125605-10-9

Basic information

• Product Name: (R)-4-CHLORO-1,3-BUTANEDIOL
• Synonyms: (R)-4-CHLORO-1,3-BUTANEDIOL;(R)-4-Chlor-1,3-butanediol;4-Chloro-(R)-1,3-butanediol
• CAS NO: 125605-10-9
• Molecular Formula: C₄H₉ClO₂
• Molecular Weight: 124.57
• Product Categories: Chiral Compounds;Diols
• Mol File: 125605-10-9.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 270.2 °C at 760 mmHg
• Flash Point: 117.2 °C
• Appearance: /
• Density: 1.229 g/cm³
• Vapor Pressure: 0.000914mmHg at 25°C
• Refractive Index: 1.473
• PKA: 13.61±0.20(Predicted)
• CAS DataBase Reference: (R)-4-CHLORO-1,3-BUTANEDIOL(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-4-CHLORO-1,3-BUTANEDIOL(125605-10-9)
• EPA Substance Registry System: (R)-4-CHLORO-1,3-BUTANEDIOL(125605-10-9)

Safety Data

• Hazardous Substances Data: 125605-10-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C4H9ClO2/c5-3-4(7)1-2-6/h4,6-7H,1-3H2/t4-/m1/s1

Synthetic route

ethyl (L)-4-chloro-3-hydroxybutyrate (10488-69-4, 86728-85-0, 87068-18-6, 90866-33-4) → (3R)-4-chloro-1,3-butanediol (125605-10-9)

Conditions	Yield
Stage #1: ethyl (L)-4-chloro-3-hydroxybutyrate With sodium tetrahydroborate In methanol; toluene at 20℃; for 12h; Stage #2: With hydrogenchloride; water In methanol; toluene at 10℃;	97%
With sodium tetrahydroborate In tetrahydrofuran at 40℃; for 5h;	96%
Stage #1: ethyl (L)-4-chloro-3-hydroxybutyrate With sodium tetrahydroborate In tetrahydrofuran at 20 - 40℃; for 16h; Stage #2: With hydrogenchloride In tetrahydrofuran; methanol; water at 0℃; for 0.5h;	95%
Stage #1: ethyl (L)-4-chloro-3-hydroxybutyrate With sodium tetrahydroborate In toluene at -5 - 5℃; for 0.5h; Inert atmosphere; Stage #2: With methanol In toluene at -5 - 25℃;

ethyl 4-chloro-3-hydroxybutanoate (86728-85-0, 87068-18-6, 90866-33-4, 10488-69-4) → (3S)-4-chloro-1,3-butanediol (139013-68-6) + (3R)-4-chloro-1,3-butanediol (125605-10-9)

Conditions	Yield
With sodium tetrahydroborate In tetrahydrofuran for 1h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

(3R)-4-chloro-1,3-butanediol (125605-10-9) → (R)-3-Hydroxytetrahydrofuran (86087-24-3)

Conditions	Yield
With hydrogenchloride; sodium hydroxide In methanol; water	99.1%
In toluene for 16h; Heating / reflux;	88%
With hydrogenchloride for 2h; Reflux;	73.62 g

4,4'-dimethoxytrityl chloride (40615-36-9) + (3R)-4-chloro-1,3-butanediol (125605-10-9) → (3R)-4-chloro-1-(bis(4-methoxyphenyl)(phenyl)methoxy)-3-butanol (1574389-67-5)

Conditions	Yield
With triethylamine In dichloromethane at 0℃; Inert atmosphere;	90%

p-toluenesulfonyl chloride (98-59-9) + (3R)-4-chloro-1,3-butanediol (125605-10-9) → (R)-4-chloro-3-hydroxy-1-p-toluenesulfonyloxybutane (138915-39-6)

Conditions	Yield
With 2,6-dimethylpyridine at 0 - 20℃; for 15h;	70.8%

methyl (R)-4-chloro-3-hydroxybutyrate (88496-70-2) + p-toluenesulfonyl chloride (98-59-9) + (3R)-4-chloro-1,3-butanediol (125605-10-9) → (R)-4-chloro-3-hydroxy-1-p-toluenesulfonyloxybutane (138915-39-6)

Conditions	Yield
With hydrogenchloride; triethylamine In ice-water; dichloromethane	54%

Upstream product

• 10488-69-4 ethyl (L)-4-chloro-3-hydroxybutyrate 
• 86728-85-0 ethyl 4-chloro-3-hydroxybutanoate 

Downstream Products

• 138915-39-6 (R)-4-chloro-3-hydroxy-1-p-toluenesulfonyloxybutane 
• 86087-24-3 (R)-3-Hydroxytetrahydrofuran 
• 1574389-67-5 (3R)-4-chloro-1-(bis(4-methoxyphenyl)(phenyl)methoxy)-3-butanol 

Relevant articles and documents

Practical syntheses of (S)-4-hydroxytetrahydrofuran-2-one, (S)-3-hydroxytetrahydrofuran and their (R)-enantiomers

Optically active 4-hydroxytetrahydrofuran-2-one (3) has been synthesized in good yield from optically active ethyl 4-chloro-3-hydroxybutanoate (2) by refluxing with dilute hydrochloric acid. In a similar manner, optically active 3-hydroxytetrahydrofuran (5) was prepared from optically active 4-chloro-1,3-butanediol (4), which was derived from 2 by NaBH4 reduction. These new cyclizations proceed without racemization. VCH Verlagsgesellschaft mbH, 1997.

Design, synthesis and properties of artificial nucleic acids from (R)-4-amino-butane-1,3-diol

A new artificial nucleic acid analogue, (R)-Am-BuNA, was developed with a simplified acyclic (R)-4-amino-butane-1,3-diol phosphodiester backbone. Phosphoramidite monomers of (R)-Am-BuNA were incorporated into DNA oligonucleotides (ODNs) and G-quadruplexes. Their thermal stability, conformation change and biological stability were further investigated using UV-melting, circular dichroism (CD) and gel electrophoresis. The results suggested that thermal stability of the duplexes of (R)-Am-BuNA modified ODNs and their complementary ODN is highly dependent on the substitution position. Substitution of thymidine at the 7th position in a thrombin-binding DNA aptamer (TBA) results in a slight increase in Tm with no effect on quadruplex conformation on the CD spectrum in comparison to that of the natural G-quadruplex. Further enzymatic experiments with fetal bovine serum (FBS) and snake venom phosphodiesterase (SVPDE) indicated that only single replacement of a (R)-Am-BuNA modified nucleobase greatly inhibited oligonucleotide degradation, which shows their promising applications as capping nucleotides in nucleic acid drugs. This journal is

Process for preparing 3-Hydroxythiolane

A process for preparing 3-hydroxythiolane which is characterized by reacting a compound of the following formula, ???wherein X is a halogen atom, and R2 is a substituted or unsubstituted alkyl group, substituted or unsubstituted aralkyl group, or substituted or unsubstituted aryl group, with a metal sulfide.