N-Benzylbenzamide

Base Information

• Chemical Name: N-Benzylbenzamide
• CAS No.: 1485-70-7
• Molecular Formula: C14H13NO
• Molecular Weight: 211.263
• Hs Code.: 29242990
• European Community (EC) Number: 216-063-4
• NSC Number: 31622
• UNII: JMX9K7MD23
• DSSTox Substance ID: DTXSID50164000
• Nikkaji Number: J80.127E
• Wikidata: Q83033025
• ChEMBL ID: CHEMBL207313
• Mol file: 1485-70-7.mol

Synonyms:N-Benzylbenzamide;1485-70-7;Benzamide, N-(phenylmethyl)-;N-benzyl-benzamide;N-Benzoylbenzylamine;N-(phenylmethyl)benzamide;MFCD00003070;JMX9K7MD23;MLS002639410;CHEMBL207313;EINECS 216-063-4;NSC-31622;AI3-00504;Benzbenzylamid;benzoylbenzylamine;NSC31622;N~1~-benzylbenzamide;Benzamide, N-benzyl-;UNII-JMX9K7MD23;TimTec1_000762;N-Benzylbenzamide, >=98%;SCHEMBL457082;BENZOIC ACID BENZYLAMIDE;LKQUCICFTHBFAL-UHFFFAOYSA-;DTXSID50164000;HMS1536C14;AMY41905;AC8756;BDBM50183710;NSC 31622;STK067759;AKOS000485547;NCGC00175147-01;MS-10602;SMR001548855;SY061592;CS-0149864;FT-0633601;A808786;AN-329/13082042;methyl N-[2-(methoxycarbonylamino)phenyl]carbamate;SR-01000358526;J-008489;SR-01000358526-1;BRD-K68080625-001-01-9;Z27749565

Chemical Property of N-Benzylbenzamide

Chemical Property:

• Appearance/Colour: White fine crystalline powder
• Vapor Pressure: 1.56E-07mmHg at 25°C
• Melting Point: 104-106 °C(lit.)
• Refractive Index: 1.59
• Boiling Point: 428 °C at 760 mmHg
• PKA: 14.86±0.46(Predicted)
• Flash Point: 256.6 °C
• PSA: 29.10000
• Density: 1.109 g/cm³
• LogP: 3.00750
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Soluble in Acetone (25 mg/ml).
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 211.099714038
• Heavy Atom Count: 16
• Complexity: 215

Purity/Quality:

97% ^*data from raw suppliers

N-Benzylbenzamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CNC(=O)C2=CC=CC=C2
• Uses: A convenient precursor to α-substituted benzylamines and an indicator for the titration of butyllithium and other lithium bases. For references see Aldrichimica Acta .

Technology Process of N-Benzylbenzamide

There total 604 articles about N-Benzylbenzamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 88.0%

3-benzoyl-2-oxa-3-azabicyclo<2.2.1>hept-5-ene (59438-62-9) + benzylamine (100-46-9) → N-benzylbenzamide (1485-70-7) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8)

Guidance literature:

In toluene; at 80 ℃; for 20h; Product distribution; Mechanism; var. amine; determination of formed N₂O; retro-Diels Alder dissociation;

DOI:10.1016/S0040-4039(97)82943-7

Reference yield: 87.0%

diisopropyl benzoylphosphonate (22950-57-8) + benzylamine (100-46-9) → diisopropyl hydrogenphosphonate (1809-20-7) + N-benzylbenzamide (1485-70-7) + [(Diisopropoxy-phosphoryloxy)-phenyl-methyl]-phosphonic acid diisopropyl ester (74449-29-9)

Guidance literature:

In diethyl ether; for 20h; Ambient temperature;

DOI:10.1021/jo01309a019

Reference yield: 83.0%

N-benzylidenebenzamide (10374-29-5) + acetaldehyde (75-07-0,9002-91-9) → (S)-3-benzoylamino-3-phenylpropanol (1072916-80-3) + C30H28N2O3 (1094216-86-0) + N-benzylbenzamide (1485-70-7) + benzyl alcohol (100-51-6,185532-71-2)

Guidance literature:

N-benzylidenebenzamide; acetaldehyde; With (S)-(-)-α,α-bis[3,5-bis(trifluoromethyl)phenyl]-2-pyrrolidinemethanol; In tetrahydrofuran; at 4 ℃; for 48h; Sealed tube;

With lithium aluminium tetrahydride; In tetrahydrofuran; at -50 ℃; for 1h;

DOI:10.1002/anie.200802073

upstream raw materials:

ethanol

N-benzyl-N-nitrosobenzamide

N-(hydroxymethyl)benzamide

N-Benzylidenebenzylamine N-oxide

Downstream raw materials:

benzoyl-benzyl-dichloroacetyl-amine

N,N-dimethyl-N'-benzyl-1,2-ethanediamine

N-benzyl-N-nitrosobenzamide

5-benzyl-1-phenyl-1H-tetrazole

Refernces

Mild rhodium(III)-catalyzed cyclization of amides with α,β- unsaturated aldehydes and ketones to azepinones: Application to the synthesis of the homoprotoberberine framework

10.1002/anie.201301426

The key substrate used in this study, N-methoxybenzamide (1a), is an amide with a methoxy group attached to the nitrogen atom. It is key for the initial reaction with a,b-unsaturated aldehydes and ketones. Another amide substrate used in this study, N-methylbenzamide (1b), has a methyl group attached to the nitrogen atom, which affects the reactivity and selectivity of the C-H activation process. N-n-butylbenzamide (1c), an amide with a butyl group attached to the nitrogen atom, demonstrates the versatility of the method towards different alkyl groups. N-benzylbenzamide (1d), an amide with a benzyl group attached to the nitrogen atom, is used to demonstrate the tolerance of the reaction towards aromatic groups. Acrolein (2a), the simplest unsaturated aldehyde used in this study, acts as the electrophilic component in the cyclization process and reacts with the amide to generate the desired azacyclopentane product.