2,3-Pentanedione Property

Melting point:

-52 °C (lit.)

Boiling point:

110-112 °C (lit.)

Density 

0.957 g/mL at 25 °C (lit.)

vapor pressure 

28.5 hPa (20 °C)

FEMA 

2841 | 2,3-PENTANEDIONE

refractive index 

n20/D 1.404(lit.)

Flash point:

66 °F

storage temp. 

2-8°C

solubility 

60g/l

form 

Liquid

color 

very deep green-yellow

PH

4 (H2O)

Odor

at 1.00 % in dipropylene glycol. pungent sweet butter creamy caramel nutty cheese

Odor Type

buttery

explosive limit

1.8-10.9%(V)

Water Solubility 

60 g/L (15 ºC)

JECFA Number

410

BRN 

1699638

Exposure limits

NIOSH: TWA 9.3 ppb; STEL 31 ppb

Stability:

Stable. Highly flammable - store cool. Incompatible with strong oxidizing agents, reducing agents, strong bases.

InChIKey

TZMFJUDUGYTVRY-UHFFFAOYSA-N

LogP

-0.85

CAS DataBase Reference

600-14-6(CAS DataBase Reference)

NIST Chemistry Reference

2,3-Pentanedione(600-14-6)

EPA Substance Registry System

2,3-Pentanedione (600-14-6)

Safety

Hazard Codes 

F,Xi

Risk Statements 

11-36/37/38

Safety Statements 

16-26-36-37/39

RIDADR 

UN 1224 3/PG 2

WGK Germany 

1

RTECS 

SA1850000

F 

9-23

Autoignition Temperature

265 °C

TSCA 

Yes

HazardClass 

3

PackingGroup 

II

HS Code 

29141990

Hazardous Substances Data

600-14-6(Hazardous Substances Data)

Toxicity

LD50 orally in Rabbit: 3000 mg/kg LD50 dermal Rabbit > 2500 mg/kg

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H225Highly Flammable liquid and vapour

H317May cause an allergic skin reaction

H373May cause damage to organs through prolonged or repeated exposure

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P233Keep container tightly closed.

P240Ground/bond container and receiving equipment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P314Get medical advice/attention if you feel unwell.

2,3-Pentanedione Chemical Properties,Usage,Production

Chemical Properties

2,3-Pentanedione is a colourless or deep green-yellow colour liquid that has a somewhat sweet odor similar to quinone. This compound has a penetrating, buttery taste on dilution. It is used as flavoring agent or adjuvant.

Occurrence

2,3-Pentanedione occurs in butter, bread, milk, yogurt, chicken, meat, cocoa, coffee, potato chips, roasted almonds, pecans, beer, red and white wine, rum and whiskey. The organoleptic profile can be described as creamy, penetrating, cheesy, oily, sweet, buttery, almondlike, brown roasted, and somewhat caramellic, with a fruity nuance.

Uses

2,3-Pentanedione may be used as a reference standard in the determination of 2,3-pentanedione in beer samples using headspace-gas chromatographic technique (HS-GC).

Application

2,3-Pentanedione can be used as a reactant to synthesize:
Bisphenol derivatives by acid-catalyzed condensation reaction with phenols.
2-Ethyl-3-methyl-1H-indole by Pd-catalyzed reaction with aniline under reductive conditions.
2-Ethyl-3-methylquinoxaline by condensation reaction with o-phenylenediamine using citric acid as a catalyst.

Definition

ChEBI: 2,3-Pentanedione is an alpha-diketone that is pentane substituted at the 2- and 3-positions by oxo groups. It has a role as a flavouring agent. It is an alpha-diketone and a methyl ketone. It derives from a hydride of a pentane.

Preparation

By oxidation of methyl propyl ketone with excess NaNO2 and diluted HCl in the presence of hydroxylamine hydrochloride under a nitrogen blanket.

Aroma threshold values

Detection: 20 ppb. Aroma characteristics at 1.0%: buttery diacetyl-like, fermented dairy and creamy, popcorn buttery.

Taste threshold values

Taste characteristics at 1 to 5 ppm: sweet buttery, creamy, cheesy, slightly toasted dairy, with a rich baked goods nuance and a good mouthfeel.

General Description

2,3-Pentanedione (acetylpropionyl) is one of the aroma active compounds of cereal coffee brew.

Biochem/physiol Actions

Taste at 1-5.0 ppm

Safety Profile

Confirmed human carcinogen. Poison by intraperitoneal route. When heated to decomposition it emits acrid smoke and irritating fumes. See also NICKEL COMPOUNDS