[ CAS No. 73391-96-5 ]

Name: 73391-96-5|N-Benzyl-2-bromo-N-methylacetamide|97%
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SKU: A986946
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Quality Control of [ 73391-96-5 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 73391-96-5 ]

CAS No. :	73391-96-5	MDL No. :	MFCD02751705
Formula :	C₁₀H₁₂BrNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	242.11 g/mol	Pubchem ID :	-
Synonyms :

Calculated chemistry of of [ 73391-96-5 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.3
Num. rotatable bonds :	4
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	56.8
TPSA :	20.31 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.35 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.11
Log Po/w (XLOGP3) :	2.01
Log Po/w (WLOGP) :	1.89
Log Po/w (MLOGP) :	2.31
Log Po/w (SILICOS-IT) :	2.17
Consensus Log Po/w :	2.1

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.68
Solubility :	0.5 mg/ml ; 0.00207 mol/l
Class :	Soluble
Log S (Ali) :	-2.06
Solubility :	2.09 mg/ml ; 0.00864 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.74
Solubility :	0.0443 mg/ml ; 0.000183 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.34

Safety of [ 73391-96-5 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P310-P332+P313-P362-P403+P233-P405-P501	UN#:	3265
Hazard Statements:	H315-H318-H335	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 73391-96-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 73391-96-5 ]

[ 73391-96-5 ] Synthesis Path-Downstream 1~33

1
[ 73391-96-5 ]
[ 294-90-6 ]
[ 132930-14-4 ]

Yield	Reaction Conditions	Operation in experiment
30%	With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 24h;

Reference： [1]Broan, Christopher J.; Cox, Jonathan P. L.; Craig, Andrew S.; Kataky, Ritu; Parker, David; et al. [Journal of the Chemical Society. Perkin transactions II, 1991, # 1, p. 87 - 99]

2
[ 73391-96-5 ]
[ 178739-07-6 ]
(2R,3R,4S)-4-Benzo[1,3]dioxol-5-yl-1-[(benzyl-methyl-carbamoyl)-methyl]-2-(4-methoxy-phenyl)-pyrrolidine-3-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; N-ethyl-N,N-diisopropylamine 1.) CH₃CN, 50 deg C, 1 h, 2.) C₂H₅OH, RT, 3 h; Yield given. Multistep reaction;

Reference： [1]Winn, Martin; Von Geldern, Thomas W.; Opgenorth, Terry J.; Jae, Hwan-Soo; Tasker, Andrew S.; Boyd, Steven A.; Kester, Jeffrey A.; Mantei, Robert A.; Bal, Radhika; Sorensen, Bryan K.; Wu-Wong, Jinshyun R.; Chiou, William J.; Dixon, Douglas B.; Novosad, Eugene I.; Hernandez, Lisa; Marsh, Kennan C. [Journal of Medicinal Chemistry, 1996, vol. 39, # 5, p. 1039 - 1048]

3
[ 4383-22-6 ]
[ 73391-96-5 ]
2-(allylbenzylamino)-N-benzyl-N-methylacetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With triethylamine In tetrahydrofuran at 20℃; for 20h;

Reference： [1]Gensini, Martina; Kozhushkov, Sergei I.; Yufit, Dmitrii S.; Howard, Judith A. K.; Es-Sayed, Mazen; De Meijere, Armin [European Journal of Organic Chemistry, 2002, # 15, p. 2499 - 2507]

4
[ 73391-96-5 ]
N,3-dibenzyl-N-methyl-3-azabicyclo[3.1.0]hex-1-ylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 85 percent / Et₃N / tetrahydrofuran / 20 h / 20 °C 2: 56 percent / methyltitanium triisopropoxide; cyclohexylmagnesium bromide / diethyl ether; tetrahydrofuran / 12 h / 20 °C

5
[ 73391-96-5 ]
[ 132930-10-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 30 percent / potassium carbonate / dimethylformamide / 24 h / 50 °C 2: 16 percent / potassium carbonate / dimethylformamide / 10 h / 60 °C 3: 15 percent / tetramethylammonium hydroxide / methanol; H₂O / 6 h / 100 °C

Reference： [1]Broan, Christopher J.; Cox, Jonathan P. L.; Craig, Andrew S.; Kataky, Ritu; Parker, David; et al. [Journal of the Chemical Society. Perkin transactions II, 1991, # 1, p. 87 - 99]

6
[ 73391-96-5 ]
[ 132930-15-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 30 percent / potassium carbonate / dimethylformamide / 24 h / 50 °C 2: 16 percent / potassium carbonate / dimethylformamide / 10 h / 60 °C

Reference： [1]Broan, Christopher J.; Cox, Jonathan P. L.; Craig, Andrew S.; Kataky, Ritu; Parker, David; et al. [Journal of the Chemical Society. Perkin transactions II, 1991, # 1, p. 87 - 99]

7
[ 1337537-34-4 ]
[ 73391-96-5 ]
[ 1337537-45-7 ]

Yield	Reaction Conditions	Operation in experiment
62%	Stage #1: 4-methyl-2-phenyl-1H-pyrazolo[3,4-b]quinolin-3(2H)-one With sodium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: N-methyl-N-(phenylmethyl)-2-bromoacetamide In N,N-dimethyl-formamide at 20℃;

Reference： [1]Location in patent: experimental part Cappelli, Andrea; Bini, Giulia; Valenti, Salvatore; Giuliani, Germano; Paolino, Marco; Anzini, Maurizio; Vomero, Salvatore; Giorgi, Gianluca; Giordani, Antonio; Stasi, Luigi Piero; Makovec, Francesco; Ghelardini, Carla; Di Cesare Mannelli, Lorenzo; Concas, Alessandra; Porcu, Patrizia; Biggio, Giovanni [Journal of Medicinal Chemistry, 2011, vol. 54, # 20, p. 7165 - 7175]

8
[ 598-21-0 ]
[ 103-67-3 ]
[ 73391-96-5 ]

Yield	Reaction Conditions	Operation in experiment
89%	In dichloromethane at 0 - 20℃; for 1h;
76%	In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere;
72%	In acetonitrile at 0 - 20℃; for 1h;

	With sodium hydrogencarbonate In dichloromethane at 0 - 20℃; for 6h; Inert atmosphere;	Synthesis of N-benzyl-N-methyl diazoacetamide (2a) Using the procedure of Fukuyama,1 N-methyl-benzylamine (605.4 mg, 5.0 mmol) and NaHCO3 (1266.1 mg, 15.0 mmol) were dissolved in CH2Cl2 (10.0 mL) and bromoacetyl bromide (976 μL, 10.0 mmol) was added slowly at 0 °C and stirred for 6 hours at room temperature, the reaction was quenched with H2O (50 mL) and the solution was extracted with CH2Cl2 (100 mL) three times. After washed with water and dried over Na2SO4, the solvent was evaporated and the residue was used in the next step without purification. The resulting bromoacetamide and N,N'-ditosylhydrazine (1036.0 mg, 3.04 mmol) were dissolved in THF (10.0 mL) and cooled down to 0 C, then DBU (1158.2 mg, 7.60 mmol) was added drop wise and stirred at room temperature for 1 h. After quenched with NaHCO3 aq and extracted with diethyl ether three times, the organic phase was dried over Na2SO4 and evaporated to give crude product. Purification was performed with flash column chromatography on silica gel eluted with hexane:EtOAc = 5:1 to give N-benzyl-N-methyl-diazoacetamide (242.0 mg, 69% yield in two steps) as a yellow oil. Rf = 0.5 (hexane:EtOAc = 1:1). 1H NMR (300 MHzCDCl3) δ 7.38-7.16 (m, 5H), 4.99 (s, 1H), 4.48 (br s, 2H), 2.84 (br s, 3H) ppm. 13C NMR (75 MHzCDCl3) δ 166.3, 137.2, 128.9, 127.7, 127.6 , 52.1, 46.6, 34.5 ppm. IR (NaCl, cm-1) 3739, 3088, 2920, 2361, 2104, 1749. EA Anal. Calcd. for C10H11N3O×0.1CH2Cl2×0.1CH3CO2CH2CH3: C 61.07, H 5.86, N 20.35%; Found C 61.44, H 5.79, N 20.72%.
	With triethylamine In dichloromethane at 20℃; Inert atmosphere;	Synthesis of 18, 22, 23, and 24 General procedure: Toa chilled solution (ice/water) of Benzylamine or N-Benzylmethylamine andTriethylamine(1.2 equiv.) in dry CH2Cl2 (5 mL/gbenzylamine)was added Bromoacetyl bromide (1.2equiv.) The reaction was allowed to warm to ambient temperature and monitoredby GC/MS. Upon consumption of the starting amine, The reaction was diluted with5 vol CH2Cl2 and washed 3x 5vol H2O. The aqueouslayer was back extracted 3x1 vol. The combined organics were dried over Na2SO4.The crude material was concentrated and subjected to the next reaction. Whennecessary, purification via flash chromatography was employed Toa chilled solution solution of the α-Bromoamide in acetonitrile (5 vol) wasadded 4 equiv. of benzylamine or N-benzylmethylamine. The reactions weremonitored by GC/MS. Upon completion, the reactions were diluted with 7.15 vol ethylacetate, washed 3x7.15 vol H2O, and 1x4vol saturated aqueous NaClsolution. Finally, the organics weredried over Na2SO4, decanted, concentrated en vacuo, and purified by flashchromatography
	In dichloromethane at 0 - 20℃; for 24h;
	With triethylamine In dichloromethane at 0 - 20℃; for 4h; Schlenk technique; Inert atmosphere;
	With potassium carbonate In dichloromethane at 0 - 20℃; for 0.5h; Inert atmosphere;
	With triethylamine In dichloromethane at 0 - 20℃; for 4h;
	With triethylamine In acetonitrile at 20℃; for 3h;

Reference： [1]Cappelli, Andrea; Bini, Giulia; Valenti, Salvatore; Giuliani, Germano; Paolino, Marco; Anzini, Maurizio; Vomero, Salvatore; Giorgi, Gianluca; Giordani, Antonio; Stasi, Luigi Piero; Makovec, Francesco; Ghelardini, Carla; Di Cesare Mannelli, Lorenzo; Concas, Alessandra; Porcu, Patrizia; Biggio, Giovanni [Journal of Medicinal Chemistry, 2011, vol. 54, # 20, p. 7165 - 7175]
[2]Fetzer, Christian; Korotkov, Vadim S.; Sieber, Stephan A. [Organic and Biomolecular Chemistry, 2019, vol. 17, # 30, p. 7124 - 7127]
[3]Samanta, Sanjay; Lim, Ting Liang; Lam, Yulin [ChemMedChem, 2013, vol. 8, # 6, p. 994 - 1001]
[4]Chanthamath, Soda; Thongjareun, Songkharm; Shibatomi, Kazutaka; Iwasa, Seiji [Tetrahedron Letters, 2012, vol. 53, # 36, p. 4862 - 4865]
[5]Mitra, Aurpon W.; Hansen, Marvin M.; Laurila, Michael E.; Kolis, Stanley P.; Martinelli, Joseph R. [Tetrahedron Letters, 2013, vol. 54, # 48, p. 6580 - 6583]
[6]Wiȩckowska, Anna; Wichur, Tomasz; Godyń, Justyna; Bucki, Adam; Marcinkowska, Monika; Siwek, Agata; Wiȩckowski, Krzysztof; Zarȩba, Paula; Knez, Damijan; Głuch-Lutwin, Monika; Kazek, Grzegorz; Latacz, Gniewomir; Mika, Kamil; Kołaczkowski, Marcin; Korabecny, Jan; Soukup, Ondrej; Benkova, Marketa; Kieć-Kononowicz, Katarzyna; Gobec, Stanislav; Malawska, Barbara [ACS Chemical Neuroscience, 2018, vol. 9, # 5, p. 1195 - 1214]
[7]Zhou, Zijun; Chen, Shuming; Qin, Jie; Nie, Xin; Zheng, Xingwen; Harms, Klaus; Riedel, Radostan; Houk; Meggers, Eric [Angewandte Chemie - International Edition, 2019, vol. 58, # 4, p. 1088 - 1093][Angew. Chem., 2019, vol. 131, # 4, p. 1100 - 1105,6]
[8]Phan Thi Thanh, Nga; Tone, Masaya; Inoue, Hayato; Fujisawa, Ikuhide; Iwasa, Seiji [Chemical Communications, 2019, vol. 55, # 89, p. 13398 - 13401]
[9]Abularrage, Nile S.; Gold, Brian; Khanal, Namrata; Raines, Ronald T.; Dones, Jesús M. [Journal of the American Chemical Society, 2021, vol. 143, # 25, p. 9489 - 9497]
[10]Fallica, Antonino N.; Sorrenti, Valeria; D’Amico, Agata G.; Salerno, Loredana; Romeo, Giuseppe; Intagliata, Sebastiano; Consoli, Valeria; Floresta, Giuseppe; Rescifina, Antonio; D’Agata, Velia; Vanella, Luca; Pittalà, Valeria [Journal of Medicinal Chemistry, 2021, vol. 64, # 18, p. 13373 - 13393]

9
[ 73391-96-5 ]
[ 122-52-1 ]
[ 883231-60-5 ]

Yield	Reaction Conditions	Operation in experiment
98%	With sodium iodide In N,N-dimethyl-formamide for 0.025h; Microwave irradiation;

Reference： [1]Location in patent: experimental part Gruber, Nadia; Mollo, Mara C.; Zani, Mariana; Orelli, Liliana R. [Synthetic Communications, 2012, vol. 42, # 5, p. 738 - 746]

10
[ 73391-96-5 ]
[ 1394816-74-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: N,N'-ditosylhydrazine; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere 2: [(4,5-dihydro-4,4-dimethyl-2-phenyloxazole)Ru(CH₃CN)₄]PF₆ / dichloromethane / 0.08 h / 20 °C / Inert atmosphere