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Chemistry
Organic Building Blocks
Aryls
benzyl
Methyl 4-(bromomethyl)-2-methylbenzoate
Chemistry
Organic Building Blocks
Aryls
Bromides Esters Benzene Compounds Benzyl Bromides
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methyl 2-methylbenzoate 1-(bromomethyl)-3-methylbenzene p-tolyl benzoyl benzyloxymethyl

[ CAS No. 74733-28-1 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
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Chemical Structure| 74733-28-1
Chemical Structure| 74733-28-1
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Quality Control of [ 74733-28-1 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification
Alternatived Products of [ 74733-28-1 ]

Product Details of [ 74733-28-1 ]

CAS No. :74733-28-1 MDL No. :MFCD27928283
Formula : C10H11BrO2 Boiling Point : -
Linear Structure Formula :- InChI Key :MABHQNNTZZMWCU-UHFFFAOYSA-N
M.W : 243.10 Pubchem ID :19372658
Synonyms :

Calculated chemistry of [ 74733-28-1 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.3
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 55.52
TPSA : 26.3 Ų

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) : -5.43 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.59
Log Po/w (XLOGP3) : 3.31
Log Po/w (WLOGP) : 2.52
Log Po/w (MLOGP) : 2.99
Log Po/w (SILICOS-IT) : 3.19
Consensus Log Po/w : 2.92

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.58
Solubility : 0.0645 mg/ml ; 0.000265 mol/l
Class : Soluble
Log S (Ali) : -3.54
Solubility : 0.0704 mg/ml ; 0.00029 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.12
Solubility : 0.0183 mg/ml ; 0.0000752 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.91

Safety of [ 74733-28-1 ]

Signal Word:Danger Class:8
Precautionary Statements:P260-P264-P270-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P405-P501 UN#:3261
Hazard Statements:H302-H314 Packing Group:Ⅱ
GHS Pictogram:

Application In Synthesis of [ 74733-28-1 ]

* 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 [ 74733-28-1 ]

[ 74733-28-1 ] Synthesis Path-Downstream   1~25

  • 1
  • [ 74733-28-1 ]
  • 4-(hydroxymethyl)-2-methylbenzoic acid [ No CAS ]
  • 2,2'-dimethyl-4,4'-(2-oxa-propanediyl)-di-benzoic acid [ No CAS ]
Reference： [1]Journal of the Chemical Society,1925,vol. 127,p. 2292
  • 2
  • [ 21900-42-5 ]
  • [ 74733-28-1 ]
  • [ 622847-32-9 ]
Reference： [1]Journal of the Chemical Society,1925,vol. 127,p. 2292
  • 3
  • [ 5851-44-5 ]
  • [ 74733-28-1 ]
  • [ 133052-57-0 ]
Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 877 - 885
  • 4
  • [ 23617-71-2 ]
  • [ 54120-64-8 ]
  • [ 74733-28-1 ]
Reference： [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 583 - 592
  • 5
  • [ 74733-28-1 ]
  • [ 71441-11-7 ]
Reference： [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 583 - 592
YieldReaction ConditionsOperation in experiment
48% With phosphorus tribromide; In dichloromethane; at 0 - 20℃; for 0.5h; General procedure: To a stirred solution of 18-4B (1.2 g, 6.6 mmol) in DCM, was added phosphorous tribromide (0.64 mL, 6.6 mmol) at 0 C and stirred to RT for 30 min. After consumption of the starting material (by TLC), reaction was quenched with saturated NaHC03 solution and extracted with DCM. The organic layer was dried over Na2S04, and concentrated under reduced pressure. The crude compound was purified by flash column chromatography (100-200 silica) using 5% EtOAc in hexane to afford 18-5B (0.95 g, 3.9 mmol, 59% yield) as a colorless semi-solid. adapted using 18-4A (1.42 g, 7.88 mmol) to prepare 18-5A (920 mg, 48%).
(ii) Oxalyl chloride (2.3 ml) was added to a solution of compound (B) (3.9 g) and DMF (0.3 ml) in dry dichloromethane (100 ml) and the mixture was stirred for 3 hours. The solvent and excess oxalyl chloride were removed by evaporation and dry methanol (50 ml) was added to the residue. The mixture was then stirred for 2 hours and the solvent removed by evaporation. The residue was partitioned between dichloromethane and aqueous sodium bicarbonate solution. The organic layer was separated, dried (MgSO4) and evaporated. The residue was triturated with a mixture of hexane and ether to give methyl 4-bromomethyl-2-methylbenzoate (C) (3.51 g) as a white solid, m.p. 51-53 C.; NMR (CDCl3): 2.59 (s, 3H), 3.89 (s, 3H), 4.44(s, 2H), 7.2-7.3(complex m, 2H), 7.88(d, 1H).
Addition of hot petrol and filtration from the phthalide gave after evaporation the title compound. tau(CDCl3) 7.48 (3H, s), 6.21 (3H, s), 5.65 (2H, s), 2.6-2.93 (2H, m), 2.18 (1H, d, J=8 Hz).
  • 7
  • [ 74733-28-1 ]
  • KOH-solution [ No CAS ]
  • 4-(hydroxymethyl)-2-methylbenzoic acid [ No CAS ]
  • 2,2'-dimethyl-4,4'-(2-oxa-propanediyl)-di-benzoic acid [ No CAS ]
Reference： [1]Journal of the Chemical Society,1925,vol. 127,p. 2292
  • 8
  • [ 74733-28-1 ]
  • [ 77837-67-3 ]
Reference： [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 583 - 592
  • 9
  • [ 74733-28-1 ]
  • [ 77837-80-0 ]
Reference： [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 583 - 592
  • 10
  • [ 74733-28-1 ]
  • [ 77837-69-5 ]
Reference： [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 583 - 592
  • 11
  • [ 74733-28-1 ]
  • [ 77837-63-9 ]
Reference： [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 583 - 592
[2]Journal of Medicinal Chemistry,1981,vol. 24,p. 583 - 592
  • 12
  • [ 74733-28-1 ]
  • [ 77837-64-0 ]
Reference： [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 583 - 592
  • 13
  • [ 74733-28-1 ]
  • [ 77837-62-8 ]
Reference： [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 583 - 592
[2]Journal of Medicinal Chemistry,1981,vol. 24,p. 583 - 592
  • 14
  • [ 74733-28-1 ]
  • [ 133052-40-1 ]
Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 877 - 885
  • 15
  • [ 74733-28-1 ]
  • [ 20277-69-4 ]
  • [ 1268243-58-8 ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide; at 120℃; for 0.0833333h;Microwave irradiation; O: Sodium Methanesulfmate displacement of Bromine To the bromine starting material (leq) was added sodium methanesulfmate (2eq) in DMF and heated to 120C in the microwave for 5 minutes. Alternatively, the reaction was heated to 60C in an oil bath for several hours until completed. Reaction mixture was concentrated under reduced pressure and extracted in ethyl acetate and water. The organic layer was dried over Magnesium Sulfate, filtered and concentrated in vacuo to yield generic methylsulfone. 255 mg of <strong>[74733-28-1]methyl 4-(bromomethyl)-2-methylbenzoate</strong> was reacted via Procedure O to give methyl 2-methyl-4-(methylsulfonylmethyl)benzoate
In N,N-dimethyl-formamide; at 120℃; for 0.0833333h;Microwave irradiation; O: Sodium Methanesulfinate displacement of Bromine To the bromine starting material (1 eq) was added sodium methanesulfinate (2 eq) in DMF and heated to 120 C. in the microwave for 5 minutes. Alternatively, the reaction was heated to 60 C. in an oil bath for several hours until completed. Reaction mixture was concentrated under reduced pressure and extracted in ethyl acetate and water. The organic layer was dried over Magnesium Sulfate, filtered and concentrated in vacuo to yield generic methylsulfone.; 255 mg of <strong>[74733-28-1]methyl 4-(bromomethyl)-2-methylbenzoate</strong> was reacted via Procedure O to give methyl 2-methyl-4-(methylsulfonylmethyl)benzoate. 250 mg of methyl 2-methyl-4-(methylsulfonylmethyl)benzoate was then hydrolyzed upon heating to 45 C. for 1 hour via Procedure M to give 2-methyl-4-(methylsulfonylmethyl)benzoic acid. 202 mg of 4-chloro-3-(pyridin-2-yl)aniline was coupled to 2-methyl-4-(methylsulfonylmethyl)benzoic acid via Procedure G. The crude product was purified by reverse phase HPLC to yield N-(4-chloro-3-(pyridin-2-yl)phenyl)-2-methyl-4-(methylsulfonylmethyl)benzamide. MS (Q1) 415 (M)+.
In N,N-dimethyl-formamide; at 60℃; O: Sodium Methanesulfinate displacement of Bromine To the bromine starting material (1 eq) was added sodium methanesulfinate (2 eq) in DMF and heated to 120 C. in the microwave for 5 minutes. Alternatively, the reaction was heated to 60 C. in an oil bath for several hours until completed. Reaction mixture was concentrated under reduced pressure and extracted in ethyl acetate and water. The organic layer was dried over Magnesium Sulfate, filtered and concentrated in vacuo to yield generic methylsulfone.; 255 mg of <strong>[74733-28-1]methyl 4-(bromomethyl)-2-methylbenzoate</strong> was reacted via Procedure O to give methyl 2-methyl-4-(methylsulfonylmethyl)benzoate. 250 mg of methyl 2-methyl-4-(methylsulfonylmethyl)benzoate was then hydrolyzed upon heating to 45 C. for 1 hour via Procedure M to give 2-methyl-4-(methylsulfonylmethyl)benzoic acid. 202 mg of 4-chloro-3-(pyridin-2-yl)aniline was coupled to 2-methyl-4-(methylsulfonylmethyl)benzoic acid via Procedure G. The crude product was purified by reverse phase HPLC to yield N-(4-chloro-3-(pyridin-2-yl)phenyl)-2-methyl-4-(methylsulfonylmethyl)benzamide. MS (Q1) 415 (M)+.
Reference： [1]Patent: WO2009/126863,2009,A2 .Location in patent: Page/Page column 74; 167-168
[2]Patent: US2006/63779,2006,A1 .Location in patent: Page/Page column 68; 113
[3]Patent: US2006/63779,2006,A1 .Location in patent: Page/Page column 68; 113
  • 16
  • [ 530145-28-9 ]
  • [ 74733-28-1 ]
YieldReaction ConditionsOperation in experiment
With N-Bromosuccinimide; triphenylphosphine; In dichloromethane; at 0℃; 220 mg of methyl 4-(hydroxymethyl)-2-methylbenzoate was cooled to 0C in 5 mL of DCM before adding 260 mg of Triphenylphosphine and 395 mg of NBS. The reaction was concentrated and directly purified via ISCO Combi-Flash to give pure methyl 4-(bromomethyl)-2-methylbenzoate.
With N-Bromosuccinimide; triphenylphosphine; In dichloromethane; at 0℃; 220 mg of methyl 4-(hydroxymethyl)-2-methylbenzoate was cooled to 0 C. in 5 mL of DCM before adding 260 mg of Triphenylphosphine and 395 mg of NBS. The reaction was concentrated and directly purified via ISCO Combi-Flash to give pure methyl 4-(bromomethyl)-2-methylbenzoate.
Reference： [1]Patent: WO2009/126863,2009,A2 .Location in patent: Page/Page column 167-168
[2]Patent: US2006/63779,2006,A1 .Location in patent: Page/Page column 113
YieldReaction ConditionsOperation in experiment
EXAMPLE 238 4-[6-(4-Methoxy-benzylcarbamoyl)-1-methyl-2,4-dioxo-1,4-dihydro-2H-thieno[2,3-d]pyrimidin-3-ylmethyl]-2-methyl-benzoic acid methyl ester Made by the procedure of Example 217 with 4-bromomethyl-2-methylbenzoic acid methyl ester; mp 179-181 C.
YieldReaction ConditionsOperation in experiment
EXAMPLE 241 4-[6-(3-Methoxy-benzylcarbamoyl)-1-methyl-2,4-dioxo-1,4-dihydro-2H-thieno[2,3-d]pyrimidin-3-ylmethyl]-2-methyl-benzoic acid methyl ester Made by the procedure of Example 217 with 4-bromomethyl-2-methyl-benzoic acid methyl ester; mp 175-177 C.
  • 19
  • [ 1398395-52-2 ]
  • [ 74733-28-1 ]
  • [ 1398397-78-8 ]
  • [ 1398397-72-2 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; at 0 - 20℃; Step-1: Methyl 4-((2-(2-(((R)-1-(naphthalen-1-yl)ethyl)amino)ethyl)morpholino)methyl)benzoate To a stirred solution of Intermediate-11 (0.2 g, 0.740 mmol) in dichloromethane (5 ml), triethylamine (0.155 ml, 1.110 mmol) at 0 C., ethyl 4-(bromomethyl)-2-methylbenzoate (0.228 g, 0.888 mmol) was added. The reaction mixture stirred for 2 h at room temperature. Reaction mixture quenched with water and extracted with dichloromethane to get crude oil. Further compound was purified by prep HPLC and diasteromers were separated by chiral HPLC [CHIRAL PAK IA, 250 mm*4.6, 5mu; A=n-hexane:IPA (90:10% v/v, 0.1% DEA), B=IPA, A: B=70/30% V/V] offered title compound of isomer-a, tR=5.63 (120 mg) m/z 419.04 and isomer-b, tR=7.45 (130 mg) m/z 419.04.
Reference： [1]Patent: US2013/345213,2013,A1 .Location in patent: Paragraph 0459
  • 20
  • [ 23617-71-2 ]
  • [ 74733-28-1 ]
YieldReaction ConditionsOperation in experiment
93% With tert.-butylhydroperoxide; cetyltrimethylammonim bromide; potassium bromide; In water; at 120℃; under 750.075 Torr;Microwave irradiation; General procedure: The reaction mixture was treated in a controlled microwavesynthesizer (Biotage Initiator+SP Wave model, 0-200 W at2.45 GHz, capped at 60 W during steady state) for severalminutes (the reaction attained 120 C at 1 bar pressure). Thefinal products were isolated by column chromatographyusing an EtOAc-hexane gradient
Reference： [1]Synlett,2014,vol. 25,p. 2485 - 2487
  • 21
  • [ 67-56-1 ]
  • [ 611-01-8 ]
  • [ 74733-28-1 ]
Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 7703 - 7724
  • 22
  • [ 74733-28-1 ]
  • C10H11N3O2 [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 7703 - 7724
  • 23
  • [ 74733-28-1 ]
  • C10H13NO2 [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 7703 - 7724
  • 24
  • [ 74733-28-1 ]
  • methyl 4-(4-tert-butylbenzylamidomethyl)-2-methylbenzoate [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 7703 - 7724
  • 25
  • [ 74733-28-1 ]
  • 4-(4-tert-butylbenzamidomethyl)-2-methylbenzoic acid [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 7703 - 7724

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