2-one 
• 1426140-06-8 (3Z,5E)-1-[(4R,6S)-6-allyl-2,2-dimethyl-1,3-dioxan-4-yl]-4-hydroxy-6-phenylhexa-3,5-dien-2-one 
• 1061330-08-2 (R)-4-(4-methoxyphenylmethoxy)cyclopent-2-enone 
• 59995-48-1 (R)-4-acetoxycyclopent-2-en-1-one 
• 135943-83-8 (2S,4S)-1,5-diphenyl-2,4-pentanediol 
• 135943-79-2 (3S,5R)-5,6-epoxy-1-phenyl-3-hexanol 
• 135943-80-5 (3R,5R)-3-benzoyl-5,6-epoxy-1-phenylhexanol 
• 135943-91-8 (2S,4S)-1-phenyl-2,4-nonanediol 
• 135943-81-6 (+)-(4S,6R)-8-phenyloct-1-ene-4,6-diol 
• 135943-93-0 (5S,7S)-8-phenyl-1-octene-5,7-diol 
• 135943-90-7 (2S,4R)-4,5-epoxy-1-phenyl-2-pentanol 
• 129212-21-1 (3S,5S)-3,5-heptanediol 

Relevant articles and documents

Synthesis of a key building block for a butyrolactone → 1,3-diol approach to the polyol part of roflamycoin

For preparing tris(γ-lactone) 3 the mono(γ-lactone) 6 was synthesized from the dichlorodiol 12 (99.8% ee). Bisepoxide 9 - derived from dichlorodiol 12 (99.8% ee) - was ring-opened with the Gilman cuprate from 2-lithio-1,5-hexadiene and Cul giving almost exclusively the monoepoxide 21; in five more steps, γ-lactone 30 with the same stereotriad as the target molecule 6 but a different protecting group was obtained. Monoepoxide 33 - also derived from dichlorodiol 12 - was ring-opened with the same Gilman cuprate affording compound 35. It was transformed into the correctly protected γ-lactone 6 in seven steps, key reactions being the ozonolysis 35 → 36 and the diastereoselective reduction 36 → anti-37.