[ CAS No. 33842-18-1 ]

Name: 33842-18-1|Methyl 6-bromobenzo[d][1,3]dioxole-4-carboxylate|97%
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SKU: A158542
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Quality Control of [ 33842-18-1 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 33842-18-1 ]

CAS No. :	33842-18-1	MDL No. :	MFCD23701705
Formula :	C₉H₇BrO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	259.05 g/mol	Pubchem ID :	71463973
Synonyms :

Calculated chemistry of of [ 33842-18-1 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.22
Num. rotatable bonds :	2
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	51.48
TPSA :	44.76 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) :	-6.26 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.47
Log Po/w (XLOGP3) :	2.28
Log Po/w (WLOGP) :	1.96
Log Po/w (MLOGP) :	1.79
Log Po/w (SILICOS-IT) :	2.4
Consensus Log Po/w :	2.18

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.07
Solubility :	0.222 mg/ml ; 0.000856 mol/l
Class :	Soluble
Log S (Ali) :	-2.86
Solubility :	0.36 mg/ml ; 0.00139 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.08
Solubility :	0.214 mg/ml ; 0.000828 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.47

Safety of [ 33842-18-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 33842-18-1 ]

* 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 [ 33842-18-1 ]

[ 33842-18-1 ] Synthesis Path-Downstream 1~19

Yield	Reaction Conditions	Operation in experiment
	Rk. mit Cu(I)CN;
	Rk. mit HNO3;
	Hydrierung;

Umsetzung mit Cu(I)CN, sowie HNO3 u. Hydrierung ?;

Yield	Reaction Conditions	Operation in experiment
	(1b), Brom in H2O/CHCl3;
	aus (1b), Brom in H2O/ CHCl3;

3
[ 72517-15-8 ]
[ 33842-18-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: thionyl chloride / 0 °C / Reflux; Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide / 100 °C

Reference： [1]Current Patent Assignee: JEIL PHARMA HOLDINGS INC - EP3404033, 2018, A1

4
[ 303-38-8 ]
[ 33842-18-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: bromine; acetic acid / 12 h / 20 °C 2: thionyl chloride / 0 °C / Reflux; Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 100 °C

Reference： [1]Current Patent Assignee: JEIL PHARMA HOLDINGS INC - EP3404033, 2018, A1

5
[ 105603-49-4 ]
[ 74-95-3 ]
[ 33842-18-1 ]

Yield	Reaction Conditions	Operation in experiment
97%	With potassium carbonate; In N,N-dimethyl-formamide; at 100℃;	Dibromomethane (3.2 mL, 45.3 mmol) was added dropwise into a mixture of the compound (17-2) (7.5 g, 30.2 mmol) obtained in Step 102 2 of Example 17 in 30 DMF (100 mL) as well as 67 K2CO3 (12.5 g, 95.0 mmol). A reaction mixture was heated at 100C overnight, after which a reaction thereof was completed with water. A water layer was extracted with EtOAc, after which a combined organic layer was washed with brine, such that the resulting product was dried over anhydrous MgSO4, filtered and concentrated under vacuum. A resulting residue was purified by means of a silica gel column chromatography, so as to obtain the 127 title compound (19-1) (7.6 g, 29.3 mmol, 97%). (0166) 1H NMR (400 MHz, CDCl3); delta 7.55 (d, J = 2.0 Hz, 1H), 7.08 (d, J = 1.6 Hz, 1H), 6.12 (s, 2H), 3.92 (s, 3H)

Reference： [1]Patent: EP3404033,2018,A1 .Location in patent: Paragraph 0165-0166

6
[ 33842-18-1 ]
[ 72744-57-1 ]

Yield	Reaction Conditions	Operation in experiment
99%	With water; sodium hydroxide In tetrahydrofuran; methanol at 20℃; for 4h;	19.2 Step 2. Synthesis of 6-bromobenzo[d][1,3]dioxol-4-carboxylic acid (19-2) A 1N-NaOH aqueous solution (58.7 mL) was added into the compound (19-1) (7.6 g, 29.3 mmol) in THF/MeOH (40 mL/80 mL) at room temperature. A reaction mixture was stirred at room temperature for 4 hours. After a reaction was completed, a volatile substance was removed under reduced pressure. A 1N-HCl aqueous solution was added into a residue to carry out acidification, during which a resulting mixture was stirred to precipitate a crude product. The crude product was filtered, washed with water and dried under high vacuum, so as to obtain the title compound (19-2) (7.2 g, 29.3 mmol, 99%). (0169) 1H NMR (400 MHz, CDCl3); δ 7.59 (d, J = 2.0 Hz, 1H), 7.13 (d, J = 2.0 Hz, 1H), 6.16 (s, 2H).

Reference： [1]Current Patent Assignee: JEIL PHARMA HOLDINGS INC - EP3404033, 2018, A1 Location in patent: Paragraph 0168-0169

7
[ 2411-83-8 ]
[ 33842-18-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: potassium fluoride / N,N-dimethyl-formamide / 0.5 h 1.2: 30 h / 110 °C 2.1: acetic acid; sodium acetate; bromine / 12 h / 20 °C

Reference： [1]Hermane, Jekaterina; Eichner, Simone; Mancuso, Lena; Schröder, Benjamin; Sasse, Florenz; Zeilinger, Carsten; Kirschning, Andreas [Organic and Biomolecular Chemistry, 2019, vol. 17, # 21, p. 5269 - 5278]

8
[ 33842-16-9 ]
[ 33842-18-1 ]

Yield	Reaction Conditions	Operation in experiment
84%	With bromine; sodium acetate; acetic acid at 20℃; for 12h;

9
[ 33842-18-1 ]
[ 33842-32-9 ]

Yield	Reaction Conditions	Operation in experiment
30%	With copper(l) iodide; ammonia; caesium carbonate In N,N-dimethyl-formamide; acetylacetone at 70℃; for 12h;

10
[ 33842-18-1 ]
6-aminobenzo[d][1,3]dioxole-4-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: caesium carbonate; copper(l) iodide; ammonia / N,N-dimethyl-formamide; acetylacetone / 12 h / 70 °C 2: lithium hydroxide / methanol; water / 4 h / 20 °C

11
[ 33842-18-1 ]
[ 74-88-4 ]
methyl 6-bromo-7-methylbenzo[d][1,3]dioxole-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
17%	Stage #1: methyl 6-bromobenzo[d][1,3]dioxole-4-carboxylate With lithium diisopropyl amide In tetrahydrofuran; n-heptane; ethylbenzene at -78℃; for 0.25h; Stage #2: methyl iodide In tetrahydrofuran; n-heptane; ethylbenzene at 20℃; for 1.5h;	2 Methyl 6-bromo-7-methylbenzo[d][1,3]dioxole-4-carboxylate. To a solution of lithium diisopropyl amide (0.32 mL, 0.64 mmol, 1.1 eq, 2.0 M solution in THF/heptane/ethylbenzene) in THF (2 mL) at -78 °C was added methyl 6- bromobenzo[d][l,3]dioxole-4-carboxylate (150 mg, 0.58 mmol, 1 eq) dissolved in THF (1 mL) dropwise. The resulting solution was stirred at -78 °C for 15 min, after which time methyl iodide (0.11 mL, 1.74 mmol, 3 eq) was added dropwise. The resulting solution was slowly warmed to r.t. over 30 min, and stirred for 1 h at r.t. The reaction mixture was quenched with H2O, and diluted with DCM. 1M HC1 was then added, and the aqueous layer was extracted with DCM. The combined organic extracts were filtered through a phase separator and concentrated, and the crude residue was purified by column chromatography (3-50% EtOAc in hexanes) to give the title compound as a white solid (27 mg, 17%). 1H-NMR (400 MHz, CDCl3) d 7.61 (s, 1H), 6.11 (s, 2H), 3.90 (s, 3H), 2.27 (s, 3H). ES-MS [M+H]+ = 273.2, 275.2.

Reference： [1]Current Patent Assignee: VANDERBILT UNIVERSITY - WO2020/86864, 2020, A1 Location in patent: Paragraph 00228-00229

12
[ 33842-18-1 ]
methyl 6-(4-(1H-pyrazol-1-yl)benzyl)benzo[d][1,3]dioxole-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / dimethyl sulfoxide / 0.17 h / 120 °C / Microwave irradiation; Sealed tube; Inert atmosphere 2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂; caesium carbonate / 1,4-dioxane; water / 2 h / 90 °C / Sealed tube; Inert atmosphere