1,2,4-Butanetriol

Names
Preferred IUPAC name

Butane-1,2,4-triol

Other names

1,2,4-Butanetriol
1,2,4-Trihydroxybutane
Triol 124
2-Deoxyerthritol

Identifiers

CAS Number

* 3068-00-6 Y

3D model (JSmol)

* Interactive image
* Interactive image

ChEBI |

* CHEBI:88063 Y

ChEMBL |

* ChEMBL1356759

ChemSpider |

* 17287 Y

EC Number |

* 221-323-5

PubChem CID

* 18302

RTECS number |

* EK7176000

UNII |

* NK798C370H Y

InChI

* InChI=1S/C4H10O3/c5-2-1-4(7)3-6/h4-7H,1-3H2 Y

Key: ARXKVVRQIIOZGF-UHFFFAOYSA-N Y

* InChI=1/C4H10O3/c5-2-1-4(7)3-6/h4-7H,1-3H2

Key: ARXKVVRQIIOZGF-UHFFFAOYAQ

SMILES

* OCC(O)CCO

* OCCC(O)CO

Properties

Chemical formula

| C4H10O3
Molar mass | 106.121 g·mol−1
Density | 1.19
Boiling point |  190 to 191 °C (374 to 376 °F; 463 to 464 K) 18 torr
Hazards
GHS pictograms |
GHS Signal word | Warning

GHS hazard statements

| H315, H319, H335

GHS precautionary statements

| P261, P264, P271, P280, P302+352, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362, P403+233, P405, P501
NFPA 704 (fire diamond)  |

Flash point |  112 °C (234 °F; 385 K)

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

N verify (what is YN ?)
Infobox references

1,2,4-Butanetriol is a clear or slightly yellow, odorless, hygroscopic, flammable, viscous liquid. It is an alcohol with three hydrophilic alcoholic hydroxyl groups. It is similar to glycerol and erythritol. It is chiral, with two possible enantiomers.

1,2,4-Butanetriol is used in the manufacture of butanetriol trinitrate (BTTN), an important military propellant.

1,2,4-Butanetriol is also used as a precursor for two cholesterol-lowering drugs, Crestor and Zetia, which are derived from D-3,4-dihydroxybutanoic acid, by using 3-hydroxy-gamma-butyrolactone as a chiral synthon[1][2] It is used as one of the monomers for manufacture of some polyesters and as a solvent.

1,2,4-Butanetriol can be prepared synthetically by several different methods such as hydroformylation of glycidol and subsequent reduction of the product, sodium borohydride reduction of esterified malic acid, or catalytic hydrogenation of malic acid.[3] However, of an increasing importance is the biotechnological synthesis using genetically engineered Escherichia coli and Pseudomonas fragi bacteria.[4]

## References

1. ↑ Niu, Wei; Molefe, Mapitso N.; Frost, J. W. (2003). "Microbial Synthesis of the Energetic Material Precursor 1,2,4-Butanetriol". Journal of the American Chemical Society 125 (43): 12998–12999. doi:10.1021/ja036391+. ISSN 0002-7863. PMID 14570452.
2. ↑ "Biosynthetic Pathways". http://www.frostchemlab.com/biosynthetic-pathways.htm. Retrieved 24 November 2010.
3. ↑ Ritter, Stephen K. (May 31, 2004). "Biomass or Bust". Chemical & Engineering News. p. 31-34. http://pubsapp.acs.org/email/cen/html/060804150713.html.
4. ↑ Gilbert, Meghan (February 12, 2004). "Propelling Research". The State News. https://statenews.com/article/2004/02/propelling_research.

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*[CID]: Compound ID
*[H315]: Causes skin irritation
*[H319]: Causes serious eye irritation
*[H335]: May cause respiratory irritation
*[P261]: Avoid breathing dust/fume/gas/mist/vapours/spray
*[P264]: Wash … thoroughly after handling
*[P271]: Use only outdoors or in a well-ventilated area
*[P280]: Wear protective gloves/protective clothing/eye protection/face protection
*[P302+352]: IF ON SKIN: Wash with soap and water
*[P304+340]: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
*[P305+351+338]: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do – continue rinsing
*[P312]: Call a POISON CENTER or doctor/physician if you feel unwell
*[P321]: Specific treatment (see … on this label)
*[P332+313]: If skin irritation occurs: Get medical advice/attention
*[P337+313]: Get medical advice/attention
*[P362]: Take off contaminated clothing and wash before reuse
*[P403+233]: Store in a well ventilated place. Keep container tightly closed
*[P405]: Store locked up
*[P501]: Dispose of contents/container to …