2,2-Dimethylsuccinic acid
Basic information
- CAS
597-43-3- Standard SMILES
CC(C)(CC(=O)O)C(=O)O- InChIKey
GOHPTLYPQCTZSE-UHFFFAOYSA-N- Molecular formula
- C6H10O4
- Average molar mass
- 146.14 g/mol
- Monoisotopic mass
- 146.0579088
Overview
2,2-dimethylsuccinic acid is an alpha,-dicarboxylic acid that is succinic acid substituted by two methyl groups at positions 2 and 2 respectively. It is functionally related to a succinic acid. It is a conjugate acid of a 2,2-dimethylsuccinate(2-).
Names & identifiers
- Preferred name
- 2,2-Dimethylsuccinic acid
- IUPAC
- 2,2-dimethylbutanedioic acid
- English name
- 2,2-Dimethylsuccinic acid
- Molecular formula
- C6H10O4
- Molecular weight
- 146.14
Names & synonyms
2,2-DIMETHYLSUCCINIC ACID597-43-32,2-Dimethylbutanedioic acidButanedioic acid, 2,2-dimethyl-DTXSID6021581MX6TVR2107NSC-408419DTXCID901581CHEBI:86537RefChem:441478209-899-62,2-DimethylsuccinicAcid
Show more names
DiMethylsuccinic Aci2-DiMethylsuccinic acid2,2-dimethylsuccinicaci2,2-Dimethlsuccinic acid3,3-Dimethylsuccinic acid2,2-Dimethylbernsteinsure2,2-DimethylsuccinicAcid>
MFCD000041962,2-dimethyl-butanedioic acidSuccinic acid, 2,2-dimethyl-2,2-dimethyl-succinic acid2,2-Dimethyl SuccinateEINECS 209-899-62.2-Dimethylsuccinic acid3,3-dimethyl succinic acid
Database identifiers
- CAS
597-43-3- PubChem CID
- 11701
- DTXSID
DTXSID6021581- ChEMBL
CHEMBL3186607- ChEBI
CHEBI:86537- UNII
- MX6TVR2107
- EC Number
Properties
Computed structural properties
- XLogP
- 0.2
- Topological polar surface area
- 74.6 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 3
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 159
Experimental & physicochemical properties
LipidsFatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Dicarboxylic acids [FA0117]
SpringerMaterials PropertiesBoiling point
Solubility70 mg/mL at 14 °C
Melting Point140.5 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 138 · 138-142 °C (lit.)
- Boiling point
- 311.39 °C · 311.39°C (rough estimate)
- Density
- 1.4528 · 1.4528 (rough estimate)
- refractive index
- 1.4328 · 1.4328 (estimate)
- storage temp.
- Sealed in dry,Room Temperature
- form
- powder to crystal
- pka
- 3.8 · 3.80±0.10(Predicted)
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
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 46 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- hs_code
- 29171900
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36-37/39
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P261-P264-P271-P280-P302+P352-P305+P351+P338
Chemistry & industry
Applications
UsesDerivatives of 2,2-dimethylsuccinic acid serve as precursors for the synthesis of specific isoprenoids[1]. The compound acts as a starting material for synthesizing dimethyl 2,2-dimethylsuccinate via esterification with methanol and sulfuric acid, and serves as a ligand in the preparation of the bio-MOF Cu-AD-DMSA alongside copper nitrate and adenine[1][3]. It reacts with (PyH)5[MoOCl4(H2O)]3Cl2 in the presence of base to afford pyridinium salts of the [Mo2O4Cl4(μ2-dmsH)]3− complex[2].
Upstream & downstream products
Upstream raw materials
Downstream products
Additional notes
DefinitionChEBI: An alpha,omega-dicarboxylic acid that is succinic acid substituted by two methyl groups at positions 2 and 2 respectively.
Suppliers
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Related reactions
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Compound notes
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