84803-57-6

Basic information

• Product Name: (4-tert-butyl-2,6-dimethylphenyl)acetonitrile
• Synonyms: 4-(1,1-Dimethylethyl)-2,6-dimethylbenzeneacetonitrile;[4-(1,1-Dimethylethyl)-2,6-dimethylphenyl]acetonitrile;Xylometazoline hydrochloride impurity A
• CAS NO: 84803-57-6
• Molecular Formula: C₁₄H₁₉N
• Molecular Weight: 201.3074
• EINECS: 284-183-4
• Mol File: 84803-57-6.mol
• Article Data: 0

Chemical Properties

• Melting Point: 90℃ (ethanol )
• Boiling Point: 302.5°C at 760 mmHg
• Flash Point: 136.6°C
• Appearance: /
• Density: 0.936g/cm³
• Vapor Pressure: 0.000987mmHg at 25°C
• Refractive Index: 1.505
• CAS DataBase Reference: (4-tert-butyl-2,6-dimethylphenyl)acetonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: (4-tert-butyl-2,6-dimethylphenyl)acetonitrile(84803-57-6)
• EPA Substance Registry System: (4-tert-butyl-2,6-dimethylphenyl)acetonitrile(84803-57-6)

Safety Data

• Hazardous Substances Data: 84803-57-6(Hazardous Substances Data)

Usage

General Description

(4-tert-butyl-2,6-dimethylphenyl)acetonitrile, also known as DMTBBN, is a chemical compound with the molecular formula C14H21N. This aromatic nitrile is often used as a building block in the synthesis of complex organic compounds. It is a white crystalline solid with a strong, somewhat aromatic odor. DMTBBN is primarily used as a reagent in organic synthesis, particularly in the formation of carbon-carbon and carbon-heteroatom bonds. It has also been utilized in the production of pharmaceuticals and agrochemicals. Due to its versatile nature and utility in various chemical reactions, DMTBBN is an important tool in the field of organic chemistry.

InChI:InChI=1/C14H19N/c1-10-8-12(14(3,4)5)9-11(2)13(10)6-7-15/h8-9H,6H2,1-5H3

Synthetic route

4-tert-butyl-2,6-dimethylbenzyl chloride (19387-83-8) + potassium cyanide (151-50-8) → 4-tert-butyl-2,6-dimethylphenylacetonitrile (84803-57-6)

Conditions	Yield
With ethanol

5-tert-Butyl-m-xylene (98-19-1) → 4-tert-butyl-2,6-dimethylphenylacetonitrile (84803-57-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: HCl; ZnCl2 / 50 °C 2: ethanol View Scheme

m-xylene (108-38-3) → 4-tert-butyl-2,6-dimethylphenylacetonitrile (84803-57-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: FeCl3 2: HCl; ZnCl2 / 50 °C 3: ethanol View Scheme
Multi-step reaction with 3 steps 1: aqueous H2SO4 / 65 - 70 °C 2: HCl; ZnCl2 / 50 °C 3: ethanol View Scheme

4-tert-butyl-2,6-dimethylphenylacetonitrile (84803-57-6) → 2-(2,6-dimethyl-4-tert-butylphenyl)-1-aminoethane (93720-89-9)

Conditions	Yield
With hydrogen; 10% palladium on active carbon In methanol under 2068.6 Torr;	76%

ethanol (64-17-5) + 4-tert-butyl-2,6-dimethylphenylacetonitrile (84803-57-6) → 2-(4-tert-Butyl-2,6-dimethyl-phenyl)-acetimidic acid ethyl ester (208719-08-8)

Conditions	Yield
With hydrogenchloride In diethyl ether; ethanol at 0℃; for 2h;	56%

4-tert-butyl-2,6-dimethylphenylacetonitrile (84803-57-6) → (4-tert-butyl-2,6-dimethyl-phenyl)-acetic acid (854646-92-7)

Conditions	Yield
With potassium hydroxide

4-tert-butyl-2,6-dimethylphenylacetonitrile (84803-57-6) → 2-(4-tert-butyl-2,6-dimethyl-phenyl)-4-phenyl-butyronitrile

Conditions	Yield
With sodium amide; toluene anschliessend Behandeln mit Phenaethylbromid;

4-tert-butyl-2,6-dimethylphenylacetonitrile (84803-57-6) + ethylenediamine (107-15-3) → xylometazoline (526-36-3)

Conditions	Yield
With carbon disulfide

methyl magnesium iodide (917-64-6) + 4-tert-butyl-2,6-dimethylphenylacetonitrile (84803-57-6) → 1-(4-tert-Butyl-2,6-dimethyl-phenyl)-propan-2-one

4-tert-butyl-2,6-dimethylphenylacetonitrile (84803-57-6) + Trimethylenediamine (109-76-2) → 2-(4-t-butyl-2,6-dimethylbenzyl)-1,4,5,6-tetrahydropyrimidine

Conditions	Yield
With ethylenediamine p-toluenesulfonate at 200℃; for 1h;

4-tert-butyl-2,6-dimethylphenylacetonitrile (84803-57-6) → N-monomethyl-2-(2,6-dimethyl-4-tert-butylphenyl)-1-aminoethane (208718-97-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: 76 percent / H2 / 10percentPd/C / methanol / 2068.6 Torr 2: Et3N / tetrahydrofuran / Ambient temperature 3: LiAlH4 / tetrahydrofuran / 4 h / Heating View Scheme

4-tert-butyl-2,6-dimethylphenylacetonitrile (84803-57-6) → [2-(4-tert-Butyl-2,6-dimethyl-phenyl)-ethyl]-carbamic acid ethyl ester

Conditions	Yield
Multi-step reaction with 2 steps 1: 76 percent / H2 / 10percentPd/C / methanol / 2068.6 Torr 2: Et3N / tetrahydrofuran / Ambient temperature View Scheme

4-tert-butyl-2,6-dimethylphenylacetonitrile (84803-57-6) → 4-t-butyl-2,6-dimethylbenzeneethanimidamide

Conditions	Yield
Multi-step reaction with 2 steps 1: 56 percent / HCl(gas) / diethyl ether; ethanol / 2 h / 0 °C 2: NH3(gas) / ethanol / Ambient temperature View Scheme

4-tert-butyl-2,6-dimethylphenylacetonitrile (84803-57-6) → 2-[(4-t-butyl-2,6-dimethylphenyl)methyl]-4,5-dihydro-1-methylimidazole (208718-93-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 56 percent / HCl(gas) / diethyl ether; ethanol / 2 h / 0 °C 2: ethanol / 1.) 0 deg C, 1 h, 2.) reflux, 20 min View Scheme

4-tert-butyl-2,6-dimethylphenylacetonitrile (84803-57-6) → (4-tert-butyl-2,6-dimethyl-phenyl)-acetic acid amide

Conditions	Yield
Multi-step reaction with 2 steps 1: ethanolic KOH-solution 2: thionyl chloride / Behandeln des Saeurechlorids mit wss. Ammoniak View Scheme

4-tert-butyl-2,6-dimethylphenylacetonitrile (84803-57-6) → [2-(4-tert-Butyl-2,6-dimethyl-phenyl)-1-methyl-ethyl]-(1-methyl-3,3-diphenyl-propyl)-amine

Conditions	Yield
Multi-step reaction with 2 steps 2: (i) toluene, (ii) H2, PtO2, MeOH View Scheme

4-tert-butyl-2,6-dimethylphenylacetonitrile (84803-57-6) → [2-(4-tert-Butyl-2,6-dimethyl-phenyl)-1-methyl-ethyl]-methyl-(1-methyl-3,3-diphenyl-propyl)-amine

Conditions	Yield
Multi-step reaction with 3 steps 2: (i) toluene, (ii) H2, PtO2, MeOH 3: formic acid / water / 100 °C View Scheme

Upstream product

• 108-38-3 m-xylene 
• 98-19-1 5-tert-Butyl-m-xylene 
• 19387-83-8 4-tert-butyl-2,6-dimethylbenzyl chloride 
• 151-50-8 potassium cyanide 

Downstream Products

• 208718-93-8 2-[(4-t-butyl-2,6-dimethylphenyl)methyl]-4,5-dihydro-1-methylimidazole 
• 208718-97-2 N-monomethyl-2-(2,6-dimethyl-4-tert-butylphenyl)-1-aminoethane 
• 246544-20-7 2-(4-t-butyl-2,6-dimethylbenzyl)-1,4,5,6-tetrahydropyrimidine 
• 93720-89-9 2-(2,6-dimethyl-4-tert-butylphenyl)-1-aminoethane 
• 208719-08-8 2-(4-tert-Butyl-2,6-dimethyl-phenyl)-acetimidic acid ethyl ester 
• 526-36-3 xylometazoline 
• 854646-92-7 (4-tert-butyl-2,6-dimethyl-phenyl)-acetic acid