33375-06-3

Basic information

• Product Name: (R)-(+)-1-Phenylethyl isocyanate
• Synonyms: ISOCYANIC ACID (R)-(+)-1-PHENYLETHYL ESTER;ISOCYANIC ACID (R)-(+)-ALPHA-METHYLBENZYL ESTER;(R)-(+)-1-PHENYLETHYL ISOCYANATE;(R)-1-PHENYLETHYLISOCYANATE;(R)-(+)-A-METHYLBENZYL ISOCYANATE;(R)-(+)-ALPHA-METHYLBENZYL ISOCYANATE;(R)(+)-ALPHA-PHENETHYL ISOCYANATE;(R) METHYL BENZYLISOCYANATE
• CAS NO: 33375-06-3
• Molecular Formula: C₉H₉NO
• Molecular Weight: 147.17
• EINECS: 251-485-2
• Product Categories: chiral;Isocyanates (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;Optical Resolution;Synthetic Organic Chemistry
• Mol File: 33375-06-3.mol
• Article Data: 23

Chemical Properties

• 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 1.513(lit.)
• Storage Temp.: 2-8°C
• Water Solubility: Decomposition
• Sensitive: Moisture Sensitive
• BRN: 3196930
• CAS DataBase Reference: (R)-(+)-1-Phenylethyl isocyanate(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-1-Phenylethyl isocyanate(33375-06-3)
• EPA Substance Registry System: (R)-(+)-1-Phenylethyl isocyanate(33375-06-3)

Safety Data

• Hazard Codes: Xn,T+,T
• Statements: 36/37/38-42-26-23/24/25-23
• Safety Statements: 23-26-36-45-24/25-38-36/37/39-7/9
• RIDADR: UN 2206 6.1/PG 2
• WGK Germany: 3
• F: 3-10-21
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 33375-06-3(Hazardous Substances Data)

Usage

Chemical Properties

Colorless to light yellow liqui

Uses

(R)-1-phenylethyl isocyanate is used in the derivatisation of alcohols, thiocarbamates and hydroxy fatty acids. (R)-1-phenylethyl isocyanate moderately inhibited both BP-DNA adducts.

General Description

(R)-(+)-a-Methylbenzyl isocyanate [(R)-(+)-MBIC] is a derivatizing agent.

InChI:InChI=1/C9H9NO/c1-8(10-7-11)9-5-3-2-4-6-9/h2-6,8H,1H3/t8-/m1/s1

Upstream product

• 3315-16-0 silver cyanate 
• 585-71-7 (1-bromoethyl)benzne 
• 618-36-0 rac-methylbenzylamine 
• 503-38-8 trichloromethyl chloroformate 
• 75-44-5 phosgene 
• 10277-86-8 (R)-1-phenylethylamine hydrochloride 
• 82826-58-2 (R)-N-Hydroxy-2-phenyl-propionamide 
• 100-42-5 styrene 
• 75-13-8 isocyanic acid 
• 85548-65-8 (1-Phenyl-ethyl)-carbamic acid (1S,2S)-2-phenylsulfanyl-cyclopent-3-enyl ester 
• 14649-03-7 S-(-)-(α-Methylbenzyl)isocyanate 
• 85548-66-9 (1-Phenyl-ethyl)-carbamic acid (1R,2R)-2-phenylsulfanyl-cyclopent-3-enyl ester 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 

Downstream Products

• 16849-92-6 2,2-dimethyl-aziridine-1-carboxylic acid-((R)-1-phenyl-ethylamide) 
• 16849-91-5 (R)-(+)-N-α-methylbenzylurea 
• 80490-87-5 Piperazine-1,4-dicarboxylic acid bis-[(1-phenyl-ethyl)-amide] 
• 99541-09-0 ((R)-1-Phenyl-ethyl)-carbamic acid quinolin-8-yl ester 
• 840504-12-3 (S)-4-Phenyl-3-((R)-1-phenyl-ethyl)-1-(toluene-4-sulfonyl)-imidazolidin-2-one 
• 840504-11-2 (R)-4-Phenyl-3-((R)-1-phenyl-ethyl)-1-(toluene-4-sulfonyl)-imidazolidin-2-one 

Relevant articles and documents

Resolution of albuterol acetonide

The (R)-enantiomer of albuterol has been isolated via resolution of albuterol acetonide with (2S,3S)-di-O-benzoyl- or (2S,3S)-di-O-toluoyltartaric acid. The absolute configuration of the resolved acetonide was assessed by 1H NMR analysis of its (R)-Mosher's ester, and confirmed by an X-ray crystal structure determination of the (R)-phenylethylurea derivative of the (S)-enantiomer.

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.

Structure-activity relationship studies of pyrazolo[3,4-d]pyrimidine derivatives leading to the discovery of a novel multikinase inhibitor that potently inhibits FLT3 and VEGFR2 and evaluation of its activity against acute myeloid leukemia in vitro and in vivo

We describe the structural optimization of a hit compound, 1-(4-(1H-pyrazolo[3,4-d]pyrimidin-4-ylamino)phenyl)-3-(3-methoxyphenyl)urea (1), which exhibits inhibitory activity but low potency against FLT3 and VEGFR2. A series of pyrazolo[3,4-d]pyrimidine derivatives were synthesized, and structure-activity relationship analysis using cell- and transgenic-zebrafish- based assays led to the discovery of a number of compounds that exhibited both high potency against FLT3-driven human acute myeloid leukemia (AML) MV4-11 cells and a considerable antiangiogenic effect in transgenic-zebrafish-based assays. The compound 1-(4-(1H-pyrazolo[3,4-d]pyrimidin -4-yloxy)phenyl)-3-(4-chloro-3- (trifluoromethyl)phenyl)urea (33), which exhibited the highest activity in preliminary in vivo anti-AML assays, was chosen for further anti-AML studies. The results demonstrated that compound 33 is a multikinase inhibitor that potently inhibits FLT3 and VEGFR2. In an MV4-11 xenograft mouse model, a once-daily dose of compound 33 at 10 mg/kg for 18 days led to complete tumor regression without obvious toxicity. Western blot and immunohistochemical analyses were performed to determine the mechanism of action of compound 33.