BUTOPYRONOXYL Chemical Properties

Melting point:

25°C

Boiling point:

bp760 256-270°

Density 

1.054 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.477(lit.)

Flash point:

>230 °F

storage temp. 

4°C, protect from light

solubility 

DMSO: 100 mg/mL (441.95 mM)

form 

clear liquid

color 

Light orange to Yellow to Green

CAS DataBase Reference

532-34-3

EPA Substance Registry System

Butopyronoxyl (532-34-3)

Safety Information

Risk Statements 

38

Safety Statements 

37/39

WGK Germany 

3

RTECS 

UP7000000

HS Code 

29329990

Hazardous Substances Data

532-34-3(Hazardous Substances Data)

Toxicity

LD50 in mice, rats (ml/kg): 11.6, 7.4 orally (Draize)

MSDS

• Language:English Provider:SigmaAldrich

BUTOPYRONOXYL Usage And Synthesis

Synthesis

To a 25-mL flflame-dried flflask under a nitrogen atmosphere were added freshly distilled Rawal’s diene (227 mg, 1 mmol, 1.0 equivalents) and 2 mL of CHCl3. Benzaldehyde (1.5 mmol, 1.5 equivalents) was added dropwise via a gas-tight syringe. The reaction mixture was stirred at room temperature for 2 h and then diluted with 15 mL of CH2Cl2. The yellow solution was cooled to −78 °C and treated with 142 µL acetyl chloride (2 mmol, 2 equivalents). After stirring for about 30 min, saturated Na2CO3 was added. The organic layer was separated and the water phase was diluted with 15 mL of water and extracted twice with CH2Cl2. The combined organic phase was dried with MgSO4, fifiltered, and concentrated to give a yellow oil, which was subjected to flflash chromatography to afford the desired dihydropyrone in 86% overall yield. Reference: Huang, Y.; Rawal, V. H. Org. Lett. 2000, 2, 3321−3322.

Chemical Properties

Yellow to pale reddish-brown liquid; aromatic odor. Reasonably stable in air. Slowly affected by light. Insoluble in water; miscible with alcohol, chloroform, ether, glacial acetic acid.

Uses

Insect repellents that can be applied directly on the skin.

Uses

Indalon is an insect repellent.

Definition

ChEBI: Butopyronoxyl is a member of pyrans and a carbonyl compound.

Indications

Butopyronoxyl is not water soluble and can be applied to skin and clothing to repel biting stable flies, Lone Star ticks, dog and cat fleas, and chiggers.

Hazard

Toxic by ingestion. May cause liver dam- age.

Safety Profile

Moderately toxic by ingestion. Produces liver necrosis in experimental animals. A rmld skin irritant. See also OXALATES and ESTERS. Combustible when exposed to heat or flame. When heated to decomposition it emits acrid fumes.

BUTOPYRONOXYL(532-34-3)Related Product Information

• Methyl methoxyacetate
• Methoxyacetic acid
• Vinyl isopropyl ether
• 5,6-DIHYDRO-4H-PYRAN-2-CARBOXYLIC ACID
• 2-Ethoxypropene
• ETHYL CROTONATE
• (E)-4-Hexen-1-ol
• METHYL 2-PENTENOATE
• Ethylene Glycol Dibutyl Ether
• TERT-AMYL METHYL ETHER
• Butyl hydroxyacetate
• ETHYLENE GLYCOL MONO-TERT-BUTYL ETHER
• BUTYL CROTONATE
• BUTOPYRONOXYL
• Diacetone Alcohol
• Ethyl glycolate
• N-PROPYL ACRYLATE
• TRANS-2-HEXENOIC ACID