[ CAS No. 145908-29-8 ] {[proInfo.proName]}

Name: 145908-29-8|Methyl 2-(bromomethyl)-4-chlorobenzoate|98%
Brand: Ambeed
SKU: A396786
Price: 18.0 USD
Availability: InStock
Rating: 99 (29 reviews)

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

HazMat Fee +

There will be a HazMat fee per item when shipping a dangerous goods. The HazMat fee will be charged to your UPS/DHL/FedEx collect account or added to the invoice unless the package is shipped via Ground service. Ship by air in Excepted Quantity (each bottle), which is up to 1g/1mL for class 6.1 packing group I or II, and up to 25g/25ml for all other HazMat items.

Type	HazMat fee for 500 gram (Estimated)
Excepted Quantity	USD 0.00
Limited Quantity	USD 15-60
Inaccessible (Haz class 6.1), Domestic	USD 80+
Inaccessible (Haz class 6.1), International	USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic	USD 100+
Accessible (Haz class 3, 4, 5 or 8), International	USD 200+

DV 2D 3D

3d Animation Molecule Structure of 145908-29-8

Structure of 145908-29-8 * Storage: {[proInfo.prStorage]}

Please Login or Create an Account to: See VIP prices and availability

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

* Shipping: {[proInfo.prShipping]}

For Research Only 120K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 145908-29-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 145908-29-8 ]

SDS Specification

Alternatived Products of [ 145908-29-8 ]

Product Details of [ 145908-29-8 ]

CAS No. :	145908-29-8	MDL No. :	MFCD11505950
Formula :	C₉H₈BrClO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LGLIPOQXOPCFRN-UHFFFAOYSA-N
M.W :	263.52	Pubchem ID :	20814722
Synonyms :

Calculated chemistry of [ 145908-29-8 ] Expand+

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.22
Num. rotatable bonds :	3
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	55.57
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) :	-5.81 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.59
Log Po/w (XLOGP3) :	2.96
Log Po/w (WLOGP) :	2.87
Log Po/w (MLOGP) :	3.25
Log Po/w (SILICOS-IT) :	3.36
Consensus Log Po/w :	3.01

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.48
Solubility :	0.0868 mg/ml ; 0.00033 mol/l
Class :	Soluble
Log S (Ali) :	-3.18
Solubility :	0.176 mg/ml ; 0.000668 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.35
Solubility :	0.0118 mg/ml ; 0.0000448 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.04

Safety of [ 145908-29-8 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P501-P260-P234-P264-P280-P390-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P406-P405	UN#:	3261
Hazard Statements:	H314-H290	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 145908-29-8 ]

* 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 [ 145908-29-8 ]
Downstream synthetic route of [ 145908-29-8 ]

[ 145908-29-8 ] Synthesis Path-Upstream 1~2

1
[ 99585-12-3 ]
[ 145908-29-8 ]

Yield	Reaction Conditions	Operation in experiment
45.8%	With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethaneHeating / reflux	Compound C (10.86 g, 58.8 mmol, 1.0 eq.) was dissolved in carbon tetrachloride (100 mL), and N-bromosuccinimide (15.7 g, 88.2 mmol., 1.5 eq.) was added followed by benzoylperoxide (0.05 g). The mixture was refluxed overnight. The reaction mixture was then filtered, and the solids were washed with dichloromethane. The combined organic filtrate was concentrated and dried to give compound D (7.1 g, 45.8percent). The structure was confirmed by ¹H NMR.
45.8%	With N-Bromosuccinimide In tetrachloromethaneHeating / reflux	Compound C (10.86 g, 58.8 mmol, 1.0 eq.) was dissolved in carbon tetrachloride (100 mL), and N-bromosuccinimide (15.7 g, 88.2 mmol., 1.5 eq.) was added followed by benzoylperoxide (0.05 g). The mixture was refluxed overnight. The reaction mixture was then filtered, and the solids were washed with dichloromethane. The combined organic filtrate was concentrated and dried to give compound D (7.1 g, 45.8percent). The structure was confirmed by ¹H NMR.
45%	With N-Bromosuccinimide In tetrachloromethaneHeating / reflux	Step B 2-Bromomethyl-4-chloro-benzoic acid methyl ester; The compound from Step A (1.0 g, 5.4 mmol), N-bromosuccinimide (1.1 g, 6.0 mmol), and benzoylperoxide (catalytic amount) are refluxed overnight in carbon tetrachloride (10 mL) under nitrogen. Upon cooling the solid is removed by filtration and the filtrate is concentrated under reduced pressure. Ether is added, and the mixture is washed with water and brine, and then dried over sodium sulfate, and concentrated under reduced pressure. The remaining solid is triturated with hexane and collected by filtration providing the title compound (0.65 g, 45 percent). GC/MS: M-'*'263/264 ; HNMR (400 MHz, CDCl3).

Reference： [1] Patent: US2005/143348, 2005, A1, . Location in patent: Page/Page column 45; 49; 55
[2] Patent: US2005/239838, 2005, A1, . Location in patent: Page/Page column 41
[3] Patent: WO2005/54176, 2005, A1, . Location in patent: Page/Page column 136
[4] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 5, p. 1628 - 1631
[5] Patent: US2009/270393, 2009, A1, . Location in patent: Page/Page column 43-44
[6] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 1, p. 360 - 365
[7] Patent: WO2015/8230, 2015, A1, . Location in patent: Page/Page column 318

2
[ 7499-07-2 ]
[ 145908-29-8 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 1, p. 360 - 365
[2] Patent: WO2015/8230, 2015, A1,

[ 145908-29-8 ] Synthesis Path-Downstream 1~39

1
[ 145908-29-8 ]
[ 854531-85-4 ]
2-{4-[3-(5-chloro-1-oxo-1,3-dihydro-isoindol-2-ylmethyl)-5-fluoro-phenoxy]-2-methyl-phenoxy}-2-methyl-propionic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
26%	With potassium carbonate; In DMF (N,N-dimethyl-formamide); at 20℃;	Step C 2- {4- [3- (5-Chloro-1-oxo-1, 3-dihydro-isoindol-2-ylmethyl)-5-fluoro-phenoxy]-2-methyl- phenoxy}-2-methyl-propionic acid ethyl ester; Compound from Step B (76 mg, 0.29mmol), 2- [4- (3-aminomethyl-5- < fluoro-phenoxy)-2-methyl-phenoxy]-2-methyl-propionic acid ethyl ester (Intermediate 47) (120 mg, 0.33 mmol), and potassium carbonate (92 mg, 0.66 mmol) are dissolved in dry DMF (10 mL) and stirred at rt overnight under nitrogen. Water is added to the reaction, and the mixture is extracted with ethyl acetate, washed with brine, dried over sodium sulfate and concentrated under reduced pressure. Purification by flash chromatography, eluting with 10 % EtOAc in hexane then 25 % EtOAc in hexane provides the title compound (38 g, 26 %). MS (ES+) : 512 (M+H+) ; 1HNMR (400 MHz, CDCl3)

Reference： [1]Patent: WO2005/54176,2005,A1 .Location in patent: Page/Page column 136-137

2
[ 99585-12-3 ]
[ 145908-29-8 ]

Yield	Reaction Conditions	Operation in experiment
45.8%	With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane;Heating / reflux;	Compound C (10.86 g, 58.8 mmol, 1.0 eq.) was dissolved in carbon tetrachloride (100 mL), and N-bromosuccinimide (15.7 g, 88.2 mmol., 1.5 eq.) was added followed by benzoylperoxide (0.05 g). The mixture was refluxed overnight. The reaction mixture was then filtered, and the solids were washed with dichloromethane. The combined organic filtrate was concentrated and dried to give compound D (7.1 g, 45.8%). The structure was confirmed by 1H NMR.
45.8%	With N-Bromosuccinimide;dibenzoyl peroxide; In tetrachloromethane;Heating / reflux;	Compound C (10.86 g, 58.8 mmol, 1.0 eq.) was dissolved in carbon tetrachloride (100 mL), and N-bromosuccinimide (15.7 g, 88.2 mmol., 1.5 eq.) was added followed by benzoylperoxide (0.05 g). The mixture was refluxed overnight. The reaction mixture was then filtered, and the solids were washed with dichloromethane. The combined organic filtrate was concentrated and dried to give compound D (7.1 g, 45.8%). The structure was confirmed by 1H NMR.
45%	With N-Bromosuccinimide;dibenzoyl peroxide; In tetrachloromethane;Heating / reflux;	Step B 2-Bromomethyl-4-chloro-benzoic acid methyl ester; The compound from Step A (1.0 g, 5.4 mmol), N-bromosuccinimide (1.1 g, 6.0 mmol), and benzoylperoxide (catalytic amount) are refluxed overnight in carbon tetrachloride (10 mL) under nitrogen. Upon cooling the solid is removed by filtration and the filtrate is concentrated under reduced pressure. Ether is added, and the mixture is washed with water and brine, and then dried over sodium sulfate, and concentrated under reduced pressure. The remaining solid is triturated with hexane and collected by filtration providing the title compound (0.65 g, 45 %). GC/MS: M-'*'263/264 ; HNMR (400 MHz, CDCl3).

	With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In acetic acid tert-butyl ester; at 90℃;	(Step 2) A solution of N-bromosuccinimide (6.33 g), 2,2'-azobis(isobutyronitrile) (0.27 g) and methyl 4-chloro-2-methylbenzoate obtained in Step 1 (5.05 g) in t-butyl acetate (80 ml) was stirred overnight at 90 C. The mixture was allowed to cool to room temperature, poured into aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, and filtered. The solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate:hexane=0:1-3:17) to give methyl 4-chloro-2-bromomethylbenzoate (6.05 g) as a white solid. 1H NMR (300 MHz, CDCl3) delta ppm 3.94 (3H, s) 4.91 (2H, s) 7.35 (1H, dd, J=8.4, 2.2 Hz) 7.47 (1H, d, J=2.1 Hz), 7.93 (1H, d, J=8.3 Hz).
	With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); at 90℃;	Methyl 4-chloro-2-methylbenzoate (25.7 g, 139 mmol) was placed in a flask with t-butyl acetate (400 mL). NBS (32.2 g, 181 mmol) was added followed by AIBN (1.14 g, 6.96 mmol) and the mixture was stirred at 90C overnight. The mixture was partitioned between EtOAcand water. The organic phase was washed with water and brine, dried over Mg504, filtered and the solvent was removed in vacuo. The product was purified by chromatography on silica eluting with 19:1 iso-hexane: EtOAc. The resulting material was triturated in a minimal volume of ice cold iso-hexane and filtered to afford the title compound;1H NMR (400 MHz, DMSO-d6) O 7.90 (1H, d), 7.78 (1H, d), 7.57 (1H, d of d), 5.01 (2H, 5),3.89(3H,s).
	With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; at 80℃; for 20h;Inert atmosphere;	Into a 1000-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of N2, was placed CC14 (600 ml), methyl 4-chloro-2-methylbenzoate (60 g, (0418) 325mmol), BS (87 g, 487mmol) and BPO (3.15 g, 13.00mmol). The mixture was heated to 80 C for 20 hours . The resulting solution was cooled to room temperature. The mixture was concentrated under vacuum and then purified by HPLC to give methyl 2-(bromomethyl)-4- chlorobenzoate. 1H NMR (300 MHz, CDC13) delta 7.92 (d, J= 8.4 Hz, 1H), 7.47 (d, J= 2.2 Hz, 1H), 7.35 (dd, J= 8.5, 2.2 Hz, 1H), 4.91 (s, 2H), 3.94 (s, 3H).
	With N-Bromosuccinimide; dibenzoyl peroxide; In 1,2-dichloro-ethane; at 80℃; for 12h;	General procedure: A mixture of methyl 3-bromo-2-methylbenzoate (500 mg, 3.3 mmol), NBS (770.4 mg, 4.3 mmol), and di-benzoyl peroxide (BPO, 80.7 mg, 0.3 mmol) in 1,2-dichloroethane (10 mL) was heated at 80 C for 12 h. The reaction mixture was cooled to room temperature, and the precipitated solid was removed by filtration and washed with ethers (10 mL). The filtrate was concentrated in vacuo and the residue was partitioned between 2 N NaHCO3 (15 mL) and ethers (15 mL). The organic layer was separated, dried over NaSO4, filtered and concentrated to give a crude product (683.2 mg, 89.6%), which was used in the next step reaction without further purification.

Reference： [1]Patent: US2005/143348,2005,A1 .Location in patent: Page/Page column 45; 49; 55
[2]Patent: US2005/239838,2005,A1 .Location in patent: Page/Page column 41
[3]Patent: WO2005/54176,2005,A1 .Location in patent: Page/Page column 136
[4]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 1628 - 1631
[5]Patent: US2009/270393,2009,A1 .Location in patent: Page/Page column 43-44
[6]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 360 - 365
[7]Patent: WO2015/8230,2015,A1 .Location in patent: Page/Page column 318
[8]Patent: WO2019/94312,2019,A1 .Location in patent: Page/Page column 50; 61
[9]European Journal of Medicinal Chemistry,2019,vol. 180,p. 509 - 523

3
[ 145908-29-8 ]
[ 501-94-0 ]
[ 1046494-91-0 ]

Reference： [1]Patent: US2005/143348,2005,A1 .Location in patent: Page/Page column 55

4
[ 145908-29-8 ]
[ 139-02-6 ]
[ 515133-98-9 ]

Reference： [1]Patent: US2005/143348,2005,A1 .Location in patent: Page/Page column 49

5
[ 145908-29-8 ]
[ 108-95-2 ]
[ 515133-98-9 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;potassium iodide; In butanone;Heating / reflux;	Phenol (2.79 g, 29.63 mmol, 1.1 eq.) was dissolved in 2-butanone (75.0 mL) and potassium carbonate (11.17 g, 80.82 mmol., 3.0 eq.) was added, followed by compound D (7.1 g, 26.94 mmol., 1.0 eq.) dissolved in 2-butanone (75.0 mL). A catalytic amount of potassium iodide (0.05 g) was added and the mixture was refluxed overnight. The cooled reaction mixture was filtered and the solids were washed with 2-butanone. The combined filtrate was taken up in ethyl acetate (75 mL) and was washed with 5% aqueous NaOH (2×50 mL), brine (40 mL), and water (50 mL). The organic phase was concentrated and purified on silica gel to give compound E (9.32 g). The structure confirmed product by 1H NMR.
	With potassium carbonate;potassium iodide; In butanone;Heating / reflux;	Phenol (2.79 g, 29.63 mmol, 1.1 eq.) was dissolved in 2-butanone (75.0 mL) and potassium carbonate (11.17 g, 80.82 mmol., 3.0 eq.) was added, followed by compound D (7.1 g, 26.94 mmol., 1.0 eq.) dissolved in 2-butanone (75.0 mL). A catalytic amount of potassium iodide (0.05 g) was added and the mixture was refluxed overnight. The cooled reaction mixture was filtered and the solids were washed with 2-butanone. The combined filtrate was taken up in ethyl acetate (75 mL) and was washed with 5% aqueous NaOH (2×50 mL), brine (40 mL), and water (50 mL). The organic phase was concentrated and purified on silica gel to give compound E (9.32 g). The structure confirmed product by 1H NMR.

Reference： [1]Patent: US2005/143348,2005,A1 .Location in patent: Page/Page column 45
[2]Patent: US2005/239838,2005,A1 .Location in patent: Page/Page column 41

6
[ 145908-29-8 ]
[ 877317-13-0 ]
C₁₈H₁₃BrClN₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 25 - 60℃; for 12 - 24h;	compound 14A (prepared as described in Example 1) was treated with a benzyl bromide (Compound 14B) and DIPEA base in DMF at 25 C to 60 C for 12 to 24 hours. The reaction solution was purified via C18 reverse phase chromatography to give compound 14C.

Reference： [1]Patent: WO2006/19768,2006,A1 .Location in patent: Page column 97

7
[ 145908-29-8 ]
[ 99-98-9 ]
[ 1022984-23-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 1628 - 1631

8
[ 145908-29-8 ]
[ 58483-97-9 ]
[ 1192348-24-5 ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide; at 90℃;	(Step 3) A solution of 2-amino-5-chloronicotinamide (202 mg) and <strong>[145908-29-8]methyl 4-chloro-2-bromomethylbenzoate</strong> obtained in Step 2 (470 mg) in DMF (5 ml) was stirred overnight at 90 C. The mixture was allowed to cool to room temperature, ethyl acetate was added, and the precipitated crystals were collected by filtration. The obtained crystals were recrystallized from ethanol and ethyl acetate to give the title compound (78 mg). 1H NMR (300 MHz, DMSO-d6) delta ppm 3.90 (3H, s) 5.79 (2H, s) 6.92 (1H, d, J=1.9 Hz) 7.63 (1H, dd, J=1.9, 8.5 Hz) 8.08 (1H, d, J=8.5 Hz) 8.21 (1H, s) 8.52-8.72 (3H, m) 9.12-9.78 (2H, m).

Reference： [1]Patent: US2009/270393,2009,A1 .Location in patent: Page/Page column 44

9
[ 145908-29-8 ]
[ 1224885-25-9 ]
C₁₈H₁₃ClFN₃O₃ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 1877 - 1880

10
[ 145908-29-8 ]
[ 24666-56-6 ]
[ 1416990-11-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 360 - 365

11
[ 7499-07-2 ]
[ 145908-29-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 360 - 365
[2]Patent: WO2015/8230,2015,A1
[3]Patent: WO2019/94312,2019,A1

12
[ 145908-29-8 ]
4-chloro-2-((5-methyl-2H-tetrazol-2-yl)methyl)benzyl 1H-imidazole-1-carboxylate [ No CAS ]