[ CAS No. 103440-54-6 ] {[proInfo.proName]}

Name: 103440-54-6|Methyl 5-iodo-2-methylbenzoate|95%
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SKU: A213017
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Quality Control of [ 103440-54-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 103440-54-6 ]

CAS No. :	103440-54-6	MDL No. :	MFCD11112847
Formula :	C₉H₉IO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BXVIKPGEGLOGLU-UHFFFAOYSA-N
M.W :	276.07	Pubchem ID :	25067352
Synonyms :

Calculated chemistry of [ 103440-54-6 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.22
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	55.4
TPSA :	26.3 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) :	-5.57 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.51
Log Po/w (XLOGP3) :	3.4
Log Po/w (WLOGP) :	2.39
Log Po/w (MLOGP) :	3.11
Log Po/w (SILICOS-IT) :	3.12
Consensus Log Po/w :	2.91

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.93
Solubility :	0.0323 mg/ml ; 0.000117 mol/l
Class :	Soluble
Log S (Ali) :	-3.63
Solubility :	0.0645 mg/ml ; 0.000234 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.81
Solubility :	0.0428 mg/ml ; 0.000155 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	1.87

Safety of [ 103440-54-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 103440-54-6 ]

* 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.

Upstream synthesis route of [ 103440-54-6 ]
Downstream synthetic route of [ 103440-54-6 ]

[ 103440-54-6 ] Synthesis Path-Upstream 1~9

1
[ 67-56-1 ]
[ 54811-38-0 ]
[ 103440-54-6 ]

Yield	Reaction Conditions	Operation in experiment
73%	at 0℃; for 2 h; Reflux	Preparation 42 Methyl 5-iodo-2-methylbenzoate To a solution of 5-iodo-2-methylbenzoic acid (86 g, 0.57 mol) in MeOH (0.5 L) was added thionyl chloride (74 g, 0.62 mol) dropwise at 0°C, and after complete addition the reaction was heated to reflux for 2 hours. The reaction was cooled, concentrated in vacuo, diluted with water and extracted into EtOAc (2 x 300 ml_). The organic layers were combined, washed with brine, dried over Na₂S0₄ and concentrated in vacuo to afford the title compound that was taken directly on to the next step (69 g, 73percent).

Reference： [1] Patent: WO2015/189744, 2015, A1, . Location in patent: Page/Page column 73-74
[2] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 23, p. 6273 - 6278
[3] Patent: WO2006/117669, 2006, A1, . Location in patent: Page/Page column 41; 115

2
[ 7745-93-9 ]
[ 103440-54-6 ]

Reference： [1] Patent: WO2006/117669, 2006, A1,

3
[ 939-83-3 ]
[ 103440-54-6 ]

Reference： [1] Patent: WO2006/117669, 2006, A1,

4
[ 1975-52-6 ]
[ 103440-54-6 ]

Reference： [1] Patent: WO2006/117669, 2006, A1,

5
[ 77324-87-9 ]
[ 103440-54-6 ]

Reference： [1] Patent: WO2006/117669, 2006, A1,

6
[ 2840-04-2 ]
[ 103440-54-6 ]

Reference： [1] Patent: WO2006/117669, 2006, A1,

7
[ 103440-54-6 ]
[ 73183-34-3 ]
[ 478375-39-2 ]

Yield	Reaction Conditions	Operation in experiment
87%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate In N,N-dimethyl-formamide at 100℃; for 18 h; Inert atmosphere	Preparation 37 Methyl 2-methyl-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)benzoate To a solution of methyl 5-iodo-2-methylbenzoate (Preparation 42, 69 g, 0.25 mol) in DMF (800 mL) was added bispinacolatodiboron (100 g, 0.40 mol) and potassium acetate (92 g, 0.93 mol) followed by degassing with nitrogen. [1 ,1 '- bis(diphenylphosphino)ferrocene]dichloropalladium (II) complex with dichloromethane (6 g) was added and the reaction heated to 100°C for 18 hours. The reaction was cooled and filtered through celite, washing through with EtOAc (3 x 1 L). The filtrates were combined, washed with brine (3 x 500 mL), dried over Na₂S0₄ and concentrated in vacuo. The residue was washed with petroleum ether (2 x 500 mL), filtered and dried to afford the title compound as a yellow powder (60 g, 87percent) that was taken directly on to the next step.

Reference： [1] Patent: WO2015/189744, 2015, A1, . Location in patent: Page/Page column 72

8
[ 103440-54-6 ]
[ 1004294-80-7 ]

Reference： [1] Patent: WO2015/189744, 2015, A1,

9
[ 103440-54-6 ]
[ 1313399-38-0 ]

Reference： [1] Patent: WO2015/189744, 2015, A1,

[ 103440-54-6 ] Synthesis Path-Downstream 1~42

1
[ 103440-54-6 ]
methyl 2-(bromomethyl)-5-iodobenzoate [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 5392 - 5403

3
[ 103440-54-6 ]
[ 191803-87-9 ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 5392 - 5403

4
[ 103440-54-6 ]
[ 191804-09-8 ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 5392 - 5403

5
[ 103440-54-6 ]
[ 191804-07-6 ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 5392 - 5403

6
[ 103440-54-6 ]
[ 191803-94-8 ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 5392 - 5403

7
[ 103440-54-6 ]
(S)-2-{6-[2-(2-Amino-4-oxo-3,4,5,6,7,8-hexahydro-pyrido[2,3-d]pyrimidin-6-yl)-ethyl]-1-oxo-1,3-dihydro-isoindol-2-yl}-pentanedioic acid [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 5392 - 5403

8
[ 103440-54-6 ]
(S)-2-(6-{(E)-2-[2-(2,2-Dimethyl-propionylamino)-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl]-vinyl}-1-oxo-1,3-dihydro-isoindol-2-yl)-pentanedioic acid diethyl ester [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 5392 - 5403
[2]Journal of Organic Chemistry,1997,vol. 62,p. 5392 - 5403

9
[ 103440-54-6 ]
[ 191804-12-3 ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 5392 - 5403
[2]Journal of Organic Chemistry,1997,vol. 62,p. 5392 - 5403
[3]Journal of Organic Chemistry,1997,vol. 62,p. 5392 - 5403

10
[ 103440-54-6 ]
[ 191804-08-7 ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 5392 - 5403

11
[ 103440-54-6 ]
[ 191803-75-5 ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 5392 - 5403

12
[ 103440-54-6 ]
[ 191803-76-6 ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 5392 - 5403

13
[ 103440-54-6 ]
(S)-2-{6-[2-(2-Amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl)-ethyl]-1-oxo-1,3-dihydro-isoindol-2-yl}-pentanedioic acid [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 5392 - 5403
[2]Journal of Organic Chemistry,1997,vol. 62,p. 5392 - 5403
[3]Journal of Organic Chemistry,1997,vol. 62,p. 5392 - 5403

14
[ 88-12-0 ]
[ 103440-54-6 ]
[ 914299-26-6 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride; In tetrahydrofuran; for 3h;Heating / reflux;	A solution of compound 7 (39.6 g, 0.143 mol) and 1-vinyl-2-pyrrolidinone (18.5 g, 0.143 mol) in anhydrous THF (200 mL) was added slowly to a gently refluxing suspension of sodium hydride (9.2 g, 60% in mineral oil, 0.229 mol) in THF (70 mL). After the addition, the mixture was stirred at reflux for additional 3 hours. TLC (petroleum ether: ethyl acetate = 10:1) showed the reaction was complete. The mixture was cooled and the excess sodium hydride was EPO <DP n="117"/>quenched with saturated aqueous ammonium chloride. The mixture was concentrated in vacuo to remove THF. The residue was extracted with ethyl acetate (400 ml_x2). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give crude product 8, which was used in the next step without further purification.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 6273 - 6278
[2]Patent: WO2006/117669,2006,A1 .Location in patent: Page/Page column 41; 115-116

15
[ 67-56-1 ]
[ 54811-38-0 ]
[ 103440-54-6 ]

Yield	Reaction Conditions	Operation in experiment
73%	With thionyl chloride; at 0℃; for 2h;Reflux;	Preparation 42 Methyl 5-iodo-2-methylbenzoate To a solution of <strong>[54811-38-0]5-iodo-2-methylbenzoic acid</strong> (86 g, 0.57 mol) in MeOH (0.5 L) was added thionyl chloride (74 g, 0.62 mol) dropwise at 0C, and after complete addition the reaction was heated to reflux for 2 hours. The reaction was cooled, concentrated in vacuo, diluted with water and extracted into EtOAc (2 x 300 ml_). The organic layers were combined, washed with brine, dried over Na2S04 and concentrated in vacuo to afford the title compound that was taken directly on to the next step (69 g, 73%).
	With thionyl chloride; at 0℃; for 4h;Heating / reflux;	To a solution of compound 6 (40.0 g, 0.153 mol) in MeOH (400 mL) was added dropwise a freshly prepared solution of SOCI2 (22 mL, 0.305 mol) in MeOH (400 mL) at O0C. The mixture was heated to reflux for 4 hours. TLC (petroleum ether: ethyl acetate = 10:1) showed the reaction was complete, then the mixture was concentrated in vacuo. The residue was desolved in ethyl acetate (800 mL) and washed with water (200 mLx2), saturated aqueous sodium carbonate (200 mLx2) and brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give compound 7 as a yellow solid. 1H NMR (300 MHz, CDCI3): delta 8.21 (S, 1 H), 7.67-7.70 (dd, J = 9.0 Hz, 1 H), 6.97-6.99 (d, J = 6.0 Hz, 1 H), 3.88 (s, 3H), 2.53 (s, 3H).

Reference： [1]Patent: WO2015/189744,2015,A1 .Location in patent: Page/Page column 73-74
[2]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 6273 - 6278
[3]Patent: WO2006/117669,2006,A1 .Location in patent: Page/Page column 41; 115

16
[ 103440-54-6 ]
methyl 2-(aminomethyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate [ No CAS ]

Reference： [1]Patent: WO2015/189744,2015,A1

17
[ 103440-54-6 ]
[ 1004294-80-7 ]

Reference： [1]Patent: WO2015/189744,2015,A1

18
[ 103440-54-6 ]
methyl 2-(bromomethyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate [ No CAS ]

Reference： [1]Patent: WO2015/189744,2015,A1

19
[ 103440-54-6 ]
methyl 2-[(methylamino)methyl]-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate [ No CAS ]

Reference： [1]Patent: WO2015/189744,2015,A1

20
[ 103440-54-6 ]
[ 1313399-38-0 ]

Reference： [1]Patent: WO2015/189744,2015,A1

21
[ 103440-54-6 ]
[ 73183-34-3 ]
[ 478375-39-2 ]

Yield	Reaction Conditions	Operation in experiment
87%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In N,N-dimethyl-formamide; at 100℃; for 18h;Inert atmosphere;	Preparation 37 Methyl 2-methyl-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)benzoate To a solution of <strong>[103440-54-6]methyl 5-iodo-2-methylbenzoate</strong> (Preparation 42, 69 g, 0.25 mol) in DMF (800 mL) was added bispinacolatodiboron (100 g, 0.40 mol) and potassium acetate (92 g, 0.93 mol) followed by degassing with nitrogen. [1 ,1 '- bis(diphenylphosphino)ferrocene]dichloropalladium (II) complex with dichloromethane (6 g) was added and the reaction heated to 100C for 18 hours. The reaction was cooled and filtered through celite, washing through with EtOAc (3 x 1 L). The filtrates were combined, washed with brine (3 x 500 mL), dried over Na2S04 and concentrated in vacuo. The residue was washed with petroleum ether (2 x 500 mL), filtered and dried to afford the title compound as a yellow powder (60 g, 87%) that was taken directly on to the next step.

Reference： [1]Patent: WO2015/189744,2015,A1 .Location in patent: Page/Page column 72

22
[ 103440-54-6 ]
(S)-methyl 5-(1-(diphenylsilyl)ethyl)-2-methylbenzoate [ No CAS ]
(R)-methyl 5-(1-(diphenylsilyl)ethyl)-2-methylbenzoate [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 615 - 618
Angew. Chem.,2017,vol. 129,p. 630 - 633,4

23
[ 103440-54-6 ]
methyl 5-ethynyl-2-methylbenzoate [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 615 - 618
Angew. Chem.,2017,vol. 129,p. 630 - 633,4

24
[ 103440-54-6 ]
[ 1066-54-2 ]
methyl 2-methyl-5-((trimethylsilyl)ethynyl)benzoate [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 615 - 618
Angew. Chem.,2017,vol. 129,p. 630 - 633,4

25
[ 103440-54-6 ]
(3R)-3-(2,2-dimethylchroman-6-yl)-3,5-dimethylindolin-2-one [ No CAS ]
5-[(3R)-3-(2,2-dimethylchroman-6-yl)-3,5-dimethyl-2-oxo-indolin-1-yl]-2-methyl-benzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of (3R)-3-(2,2-dimethylchroman-6-yl)-3,5-dimethylindolin-2-one (32 mg, 0.10 mmol), <strong>[103440-54-6]methyl 5-iodo-2-methylbenzoate</strong> (36 mg, 0.13 mmol), trans-N,N'-dimethylcyclohexane-1,2-diamine (10 mg, 0.07 mmol), and potassium carbonate(28 mg, 0.20 mmol)) in dioxane (3.0 mL) was added copper iodide (6.0 mg, 0.03 mmol). The mixture was purged with nitrogen and heated to 100 C.After 1 h, the mixture was cooled to room temperature and diluted with EtOAc (20 mL). The organic layer was washed with 1 M HCl (120 mL), water (120 mL), dried over Na2SO4, filtered, and concentrated in vacuo. The crude material was re-dissolved in a mixture of ethanol (2 mL) and water (1 mL). Lithium hydroxide monohydrate (100 mg, 2.4 mmol) was added and the mixture was stirred at 50 C. for 30 min. After cooling to room temperature, the reaction was quenched by the addition of 1 M HCl (25 mL) and extracted with EtOAc (50 mL).The organic layer was washed with water (1*20 mL), dried over Na2SO4, filtered, and concentrated in vacuo. Purification of the crude material by reverse-phase HPLC (C18 column, acetonitrile-H2O with 0.1% TFA as eluent) gave the titled compound. 1H NMR (400 MHz, Chloroform-d) delta 8.19 (t, J=1.9 Hz, 1H), 8.13-8.06 (m, 1H), 7.76-7.69 (m, 1H), 7.61 (t, J=7.9 Hz, 1H), 7.14-7.03 (m, 3H), 7.03-6.97 (m, 1H), 6.86-6.77 (m, 1H), 6.71 (d, J=8.6 Hz, 1H), 2.75 (t, J=6.8 Hz, 2H), 2.36 (d, J=0.9 Hz, 3H), 1.85 (s, 3H), 1.78 (t, J=6.7 Hz, 2H), 1.31 (d, J=1.8 Hz, 6H); MS: (ES) m/z calculated for C29H30NO4 [M+H]+ 456.6, found 456.0.

Reference： [1]Patent: US2017/204087,2017,A1 .Location in patent: Paragraph 0155; 0156

26
[ 103440-54-6 ]
C₁₂H₁₂FeO [ No CAS ]
C₂₁H₂₀FeO₃ [ No CAS ]

Reference： [1]Chemical Communications,2018,vol. 54,p. 689 - 692

27
[ 5765-65-1 ]
[ 103440-54-6 ]
[ 1544683-02-4 ]