14649-03-7

Basic information

• Product Name: (S)-(-)-1-Phenylethyl isocyanate
• Synonyms: Isocyanic Acid (S)-(-)-alpha-Methylbenzyl Ester Isocyanic Acid (S)-(-)-1-Phenylethyl Ester (S)-(-)-1-Phenylethyl Isocyanate;(S)-(-)-α-Methylbenzyl isocyanate, for chiral derivatization;(S)-(-)-α-Methylbenzyl Isocyanate;(S)-(-)-alpha-Methylbenzyl isocyanate 99%;Tris(pentafluorophenyl)borane(S)-(-)-1-Phenylethylisocyanate;(S)-(-)-α[(1S)-1-Isocyanatoethyl]benzene;(S) METHYL BENZYLISOCYANATE
• CAS NO: 14649-03-7
• Molecular Formula: C₉H₉NO
• Molecular Weight: 147.17
• EINECS: 238-698-6
• Product Categories: chiral;Analytical Chemistry;Chiral Building Blocks;e.e. / Absolute Configuration Determination (NMR);e.e. Determination (HPLC Labeling Reagents);Enantiomer Excess & Absolute Configuration Determination;for Resolution of Alcohols & Thiols;for Resolution of Bases;Isocyanates (Chiral);Optical Resolution;Synthetic Organic Chemistry
• Mol File: 14649-03-7.mol
• Article Data: 20

Chemical Properties

• Melting Point: 65 °C
• Boiling Point: 55-56 °C2.5 mm Hg(lit.)
• Flash Point: 150 °F
• Appearance: Clear colorless to pale yellow/Liquid
• Density: 1.045 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.268mmHg at 25°C
• Refractive Index: n20/D 1.5145(lit.)
• Storage Temp.: 2-8°C
• Water Solubility: Decomposition
• Sensitive: Moisture Sensitive
• BRN: 4230972
• CAS DataBase Reference: (S)-(-)-1-Phenylethyl isocyanate(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-1-Phenylethyl isocyanate(14649-03-7)
• EPA Substance Registry System: (S)-(-)-1-Phenylethyl isocyanate(14649-03-7)

Safety Data

• Hazard Codes: Xn,T+,T
• Statements: 36/37/38-42-26-23
• Safety Statements: 23-26-36-45-24/25
• RIDADR: UN 2206 6.1/PG 2
• WGK Germany: 3
• F: 3-10-21
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 14649-03-7(Hazardous Substances Data)

Usage

Chemical Properties

Colorless to light yellow liqui

Uses

(S)-(-)-1-Phenylethyl isocyanate act by inhibition of cell proliferation and induction of apoptosis. It helps to prevent lung cancer and esophageal cancer. It is a fine chemical intermediate.

General Description

(S)-(-)-α-Methylbenzyl isocyanate is a commonly used chiral derivatizing agent for the resolution of enantiomers.

Purification Methods

Purify the isocyanates by fractional distillation under a vacuum. With ammonia

InChI:InChI=1/C9H9NO/c1-8(10-7-11)9-5-3-2-4-6-9/h2-6,8H,1H3/t8-/m0/s1

Upstream product

• 98-85-1 1-Phenylethanol 
• 39139-87-2 tetrabutylammonium isocyanate 
• 100-42-5 styrene 
• 105966-39-0 2-(1-phenylethoxy)-tetrahydro-2H-pyran 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 503-38-8 trichloromethyl chloroformate 
• 33375-06-3 C₉H₉NO 
• 85548-65-8 (1-Phenyl-ethyl)-carbamic acid (1S,2S)-2-phenylsulfanyl-cyclopent-3-enyl ester 
• 75-44-5 phosgene 
• 26848-01-1 S-(-)-α-methylbenzylamine-(2R,3R)-(-)-2,3-dihydroxybutanedioic acid 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 124-38-9 carbon dioxide 
• 32366-25-9 1-azidoethylbenzene 
• 618-36-0 rac-methylbenzylamine 

Downstream Products

• 90432-79-4 N-<(S)-1-phenylethyl>-3-hexyl-2-pyrrolidone-1-carboxamide 
• 90432-78-3 N-<(S)-1-phenylethyl>-3-hexyl-2-pyrrolidone-1-carboxamide 
• 90432-76-1 N-<(S)-1-phenylethyl>-5-hexyl-2-pyrrolidone-1-carboxamide 
• 90432-77-2 N-<(S)-1-phenylethyl>-5-hexyl-2-pyrrolidone-1-carboxamide 
• 90432-80-7 N-<(S)-1-phenylethyl>-6-pentyl-2-piperidone-1-carboxamide 
• 90432-81-8 N-<(S)-1-phenylethyl>-6-pentyl-2-piperidone-1-carboxamide 
• 147169-48-0 (R,S)-N-(tert-butyloxycarbonyl)-α-methylbenzylamine 
• 336628-48-9 1,3-dibromo-2-propyl (S)-N-(1-phenylethyl)carbamate 
• 336628-49-0 1,3-dichloro-2-propyl (S)-N-(1-phenylethyl)carbamate 

Relevant articles and documents

Triphenylphosphine/2,3-dichloro-5,6-dicyanobenzoquinone (DDQ)/[n-Bu4N]OCN as a useful system for the efficient conversion of tetrahydropyranyl (THP) ethers to the corresponding alkyl isocyanates

Triphenylphosphine/2,3-dichloro-5,6-dicyanobenzoquinone/tetrabutylammonium cyanate was used as an efficient system for the conversion of tetrahydropyranyl ethers to the corresponding alkyl isocyanates. Taylor & Francis Group, LLC.

A new and convenient method of generating alkyl isocyanates from alcohols, thiols and trimethylsilyl ethers using triphenylphosphine/2,3-dichloro-5,6- dicyanobenzoquinone/Bu4NOCN

Alkyl isocyanates are prepared in good to excellent yields by treatment of alcohols, thiols and trimethylsilyl ethers with triphenylphosphine/2,3-dichloro- 5,6-dicyanobenzoquinone/ Bu4NOCN in acetonitrile. This method is highly selective for conversion of primary alcohols to alkyl isocyanates in the presence of secondary and tertiary alcohols, thiols and trimethysilyl ethers. Georg Thieme Verlag Stuttgart.

Benzylic C-H isocyanation/amine coupling sequence enabling high-throughput synthesis of pharmaceutically relevant ureas

C(sp3)-H functionalization methods provide an ideal synthetic platform for medicinal chemistry; however, such methods are often constrained by practical limitations. The present study outlines a C(sp3)-H isocyanation protocol that enables the synthesis of diverse, pharmaceutically relevant benzylic ureas in high-throughput format. The operationally simple C-H isocyanation method shows high site selectivity and good functional group tolerance, and uses commercially available catalyst components and reagents [CuOAc, 2,2′-bis(oxazoline) ligand, (trimethylsilyl)isocyanate, andN-fluorobenzenesulfonimide]. The isocyanate products may be used without isolation or purification in a subsequent coupling step with primary and secondary amines to afford hundreds of diverse ureas. These results provide a template for implementation of C-H functionalization/cross-coupling in drug discovery.

Amide compound, pharmaceutical composition, preparation method and application thereof

The invention provides an amide compound, a pharmaceutical composition, a preparation method and application thereof and belongs to the field of medicine. Structure of the amide compound is shown as aformula I. The preparation method includes: in an alkaline condition and in an organic solvent, allowing a compound I and a compound II to be in condensation reaction. The amide compound or pharmaceutically acceptable salt thereof have long-acting sensory and/or motion blocking activity, can be used for preparing long-acting local anesthetic or analgesic and is long in efficacy lasting time, little side effect and high in medication safety.