Dimethyl acetylenedicarboxylate
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Basic information
- CAS
762-42-5- Standard SMILES
COC(=O)C#CC(=O)OC- InChIKey
VHILMKFSCRWWIJ-UHFFFAOYSA-N- Molecular formula
- C6H6O4
- Average molar mass
- 142.11 g/mol
- Monoisotopic mass
- 142.02660867
Overview
inhibitor of oxidative phosphorylation
Names & identifiers
- Preferred name
- Dimethyl acetylenedicarboxylate
- IUPAC
- dimethyl but-2-ynedioate
- English name
- Dimethyl acetylenedicarboxylate
- Molecular formula
- C6H6O4
- Molecular weight
- 142.11
Names & synonyms
Dimethyl acetylenedicarboxylate762-42-52-Butynedioic acid, dimethyl esterDimethyl 2-butynedioateBis(methoxycarbonyl)acetyleneDi(carbomethoxy)acetylene1,2-Bis(methoxycarbonyl)acetyleneDimethyl ethynedicarboxylateAcetylenedicarboxylic acid dimethyl ester1,2-Bis(methoxycarbonyl)ethyneAcetylenedicarboxylic acid, dimethyl ester7HZA2PL15F
Show more names
DMADACETYLENEDICARBOXYLATEDimethyl acetylenediDimethyl butynedioateDimethyl But-2-yne-1,4-dioateBut-2-ynedioic acid dimethyl esterenedicarboxyL4-Diethyl-pyrrolDimethyl butyrate
2-Butynedioic acid, 1,4-dimethyl esterNSC-14912NSC-101119DTXSID0061088RefChem:552497DTXCID7047857212-098-4dimethyl but-2-ynedioate
Database identifiers
- CAS
762-42-5- PubChem CID
- 12980
- DTXSID
DTXSID0061088- ChEMBL
CHEMBL3248452- UNII
- 7HZA2PL15F
- EC Number
- 212-098-4
- Nikkaji
- J26.302H
Properties
Computed structural propertiesFilling in
- XLogP
- 0.8
- Topological polar surface area
- 52.6 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 2
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 184
Experimental & physicochemical properties
SpringerMaterials PropertiesBoiling point
Physicochemical properties
- Melting point
- -18 °C · -18 °C
- Boiling point
- 95 · 95-98 °C/19 mmHg (lit.)
- Density
- 1.156 g/mL · 1.156 g/mL at 25 °C (lit.)
- refractive index
- 20 · n20/D 1.447(lit.)
- Flash point
- 187 °F · 187 °F
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- form
- Liquid
- color
- Colorless to pale yellow
- Water Solubility
- Soluble in most organic solvents. Insoluble in water.
- Sensitive
- Light Sensitive
- BRN
- 607063 · 607063
- InChI
- 1S/C6H6O4/c1-9-5(7)3-4-6(8)10-2/h1-2H3
- InChIKey
- VHILMKFSCRWWIJ-UHFFFAOYSA-N
- SMILES
- COC(=O)C#CC(=O)OC
- CAS DataBase Reference
- 762 · 762-42-5(CAS DataBase Reference)
- FDA UNII
- 7 HZA2PL15F · 7HZA2PL15F
- NIST Chemistry Reference
- 2 · 2-Butynedioic acid, dimethyl ester(762-42-5)
- EPA Substance Registry System
- 2 · 2-Butynedioic acid, dimethyl ester (762-42-5)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 5 · GHS05,GHS07
- Signal word
- Danger
- Hazard statements
- 302 · H302-H314
- Precautionary statements
- 270 · P270-P280-P301+P312-P303+P361+P353-P304+P340+P310-P305+P351+P338
- PPE
- Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
- Hazard Codes
- C
- Risk Statements
- 34 · 34-22
- Safety Statements
- 23 · 23-26-27-36/37/39-45
- RIDADR
- 3265 · UN 3265 8/PG 2
- WGK Germany
- 3 · 3
- RTECS
- 175000 · ES0175000
- F
- 8 · 8-19
- TSCA
- TSCA listed
- HazardClass
- 8 · 8
- PackingGroup
- III
- HS Code
- 29171990 · 29171990
- Storage Class
- 8 A · 8A - Combustible corrosive hazardous materials
- Hazard Classifications
- 4 OralEye · Acute Tox. 4 OralEye Dam. 1Skin Corr. 1B
- REACH Registrations
- Active
- Limited Quantities
- 1 L · 1.0 L (0.3 gallons) (liquid) or 1 Kg (2.2 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
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
Danger
H302 (94.7%): Harmful if swallowed [Warning Acute toxicity, oral]
P260, P264, P270, P280, P301+P317, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P330, P363, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 57 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: 2-Butynedioic acid, dimethyl ester
REACH registered substance: Dimethyl butynedioate (EC: 212-098-4)
Dimethyl acetylenedicarboxylate: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesAcute Tox. 4 (94.7%)
Safety data
- F
- 8-19
- PPE
- Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- ES0175000
- ridadr
- UN 3265 8/PG 2
- hs_code
- 29171990
- risk_code
- 34-22
- Signal word
- Danger
- Symbol(GHS)
- GHS05,GHS07
- hazard_code
- C
- safety_code
- 23-26-27-36/37/39-45
- hazard_class
- 8
- Storage Class
- 8A - Combustible corrosive hazardous materials
- packing_group
- III
- Hazard statements
- H302-H314
- Limited Quantities
- 1.0 L (0.3 gallons) (liquid) or 1 Kg (2.2 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 4 OralEye Dam. 1Skin Corr. 1B
- Precautionary statements
- P270-P280-P301+P312-P303+P361+P353-P304+P340+P310-P305+P351+P338
Chemistry & industry
Uses & manufacturing
General Manufacturing Information2-Butynedioic acid, 1,4-dimethyl ester: ACTIVE
Applications
UsesDimethyl acetylenedicarboxylate as a versatile dienophile used in Diels-Alder reactions.
Upstream & downstream products
Upstream raw materials
Downstream products
Related reactions
334 records
Compound notes
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