Dicyclopentadiene dioxide

HCID 6673
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Basic information

CAS
81-21-0
Standard SMILES
C1C2OC2C2C1C1CC2C2OC12
InChIKey
BQQUFAMSJAKLNB-UHFFFAOYSA-N
Molecular formula
C10H12O2
Average molar mass
164.2 g/mol
Monoisotopic mass
164.08372962

Names & identifiers

Preferred name
Dicyclopentadiene dioxide
IUPAC
4,10-dioxapentacyclo[6.3.1.02,7.03,5.09,11]dodecane
English name
Dicyclopentadiene diepoxide
Molecular formula
C10H12O2
Molecular weight
164.2

Names & synonyms

Dicyclopentadiene diepoxideDICYCLOPENTADIENE DIOXIDEHSDB 5240Dicyclopentadiene dioxide (VAN)DTXSID4020452EINECS 201-334-11,2:5,6-Diepoxyhexahydro-4,7-methanoindanAI3-260462,4-Methano-2H-indeno(1,2-b:5,6-b')bisoxirene, octahydro-2,4-Methano-2H-indeno[1,2-b:5,6-b']bisoxirene, octahydro-Dicyclopentadiene dioxide, 70% exo isomers, 30% endo isomersDTXCID00452
Show more names
BICYCLOPENTADIENE DIEPOXIDE2,4-Methano-2H-indeno1,2-b:5,6-bbisoxirene, octahydro-ep207unox207unox207xepoxide207unoxepoxide207bicyclopentadienedioxideBicyelopentadiene dioxide
NSC-24262NSC-30544NSC-34460NSC-54738NSC-56357UNII-4UQK50194RRefChem:1332582,4-METHANO-2H-INDENO(1,2-B:5,6-B')BISOXIRENE, OCTAHYDRO-, (1A.ALPHA.,1B.BETA.,2.BETA.,2A.ALPHA.,3A.ALPHA.,4.BETA.,4A.BETA.,5A.ALPHA.)-

Database identifiers

CAS
81-21-0
PubChem CID
6673
DTXSID
DTXSID4020452
ChEMBL
CHEMBL3184982
EC Number
201-334-1
Nikkaji
J192.584I

Properties

Computed structural properties

XLogP
0.8
Topological polar surface area
25.1 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
0
Heavy atoms
12

Experimental & physicochemical properties

PolymersPlastics & Rubber -> Epoxides
OdorMILD TERPENE LIKE ODOR MAY BE MASKED BY MORE POWERFUL & DISTINCTIVE HYDROCARBON ODOR OF DICYCLOPENTADIENE.
Density1.331 @ 25 °C
Color/FormWHITE CRYSTALLINE POWDER
Solubility · 5 items

SOL IN BENZENE

1.4% IN WATER

18.6% IN METHANOL

44.7% IN ACETONE

18.7% IN ETHER

Melting Point180-184 °C

Physicochemical properties

Melting point
185 · 185-189 °C(lit.)
Boiling point
120 °C · 120°C 10mm
Density
1 · 1,331 g/cm3
refractive index
1.546 · 1.5460 (estimate)
Flash point
120 °C/10mm · 120°C/10mm subl.
storage temp.
2 · 2-8°C

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P264, P264+P265, P270, P280, P301+P316, P305+P351+P338, P321, P330, P337+P317, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 46 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 2 items

Chemical: 2,4-Methano-2H-indeno[1,2-b:5,6-b']bisoxirene, octahydro-

2,4-Methano-2H-indeno[1,2-b:5,6-b']bisoxirene, octahydro-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Hazards SummaryMild irritant on rabbit skin; Methemoglobinemia, CNS effects, and proteinuria reported in inhalation studies of rats; [RTECS] Emergency treatment: irritants; [HSDB] An eye irritant; [MSDSonline]
TSCA RequirementsSection 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 of the 51 FR 41329.
Hazard Classes and CategoriesAcute Tox. 3 (100%)

Toxicology

Adverse EffectsMethemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as secondary toxic effect
Human Toxicity ExcerptsNo cases of dermatitis or sensitization have been reported /in man/.
Non-Human Toxicity Excerpts · 2 items

CMPD IS MODERATELY TOXIC FOLLOWING ORAL OR IP ENTRY INTO BODY & PRACTICALLY NONTOXIC ON PERCUTANEOUS ABSORPTION. ... THE LETHAL RANGE WHEN GIVEN ORALLY TO RATS AS 50 TO 140 MG/KG, AND 11 TO 53 MG/KG INTRAPERITONEALLY. ... RABBITS TOLERATED 1 G/KG PERCUTANEOUSLY WITHOUT EFFECT. IN INHALATION EXPERIMENTS A DOSE OF 1 G/CU M FOR 1 HR WAS MODERATELY TOXIC, AND 10 G/CU M FOR 1 HR WAS LETHAL TO 5 OF 6 TEST ANIMALS. SATURATED VAPORS WERE NONLETHAL TO RATS IN 8 HR EXPOSURE. ... MILDLY IRRITATING BUT NO CORNEAL INJURY IN RABBITS WITH TEST QUANT OF 0.05 G. 40% SOLN WAS LEAST CONCN TO CAUSE BARELY DETECTABLE INJURY. ... SKIN IRRITATION. UNDIL MATERIAL CAUSED REDNESS OF SHORT DURATION.

DICYCLOPENTADIENE DIOXIDE DID NOT SHOW ANY ALLERGENIC PROPERTIES WHEN APPLIED IN 10-50% SOLN TO SKIN OF GUINEA PIGS FOR 5-15 DAYS.

Regulatory information

TSCA RequirementsSection 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 of the 51 FR 41329.

Safety data

PPE
dust mask type N95 (US), Eyeshields, Faceshields, Gloves
wgk
3
tsca
TSCA listed
rtecs
PB9625200
ridadr
UN 2811 6.1/PG 3
hs_code
29109000

Chemistry & industry

Uses & manufacturing

Uses · 5 items

Used as an intermediate for epoxy resins, plasticizers, and protective coatings; as a rubber additive; and for high temperature and high performance adhesives; [HSDB]

Working with Glues and Adhesives [Category: Other]

INTERMEDIATE FOR EPOXY RESINS, PLASTICIZERS, PROTECTIVE COATINGS

RUBBER ADDITIVE, EG, FOR CRACK PREVENTION & ADHESION

For high temp & high performance system, adhesives

U.S. Production · 2 items

(1979) PROBABLY GREATER THAN 2.72X10+6 G

(1980) PROBABLY GREATER THAN 2.72X10+6 G

Methods of ManufacturingPROBABLY BY DIELS-ALDER CONDENSATION OF CYCLOPENTADIENE FOLLOWED BY EPOXIDATION.
General Manufacturing Information · 2 items

2,4-Methano-2H-indeno[1,2-b:5,6-b']bisoxirene, octahydro-: ACTIVE

AVAIL IN EXPTL QUANT, THIS DIFUNCTIONAL EPOXIDE IS SUGGESTED FOR USE AS PRIMARY BUILDING BLOCK FOR EPOXY RESIN SYSTEM. IT HAS ALSO BEEN SUGGESTED IN MODIFICATION OF ALKYD RESINS, AS PLASTICIZER, & AS CHEMICAL INTERMEDIATE.

Applications · 1 item

UsesDicyclopentadiene diepoxide acts as an intermediate for epoxy resins, plasticizers and protective coatings. It finds application as a rubber additive and adhesives, which is used at high temperature. Further, it is used in the preparation of endo-3-hydroxy-exo-9-oxa-exo-tetracyclo[5.3.1.02,6.08,10]undecane using lithium aluminum hydride as a reagent.

Suppliers100 total

郑州阿尔法化工有限公司+86-18530059196 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
湖北永阔科技有限公司027-59223108 15972152991 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
湖北万得化工有限公司15377098680 15377098680 · [email protected]

Related reactions

3 records
New reaction record

Compound notes

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