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2,6-dimethylbenzoyl chloride, also known as 2,6-dimethyl-1-phenylpropan-1-one, is a chemical compound with the formula C9H9ClO. It is a white to light yellow liquid that is primarily used as a reagent in organic synthesis. 2,6-dimethylbenzoyl chloride is an important intermediate in the production of various pharmaceuticals, agrochemicals, and other fine chemicals due to its high reactivity and stability. However, it should be handled with caution as it is a corrosive and toxic substance.

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  • 21900-37-8 Structure
  • Basic information

    1. Product Name: 2,6-dimethylbenzoyl chloride
    2. Synonyms: Benzoyl chloride, 2,6-dimethyl- (6CI,7CI,8CI,9CI);2,6-DIMETHYLBENZOYL CHLORIDE 95%;2,6-Dimethylbenzoic acid chloride
    3. CAS NO:21900-37-8
    4. Molecular Formula: C9H9ClO
    5. Molecular Weight: 168.62
    6. EINECS: 244-646-3
    7. Product Categories: ACIDHALIDE
    8. Mol File: 21900-37-8.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 229.5°Cat760mmHg
    3. Flash Point: 96.2°C
    4. Appearance: /
    5. Density: 1.136g/cm3
    6. Vapor Pressure: 0.0693mmHg at 25°C
    7. Refractive Index: 1.534
    8. Storage Temp.: Inert atmosphere,Room Temperature
    9. Solubility: N/A
    10. CAS DataBase Reference: 2,6-dimethylbenzoyl chloride(CAS DataBase Reference)
    11. NIST Chemistry Reference: 2,6-dimethylbenzoyl chloride(21900-37-8)
    12. EPA Substance Registry System: 2,6-dimethylbenzoyl chloride(21900-37-8)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 21900-37-8(Hazardous Substances Data)

21900-37-8 Usage

Uses

Used in Pharmaceutical Industry:
2,6-dimethylbenzoyl chloride is used as an intermediate for the synthesis of various pharmaceuticals. It plays a crucial role in the production of drugs due to its ability to act as an acylating agent in the Friedel-Crafts acylation reaction, which is a widely used method for the synthesis of aromatic compounds.
Used in Agrochemical Industry:
In the agrochemical industry, 2,6-dimethylbenzoyl chloride is used as a key intermediate in the production of various agrochemicals. Its reactivity and stability make it a valuable component in the synthesis of pesticides and other agrochemical products.
Used in Dye and Pigment Industry:
2,6-dimethylbenzoyl chloride is used as a building block in the production of dyes, pigments, and perfumes. Its high reactivity allows for the synthesis of a wide range of organic compounds, contributing to the creation of various colorants and fragrances.
Used in Organic Synthesis:
As a versatile reagent, 2,6-dimethylbenzoyl chloride is used in organic synthesis for the preparation of a wide range of organic compounds. Its ability to act as an acylating agent makes it a valuable component in various chemical reactions, facilitating the synthesis of complex organic molecules.

Check Digit Verification of cas no

The CAS Registry Mumber 21900-37-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,1,9,0 and 0 respectively; the second part has 2 digits, 3 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 21900-37:
(7*2)+(6*1)+(5*9)+(4*0)+(3*0)+(2*3)+(1*7)=78
78 % 10 = 8
So 21900-37-8 is a valid CAS Registry Number.
InChI:InChI=1/C9H9ClO/c1-6-4-3-5-7(2)8(6)9(10)11/h3-5H,1-2H3

21900-37-8SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name 2,6-Dimethylbenzoyl chloride

1.2 Other means of identification

Product number -
Other names EINECS 244-646-3

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:21900-37-8 SDS

21900-37-8Relevant articles and documents

N-Ammonium Ylide Mediators for Electrochemical C-H Oxidation

Saito, Masato,Kawamata, Yu,Meanwell, Michael,Navratil, Rafael,Chiodi, Debora,Carlson, Ethan,Hu, Pengfei,Chen, Longrui,Udyavara, Sagar,Kingston, Cian,Tanwar, Mayank,Tyagi, Sameer,McKillican, Bruce P.,Gichinga, Moses G.,Schmidt, Michael A.,Eastgate, Martin D.,Lamberto, Massimiliano,He, Chi,Tang, Tianhua,Malapit, Christian A.,Sigman, Matthew S.,Minteer, Shelley D.,Neurock, Matthew,Baran, Phil S.

supporting information, p. 7859 - 7867 (2021/05/26)

The site-specific oxidation of strong C(sp3)-H bonds is of uncontested utility in organic synthesis. From simplifying access to metabolites and late-stage diversification of lead compounds to truncating retrosynthetic plans, there is a growing need for new reagents and methods for achieving such a transformation in both academic and industrial circles. One main drawback of current chemical reagents is the lack of diversity with regard to structure and reactivity that prevents a combinatorial approach for rapid screening to be employed. In that regard, directed evolution still holds the greatest promise for achieving complex C-H oxidations in a variety of complex settings. Herein we present a rationally designed platform that provides a step toward this challenge using N-ammonium ylides as electrochemically driven oxidants for site-specific, chemoselective C(sp3)-H oxidation. By taking a first-principles approach guided by computation, these new mediators were identified and rapidly expanded into a library using ubiquitous building blocks and trivial synthesis techniques. The ylide-based approach to C-H oxidation exhibits tunable selectivity that is often exclusive to this class of oxidants and can be applied to real-world problems in the agricultural and pharmaceutical sectors.

Synthesis of O- tert-Butyl- N,N-disubstituted Hydroxylamines by N-O Bond Formation

Hill, Jarvis,Crich, David

supporting information, p. 6396 - 6400 (2021/08/23)

The reaction of magnesium amides with tert-butyl 2,6-dimethyl perbenzoate in tetrahydrofuran at 0 °C provides a method for the synthesis O-tert-butyl-N,N-disubstituted hydroxylamines by direct N-O bond formation with a broad functional group tolerance. Less sterically hindered magnesium amides require ortho,ortho-disubstitution on the perester electrophile component, whereas sterically encumbered magnesium amides perform comparably with either tert-butyl perbenzoate or tert-butyl 2,6-dimethyl perbenzoate. A reaction mechanism is presented to account for the observed reactivity.

DIVERSITY-ORIENTED SYNTHESIS OF N,N,O-TRISUBSTITUTED HYDROXYLAMINES FROM ALCOHOLS AND AMINES BY N-O BOND FORMATION

-

Paragraph 0295; 0304-0305, (2021/11/26)

In one aspect, the disclosure relates to a method for the direct synthesis of complex N,N,O-trisubstituted hydroxylamines by N—O bond formation. In another aspect, the method can successfully be employed using a wide variety of commercially available alcohols and secondary amines and enables the construction of large fragment-based libraries of trisubstituted hydroxylamines for drug discovery purposes. Also disclosed are N,N,O-trisubstituted hydroxylamines having low basicity, high stability at ambient temperatures, and an inherent lack of reactivity towards acetylating and sulfonylating enzymes that confer mutagenicity on less-substituted hydroxylamines.

MODIFIED PROTEINS AND PROTEIN DEGRADERS

-

Paragraph 001674-001675, (2021/12/08)

Provided herein are compounds, pharmaceutical compositions, and methods for binding or degrading target proteins. Further provided herein are compounds having a DNA damage-binding protein 1 (DDB1) binding moiety. Some such embodiments include a linker. Some such embodiments include a target protein binding moiety. Further provided herein are ligand-DDB1 complexes. Further provided herein are in vivo modified DDB1 proteins.

OPTIMIZATION of NAMPT (NICOTINAMIDE PHOSPHORIBOSYLTRANSFERASE) ACTIVATORS: DISCOVERY of N,N-DIETHYL-1,2-BENZOXAZOLE-3-CARBOXAMIDE DERIVATIVES AS POTENT NAMPT ACTIVATORS with MITIGATED MUTAGENIC RISKS

Akiu, Mayuko,Asano, Daigo,Hasegawa, Tomoko,Honda, Tomohiro,Ishizaka, Tomomichi,Nakamura, Tsuyoshi,Pinkerton, Anthony B.,Sogawa, Yoshitaka,Terayama, Koji,Tsuji, Takashi,Yokoyama, Mika

, p. 94 - 122 (2022/01/08)

DS68702229, a potent NAMPT activator developed from HTS followed by a hit-to-lead campaign, is a promising candidate compound that significantly reduced body weight when orally administered to mice with high fat diet-induced obesity. However, in vitro toxicology profiling of DS68702229 revealed bacterial mutagenicity using Salmonella typhimurium TA98 and TA100 strains upon S9 activation. Hypothesizing that DNA intercalation is the likely cause, we employed several approaches to disrupt the putative DNA intercalation, including modulation of the molecular shape. Our efforts culminated in the discovery of compounds 20k and 20l, which increased intracellular NAD+ levels in a cell-based assay without inducing mutagenicity, along with acceptable plasma exposure in mice after oral administration.

Enantioselective 1,3-Dipolar [6+4] Cycloaddition of Pyrylium Ions and Fulvenes towards Cyclooctanoids

McLeod, David,Cherubini-Celli, Alessio,Sivasothirajah, Nisanhi,McCulley, Christina H.,Christensen, Mette Louise,J?rgensen, Karl Anker

supporting information, p. 11417 - 11422 (2020/08/06)

Organocatalytic enantioselective 1,3-dipolar [6+4] cycloadditions of pyrylium ion intermediates with fulvenes promoted by a chiral primary amine catalyst have been developed to proceed in moderate to good yields and high enantioselectivities. The resultant chiral bicyclo[6.3.0]undecane scaffold containing a transannular bridging ether is densely functionalised providing a rigid scaffold for further manipulations. Computational studies give important insights into the role of the primary amine catalyst. Analysis of the reaction shows that the catalytic reaction proceeds in a step-wise manner and rationalises the stereochemical outcome of the reaction. Several stereoselective complexity-generating transformations, facilitated by the diverse functional groups and transannular bridge, are presented, highlighting the versatility of the core towards a number of the cyclooctanoid natural products.

N-Heterocyclic Carbene Catalyzed Photoenolization/Diels–Alder Reaction of Acid Fluorides

Agrawal, Arush,G?tze, Jan P.,Golz, Paul,Hopkinson, Matthew N.,Mavroskoufis, Andreas,Rajes, Keerthana,Ru?, Vincent

supporting information, p. 3190 - 3194 (2020/01/24)

The combination of light activation and N-heterocyclic carbene (NHC) organocatalysis has enabled the use of acid fluorides as substrates in a UVA-light-mediated photochemical transformation previously observed only with aromatic aldehydes and ketones. Stoichiometric studies and TD-DFT calculations support a mechanism involving the photoactivation of an ortho-toluoyl azolium intermediate, which exhibits “ketone-like” photochemical reactivity under UVA irradiation. Using this photo-NHC catalysis approach, a novel photoenolization/Diels–Alder (PEDA) process was developed that leads to diverse isochroman-1-one derivatives.

ORGANIC LIGHT-EMITTING DEVICE

-

Paragraph 0149; 0170; 0171; 0172; 0173; 0174, (2019/02/25)

An organic white light-emitting device comprising an anode, a cathode and at least one light-emitting layer between the anode and the cathode, wherein a first light-emitting layer comprises a first light-emitting compound of formula (I): wherein R1, R2 and R3 independently in each occurrence is a substituent; M1 is a transition metal; L1 is a ligand other than a ligand of formula: (II) a and b are each 0 or a positive integer; x is at least 1; and y is 0 or a positive integer, a light-emitting layer of the device comprising at least one further light-emitting material.

Photo-Fries rearrangement of 1-pyrenyl esters

Maeda, Hajime,Akai, Tomomi,Segi, Masahito

supporting information, p. 4377 - 4380 (2017/10/23)

Photo-Fries rearrangement reactions of 1-pyrenyl esters were investigated. Photoreaction of 1-pyrenyl benzoate in benzene generates 1-hydroxy-2-pyrenyl phenyl ketone along with 1-pyrenol. The exceptionally down field 1H NMR chemical shift of OH proton in the photoproduct indicates the existence of intramolecular hydrogen bonding. Photorearrangements of analogs that have electron-withdrawing or electron-releasing group on the phenyl ring, and related heteroaromatic carboxylates also take place to form the corresponding ketones. However, photoreactions of 1-pyrenyl aliphatic carboxylate esters do not occur. The results of spectroscopic and theoretical studies suggest the mechanistic pathway for this process is initiated by homolytic C–O bond cleavage in an aroyl group localized 1(π → π?) excited state of the 1-pyrenyl esters. The radical pair generated in this fashion then undergoes in-solvent-cage coupling to yield the 1-hydroxy-2-pyrenyl aryl ketone selectively.

SUBSTITUTED AMINOPYRIMIDINE COMPOUNDS AND METHODS OF USE

-

Paragraph 379, (2016/10/04)

The invention relates to the preparation and use of new aminopyrimidine derivatives as drug candidates in free form or in pharmaceutically acceptable salt form and formulations thereof for the modulation of a disorder or disease which is mediated by the activity of the PI3K enzymes. The invention also provides pharmaceutically acceptable compositions comprising such compounds and methods of using the compositions in the treatment of disorders or diseases, such as disorders of immunity and inflammation in which PI3K enzymes play a role in leukocyte function, and hyperproliferative disorders associated with PI3K activity, including but not restricted to leukemias and solid tumors, in mammals, especially humans.

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