56651-58-2

Basic information

• Product Name: 2-METHYLBENZYL ISOCYANATE
• Synonyms: 2-Methylbenzyl isocyanate,98%;2-Methylbenzyl isocyanate 98%;1-(isocyanatomethyl)-2-methylbenzene;2-METHYLBENZYL ISOCYANATE
• CAS NO: 56651-58-2
• Molecular Formula: C₉H₉NO
• Molecular Weight: 147.17
• Product Categories: Nitrogen Compounds;Organic Building Blocks;Building Blocks;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks;Isocyanates
• Mol File: 56651-58-2.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 226 °C(lit.)
• Flash Point: 210 °F
• Appearance: clear colorless to yellow liquid
• Density: 1.059 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0955mmHg at 25°C
• Refractive Index: n20/D 1.528(lit.)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-METHYLBENZYL ISOCYANATE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-METHYLBENZYL ISOCYANATE(56651-58-2)
• EPA Substance Registry System: 2-METHYLBENZYL ISOCYANATE(56651-58-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22-37/38-41
• Safety Statements: 26-39
• RIDADR: UN 3334
• WGK Germany: 3
• Hazardous Substances Data: 56651-58-2(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to yellow liquid

General Description

2-Methylbenzyl isocyanate, also known as 1-(isocyanatomethyl)-2-methylbenzene, is an organic building block containing an isocyanate group. Its vapor pressure has been reported.

InChI:InChI=1/C9H9NO/c1-8-4-2-3-5-9(8)6-10-7-11/h2-5H,6H2,1H3

Synthetic route

(o-tolyl)acetyl chloride (10166-09-3) → R-(+)-methylbenzyl isocyanate (56651-58-2)

Conditions	Yield
With trimethylsilylazide In toluene for 5h; Heating;	63%
Multi-step reaction with 2 steps 1: NaN3 / acetone; H2O / 0.5 h / 0 - 5 °C 2: CHCl3 / 0.5 h / Heating View Scheme

o-Tolyl-acetyl azide → R-(+)-methylbenzyl isocyanate (56651-58-2)

Conditions	Yield
In chloroform for 0.5h; Heating;

chloromethyl isocyanate (7093-91-6) + toluene (108-88-3) → 1-chloromethyl-2-methylbenzene (552-45-4) + R-(+)-methylbenzyl isocyanate (56651-58-2) + 4-Methylbenzyl chloride (104-82-5) + 4-tolylmethyl isocyanate (56651-57-1)

Conditions	Yield
With iron(III) chloride at 40 - 150℃; for 2h;	A n/a B 23 % Spectr. C n/a D n/a
With iron(III) chloride at 40 - 150℃; for 2h;	A n/a B 20 % Spectr. C n/a D n/a

o-methylphenylacetic acid (644-36-0) → R-(+)-methylbenzyl isocyanate (56651-58-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: oxalyl chloride, dimethylformamide / CH2Cl2 / 0.42 h 2: NaN3 / acetone; H2O / 0.5 h / 0 - 5 °C 3: CHCl3 / 0.5 h / Heating View Scheme

ortho-methylbenzylamine (89-93-0) + bis(trichloromethyl) carbonate (32315-10-9) → R-(+)-methylbenzyl isocyanate (56651-58-2)

Conditions	Yield
In toluene for 4h; Reflux;

R-(+)-methylbenzyl isocyanate (56651-58-2) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → C31H30NO3P

Conditions	Yield
In 1,2-dichloro-ethane at 20℃; for 1h; Inert atmosphere; Sealed tube;	96%

R-(+)-methylbenzyl isocyanate (56651-58-2) + aniline (62-53-3) → 1-(2-methylbenzyl)-3-phenylurea (92277-79-7)

Conditions	Yield
In diethyl ether	92%

benzo[d]oxazol-2-yl-(4-hydroxyphenyl)methanone (946837-64-5) + R-(+)-methylbenzyl isocyanate (56651-58-2) → C23H18N2O4

Conditions	Yield
With triethylamine In toluene at 20℃; for 12h;	90%

R-(+)-methylbenzyl isocyanate (56651-58-2) + benzylamine (100-46-9) → 1-benzyl-3-(2-methylbenzyl)urea (92277-81-1)

Conditions	Yield
In diethyl ether	79%

C33H41N5O2 (1430093-77-8) + R-(+)-methylbenzyl isocyanate (56651-58-2) → LLW62

Conditions	Yield
In dichloromethane; acetonitrile at 20℃; for 2h; Inert atmosphere;	75%

benzoimidazole (51-17-2) + R-(+)-methylbenzyl isocyanate (56651-58-2) → N-(o-tolylmethyl)benzimidazole-1-carboxamide

Conditions	Yield
With dmap In pyridine at 20℃; for 5h; Inert atmosphere;	66%

2-methyl-8-aminoquinoline (18978-78-4) + R-(+)-methylbenzyl isocyanate (56651-58-2) → C19H19N3O

Conditions	Yield
In toluene at 20℃; Inert atmosphere;	65%

1H-benzimidazol-2-amine (934-32-7) + R-(+)-methylbenzyl isocyanate (56651-58-2) → 2-amino-N-(o-tolylmethyl)benzimidazole-1-carboxamide

Conditions	Yield
With dmap In pyridine at 20℃; for 5h; Inert atmosphere;	64%

S-4-hydroxybenzyl 4-tert-butoxycarbonylpiperazine-1-thiocarboxylate (438049-39-9) + R-(+)-methylbenzyl isocyanate (56651-58-2) → S-4-[[(2-Methylbenzyl)amino]carbonyl]oxybenzyl piperazine-1-thiocarboxylate hydrochloride (438047-15-5)

Conditions	Yield
	62.1%

4-chloro-aniline (106-47-8) + R-(+)-methylbenzyl isocyanate (56651-58-2) → 1-(4-Chloro-phenyl)-3-(2-methyl-benzyl)-urea (92308-84-4)

Conditions	Yield
In diethyl ether	60%

1,2-benzisothiazolin-3-one (2634-33-5) + R-(+)-methylbenzyl isocyanate (56651-58-2) → 3-oxo-3H-benzo[d]isothiazole-2-carboxylic acid 2-methylbenzylamide

Conditions	Yield
In tetrahydrofuran at 45℃; for 1h;	56%

R-(+)-methylbenzyl isocyanate (56651-58-2) + 2-(4-hydroxyphenyl)-4,5-dihydro-1,3-thiazole (90563-68-1) → (2-methyl)-benzylcarbamic acid 4-(4,5-dihydrothiazol-2-yl)phenyl ester (1165760-77-9)

Conditions	Yield
With triethylamine In toluene for 2.5h; Inert atmosphere; Reflux;	53%

ethyl 5-cyano-6-(piperazin-1-yl)-2-(trifluoromethyl)nicotinate (266680-09-5) + R-(+)-methylbenzyl isocyanate (56651-58-2) → ethyl 5-cyano-6-(4-{[(2-methylbenzyl)amino]carbonyl}piperazin-1-yl)-2-(trifluoromethyl)nicotinate

Conditions	Yield
In tetrahydrofuran at 20℃; for 16h;	53%

R-(+)-methylbenzyl isocyanate (56651-58-2) + 6-chloro-4-methyl-1,2-dihydro-pyrazolo[3,4-b]pyridin-3-one (28491-61-4) → 6-chloro-4-methyl-3-oxo-1,3-dihydropyrazolo[3,4-b]pyridine-2-carboxylic acid 2-methylbenzylamide

Conditions	Yield
In tetrahydrofuran; N,N-dimethyl-formamide at 20℃;	51%

R-(+)-methylbenzyl isocyanate (56651-58-2) + 3-amino-6-chloro-2-hydroxybenzenesulfonamide (276702-20-6) → N-(3-aminosulfonyl4-chloro-2-hydroxyphenyl)-N'-(2-methyl)benzylurea (361378-87-2)

Conditions	Yield
In N,N-dimethyl-formamide	50%

4-(4,5-dihydro-2-oxazolyl)phenol (81428-58-2) + R-(+)-methylbenzyl isocyanate (56651-58-2) → (2-methyl)-benzylcarbamic acid 4-(4,5-dihydrooxazol-2-yl)phenyl ester (1165760-91-7)

Conditions	Yield
With triethylamine In toluene for 2.5h; Inert atmosphere; Reflux;	50%

2-Benzoxazolinone (59-49-4) + R-(+)-methylbenzyl isocyanate (56651-58-2) → 2-oxo-benzooxazol-3-carboxylic acid 2-methyl-benzylamide

Conditions	Yield
In 1,4-dioxane at 60℃;	36%

2,3-dihydro[1,3]oxazolo[4,5-b]pyridin-2-one (60832-72-6) + R-(+)-methylbenzyl isocyanate (56651-58-2) → 2-oxo-oxazolo[4,5-b]pyridine-3-carboxylic acid 2-methyl-benzylamide

Conditions	Yield
In tetrahydrofuran at 70℃; for 10h;	26%

R-(+)-methylbenzyl isocyanate (56651-58-2) + 3,3-diethyl-4-<<4-<(1,1-dimethylethoxy)carbonyl>phenyl>oxy>-2-azetidinone (143818-55-7) → 4-[3,3-Diethyl-1-(2-methyl-benzylcarbamoyl)-4-oxo-azetidin-2-yloxy]-benzoic acid tert-butyl ester

Conditions	Yield
With dmap; triethylamine In dichloromethane for 24h;

R-(+)-methylbenzyl isocyanate (56651-58-2) → 4-[3,3-Diethyl-1-(2-methyl-benzylcarbamoyl)-4-oxo-azetidin-2-yloxy]-benzoic acid (143818-85-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine, 4-(dimethylamino)pyridine / CH2Cl2 / 24 h 2: trifluoroacetic acid, anisole / 1 h / 0 °C View Scheme

4amino-6-methoxy-7-(-methylpiperidin-4-ylmethoxy)quinazoline (320365-82-0) + R-(+)-methylbenzyl isocyanate (56651-58-2) → 1-[6-methoxy-7-(N-methylpiperidin-4-ylmethoxy)quinazolin-4-yl]-3-(2-methylbenzyl)urea (320364-75-8)

1H-indazol-3-ol (7364-25-2, 100922-96-1, 70010-33-2) + R-(+)-methylbenzyl isocyanate (56651-58-2) → 3-oxo-1,3-dihydro-indazole-2-carboxylic acid 2-methylbenzylamide (787578-91-0)

Conditions	Yield
In tetrahydrofuran

R-(+)-methylbenzyl isocyanate (56651-58-2) → 1-(2-methyl-1,2,3,4-tetrahydroquinolin-8-yl)-3-(2-methylbenzyl)urea + 1-(2-methyl-1,2,3,4-tetrahydroquinolin-8-yl)-3-(2-methylbenzyl)urea

Conditions	Yield
Multi-step reaction with 2 steps 1: toluene / 20 °C / Inert atmosphere 2: C41H49N4O11PS; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate / dichloromethane / 24 h / 20 °C View Scheme

R-(+)-methylbenzyl isocyanate (56651-58-2) → 1-(2-methyl-1,2,3,4-tetrahydroquinolin-8-yl)-3-(2-methylbenzyl)urea

Conditions	Yield
Multi-step reaction with 2 steps 1: toluene / 20 °C / Inert atmosphere 2: acetic acid; sodium cyanoborohydride / 20 °C View Scheme

C16H27N2O2(1+)*Cl(1-) + R-(+)-methylbenzyl isocyanate (56651-58-2) → C25H36N3O3(1+)*Cl(1-)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 12h;	0.96 g

Upstream product

• 89-93-0 ortho-methylbenzylamine 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 10166-09-3 (o-tolyl)acetyl chloride 
• 7093-91-6 chloromethyl isocyanate 
• 108-88-3 toluene 
• 644-36-0 o-methylphenylacetic acid 

Relevant articles and documents

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ARYLMETHYL ISOCYANATES

Chloromethyl isocyanate reacts readily with aromatic hydrocarbons in the presence of anhydrous ferric chloride or other catalysts of the Friedel-Crafts reaction with the formation of arylmethyl isocyanates.The latter add alcohols and amines readily, being converted into the corresponding substituted urethanes and ureas.When heated in the presence of catalytic amounts of 1,3-dimethylphosphol-3-ene they give substituted carbodiimides.