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Phenylcarbamic acid phenylmethyl ester, also known as phenylmethyl carbamate, is a chemical compound with the molecular formula C9H11NO2. It is a carbamate insecticide that inhibits cholinesterase enzymes, leading to the accumulation of acetylcholine in the nervous system of pests, causing paralysis and death. Additionally, it serves as a reagent in organic synthesis and a precursor in the production of other chemicals. However, it is crucial to handle and use this chemical with caution due to its potential toxicity and harmful effects on human and environmental health.

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  • 3422-02-4 Structure
  • Basic information

    1. Product Name: Phenylcarbamic acid phenylmethyl ester
    2. Synonyms: Phenylcarbamic acid phenylmethyl ester
    3. CAS NO:3422-02-4
    4. Molecular Formula: C14H13NO2
    5. Molecular Weight: 227.25852
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 3422-02-4.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 325.2 °C at 760 mmHg
    3. Flash Point: 150.5 °C
    4. Appearance: /
    5. Density: 1.198 g/cm3
    6. Vapor Pressure: 0.000234mmHg at 25°C
    7. Refractive Index: 1.621
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. CAS DataBase Reference: Phenylcarbamic acid phenylmethyl ester(CAS DataBase Reference)
    11. NIST Chemistry Reference: Phenylcarbamic acid phenylmethyl ester(3422-02-4)
    12. EPA Substance Registry System: Phenylcarbamic acid phenylmethyl ester(3422-02-4)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 3422-02-4(Hazardous Substances Data)

3422-02-4 Usage

Uses

Used in Pest Control Industry:
Phenylcarbamic acid phenylmethyl ester is used as an insecticide for controlling various pests. It acts by inhibiting cholinesterase enzymes, leading to the accumulation of acetylcholine in the nervous system and ultimately causing paralysis and death in pests.
Used in Organic Synthesis:
Phenylcarbamic acid phenylmethyl ester is used as a reagent in organic synthesis, contributing to the production of various chemical compounds and intermediates.
Used in Chemical Production:
Phenylcarbamic acid phenylmethyl ester is used as a precursor in the production of other chemicals, playing a crucial role in the synthesis of various compounds and materials.

Check Digit Verification of cas no

The CAS Registry Mumber 3422-02-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,4,2 and 2 respectively; the second part has 2 digits, 0 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 3422-02:
(6*3)+(5*4)+(4*2)+(3*2)+(2*0)+(1*2)=54
54 % 10 = 4
So 3422-02-4 is a valid CAS Registry Number.
InChI:InChI=1/C14H13NO2/c16-14(15-13-9-5-2-6-10-13)17-11-12-7-3-1-4-8-12/h1-10H,11H2,(H,15,16)

3422-02-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name benzyl N-phenylcarbamate

1.2 Other means of identification

Product number -
Other names Benzyl phenylcarbamate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:3422-02-4 SDS

3422-02-4Relevant articles and documents

Design, synthesis and SAR of antitubercular benzylpiperazine ureas

Satish, Sohal,Chitral, Rohan,Kori, Amitkumar,Sharma, Basantkumar,Puttur, Jayashree,Khan, Afreen A.,Desle, Deepali,Raikuvar, Kavita,Korkegian, Aaron,Martis, Elvis A. F.,Iyer, Krishna R.,Coutinho, Evans C.,Parish, Tanya,Nandan, Santosh

, (2021/01/04)

Abstract: N-furfuryl piperazine ureas disclosed by scientists at GSK Tres Cantos were chosen as antimycobacterial hits from a phenotypic whole-cell screen. Bioisosteric replacement of the furan ring in the GSK Tres Cantos molecules with a phenyl ring led to molecule (I) with an MIC of 1?μM against Mtb H37Rv, low cellular toxicity (HepG2 IC50 ~ 80?μM), good DMPK properties and specificity for Mtb. With the aim of delineating the SAR associated with (I), fifty-five analogs were synthesized and screened against Mtb. The SAR suggests that the piperazine ring, benzyl urea and piperonyl moieties are essential signatures of this series. Active compounds in this series are metabolically stable, have low cellular toxicity and are valuable leads for optimization. Molecular docking suggests these molecules occupy the Q0 site of QcrB like Q203. Graphic Abstract: Bioisosteric replacement of N-furfuryl piperazine-1-carboxamides yielded molecule (I) a novel lead with satisfactory PD, metabolism, and toxicity profiles.[Figure not available: see fulltext.]

Copper-Catalyzed Coupling of Amines with Carbazates: An Approach to Carbamates

Wang, Song-Ning,Zhang, Guo-Yu,Shoberu, Adedamola,Zou, Jian-Ping

, p. 9067 - 9075 (2021/07/19)

A new approach for the preparation of carbamatesviathe copper-catalyzed cross-coupling reaction of amines with alkoxycarbonyl radicals generated from carbazates is described. This environmentally friendly protocol takes place under mild conditions and is compatible with a wide range of amines, including aromatic/aliphatic and primary/secondary substrates.

Interrupted aza-Wittig reactions using iminophosphoranes to synthesize 11C-carbonyls

Ismailani, Uzair S.,Munch, Maxime,Mair, Braeden A.,Rotstein, Benjamin H.

supporting information, p. 5266 - 5269 (2021/06/06)

A direct CO2-fixation methodology couples structurally diverse iminophosphoranes with various nucleophiles to synthesize ureas, carbamates, thiocarbamates, and amides, and is amenable for 11C radiolabeling. This methodology is practical, as demonstrated by the synthesis of >35 products and isolation of the molecular imaging radiopharmaceuticals [11C]URB694 and [11C]glibenclamide. This journal is

Metal-free late-stage C(sp2)-H functionalization of: N -aryl amines with various sodium salts

Mudithanapelli, Chandrashekar,Kim, Mi-Hyun

, p. 450 - 464 (2020/02/03)

Metal-free consecutive C(sp2)-X (X = Cl, Br, S, N) bond formations of N-aryl amines (cyclic, fused, carbamate, and aminium radicals) were achieved under mild conditions using [bis(trifluoroacetoxy)iodo]benzene (PIFA) and simple nonharmful sodium salts. This direct and selective C(sp2)-H functionalization showed excellent functional group compatibility, cost effectiveness, and late-stage applicability for the synthesis of biologically active natural products. Two mechanisms were proposed to explain the ortho- or para-preference, as well as the accelerating effect of CH3NO2

Nickel-Catalyzed Synthesis of N-(Hetero)aryl Carbamates from Cyanate Salts and Phenols Activated with Cyanuric Chloride

Dindarloo Inaloo, Iman,Esmaeilpour, Mohsen,Majnooni, Sahar,Reza Oveisi, Ali

, p. 5486 - 5491 (2020/09/04)

A simple and efficient domino reaction has been designed and employed for the one-pot synthesis of N-(hetero)aryl carbamates through the reaction between alcohols and in-situ produced (hetero)aryl isocyanates in the presence of a nickel catalyst. The phenolic C?O bond was activated via the reaction of phenol with cyanuric chloride (2,4,6-trichloro-1,3,5-triazine (TCT)) as an inexpensive and readily available reagent. This strategy provides practical access to N-(hetero)aryl carbamates in good yields with high functional groups compatibility.

Zn(ii)@TFP-DAQ COF: An efficient mesoporous catalyst for the synthesis of: N -methylated amine and carbamate through chemical fixation of CO2

Sarkar, Priyanka,Chowdhury, Arpita Hazra,Riyajuddin, Sk.,Biswas, Surajit,Ghosh, Kaushik,Islam, Sk. Manirul

, p. 744 - 752 (2020/01/31)

Selective N-methylation and carbamate formation reactions were demonstrated via the chemical incorporation of CO2 using a Zn-loaded TFP-DAQ COF (covalent organic framework) as an active catalyst under mild reaction conditions. The selective N-methylation and N-formylation reactions were performed by simply varying the type of solvent. The Zn(ii)@TFP-DAQ COF catalyst was characterized via different characterization techniques such as PXRD, FTIR, UV-vis, N2 adsorption-desorption studies, FESEM and TEM. The catalyst material showed pores in the mesoporous region with a high surface area of 1117.375 m2 g-1. The as-synthesized material was applied as a cheap catalyst for the N-methylation of secondary amines and in carbamate formation reactions with high yields of the desired products up to 98.5% and 97%, respectively, with >99% selectivity. The catalyst was found to be completely heterogeneous and reusable for multiple reaction cycles.

Carbon dioxide utilization in the efficient synthesis of carbamates by deep eutectic solvents (DES) as green and attractive solvent/catalyst systems

Dindarloo Inaloo, Iman,Majnooni, Sahar

, p. 11275 - 11281 (2019/07/31)

A green and eco-friendly solvent/catalyst system based on a deep eutectic solvent (DES) was devised and developed for the simple synthesis of carbamates through three-component coupling of amines, alkyl halides and carbon dioxide (CO2). It was found that choline chloride:zinc(ii) chloride ([ChCl][ZnCl2]2) was very proficient and effective for the activation and utilization of CO2 in carbamate formation reactions from a wide scope of amines. Surprisingly, this strategy provides the desired carbamates under atmospheric CO2 pressure at room temperature. In particular, both aromatic and aliphatic amines were effective and demonstrated excellent yields. Besides, the [ChCl][ZnCl2]2 exhibited very high stability and also could be reused for at least five consecutive cycles without any significant loss of activity. It is worth noting that this is the first solvent/catalyst system which can be recycled successfully from the reaction mixture.

CaI2-Catalyzed direct transformation of: N -Alloc-, N -Troc-, and N -Cbz-protected amines to asymmetrical ureas

Tran, Van Hieu,Kim, Hee-Kwon

, p. 14093 - 14101 (2019/09/18)

A novel and facile CaI2-catalyzed direct synthesis of asymmetrical ureas from N-Alloc-, N-Troc-, and N-Cbz-protected amines is developed. In this study, the efficient reaction of Alloc-, Troc-, and Cbz-carbamates with amines in the presence of catalytic CaI2 successfully generated various asymmetrical ureas. This catalytic synthetic procedure provided the desired ureas via reactions of these protected aromatic and aliphatic amines with various amines in high yields without side products. This suggests that novel direct synthesis of ureas from Alloc-, Troc-, and Cbz-carbamates can be a promising approach for the synthesis of useful ureas.

Visible-Light-Promoted Oxo-Sulfonylation of Ynamides with Sulfonic Acids

Wang, Lu,Lu, Chengrong,Yue, Yanni,Feng, Chao

supporting information, p. 3514 - 3517 (2019/05/16)

A visible-light-promoted oxo-sulfonylation of ynamides with sulfonic acids is reported, giving rise to a collection of functionalized α-sulfonylated amides in a straightforward manner. The reaction proceeds sequentially through a cascade of electrophilic addition and photoinduced sulfonyl radical-sustained skeleton rearrangement. The high atom economy, mild reaction conditions, and wide substrate scope comprised the merits of this synthetic transformation.

A General Copper-Catalyzed Synthesis of Ynamides from 1,2-Dichloroenamides

Mansfield, Steven J.,Smith, Russell C.,Yong, Jonathan R. J.,Garry, Olivia L.,Anderson, Edward A.

supporting information, p. 2918 - 2922 (2019/04/25)

Ynamides are accessed via copper-catalyzed coupling of Grignard or organozinc nucleophiles with chloroynamides, formed in situ from 1,2-dichloroenamides. The reaction exhibits a broad substrate scope, is readily scaled, and overcomes typical limitations in ynamide synthesis such as the use of ureas, carbamates, and bulky or aromatic amide derivatives. This modular approach contrasts with previous routes by installing both the N- and C-substituents of the ynamide as nucleophilic components.

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