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4,4-Dimethyl-2-pyrrolidinone, also known as DMP, is an organic compound with the chemical formula C6H11NO. It is a colorless liquid with a low melting point and a low boiling point. DMP is a polar aprotic solvent that is widely used in various industries due to its unique properties, such as high solubility, low toxicity, and good stability.

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  • 66899-02-3 Structure
  • Basic information

    1. Product Name: 4,4-dimethyl-2-pyrrolidinone
    2. Synonyms: 4,4-dimethyl-2-pyrrolidinone;4,4-diMethylpyrrolidin-2-one;4,4-Dimethyl-2-pyrrolidone;2-pyrrolidinone, 4,4-dimethyl-;2-PYRROLIDONE,4,4-DIMETHYL
    3. CAS NO:66899-02-3
    4. Molecular Formula: C6H11NO
    5. Molecular Weight: 113.16
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 66899-02-3.mol
  • Chemical Properties

    1. Melting Point: 38-40°
    2. Boiling Point: 150-155℃ (18 Torr)
    3. Flash Point: 121.7°C
    4. Appearance: White to cream/Solid
    5. Density: 0.945g/cm3
    6. Vapor Pressure: 0.0704mmHg at 25°C
    7. Refractive Index: 1.435
    8. Storage Temp.: Sealed in dry,Room Temperature
    9. Solubility: N/A
    10. PKA: 16.70±0.40(Predicted)
    11. Water Solubility: Sparingly soluble in water.(0.26 g/L) (25°C),
    12. Sensitive: Air Sensitive
    13. CAS DataBase Reference: 4,4-dimethyl-2-pyrrolidinone(CAS DataBase Reference)
    14. NIST Chemistry Reference: 4,4-dimethyl-2-pyrrolidinone(66899-02-3)
    15. EPA Substance Registry System: 4,4-dimethyl-2-pyrrolidinone(66899-02-3)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: IRRITANT
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 66899-02-3(Hazardous Substances Data)

66899-02-3 Usage

Uses

Used in Pharmaceutical Industry:
4,4-Dimethyl-2-pyrrolidinone is used as a pharmaceutical intermediate for the synthesis of various drugs, including benzoylthiophenes, which are allosteric enhancers of agonist activity at the A1 adenosine receptor. This application takes advantage of DMP's solubility and reactivity in facilitating chemical reactions.
Used in Chemical Synthesis:
In the chemical synthesis industry, 4,4-dimethyl-2-pyrrolidinone is used as a solvent for various organic reactions, such as esterification, transesterification, and hydrogenation. Its polar aprotic nature makes it an ideal choice for reactions involving sensitive functional groups, as it does not participate in unwanted side reactions.
Used in Polymer Industry:
4,4-Dimethyl-2-pyrrolidinone is used as a solvent in the polymer industry for the production of polyurethanes, polyamides, and other polymers. Its ability to dissolve a wide range of polymers makes it a versatile choice for various applications, such as coatings, adhesives, and elastomers.
Used in Battery Industry:
In the battery industry, 4,4-dimethyl-2-pyrrolidinone is used as an electrolyte solvent in lithium-ion batteries. Its high dielectric constant and low viscosity contribute to improved battery performance and energy density.
Used in Extraction Processes:
4,4-Dimethyl-2-pyrrolidinone is used in extraction processes to separate various compounds, such as metal ions, organic acids, and pharmaceuticals, from complex mixtures. Its high solubility and selectivity make it an effective choice for purification and separation applications.

Check Digit Verification of cas no

The CAS Registry Mumber 66899-02-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,6,8,9 and 9 respectively; the second part has 2 digits, 0 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 66899-02:
(7*6)+(6*6)+(5*8)+(4*9)+(3*9)+(2*0)+(1*2)=183
183 % 10 = 3
So 66899-02-3 is a valid CAS Registry Number.
InChI:InChI=1/C6H11NO/c1-6(2)3-5(8)7-4-6/h3-4H2,1-2H3,(H,7,8)

66899-02-3 Well-known Company Product Price

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  • (Code)Product description
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  • Packaging
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  • Alfa Aesar

  • (H33209)  4,4-Dimethyl-2-pyrrolidinone, 95%   

  • 66899-02-3

  • 250mg

  • 1159.0CNY

  • Detail
  • Alfa Aesar

  • (H33209)  4,4-Dimethyl-2-pyrrolidinone, 95%   

  • 66899-02-3

  • 1g

  • 3217.0CNY

  • Detail

66899-02-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name 4,4-Dimethyl-2-pyrrolidinone

1.2 Other means of identification

Product number -
Other names 4,4-dimethylpyrrolidin-2-one

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:66899-02-3 SDS

66899-02-3Relevant articles and documents

Pyridineacetamide derivative serving as CDK inhibitor, and preparation method and application thereof

-

Paragraph 0603; 0606; 0615-0616, (2021/07/28)

The invention belongs to the technical field of pyridineacetamide derivatives, and particularly relates to a pyridineacetamide derivative serving as a CDK inhibitor and a preparation method and application of the pyridine acetamide derivative. The pyridineacetamide derivative shows excellent CDK9/CDK7 enzyme inhibitory activity, and can be used for preparing drugs used for treating cancers, especially hematologic cancers including acute myeloid leukemia, multiple myeloma, chronic lymphocytic leukemia, follicular lymphoma and the like and solid tumors such as breast cancer, prostate cancer, ovarian cancer, hepatocellular carcinoma, pancreatic cancer, kidney cancer, stomach cancer, colorectal cancer, lung cancer and the like.

Highly Robust Iron Catalyst System for Intramolecular C(sp3)?H Amidation Leading to γ-Lactams

Kweon, Jeonguk,Chang, Sukbok

supporting information, p. 2909 - 2914 (2020/12/11)

Disclosed here is the use of an iron catalyst system for an intramolecular C?H amidation toward γ-lactam synthesis from dioxazolone precursors. (Phthalocyanine)FeIIICl was found to catalyze this cyclization with extremely high turnover numbers of up to 47 000 under mild and aerobic conditions. On the basis of experimental and computational mechanistic studies, the reaction is suggested to proceed by a stepwise radical pathway involving fast hydrogen atom abstraction followed by radical rebound. A plausible origin for the high turnover numbers along with air-compatibility is also rationalized.

Structural insight into hybrid peptide ?-helices

Misra, Rajkumar,George, Gijo,Reja, Rahi M.,Dey, Sanjit,Raghothama, Srinivasarao,Gopi, Hosahudya N.

, p. 2171 - 2173 (2020/02/27)

Unique ?-helical organizations (11-helices) from β,γ-hybrid peptides composed of chiral β3-amino acids along with achiral 3,3- or 4,4-dimethyl substituted γ-amino acids are disclosed.

Ambidextrous α,γ-Hybrid Peptide Foldamers

Misra, Rajkumar,George, Gijo,Saseendran, Abhijith,Raghothama, Srinivasarao,Gopi, Hosahudya N.

, p. 4408 - 4414 (2019/11/25)

Molecular chirality is ubiquitous in nature. The natural biopolymers, proteins and DNA, preferred a right-handed helical bias due to the inherent stereochemistry of the monomer building blocks. Here, we are reporting a rare co-existence of left- and right-handed helical conformations and helix-terminating property at the C-terminus within a single molecule of α,γ-hybrid peptide foldamers composed of achiral Aib (α-aminoisobutyric acid) and 3,3-dimethyl-substituted γ-amino acid (Adb; 4-amino-3,3-dimethylbutanoic acid). At the molecular level, the left- and right-handed helical screw sense of α,γ-hybrid peptides are representing a macroscopic tendril perversion. The pronounced helix-terminating behaviour of C-terminal Adb residues was further explored to design helix–Schellman loop mimetics and to study their conformations in solution and single crystals. The stereochemical constraints of dialkyl substitutions on γ-amino acids showed a marked impact on the folding behaviour of α,γ-hybrid peptides.

Selective formation of γ-lactams via C-H amidation enabled by tailored iridium catalysts

Hong, Seung Youn,Park, Yoonsu,Hwang, Yeongyu,Kim, Yeong Bum,Baik, Mu-Hyun,Chang, Sukbok

, p. 1016 - 1021 (2018/03/09)

Intramolecular insertion of met al nitrenes into carbon-hydrogen bonds to form γ-lactam rings has traditionally been hindered by competing isocyanate formation. We report the application of theory and mechanism studies to optimize a class of pentamethylcyclopentadienyl iridium(III) catalysts for suppression of this competing pathway. Modulation of the stereoelectronic properties of the auxiliary bidentate ligands to be more electron-donating was suggested by density functional theory calculations to lower the C-H insertion barrier favoring the desired reaction. These catalysts transform a wide range of 1,4,2-dioxazol-5-ones, carbonylnitrene precursors easily accessible from carboxylic acids, into the corresponding γ-lactams via sp3 and sp2 C-H amidation with exceptional selectivity. The power of this method was further demonstrated by the successful late-stage functionalization of amino acid derivatives and other bioactive molecules.

FUNCTIONALIZED 9-BROMO-CAMPTOTHECIN DERIVATIVES

-

, (2014/05/24)

The present invention relates to new functionalized 9-bromo-camptothecin derivatives which have cytotoxic activity and are useful in treating diseases such as cancer, cellular proliferation disorders and viral infections. The present invention also provides methods for preparing these compounds, pharmaceutical compositions comprising them and methods of treating diseases utilizing such compounds or the pharmaceutical composition containing them. The invention also relates to the use of these functionalized 9-bromo-camptothecin derivatives in the preparation of conjugates.

NOVEL AMINO-PYRROLINE DERIVATIVES, AND USE THEREOF IN THE PREVENTION AND/OR TREATMENT OF METABOLIC SYNDROME

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Paragraph 0183; 0184, (2014/03/21)

Novel amino-pyrrolinic derivatives, their pharmacologically acceptable salts and use thereof in the prevention and/or treatment of metabolic syndrome.

GSK-3BETA INHIBITOR

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Page/Page column 31, (2011/04/13)

For the purpose of providing a GSK-3β inhibitor containing a 2-aminopyridine compound or a salt thereof or a prodrug thereof useful as an agent for the prophylaxis or treatment of a GSK-3β-related pathology or disease, the present invention provides a GSK-3β inhibitor containing a compound represented by the formula (IA): wherein each symbol is as defined in the specification. or a salt thereof or a prodrug thereof.

Rigidified Compounds for Modulating Heparanase Activity

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, (2010/11/30)

Disclosed are novel rigidified compounds having a rhodanine-like residue and at least one aryl or heteroaryl residue linked to the rhodanine-like residue, whereby a core structure of these compounds, as defined in the specification, is characterized as having one or zero free-to-rotate bonds. Also disclosed are pharmaceutical compositions containing these rigidified compounds and uses thereof for modulating the activity of heparanase and hence in the treatment of heparanase-associated diseases and disorders, and uses thereof for modulating the activity of heparin-binding proteins and hence in the treatment of heparin-binding proteins-associated diseases and disorders as well as in the treatment of medical conditions that are at least partially treatable by rhodanine or a rhodanine analog.

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