2958-62-5

Basic information

• Product Name: 2,4,6-TRIMETHYLPHENYL ISOCYANATE
• Synonyms: 2,4,6-TRIMETHYLPHENYL ISOCYANATE;Mesityl isocyanate;2,4,6-Trimethylphenyl isocyanate 99%
• CAS NO: 2958-62-5
• Molecular Formula: C₁₀H₁₁NO
• Molecular Weight: 161.2
• Product Categories: Isocyanates;Nitrogen Compounds;Organic Building Blocks
• Mol File: 2958-62-5.mol

Chemical Properties

• Melting Point: 44-48 °C(lit.)
• Boiling Point: 218-220°C
• Flash Point: 220 °F
• Appearance: /
• Density: 0.98g/cm³
• Vapor Pressure: 0.0288mmHg at 25°C
• Refractive Index: 1.513
• Storage Temp.: 2-8°C
• Water Solubility: It hydrolyzes in water.
• Sensitive: Moisture Sensitive
• BRN: 2085601
• CAS DataBase Reference: 2,4,6-TRIMETHYLPHENYL ISOCYANATE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,6-TRIMETHYLPHENYL ISOCYANATE(2958-62-5)
• EPA Substance Registry System: 2,4,6-TRIMETHYLPHENYL ISOCYANATE(2958-62-5)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36-42-36/37/38-23/25
• Safety Statements: 26-60-45-36/37-22-20-9-4
• RIDADR: 2811
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 2958-62-5(Hazardous Substances Data)

Usage

Uses

2,4,6-Trimethylphenyl isocyanate is used as an organic chemical synthesis intermediate.

Preparation

A solution of Boc2O (619 mg, 2.84 mmol) in acetonitrile (2 mL) was treated successively with a solution of 4-dimethylaminopyridine (33 mg, 0.27 mmol) in acetonitrile (2 mL) and a solution of 348 (365 mg, 2.7 mmol) in acetonitrile (2 mL). The reaction mixture was stirred vigorously for 10 min. After the addition of concentrated sulfuric acid in acetonitrile (40% solution, ρ= 1:03 g cm-3, 0.47 mL), the resulting mixture was stirred for 5 min. Water (0.47 mL) was then added, and the mixture was stirred for a further 5 min. The reaction mixture was then poured into an equal volume of water. The solution was extracted three times with hexane, and the combined hexane layers were dried over magnesium sulfate. Removal of the solvent in vacuo afforded mesityl isocyanate 349 (420 mg, 97%) as colorless crystals; mp 42 °C.

InChI:InChI=1/C10H11NO/c1-7-4-8(2)10(11-6-12)9(3)5-7/h4-5H,1-3H3

Upstream product

• 51977-16-3 ethyl N-mesitylcarbamate 
• 75-44-5 phosgene 
• 88-05-1 2,4,6-trimethylaniline 
• 201230-82-2 carbon monoxide 
• 603-71-4 nitromesitylene 
• 85288-17-1 5,7,9-Trimethyl-1H-oxazolo[3,4-a]azepin-3-one 
• 63105-14-6 1,3-bis(2,4,6-trimethylphenyl)carbodiimide 
• 99-94-5 p-Toluic acid 
• 2904-57-6 mesitylenecarbonitrile oxide 
• 65-85-0 benzoic acid 
• 503-38-8 trichloromethyl chloroformate 
• 66241-35-8 N-(2,4,6-Trimethylbenzoyl)-S,S-diphenylsulfinilimin 
• 5070-13-3 bis-(p-nitrophenyl) carbonate 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 93814-13-2 mesityl-carbamic acid-(2-piperidino-ethyl ester) 
• 107773-39-7 N-mesityl-N'-(3-piperidino-propyl)-urea 
• 114279-58-2 1-mesitylcarbamoyloxy-2-phenylcarbamoyloxy-3-piperidino-propane 
• 93151-96-3 mesityl-carbamic acid-(β-dimethylamino-isopropyl ester) 
• 51977-16-3 ethyl N-mesitylcarbamate 
• 100861-71-0 N,N-diethyl-N'-mesityl-urea 
• 101426-77-1 N-(2-diethylamino-ethyl)-N'-mesityl-urea 
• 6095-81-4 N,N'-di(2,4,6-trimethylphenyl)urea 
• 93162-13-1 mesityl-carbamic acid-(2-diethylamino-ethyl ester) 
• 101428-02-8 mesityl-thiocarbamic acid S-(2-diethylamino-ethyl ester) 
• 100141-59-1 mesityl-carbamic acid-(2-chloro-ethyl ester) 
• 29848-33-7 (2,4,6-trimethyl-phenyl)-carbamic acid 2-morpholin-4-yl-cyclohexyl ester 
• 2904-67-8 N-(2,4,6-trimethylphenyl)-N'-phenylurea 
• 97627-26-4 N-(2,4,6-trimethylphenyl)-N'-4-pyridinyl urea 

Relevant articles and documents

A P?P Bond as a Redox Reservoir and an Active Reaction Site

The carbonylation of a nickel(II) anilido species 2 led to the formation of a dinickel(0)–CO complex (P2P-PP2){Ni(CO)}2 3 with a P?P bond along with isocyanate generation. In this reaction, the central phosphide moiety of an anionic PPP ligand (PPP?=?P[2-PiPr2C6H4]2) acts as a single-electron donor to form a P radical. Alternatively, 3 can be synthesized from the reduction of (PPP)NiCl (1) in the presence of CO; thus, the reaction proceeds by radical coupling of a .P?Ni0?CO species. The reverse reaction occurred to generate 1 when 3 was treated with AgCl. Since the P?P bond is light-sensitive, its homolysis is possible and was explored by EPR spectroscopy and DFT analysis. Finally, various bond-activation reactions of 3 occurred under visible-light conditions, thus indicating that a P?P bond can act as an active reaction site.

1,1′-Dicarbodiimidoferrocenes: Synthesis, Characterization, and Group IV 1,1′-Bisguanidinateferrocene Complexes

We report the two-step one-pot preparation of a series of bulky substituted 1,1′-dicarbodiimidoferrocene proligands. In solution the compounds achieve equilibrium with the corresponding 2,4-diimino-1,3-azetidine products which exhibit distinct spectroscopic and electrochemical features. Metalation of the carbodiimides with M(NMe2)4 (M = Zr, Hf) leads to fluxional six-coordinate compounds that exhibit intermediate Bailar twist features in solution and in the solid state. Coordination of the 2,4-diimino-1,3-diazetidines to Zr(NMe2)4 results in a metal-mediated carbodiimide metathesis into two zirconium guanidinate complexes, which can be rationalized by a two-step reaction mechanism.

Di-tert-butyl dicarbonate and 4-(dimethylamino)pyridine revisited. Their reactions with amines and alcohols

The reaction of BOC2O in the presence and absence of DMAP was examined with some amines, alcohols, diols, amino alcohols, and aminothiols. Often, unusual products were observed depending on the ratio of reagents, reaction time, polarity of solvent, pK(a) of alcohols, or type of amine (primary or secondary). In reactions of aliphatic alcohols with BOC2O/DMAP, we isolated for the first time carbonic-carbonic anhydride intermediates; this helps explain the formation of symmetrical carbonates in addition to the O-BOC products. In the case of secondary amines, we succeeded to isolate unstable carbamic-carbonic anhydride intermediates that in the presence of DMAP led to the final N-BOC product. The effect of N-methylimidazole in place of DMAP was also examined.

Substituted N-phenylcarbamates as histamine H3 receptor antagonists with improved in vivo potency

Novel substituted N-phenylcarbamates as derivatives of 3-(1 H-imidazol- 4-yl)propanol were prepared and tested for their antagonist potency in vitro and in vivo at histamine H3 receptors. Structural modifications with different alkyl and acetyl moieties were performed in an attempt to optimize pharmacodynamic and pharmacokinetic effects. Most compounds are active in a functional test for histamine H3 receptors on rat cerebral cortex synaptosomes as well as in a peripheral model on guinea pig ileum. But only carbamates without too bulky lipophilic residues showed pronounced to high antagonist potency on the enhancement of endogenous histamine in brain after p.o. administration to mice (ED50 values of 5.5 to 0.86 mg · kg-1). The tested compounds presented weak activities at histamine H1, H2, and muscarinic M3 receptors thus demonstrating their H3-receptor selectivity.

A novel synthesis of isocyanates and ureas via β-elimination of haloform

A novel synthesis of isocyanates via base-induced β-elimination of haloform from N-monosubstituted trihaloacetamides is described. The rate of reaction exhibits a strong dependence on the nature of the trihalomethyl group. Thus, while the reaction of tribromoacetamides proceeds at room temperature and the reaction of trichloroacetamides requires heating in polar solvents, no reaction could be observed for any of the corresponding trifluoro derivatives. This novel β-elimination of haloform from stable and readily available trihaloacetamides was applied to a 'one-pot' synthesis of ureas which avoids the use of phosgene and isolation of isocyanates.

Preparation of isocyanates from primary amines and carbon dioxide using Mitsunobu chemistry

Primary alkylamines 1 and hindered arylamines 1 give high yields of isocyanates 5 when reacted with carbon dioxide and the Mitsunobu zwitterions 4 generated from dialkyl azodicarboxylates and Bu3P in dichloromethane at - 78°C. Use of Ph3P still gave high yields of isocyanates from reactions of primary alkylamines, but only low yields were obtained from reactions of aromatic amines. Reactions which failed to give high yields of isocyanates gave either carbamoylhydrazines 6 and/or dicarbamoylhydrazines 10 and/or triazolinones 7. The triazolinones were shown to arise from reactions of reactive aryl isocyanates with the Mitsunobu zwitterion. The carbamoylhydrazines were shown not to arise from reaction of isocyanate with reduced dialkyl azodicarboxylates, and a mechanism for their formation is proposed. Single-crystal X-ray analyses confirmed the structures of 6, 7, and 10.

A Mitsunobu-based procedure for the preparation of alkyl and hindered aryl isocyanates from primary amines and carbon dioxide under mild conditions

A Mitsunobu-based procedure for the preparation of alkyl and hindered aryl isocyanates in excellent yields from primary amines and carbon dioxide under very mild conditions is described.

Thermolysis of Alkyl N-Phenylcarbamates in the Presence of Hydroxy Compounds

Kinetic and activation parameters of thermolysis of alkyl N-phenylcarbamates in the presence of hydroxy compounds in diglyme are determined. Hydroxy compounds accelerate thermolysis of carbamates. The initial stage of the reaction in the presence of alcohols and phenols is formation of a complex of carbamate with the hydroxy compound. The compositions of the complexes are determined thermochemically, and the stability constants and enthalpies of formation are calculated.

Neue Methode zur Synthese von Isocyanaten unter milden Bedingungen

Keywords: Arendiyldiisocyanate; Di-tert-butyldicarbonat; 4-Dimethylaminopyridin; Isocyanate