Basic information
- Standard SMILES
CC12C=CC(C1)C1C(=O)OC(=O)C12- InChIKey
LTVUCOSIZFEASK-MPXCPUAZSA-N- Molecular formula
- C10H10O3
- Average molar mass
- 178.18 g/mol
Names & identifiers
- Preferred name
- Methyl nadic anhydride
- IUPAC
- 1-methyl-4-oxatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione
- English name
- Methyl-5-norbornene-2,3-dicarboxylic anhydride
- Molecular formula
- C10H10O3
- Molecular weight
- 178.18
Names & synonyms
Nadic methyl anhydrideKayahard MCDHardener HY906Methylendic anhydrideHSDB 6093MEA 610EINECS 246-644-8BRN 0162395TK 10 524CCRIS 9477endo-Methylenemethyltetrahydrophthalic anhydride5-Norbornene-2,3-dicarboxylic anhydride, methyl-
Show more names
MNAMETHYL NADIC ANHYDRIDENMAXMNAmea610tk10524epicurenmaEpicure NMA
Methyl-tetrahydro-3,6-endomethylenephthalic anhydrideMethylbicyclo(2.2.1)heptene-2,3-dicarboxylic anhydrideMethyl-1,2,3,6-tetrahydro-3,6-endomethylenephthalic anhydrideMethylbicyclo(2.2.1)heptene-2,3-dicarboxylic anhydride isomersEC 246-644-84,7-Methanoisobenzofuran-1,3-dione, 3a,4,7,7a-tetrahydromethyl-, (3aalpha,4alpha,7alpha,7aalpha)-5-17-11-00199 (Beilstein Handbook Reference)RefChem:157957
Database identifiers
- CAS
25134-21-8- PubChem CID
- 32802
- EC Number
- 246-644-8
- Nikkaji
- J1.864.179H
Properties
Computed structural properties
- XLogP
- 1.2
- Topological polar surface area
- 43.4 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 0
- Heavy atoms
- 13
- Formal charge
- 0
- Complexity
- 344
Experimental & physicochemical properties
PolymersPlastics & Rubber -> Acid Anhydrides, Cyclic
Density
1.200-1.250 @ 20 °C/20 °C
1.232 @25 °C
Viscosity175-225 CP @ 25 °C
Color/FormCOLORLESS TO LIGHT-YELLOW VISCOUS LIQ
SolubilityMISCIBLE IN ALL PROPORTIONS WITH ACETONE, BENZENE, NAPHTHA, & XYLENE
Melting Point18 °C
Vapor Pressure0.1 [mmHg]
Food Contact Substances
FCS -> FDA Cumulative Estimated Daily Intake (CEDI)
FCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR
Refractive IndexINDEX OF REFRACTION: 1.500-1.506 @ 20 °C/D
Physical Description
Liquid
Colorless to light yellow liquid; [HSDB] Colorless liquid; [MSDSonline]
Physicochemical properties
- Boiling point
- 140 °C · 140°C (10 mmHg)
- Density
- 1.232 g/mL · 1.232 g/mL at 25 °C(lit.)
- vapor density
- 6.1 · 6.1 (20 °C, vs air)
- vapor pressure
- 5 mm · 5 mm Hg ( 120 °C)
- refractive index
- 20 · n20/D 1.506(lit.)
- Flash point
- 230 °F · >230 °F
- storage temp.
- room temp
- solubility
- Miscible with acetone, benzene, naphtha and xylene.
- pka
- 4.42 · 4.42[at 20 ℃]
- form
- Oily Liquid
- color
- Clear light yellow
- biological source
- synthetic
- Water Solubility
- REACTS
- Sensitive
- Moisture Sensitive
- BRN
- 162395 · 162395
- Major Application
- hematologyhistology
- InChI
- 1S/C10H10O3/c1-10-6-3-2-5(4-6)7(10)8(11)13-9(10)12/h2-3,5-7H,4H2,1H3/t5-,6+,7+,10+/m0/s1
- InChIKey
- LTVUCOSIZFEASK-MPXCPUAZSA-N
- SMILES
- [H][C@]12C3CC(C(C)=C3)[C@@]1([H])C(=O)OC2=O
- LogP
- -4.01 at · -4.01 at 20℃
- CAS DataBase Reference
- 25134 · 25134-21-8(CAS DataBase Reference)
- Indirect Additives used in Food Contact Substances
- -5 · METHYL-5-NORBORNENE-2,3-DICARBOXYLIC ANHYDRIDE
- FDA 21 CFR
- 177.152 · 177.1520
- EWG's Food Scores
- 1 · 1
- NIST Chemistry Reference
- 4 · 4,7-Methanoisobenzofuran-1,3-dione, 3a,4,7,7a-tetrahydromethyl-(25134-21-8)
- EPA Substance Registry System
- 4 · 4,7-Methanoisobenzofuran-1,3-dione, 3a,4,7,7a-tetrahydromethyl-, (3aR,4S,7R,7aS)-rel- (25134-21-8)
- UNSPSC Code
- 41102904 · 41102904
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 5 · GHS05,GHS07,GHS08
- Signal word
- Danger
- Hazard statements
- 302 · H302-H314-H317-H334
- Precautionary statements
- 280 · P280-P301+P312+P330-P301+P330+P331-P303+P361+P353-P305+P351+P338
- PPE
- Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
- Hazard Codes
- Xn,C
- Risk Statements
- 22 · 22-36/37/38-42-34
- Safety Statements
- 39 · 39-45-36/37/39-26
- RIDADR
- 3265 · UN 3265 8/PG 2
- WGK Germany
- 3 · 3
- RTECS
- 9100000 · RB9100000
- TSCA
- TSCA listed
- HazardClass
- 6.1 · 6.1
- PackingGroup
- III
- HS Code
- 29172000 · 29172000
- Storage Class
- 8 A · 8A - Combustible corrosive hazardous materials
- Hazard Classifications
- 4 OralResp · Acute Tox. 4 OralResp. Sens. 1Skin Corr. 1CSkin Sens. 1
- Hazardous Substances Data
- 25134 · 25134-21-8(Hazardous Substances Data)
- Toxicity
- 50 oral · LD50 oral in rat: 914mg/kg
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
Danger
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P233, P260, P261, P264, P264+P265, P270, P271, P272, P280, P284, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P319, P321, P330, P332+P317, P333+P317, P337+P317, P342+P316, P362+P364, P363, P403, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 295 reports by companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Warning
H302: Harmful if swallowed [Warning Acute toxicity, oral]
Hazard information
Regulatory Information
Chemical: 4,7-Methanoisobenzofuran-1,3-dione, 3a,4,7,7a-tetrahydromethyl-, (3a.alpha.,4.alpha.,7.alpha.,7a.alpha.)-
4,7-Methanoisobenzofuran-1,3-dione, 3a,4,7,7a-tetrahydromethyl-, (3aR,4S,7R,7aS)-rel- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 4,7-Methanoisobenzofuran-1,3-dione, 3a,4,7,7a-tetrahydromethyl-, (3aR,4S,7R,7aS)-rel- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
REACH registered substance: 1,2,3,6-tetrahydromethyl-3,6-methanophthalic anhydride (EC: 246-644-8)
Methylnorbornen-2,3-dicarboxylic anhydride: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryA skin and eye irritant; May cause respiratory sensitization; [eChemPortal: ERMA] An irritant; Inhalation may cause respiratory sensitization; [MSDSonline] See ACID ANHYDRIDES.
Hazard Classes and Categories
Acute Tox. 4 (100%)
Acute toxicity (Oral) - Category 4
Acute toxicity (Oral) - Category 4
Safety & protection
Protective Action Criteria (PAC)
0.49 [mg/m3]
5.4 [mg/m3]
32 [mg/m3]
Toxicology
Adverse EffectsAsthma - Reversible bronchoconstriction (narrowing of bronchioles) initiated by the inhalation of irritating or allergenic agents.
Toxicity DataLCLo (rat) = 750 mg/m3/4h
Safety data
- PPE
- Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- RB9100000
- ridadr
- UN 3265 8/PG 2
- hs_code
- 29172000
- Toxicity
- LD50 oral in rat: 914mg/kg
- risk_code
- 22-36/37/38-42-34
- Signal word
- Danger
- Symbol(GHS)
- GHS05,GHS07,GHS08
- hazard_code
- Xn,C
- safety_code
- 39-45-36/37/39-26
- hazard_class
- 6.1
- Storage Class
- 8A - Combustible corrosive hazardous materials
- packing_group
- III
- Hazard statements
- H302-H314-H317-H334
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 4 OralResp. Sens. 1Skin Corr. 1CSkin Sens. 1
- Precautionary statements
- P280-P301+P312+P330-P301+P330+P331-P303+P361+P353-P305+P351+P338
- Hazardous Substances Data
- 25134-21-8(Hazardous Substances Data)
Chemistry & industry
Uses & manufacturing
Uses
Used as a curing agent (epoxy resins), an intermediate (polyesters, alkyd resins, and plasticizers), and in electrical laminating and filament-winding; [HSDB]
Plastic Composites Manufacturing [Category: Industry]
CURING AGENT FOR EPOXY RESINS; INTERMEDIATE FOR POLYESTERS, ALKYD RESINS, & PLASTICIZERS; ELECTRICAL LAMINATING & FILAMENT-WINDING
CURING AGENT FOR EPOXY RESINS-EG, FOR ELECTRICAL CASTINGS
CHEM INT FOR POLYESTER RESINS
U.S. Exports
(1979) No Data
(1981) No Data
U.S. Imports
(1979) No Data
(1981) No Data
U.S. Production
2023: 154,070 lb
(1981) PROBABLY GREATER THAN 2.27X10+6 GRAMS
(1982) MORE THAN 2.27X10+6 G (MIXED ISOMERS)
Consumer UsesIntermediate
Industry UsesIntermediate
Methods of ManufacturingREACTION OF METHYLCYCLOPENTADIENE WITH MALEIC ANHYDRIDE
General Manufacturing Information
All Other Basic Organic Chemical Manufacturing
4,7-Methanoisobenzofuran-1,3-dione, 3a,4,7,7a-tetrahydromethyl-, (3aR,4S,7R,7aS)-rel-: ACTIVE
Applications
UsesMethyl-5-norbornene-2,3-dicarboxylic anhydride is used as a curing agent in epoxy resins and in the preparation of vertically aligned and penetrated carbon nanotube/polymer film. It serves as an intermediate in polyesters, alkyd resins and plasticizers. It is also used in electrical laminating and filament-winding. Further, it is used in the preparation of methyl nadimides endcapped resins based on tris(3-aminophenyl)phosphine oxide. It is utilized in the flame retarding treatment.
General Descriptionadditional information see 45359 Epoxy Embedding Medium kit
Upstream & downstream products
Upstream raw materials
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