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100-23-2

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100-23-2 Usage

Chemical Properties

Yellow Solid

Uses

It is an aromatic intermediate and in the experimental and theoretical study of the structure of N,N-dimethyl-4-nitroaniline derivatives as model compounds for non-linear optical organic materials.

Purification Methods

Crystallise the nitroaniline from aqueous EtOH, EtOH or MeOH (m 163.5-164o). Dry it in vacuo. The N-methiodide has m 161o(dec) (from H2O). [Beilstein 12 H 714, 12 III 1584, 12 IV 1616.]

Check Digit Verification of cas no

The CAS Registry Mumber 100-23-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 0 respectively; the second part has 2 digits, 2 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 100-23:
(5*1)+(4*0)+(3*0)+(2*2)+(1*3)=12
12 % 10 = 2
So 100-23-2 is a valid CAS Registry Number.
InChI:InChI=1/C8H10N2O2/c1-9(2)7-3-5-8(6-4-7)10(11)12/h3-6H,1-2H3

100-23-2 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
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  • Price
  • Detail
  • Alfa Aesar

  • (L00404)  N,N-Dimethyl-4-nitroaniline, 98+%   

  • 100-23-2

  • 5g

  • 293.0CNY

  • Detail
  • Alfa Aesar

  • (L00404)  N,N-Dimethyl-4-nitroaniline, 98+%   

  • 100-23-2

  • 25g

  • 608.0CNY

  • Detail

100-23-2SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name N,N-DIMETHYL-4-NITROANILINE

1.2 Other means of identification

Product number -
Other names N,N-Dimethyl-4-nitroaniline

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:100-23-2 SDS

100-23-2Relevant articles and documents

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Downie et al.

, p. 3951 (1975)

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Photochemical Reaction of N,N-Dimethylanilines with N-Substituted Maleimides Utilizing Benzaldehyde as the Photoinitiator

Nikitas, Nikolaos F.,Theodoropoulou, Maria A.,Kokotos, Christoforos G.

, p. 1168 - 1173 (2021)

Photoorganocatalysis constitutes a powerful domain of photochemistry and organic synthesis. The scaffold of pyrrolo[3,4-c]quinolinoles exhibits interesting and potent inhibition against various enzymes, making them really promising pharmaceutical targets. Herein, we describe a photochemical methodology for the reaction of N,N-dimethylanilines with N-substituted maleimides, utilizing benzaldehyde as the photoinitiator. A variety of substituted N,N-dimethylanilines and N-substituted maleimides were converted into the corresponding adducts in moderate to high yields.

Deoxygenation of Tertiary Amine Oxides with Carbon Disulfide

Yoshimura, Toshiaki,Asada, Kaoru,Oae, Shigeru

, p. 3000 - 3003 (1982)

Reduction of various tertiary amine oxides with carbon disulfide was examined and kinetic experiments were carried out.Trialkylamine oxides and N,N-dialkylarylamine N-oxides were readily reduced by CS2 to give the corresponding tertiary amines in good yields, while heteroaromatic amine N-oxides such as picoline N-oxide were not affected.The oxygen atom in the N-oxide was found to be transferred to CO2 upon mass spectral analysis of the gas evolved.The kinetic experiments were carried out following the UV spectra of N,N-dimethylaniline N-oxide in CH3CN containing much excess of CS2 and the rate was found to be of 2nd order in the N-oxide and CS2.Activation parameters (ΔH=55.7 kJ mol-1, ΔS=-78.2 J K-1 mol-1 at 20 deg C) are characteristic of a normal bimolecular reaction.The logarithms of the rate constants for para-substituted N,N-dimethylaniline N-oxides are nicely correlated with Hammett ? values and a small negative ρ value (ρ=-0.2) was obtained.The rate of reaction was faster in polar aprotic solvents than in nonpolar or protic solvents.These observations seem to suggest that the reaction proceeds via an initial nucleophilic attack of the N-oxide oxygen at carbon disulfide followed by the rate-determining N-O bond fission to give the tertiary amine.

Selective utilization of methoxy groups in lignin for: N -methylation reaction of anilines

Mei, Qingqing,Shen, Xiaojun,Liu, Huizhen,Liu, Hangyu,Xiang, Junfeng,Han, Buxing

, p. 1082 - 1088 (2019)

The utilization of lignin as a feedstock to produce valuable chemicals is of great importance. However, it is a great challenge to produce pure chemicals because of the complex structure of lignin. The selective utilization of specific groups on lignin molecules offers the possibility of preparing chemicals with high selectivity, but this strategy has not attracted attention. In this work, we propose a protocol to produce methyl-substituted amines by the selective reaction of the methoxy groups of lignin and aniline compounds. It was found that LiI in the ionic liquid 1-hexyl-3-methylimidazolium tetrafluoroborate could catalyze the reaction efficiently and the selectivity to the N-methylation product could be as high as 98%. Moreover, the lignin was not depolymerized in the reaction. As it was rich in hydroxyl groups, the residual material left over after the reaction was used as an efficient co-catalyst for the cycloaddition of epoxy propane with CO2, using KI as the catalyst.

-

Pedersen et al.

, p. 4211,4212 (1973)

-

Traceless Directing-Group Strategy in the Ru-Catalyzed, Formal [3 + 3] Annulation of Anilines with Allyl Alcohols: A One-Pot, Domino Approach for the Synthesis of Quinolines

Kumar, Gangam Srikanth,Kumar, Pravin,Kapur, Manmohan

, p. 2494 - 2497 (2017)

A unique, ruthenium-catalyzed, [3 + 3] annulation of anilines with allyl alcohols in the synthesis of substituted quinolines is reported. The method employs a traceless directing group strategy in the proximal C-H bond activation and represents a one-pot Domino synthesis of quinolines from anilines.

1,4-Dioxane-Tuned Catalyst-Free Methylation of Amines by CO2 and NaBH4

Guo, Zhiqiang,Zhang, Bo,Wei, Xuehong,Xi, Chanjuan

, p. 2296 - 2299 (2018)

A catalyst-free reductive functionalization of CO2 with amines and NaBH4 was developed. The N-methylation of amines was carried out with CO2 as a C1 building block and 1,4-dioxane as the solvent. Notably, the six-electron reduction of CO2 to form the methyl group occurred simultaneously with formation of the C?N bond to give the N-methylated amine.

N-methylation of aromatic amines and N-heterocycles under acidic conditions with the TTT (1,3,5-trioxane-triethylsilane-trifluoroacetic acid) system

Popp, Tobias A.,Bracher, Franz

, p. 3333 - 3338 (2015)

A novel reductive N-methylation protocol under acidic conditions with the TTT (1,3,5-trioxane-triethylsilane-trifluoroacetic acid) system is disclosed. This method is highly specific for aromatic amines and several N-heterocycles (indoles and annulated analogues, phenoxazine, phenothiazine), insensitive to steric hindrance, and compatible with a wide range of functional groups. Further the N-methylation step can be combined with an in situ N-Boc deprotection. Compounds in which the nucleophilicity of the NH group is eliminated by protonation under the reaction conditions (aliphatic amines, azaarenes of noteworthy basicity) are inert. In several examples, it was demonstrated that the TTT system is complementary to other N-methylation protocols.

Selenium-catalyzed carbonylation of nitroarenes to symmetrical 1,3-diarylureas under atmospheric pressure

Wang, Xiaofang,Lu, Shiwei,Yu, Zhengkun

, p. 929 - 932 (2004)

Selenium-catalyzed carbonylation of nitrobenzene and substituted nitroarenes with CO under atmospheric pressure afforded symmetrical 1,3-diarylureas in yields up to 94%. A mechanism has been proposed to demonstrate the formation of symmetrical ureas.

Convenient dimethylamino amination in heterocycles and aromatics with dimethylformamide

Agarwal, Anu,Chauhan, Prem M. S.

, p. 2925 - 2930 (2004)

A convenient dimethylamino amination of various heterocyclic and aromatic compounds having activated chloro group has been carried out in good yields using dimethyl formamide (DMF).

Methylation of aromatic amines and imines using formic acid over a heterogeneous Pt/C catalyst

Zhu, Lei,Wang, Lian-Sheng,Li, Bojie,Li, Wei,Fu, Boqiao

, p. 6172 - 6176 (2016)

We describe here a commercially available Pt/C catalyst capable of catalyzing the methylation of anilines and aromatic imines with formic acid in the presence of a hydrosilane reductant. Both primary aniline and secondary aniline can be methylated. The advantage of this newly described method includes operational simplicity, high TON, ready availability of the catalyst, and also good functional group compatibility.

Metal-free protodeboronation of electron-rich arene boronic acids and its application to ortho -functionalization of electron-rich arenes using a boronic acid as a blocking group

Ahn, Su-Jin,Lee, Chun-Young,Kim, Nak-Kyoon,Cheon, Cheol-Hong

, p. 7277 - 7285 (2014)

The metal-free thermal protodeboronation of various electron-rich arene boronic acids was studied. Several reaction parameters controlling this protodeboronation, such as solvent, temperature, and a proton source, have been investigated. On the basis of these studies, suitable reaction conditions for protodeboronation of several types of electron-rich arene boronic acids were provided. On the basis of this protodeboronation, a new protocol for the synthesis of ortho-functionalized electron-rich arenes from these boronic acids was developed using the boronic acid moiety as a blocking group in the electrophilic aromatic substitution reaction, followed by the removal of the boronic acid moiety via thermal protodeboronation. Mechanistic studies suggested that this protodeboronation might proceed via the complex formation of a boronic acid with a proton source, followed by the carbon-boron bond fission through σ-bond metathesis, to afford the corresponding arene compound and boric acid.

Catalyst-free N-methylation of amines using CO2

Niu, Huiying,Lu, Lijun,Shi, Renyi,Chiang, Chien-Wei,Lei, Aiwen

, p. 1148 - 1151 (2017)

Recently, utilizing CO2 as a methylation reagent to construct functional chemicals has attracted significant attention. However, the conversion of CO2 is still a challenge due to its inherent inertness. In this study, we have developed a catalyst-free N-methylation of amines to prepare numerous methylamines using CO2 as a methyl source. By utilizing 2 eq. PhSiH3 as the reductant, amines could undergo N-methylation under 1 atm of CO2 in DMF at 90 °C. Aliphatic and aromatic amines were compatible, generating the desired products in up to 95% yield.

-

Hodgson,Nicholson

, p. 470,474 (1941)

-

4-N,N-Dimethylaminophenyl azide photooxidation: effect of conditions on the reaction pathway. Ring contraction of benzene to cyclopentadiene due to a strongly electron-donating substituent

Chainikova, Ekaterina,Khursan, Sergey,Lobov, Alexander,Erastov, Alexey,Khalilov, Leonard,Mescheryakova, Ekaterina,Safiullin, Rustam

, p. 4661 - 4665 (2015)

Abstract Depending on the reaction conditions employed, the photooxidation of 4-N,N-dimethylaminophenyl azide led to the formation of 4-N,N-dimethylaminonitrosobenzene and 4-N,N-dimethylaminonitrobenzene or (5Z)-2-(dimethylamino)-5-(hydroxyimino)cyclopenta-1,3-diene-1-carbaldehyde.

Synthesis of dihydroquinazolines from 2-aminobenzylamine: N3-aryl derivatives with electron-withdrawing groups

Gruber, Nadia,Díaz, Jimena E.,Orelli, Liliana R.

, p. 2510 - 2519 (2018)

The sequential N-functionalization of 2-aminobenzylamine (2-ABA) followed by cyclodehydration allowed for a straightforward and efficient synthesis of 3,4-dihydroquinazolines with N-aryl substituents bearing electron-withdrawing groups. The sequence involves an initial SNAr displacement, N-acylation and MW-assisted ring closure. Remarkably, the uncatalyzed N-arylation of 2-ABA led to the monosubstitution product using equimolar amounts of both reagents. The individual steps were optimized achieving good to excellent overall yields of the desired heterocycles, avoiding additional protection and deprotection steps. A mechanistic interpretation for the cyclodehydration reaction promoted by trimethylsilyl polyphosphate (PPSE) is also proposed on the basis of literature data and our experimental observations.

-

Evans,Williams

, p. 1199 (1939)

-

Catalytic alternative of the Ullman reaction

Hassan, Jwanro,Penalva, Vincent,Lavenot, Laurence,Gozzi, Christel,Lemaire, Marc

, p. 13793 - 13804 (1998)

Symmetrical functionalized biaryls and biheterocycles could be obtained in good yield via homocoupling of aryl halides by using Pd(OAc)2 as catalyst with base and isopropanol. This alternative of the Ullmann reaction has proved to be compatible with sensitive functional groups.

Base-oxidant promoted metal-free N-demethylation of arylamines

Botla, Vinayak,Barreddi, Chiranjeevi,Daggupati, Ramana V,Malapaka, Chandrasekharam

, p. 1469 - 1473 (2016)

A metal-free oxidative N-demethylation of arylamines with triethylamine as a base and tert-butyl hydroperoxide (TBHP) as oxidant is reported in this paper. The reaction is general, practical, inexpensive, non-toxic, and the method followed is environmentally benign, with moderate to good yields. [Figure not available: see fulltext.]

New nitronate σ complexes and the mechanism of nucleophilic aromatic photosubstitution para to a nitro group

Wubbels, Gene G.,Johnson, Kandra M.

, p. 1451 - 1454 (2006)

Photolysis of 4-nitroanisole with aliphatic amines gives mainly N-substituted 4-nitroanilines. Reactions of this type have been widely attributed to a geminate radical mechanism. We questioned this interpretation and have searched for and found by NMR spectroscopy a new class of stable nitronate adducts generated under the reaction conditions. The adducts imply that photosubstitution by amines para to the nitro group occurs by meta σ complex formation followed by an unprecedented sigmatropic rearrangement.

Optimization of WZ4003 as NUAK inhibitors against human colorectal cancer

Yang, Huali,Wang, Xiaobing,Wang, Cheng,Yin, Fucheng,Qu, Lailiang,Shi, Cunjian,Zhao, Jinhua,Li, Shang,Ji, Limei,Peng, Wan,Luo, Heng,Cheng, Maosheng,Kong, Lingyi

, (2020/12/15)

NUAK, the member of AMPK (AMP-activated protein kinase) family of protein kinases, is phosphorylated and activated by the LKB1 (liver kinase B1) tumor suppressor protein kinase. Recent work has indicated that NUAK1 is a key component of the antioxidant stress response pathway, and the inhibition of NUAK1 will suppress the growth and survival of colorectal tumors. As a promising target for anticancer drugs, few inhibitors of NUAK were developed. With this goal in mind, based on NUAK inhibitor WZ4003, a series of derivatives has been synthesized and evaluated for anticancer activity. Compound 9q, a derivative of WZ4003 by removing a methoxy group, was found to be the most potential one with stronger inhibitory against NUAK1/2 enzyme activity, tumor cell proliferation and inducing apoptosis of tumor cells. By in vivo efficacy evaluations of colorectal SW480 xenografts, 9q suppresses tumor growth more effectively with an excellent safety profile in vivo and is therefore seen as a suitable candidate for further investigation.

Borane-Trimethylamine Complex as a Reducing Agent for Selective Methylation and Formylation of Amines with CO2

Zhang, Yanmeng,Zhang, He,Gao, Ke

, p. 8282 - 8286 (2021/10/25)

We report herein that a borane-trimethylamine complex worked as an efficient reducing agent for the selective methylation and formylation of amines with 1 atm CO2 under metal-free conditions. 6-Amino-2-picoline serves as a highly efficient catalyst for the methylation of various secondary amines, whereas in its absence, the formylation of primary and secondary amines was achieved in high yield with high chemoselectivity. Mechanistic studies suggest that the 6-amino-2-picoline-borane catalytic system operates like an intramolecular frustrated Lewis pair to activate CO2.

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