34688-71-6

Basic information

• Product Name: 2,4,6-Trimethylphenylacetonitrile
• Synonyms: BENZENEACETONITRILE, 2,4,6-TRIMETHYL-;MESITYLACETONITRILE;2,4,6-TRIMETHYL BENZYL CYANIDE;2,4,6-TRIMETHYLPHENYLACETONITRILE;Mesitylacetonitrile,98%;2-(2,4,6-Trimethylphenyl)acetonitrile;2,4,6-Trimethylbenzeneacetonitrile;2,4,6-Trimethylbenzylcyanide,90%
• CAS NO: 34688-71-6
• Molecular Formula: C₁₁H₁₃N
• Molecular Weight: 159.23
• EINECS: 252-151-9
• Product Categories: Aromatic Nitriles;pharmacetical
• Mol File: 34688-71-6.mol

Chemical Properties

• Melting Point: 76-80 °C(lit.)
• Boiling Point: 120 °C (1 mmHg)
• Flash Point: 120°C/1mm
• Appearance: /
• Density: 1.0293 (rough estimate)
• Vapor Pressure: 0.00426mmHg at 25°C
• Refractive Index: 1.5466 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• BRN: 1942677
• CAS DataBase Reference: 2,4,6-Trimethylphenylacetonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,6-Trimethylphenylacetonitrile(34688-71-6)
• EPA Substance Registry System: 2,4,6-Trimethylphenylacetonitrile(34688-71-6)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 22-26-36
• RIDADR: 3276
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 34688-71-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,4,6-Trimethylphenylacetonitrile is used as an organic building block for the synthesis of more complex compounds, such as Spiromesifen Metabolite (M225645). It plays a crucial role in the development of novel pharmaceutical agents.
Used in Anti-HIV Drug Synthesis:
2,4,6-Trimethylphenylacetonitrile is employed in the novel synthetic route for the Anti-HIV Drug MC-1220 and its analogues, contributing to the advancement of treatments for HIV/AIDS.
Used in Chemical Synthesis:
2,4,6-Trimethylphenylacetonitrile is used in the preparation of various chemical compounds, including 2,4,6-trimethyl-, 9-phenethylamine hydrochloride, ethyl mesitylacetate, α-mesitylacetoacetonitrile, mesitylacetone, β-hydroxy-α-mesitylacrylonitrile, α-mesitylpropionic acid, and α-mesityl-8-phenylpropionitrile. Its versatility in synthesis makes it valuable across different chemical applications.

InChI:InChI=1/C11H13N/c1-8-6-9(2)11(4-5-12)10(3)7-8/h6-7H,4H2,1-3H3

Upstream product

• 143-33-9 sodium cyanide 
• 1585-16-6 2-chloromethyl-1,3,5-trimethylbenzene 
• 151-50-8 potassium cyanide 
• 10531-13-2 phenylsulfonyloxyacetonitrile 
• 773837-37-9 sodium cyanide 
• 487-68-3 mesytaldehyde 
• 58047-52-2 2-(2,4,6-trimethylphenyl)acetaldehyde 
• 928664-98-6 4-isoxazoleboronic acid pinacol ester 
• 576-83-0 2,4,6-trimethylphenyl bromide 
• 108-67-8 1,3,5-trimethyl-benzene 
• 4170-90-5 2,4,6-trimethylbenzyl alcohol 
• 4761-00-6 2,4,6-trimethylbenzylbromide 
• 59146-33-7 2-mesityl-acetoacetonitrile 

Downstream Products

• 42797-68-2 1-(2,4,6-trimethylphenyl)-2-propanone 
• 5460-08-2 ethyl 2,4,6-trimethylphenylacetate 
• 5350-76-5 1-phenyl-2-(2,4,6-trimethylphenyl)ethanone 
• 4408-60-0 2-mesitylacetic acid 
• 76935-65-4 2-mesitylethan-1-amine 
• 17804-62-5 mesityl-acetic acid amide 
• 136667-11-3 α-mesitylpropionitrile 
• 205517-05-1 2,4,6-trimethyl-3-nitrobenzeneacetonitrile 
• 59146-33-7 2-mesityl-acetoacetonitrile 
• 103047-82-1 1,1,1-trichloro-2,2-bis-(2-mesityl-acetylamino)-ethane 
• 203924-71-4 2-mesityl-3-oxo-propionitrile 
• 22234-62-4 1,3,5-trimethyl-2-(nitromethyl)benzene 
• 51632-25-8 2-mesityl-3-methylbutanenitrile 
• 136667-06-6 α-mesityl-o-methylacetophenone 

Relevant articles and documents

One-Pot Preparation of C1-Homologated Aliphatic Nitriles from Aldehydes through a Wittig Reaction under Metal-Cyanide-Free Conditions

A one-pot protocol to obtain C1-homologated aliphatic nitriles was achieved by treating aromatic and aliphatic aldehydes with the (methoxymethyl)triphenylphosphonium ylide followed by hydrolysis of the resulting methyl vinyl ethers with pTsOH (Ts = para-toluenesulfonyl) and treatment with molecular iodine and aqueous ammonia under metal cyanide free conditions. Neopentyl-type nitriles, which could not be obtained by conventional methods that involved conversion of the neopentyl alcohol into a tosylate and treatment with metal cyanide, were successfully obtained by using the present method.

A 2, 4, 6-Trimethylbenzene acetyl chloride synthesis process

The invention relates to a synthesis technology for 2, 4, 6-trimethylbenzene acetyl chloride, comprising the following steps of: putting thionyl chloride, a catalyst and 2, 4, 6-trimethylbenzene acetic acid into a reaction kettle in batches, and controlling temperature to carry out reaction; and after the reaction, distilling (high vacuum) in a heating way in the reaction kettle, and acquiring a final product. The preparation method of the 2, 4, 6-trimethylbenzene acetic acid can comprise the following steps of: carrying out chloromethylation reaction by taking trimethylbenzene, formaldehyde and concentrated hydrochloric acid as raw materials, adding toluene to extract after reacting, and washing to obtain a toluene solution of 2, 4, 6-trimethyl benzyl chloride; taking the toluene solution of 2, 4, 6-trimethyl benzyl chloride and the sodium cyanide as raw materials, adding a phase transfer catalyst, reflowing in a heating way to carry out cyanation reaction, washing by adding water after reacting, distilling oil phase to recover toluene and mesitylene, and rectifying to obtain 2, 4, 6-trimethylbenzene acetonitrile; and hydrolyzing the 2, 4, 6-trimethylbenzene acetonitrile, centrifuging to obtain a 2, 4, 6-trimethylbenzeneacetic acid crude product, and optionally selecting and carrying out the aftertreatment to obtain the 2, 4, 6-trimethylbenzeneacetic acid. The content of the 2, 4, 6-trimethylbenzene acetyl chloride synthesized by the method disclosed by the invention is more than or equal to 98.0%, and the content of the 2, 4, 6-trimethylbenzene acetonitrile is less than or equal to 0.5%.

Copper-catalyzed cyanation of benzyl chlorides with non-toxic K 4[Fe(CN)6]

Copper-based catalysts were firstly introduced into the cyanation of benzyl chlorides with non-toxic K4[Fe(CN)6]. The presented method avoids the use of extremely poisonous alkali cyanides and precious palladium catalysts. No other reagent apart from CuI, K4[Fe(CN) 6] and toluene was used in the cyanation, showing that the presented protocol is simple and practical. A series of benzyl chlorides were smoothly cyanated in up to 85% yield under the optimal conditions.

Pd-catalyzed cyanation of benzyl chlorides with nontoxic K 4[Fe(CN)6]

Non-toxic K4[Fe(CN)6] was demonstrated to be effective as a green cyanating agent for the cyanation of alkyl halides using PPh3/Pd(OAc)2 as a catalyst system. The presented method allowed a series of benzyl chlorides to be smoothly cyanated in up to 88% yield. In order to avoid or suppress the deactivation of the catalyst, the reaction was required to be performed in a stringent inert ambiance.

Palladium-catalyzed cyanomethylation of aryl halides through domino Suzuki coupling-isoxazole fragmentation

A one-pot protocol for the cyanomethylation of aryl halides through a palladium-catalyzed reaction with isoxazole-4-boronic acid pinacol ester was developed. Mechanistically, the reaction proceeds through (1) Suzuki coupling, (2) base-induced fragmentation, and (3) deformylation as shown by characterization of all postulated intermediates. Under optimized conditions (PdCl2dppf, KF, DMSO/H2O, 130 °C) a broad spectrum of aryl bromides could be converted into arylacetonitriles with up to 88% yield.

NOVEL BETA MIMETICS WITH EXTENDED DURATION OF ACTION, METHOD FOR PRODUCTION AND USE THEREOF AS MEDICAMENTS

The invention relates to compounds of general formula (I), where the groups R1, R2 and R3 can have the meanings given in the claims and the description, method for production and use thereof as medicaments, in particular for the treatment of inflammatory and obstructive bronchial diseases.

Spirodiclofen and spiromesifen - Novel acaricidal and insecticidal tetronic acid derivatives with a new mode of action

The broad spectrum acaricides spirodiclofen (BAJ2740, trade name: Envidor) and spiromesifen (BSN2060, trade name: Oberon) with an additional excellent activity against whiteflies, both belong to the new chemical class of tetronic acid derivatives discovered at Bayer CropScience during the 1990s. The discovery process starting from herbicidal PPO (protoporphyrinogen oxidase) chemistry, the synthetic routes leading to the products, and some insight into process development of central intermediates is given. Spirodiclofen and spiromesifen have a new mode of action (interference with lipid biosynthesis), show no cross-resistance to any resistant mite or whitefly field population and are therefore valuable tools for resistance management.

N-heteroaryl aryl-substituted thienyl-furyl-and pyrrolyl-sulfonamides and derviatives thereof that modulate the activity of endothelin

Thienyl-, furyl- and pyrrolyl-sulfonamides, formulations of pharmaceutically-acceptable salts thereof and methods for modulating or altering the activity of the endothelin family of peptides are provided. In particular, N-(isoxazolyl)thienylsulfonamides, N-(isoxazolyl)furylsulfonamides and N-(isoxazolyl)pyrrolylsulfonamides, formulations thereof and methods using these sulfonamides for inhibiting the binding of an endothelin peptide to an endothelin receptor by contacting the receptor with the sulfonamide are provided. Methods for treating endothelin-mediated disorders by administering effective amounts of one or more of these sulfonamides or prodrugs thereof that inhibit the activity of endothelin are also provided.

Endothelin antagonists: Substituted mesitylcarboxamides with high potency and selectivity for ET(A) receptors

We have previously disclosed the discovery of 2,4-disubstituted anilinothiophenesulfonamides with potent ET(A)-selective endothelin receptor antagonism and the subsequent identification of sitaxsentan (TBC11251, 1) as a clinical development compound (Wu et al. J. Med. Chem. 1997, 40, 1682 and 1690). The orally active 1 has demonstrated efficacy in a phase II clinical trial of congestive heart failure (Givertz et al. Circulation 1998, 98, Abstr. 3044) and was active in rat models of myocardial infarction (Podesser et al. Circulation 1998, 98, Abstr. 2896) and acute hypoxia-induced pulmonary hypertension (Chen et al. FASEB J. 1996, 10 (3), A104). We now report that an additional substituent at the 6-position of the anilino ring further increases the potency of this series of compounds. It was also found that a wide range of functionalities at the 3-position of the 2,4,6-trisubstituted ring increased ETA selectivity by ~10-fold while maintaining in vitro potency, therefore rendering the compounds amenable to fine-tuning of pharmacological and toxicological profiles with enhanced selectivity. The optimal compound in this series was found to be TBC2576 (7u), which has ~10- fold higher ETA binding affinity than 1, high ET(A)/ET(B) selectivity, and a serum half-life of 7.3 h in rats, as well as in vivo activity.

Benzylimidazolines as h5-HT(1B/1D) serotonin receptor ligands: A structure-affinity investigation

Benzylimidazolines may represent a class of 5-HT(1D) ligands that has yet to be exploited. On the basis of a previous report that the 2- (substituted-benzyl)imidazoline α-adrenergic agonist oxymetazoline (8) binds with high affinity at calf brain 5-HT(1D) receptors, we explored the structure-affinity relationships of a series of related derivatives. Each of the aromatic substituents was removed and then reinstated in a systematic manner to determine the influence of the individual substituents on binding. It was found that all of the aromatic substituents of 8 act in concert to impart high affinity. However, although the 3-hydroxy group could be removed without significantly reducing affinity for h5-HT(1D) (i.e., human 5- HT(1Dα)) receptors, this modification reduced h5-HT(1B) (i.e., human 5- HT(1Dβ)) receptor affinity by nearly 50-fold. The 2,6-dimethyl groups also contribute to binding but seem to play a greater role for h5-HT(1B) binding than h5-HT(1D) binding. With the appropriate structural modifications, several compounds were identified that display 20- to > 100-fold selectivity for h5-HT(1D) versus h5-HT(1B) receptors. Preliminary functional data suggest that these compounds behave as agonists. Given that 5-HT(1D) agonists are currently being explored for their antimigraine action and that activation of h5-HT(1B) receptors might be associated with cardiovascular side effects, h5- HT(1D)selective agents may offer a new lead for the development of therapeutically efficacious agents.