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2,3:4,5-Di(2-butenyl)tetrahydrofurfural

HCID 31341
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
126-15-8
Standard SMILES
O=CC12CC=CCC1C1CC=CCC1O2
InChIKey
XNYGOEGATLFFOX-UHFFFAOYSA-N
Molecular formula
C13H16O2
Average molar mass
204.26 g/mol
Monoisotopic mass
204.11502975

Overview

topical repellent against Phlebotomus perniciosus

Names & identifiers

Preferred name
2,3:4,5-Di(2-butenyl)tetrahydrofurfural
IUPAC
4,5a,6,9,9a,9b-hexahydro-1H-dibenzofuran-4a-carbaldehyde
English name
MGK 11
Molecular formula
C13H16O2
Molecular weight
204.26

Names & synonyms

126-15-8Mgk repellent 11Dibutylene tetrafurfural1,5a,6,9,9a,9b-Hexahydro-4a(4H)-dibenzofurancarboxaldehydeCaswell No. 0894a(4H)-Dibenzofurancarboxaldehyde, 1,5a,6,9,9a,9b-hexahydro-2,3,4,5-Bis(2-butylene)tetrahydro-2-furaldehydeMGK R-11HSDB 5609UNII-C62PHK07EV2,3,4,5-Bisbutylene tetrafurfuralEINECS 204-773-7
Show more names
r-11MGK 11MGK IIMKG 11ac-r-11MGK-R 11ent17,596NSC 52965Repel 111MGK 11 0.1g
BRN 00116852,3:4,5-DI(2-BUTENYL)TETRAHYDROFURFURALAI3-17596Bis-delta(sup 2)-butylenetetrahydrofurfuralNSC-529652,3,4,5-Bis(delta-2-butylene)tetrahydrofurfural2,3,4,5-Bis(delta(sup 2)-butylene)tetrahydrofurfural2,3,4,5-Bis(delta(sup 2)-butenylene)tetrahydrofurfural

Database identifiers

CAS
126-15-8

Properties

Computed structural properties

XLogP
2.1
Topological polar surface area
26.3 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
1
Heavy atoms
15
Formal charge
0
Complexity
331

Experimental & physicochemical properties

CosmeticsViscosity controlling; Antioxidant
PesticidesPesticides -> Insect Repellents
OdorFRUITY ODOR
Density · 3 items

1.10 @ 20 °C/4 °C

DENSITY: 1.120 @ 20 °C/20 °C /TECHNICAL GRADE/

1.10 @ 20°C

Color/FormPALE YELLOW LIQUID
SolubilityPRACTICALLY INSOL IN WATER & IN DILUTE ALKALI; MISCIBLE WITH PETROLEUM OILS, TOLUENE, XYLENE, ETHANOL
Boiling Point · 2 items

307 °C

307 °C @760 [mm Hg]

Melting Point · 2 items

-80 °C

-80 °C

Physical DescriptionPale yellow liquid with a fruity odor; [HSDB]
Stability/Shelf LifeSTABLE FOR LONG PERIODS IN DRUMS

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 3 items

H411 (100%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

P273, P391, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Hazard information

Regulatory InformationChemical: 4a(4H)-Dibenzofurancarboxaldehyde, 1,5a,6,9,9a,9b-hexahydro-
Hazards SummaryMay cause irritation; [MSDSonline]
TSCA Requirements · 2 items

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, use, and exposure to EPA as cited in the preamble in 51 FR 41329.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. /4a(4H)-Dibenzofurancarboxaldehyde,1,5a,6,9,9a,9b-hexahydro/ is included on this list.

FIFRA Requirements · 1 item

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA, as amended in 1988, were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Bis(2-butylene)tetrahydro-2-furaldehyde is found on List C. Case No: 3127; Pesticide type: insecticide; Case Status: No products containing the pesticide are actively registered ... The case /is characterized/ as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.; Active ingredient (AI): Bis(2-butylene)tetrahydro-2-furaldehyde; AI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

Chemistry & industry

Uses & manufacturing

Uses · 3 items

Used as insect repellent; No longer registered with the EPA for use in the US, cancelled; [HSDB]

The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

INSECT REPELLENT

Methods of ManufacturingPRODUCED BY THE CONDENSATION OF BUTA-1,3-DIENE WITH 2-FURALDEHYDE (US PATENTS 2683511; 2934471)...
Formulations/Preparations · 4 items

USED IN COMBINATION WITH OTHER REPELLENTS SUCH AS DEET & MGK REPELLENT 326 OR TOXICANTS IN LIQUID & PRESSURIZED SPRAYS.

USED AT 0.5% TO 1.25% BY WT WITH DIETHYLTOLUAMIDE & OTHER COMPOUNDS IN REPELLENTS FOR PERSONAL USE. USED AT 0.2% TO 0.25% WITH PYRETHRINS IN SPRAYS FOR PETS & SHOW ANIMALS & HORSES.

ACTIVE INGREDIENT IN WATER EMULSION OR OIL SPRAYS USED IN INSECT REPELLENTS (FINAL RECOMMENDED CONCN 0.2-0.4%).

A typical formulation contains 0.075% pyrethins, 0.15% piperonyl butoxide, and 1% 2,3:4,5-di(2-butenyl)tetrahydrofurfural.

Household ProductsInformation on 2 consumer products that contain 2,3,4,5 Bis(2-butylene) tetrahydro 2-furaldehyde in the following categories is provided:
Use ClassificationCosmetics -> Viscosity controlling; Antioxidant
General Manufacturing Information · 3 items

4a(4H)-Dibenzofurancarboxaldehyde, 1,5a,6,9,9a,9b-hexahydro-: ACTIVE

IT IS AN INSECT REPELLENT EFFECTIVE AGAINST COCKROACHES, STABLE & HORN FLIES, MOSQUITOES & GNATS. ITS MAIN USES NOW ARE IN PET SPRAYS & IN REPELLENTS FOR PERSONAL USE IN COMBINATION WITH OTHER MATERIALS. IT IS NO LONGER RECOMMENDED FOR USE ON MILK- OR MEAT-PRODUCING ANIMALS.

The pesticide is no longer an active ingredient in any registered pesticide products. Therefore, EPA is characterizing it as cancelled.

Applications

UsesMGK 11 is an insect repellent most commonly used commercially as a mosquito repellent.

Related reactions

2 records
New reaction record
HRID 73724 reaction equation
HRID 73724As productuspto-grants-2014_09
HRID 1399474 reaction equation
HRID 1399474As productuspto-grants-2014_12

Compound notes

Loading…

On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
PubChem CID
31341
DTXSID
DTXSID3041320
UNII
C62PHK07EV
EC Number
204-773-7
Nikkaji
J5.380E

Physicochemical properties

Melting point
-80 ℃ · -80℃
Boiling point
307 ° · bp 307°
Density
420 · d420 1.10
refractive index
20 · n20/D 1.520-1.530
Flash point
154 °C · 154 °C
storage temp.
-20 °C · Amber Vial, -20°C Freezer, Under inert atmosphere
solubility
Chloroform (Slightly), Methanol (Slightly)
form
Oil
color
Pale-yellow liquid
Stability
Air Sensitive
Cosmetics Ingredients Functions
ANTIOXIDANTVISCOSITY CONTROLLING
LogP
2.29 · 2.290 (est)
EWG's Food Scores
1 · 1
FDA UNII
62 PHK07EV · C62PHK07EV
Pesticides Freedom of Information Act (FOIA)
-11 · MGK R-11
EPA Substance Registry System
2 · 2,3:4,5-Bis(2-butylene)tetrahydro-2-furaldehyde (126-15-8)
RTECS
5075000 · HP5075000
TSCA
TSCA listed
Hazardous Substances Data
126 · 126-15-8(Hazardous Substances Data)
Toxicity
50 orl-rat: · LD50 orl-rat: 2500 mg/kg MEIEDD 10,1170,83
Hazard Classes and CategoriesAquatic Chronic 2 (100%)

Safety & protection

Disposal Methods · 1 item

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Protective Action Criteria (PAC) · 3 items

7.5 [mg/m3]

83 [mg/m3]

500 [mg/m3]

Toxicology

Non-Human Toxicity ExcerptsIN 90-DAY FEEDING TRIALS RATS RECEIVING 20000 MG/KG DIET SUFFERED NO GROSS ILL-EFFECT.
Non-Human Toxicity ValuesLD50 Rat oral 2 g/kg

Regulatory information

TSCA Requirements · 2 items

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, use, and exposure to EPA as cited in the preamble in 51 FR 41329.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. /4a(4H)-Dibenzofurancarboxaldehyde,1,5a,6,9,9a,9b-hexahydro/ is included on this list.

FIFRA Requirements · 1 item

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA, as amended in 1988, were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Bis(2-butylene)tetrahydro-2-furaldehyde is found on List C. Case No: 3127; Pesticide type: insecticide; Case Status: No products containing the pesticide are actively registered ... The case /is characterized/ as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.; Active ingredient (AI): Bis(2-butylene)tetrahydro-2-furaldehyde; AI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

Safety data

tsca
TSCA listed
rtecs
HP5075000
Toxicity
LD50 orl-rat: 2500 mg/kg MEIEDD 10,1170,83
Hazardous Substances Data
126-15-8(Hazardous Substances Data)

Upstream & downstream products

Upstream raw materials

Furfural1,3-Butadiene

Suppliers21 total

Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
梯希爱(上海)化工贸易有限公司021-61109150 · [email protected]
四川库利南科技有限公司400-1166-196 18981987031 · [email protected]
艾科试剂4008-755-333 18080918076 · [email protected]
上海贺康生物技术有限公司17721021104 18939837085 · [email protected]
上海将来实业股份有限公司400-0066400 13621662912 · [email protected]
天津阿尔塔科技有限公司022-65378550-8551 · [email protected]
陕西缔都医药化工有限公司029-81024372 17792795018 · [email protected]
深圳振强药物研发有限公司+86-0755-66853366 +86-13670046396 · [email protected]
天津阿尔塔科技有限公司022-6537-8550 15522853686 · [email protected]
上海博尔森生物科技有限公司021-67681877 13166061152 · [email protected]
安耐吉化学&3A(安徽泽升科技股份有限公司)400-0056266 · [email protected]
湖北万业众诚化学试剂有限责任公司18671296875 · [email protected]
河北贞佳新材料有限公司0319-5925599 13315915972 · [email protected]
Shaanxi Dideu New Materials Co. Ltd18192503167 · [email protected]
杭州洁汉化工有限公司+86-571-86217390; +8618058761490 · [email protected]
career henan chemical co+86-0371-86658258 · [email protected]
深圳聚合生化科技有限公司+86-400-002-6226 13028896684 · [email protected]
爆牛贸易重庆有限公司+86-023-6139-8061 +86-86-13650506873 · [email protected]
上海联迈生物工程有限公司021-67680335 13052188602 · [email protected]
亚索试剂400-873-6778 18660992876 · [email protected]