80058-93-1

Basic information

• Product Name: 1,3-diisopropyl-2-isothiocyanato-5-phenoxybenzene
• Synonyms: 4-phenoxy-2，6-diisopropyl phenyl isothiocyanate;1,3-diisopropyl-2-isothiocyanato-5-phenoxybenzene;DIPPI
• CAS NO: 80058-93-1
• Molecular Formula: C₁₉H₂₁NOS
• Molecular Weight: 311.44114
• Product Categories: intermediate
• Mol File: 80058-93-1.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 411.0±45.0 °C(Predicted)
• Appearance: /
• Density: 1.04±0.1 g/cm3(Predicted)
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: Dichloromethane; Ethyl Acetate; Methanol
• CAS DataBase Reference: 1,3-diisopropyl-2-isothiocyanato-5-phenoxybenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-diisopropyl-2-isothiocyanato-5-phenoxybenzene(80058-93-1)
• EPA Substance Registry System: 1,3-diisopropyl-2-isothiocyanato-5-phenoxybenzene(80058-93-1)

Safety Data

• Hazardous Substances Data: 80058-93-1(Hazardous Substances Data)

Usage

Uses

2-Isothiocyanato-1,3-bis(1-methylethyl)-5-phenoxybenzene is a proposed intermediate in the synthesis of 6-Amino-1-(2,6-diisopropyl-4-phenoxyphenyl)-4-((2,6-diisopropyl-4-phenoxyphenyl)amino)-1,3,5-triazine-2(1H)-thione (A607450) is an impurity compound of Diafenthiuron (D310550), an insecticide.

Synthetic route

N-(4-phenoxy-2,6-diisopropylphenyl)thiourea → 2,6-diisopropyl-4-phenoxy-1-isothiocyanobenzene (80058-93-1)

Conditions	Yield
In o-xylene

2,6-diisopropyl-4-phenoxyaniline (80058-85-1) + thiophosgene (463-71-8) → 2,6-diisopropyl-4-phenoxy-1-isothiocyanobenzene (80058-93-1)

Conditions	Yield
With calcium carbonate In dichloromethane; water

2,6-diisopropyl-4-phenoxy-1-isothiocyanobenzene (80058-93-1) + methylhydrazine (60-34-4) → N-methylamino-N'-(2,6-diisopropyl-4-phenoxyphenyl)thiourea

Conditions	Yield
In water; ethyl acetate	95%

2,6-diisopropyl-4-phenoxy-1-isothiocyanobenzene (80058-93-1) + 1-(4-chlorophenyl)-3-cyanoguanidine (1482-62-8) → 4-[(4-chlorophenyl)imino]-1-(2,6-diisopropyl-4-phenoxyphenyl)-6-imino-1,3,5-triazinane-2-thione

Conditions	Yield
With sodium methylate In acetone at 80℃; for 0.0666667h; Microwave irradiation;	89%

2,6-diisopropyl-4-phenoxy-1-isothiocyanobenzene (80058-93-1) + N-cyano-N'-(3,4-dimethyl-phenyl)-guanidine (197311-81-2) → 1-(2,6-diisopropyl-4-phenoxyphenyl)-4-[(3,4-dimethylphenyl)imino]-6-imino-1,3,5-triazinane-2-thione

Conditions	Yield
With sodium methylate In acetone at 80℃; for 0.0833333h; Microwave irradiation;	88%

2,6-diisopropyl-4-phenoxy-1-isothiocyanobenzene (80058-93-1) + C10H12N4 → 1-(2,6-diisopropyl-4-phenoxyphenyl)-4-[(2,6-dimethylphenyl)imino]-6-imino-1,3,5-triazinane-2-thione

Conditions	Yield
With sodium methylate In acetone at 80℃; for 0.0833333h; Microwave irradiation;	88%

2,6-diisopropyl-4-phenoxy-1-isothiocyanobenzene (80058-93-1) + 1-phenyl-3-cyanoguanidine (41410-39-3) → 1-(2,6-diisopropyl-4-phenoxyphenyl)-6-imino-4-(phenylimino)-1,3,5-triazinane-2-thione

Conditions	Yield
With sodium methylate In acetone at 80℃; for 0.0833333h; Microwave irradiation;	84%

2,6-diisopropyl-4-phenoxy-1-isothiocyanobenzene (80058-93-1) + C9H7F3N4O → 1-(2,6-diisopropyl-4-phenoxyphenyl)-6-imino-4-{[2-(trifluoromethoxy)phenyl]imino}-1,3,5-triazinane-2-thione

Conditions	Yield
With sodium methylate In acetone at 80℃; for 0.0833333h; Microwave irradiation;	84%

2,6-diisopropyl-4-phenoxy-1-isothiocyanobenzene (80058-93-1) → diafenthiuron (80060-09-9)

Conditions	Yield
With tert-butylamine In hexane; toluene

2,2’,6,6’-tetraisopropylbenzidine (186703-54-8) + 2,6-diisopropyl-4-phenoxy-1-isothiocyanobenzene (80058-93-1) → C62H78N4O2S2

Conditions	Yield
In toluene at 90℃; for 3h; Autoclave; Industrial scale;

Upstream product

• 80058-85-1 2,6-diisopropyl-4-phenoxyaniline 
• 463-71-8 thiophosgene 

Downstream Products

• 80060-09-9 diafenthiuron 

Relevant articles and documents

Process for the preparation of isothiocyanates

There is disclosed a process for the preparation of isothiocyanates of formula STR1 wherein R1 and R2 are each independently of the other C1 -C6 alkyl and R3, R4 and R5 are each independently of the other hydrogen, halogen, C1 -C4 alkyl, C1 -C4 alkoxy, trifluoromethyl or nitro, which process comprises an amine of formula STR2 with ammonium thiocyanate or an alkali metal thiocyanate, in the presence of acid and an inert solvent, to the thiourea of formula STR3 and cleaving said thiourea by heating. The essential feature of this process consists in carrying out the reaction of the amine of the above formula with ammonium thiocyanate or an alkali metal thiocyanate in the presence of 0.5-5% by weight of water, based on the total weight of the reaction mixture. The isothiocyanates of the above formula are intermediates for the synthesis of pesticidal compounds.