[ CAS No. 585-76-2 ] {[proInfo.proName]}

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2D 3D

Structure of 585-76-2 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 585-76-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 585-76-2 ]

SDS Specification

Alternatived Products of [ 585-76-2 ]

Product Details of [ 585-76-2 ]

CAS No. :	585-76-2	MDL No. :	MFCD00002487
Formula :	C₇H₅BrO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VOIZNVUXCQLQHS-UHFFFAOYSA-N
M.W :	201.02	Pubchem ID :	11456
Synonyms :

Calculated chemistry of [ 585-76-2 ] Expand+

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	41.1
TPSA :	37.3 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.49 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.12
Log Po/w (XLOGP3) :	2.87
Log Po/w (WLOGP) :	2.15
Log Po/w (MLOGP) :	2.36
Log Po/w (SILICOS-IT) :	1.9
Consensus Log Po/w :	2.08

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-3.27
Solubility :	0.107 mg/ml ; 0.000534 mol/l
Class :	Soluble
Log S (Ali) :	-3.31
Solubility :	0.0978 mg/ml ; 0.000487 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.63
Solubility :	0.473 mg/ml ; 0.00236 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.16

Safety of [ 585-76-2 ]

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 [ 585-76-2 ]

* 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 [ 585-76-2 ]
Downstream synthetic route of [ 585-76-2 ]

[ 585-76-2 ] Synthesis Path-Upstream 1~3

1
[ 585-76-2 ]
[ 75-03-6 ]
[ 99548-72-8 ]

Reference： [1] Journal of Organic Chemistry, 2003, vol. 68, # 5, p. 2030 - 2033

2
[ 585-76-2 ]
[ 603-78-1 ]

Reference： [1] Journal of Organic Chemistry, 2003, vol. 68, # 5, p. 2030 - 2033

3
[ 585-76-2 ]
[ 190777-77-6 ]
[ 223671-15-6 ]

Reference： [1] Organic Letters, 2014, vol. 16, # 18, p. 4718 - 4721

[ 585-76-2 ] Synthesis Path-Downstream 1~14

1
[ 98-08-8 ]
[ 7726-95-6 ]
iron-powder [ No CAS ]
[ 401-78-5 ]
[ 7657-08-1 ]
[ 585-76-2 ]
[ 619-03-4 ]

Reference： [1]Journal of the American Chemical Society,1943,vol. 65,p. 389,390

2
[ 585-76-2 ]
[ 503821-94-1 ]

Reference： [1]Journal of Organic Chemistry,2003,vol. 68,p. 2030 - 2033

3
[ 585-76-2 ]
[ 3032-81-3 ]
2-(3,5-dichlorophenyl)-5-bromobenzoic acid [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 9879 - 9884

4
[ 50-43-1 ]
[ 585-76-2 ]
[ 69038-74-0 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; triethylamine; In tetrahydrofuran; tert-butyl alcohol;	a 3-Bromo-benzoic Acid Tert-butyl Ester 2,4,6-Trichlorobenzoic acid (11.7 ml, 75 mmol) was added dropwise to a solution of 3-bromobenzoic acid (15 g, 75 mmol), triethyl amine (10.5 ml, 75 mmol) in THF (25 ml) at RT. The reaction was stirred 15 min. Then, t-butanol (7.1 ml, 150 mmol) and DMAP (18.3 g, 150 mmol) were added and the reaction was stirred overnight. The crude reaction was filtered through a pad of silica gel, concentrated, and was used in the next reaction without further purification.

Reference： [1]Patent: US6518267,2003,B1

5
[ 585-76-2 ]
[ 3032-81-3 ]
2-(3,5-Dichlorophenyl)-4-Bromobenzoic Acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	With silver(I) acetate;palladium diacetate; In acetic acid; at 120℃; for 5.5h;	Palladium acetate (11.4 mg 0.05 mmol), AgOAc (217 mg 1.3 mmol), 3-bromobenzoic acid (201 mg, 1.0 mmol), <strong>[3032-81-3]3,5-dichloroiodobenzene</strong> (819 mg, 3.0 mmol) and acetic acid (200 muL) were combined and heated at 120° C. for 5.5 h. After purification light tan solid was obtained, 183 mg (53percent), mp 182-186° C. (isooctane). Rf-0.38 (1/9 ethyl acetate-dichloromethane). 1H NMR (300 MHz, acetone-d6) delta 7.32 (br s, 2H), 7.36 (d, J-8.4 Hz, 1H), 7.44 (br s, 1H), 7.79 (d, J-8.4 Hz, 1H), 8.05 (br s, 1H). Carboxylate proton signal was not observed. 13C NMR (75 MHz, acetone-d6) delta 122.2, 127.6, 127.7, 133.2, 133.3, 134.6, 135.0, 139.4, 144.5, 166.7. A signal for one aromatic carbon could not be located. FT-IR (neat, cm1) upsilon 1699, 1299, 857. Anal. calcd for C13H7BrCl2O2 (346.00 g/mol): C, 45.13; H, 2.04. Found: C, 45.17; H, 2.04. The 1H NMR and 13C NMR spectra are shown in FIGS. 27AB, respectively.

Reference： [1]Patent: US2009/12293,2009,A1 .Location in patent: Page/Page column 7; 17

6
[ 585-76-2 ]
[ 7579-20-6 ]
[ 1352995-19-7 ]

Yield	Reaction Conditions	Operation in experiment
87%		Example 1 3-[(3-Bromophenyl)carbonyl]amino}pyridine-4-carboxylic acid (A-1)3-Bromobenzoic acid (16.39 g, 81 mmol), EDC (16.65 g, 87 mmol), HOAT (13.30 g, 87 mmol), and DIEA (20.2 mL, 116 mmol) were dissolved in 500 mL of DMF and stirred at room temperature. After 30 minutes, 3-aminoisonicotinic acid (8 g, 57.9 mmol) was added. After 10 hours, the solvent was removed by rotary evaporation and then triturated with 100 mL water. After sonication, the solids were filtered off and dried under vacuum to yield 15.2 g (87%) of A-1 as a tan solid. Data for A-1: LRMS m/z (M+H): 304.64.

Reference： [1]Patent: US2011/319409,2011,A1 .Location in patent: Page/Page column 16-17

7
[ 7194-78-7 ]
[ 585-76-2 ]

Yield	Reaction Conditions	Operation in experiment
	With dihydrogen peroxide; N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid;pH 7.4;Kinetics;	A series of compounds were synthesized and kinetically analyzed (Table 1). The measured rate constants correlate well with the Hammett ? parameters giving a p value of 3.80 (Figure 4). Many of the compounds display faster reactivity with Eta202 than BFA.

Reference： [1]Patent: WO2012/27274,2012,A2 .Location in patent: Page/Page column 29; 30

8
[ 585-76-2 ]
[ 3537-14-2 ]
[ 1186224-53-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 5896 - 5899

9
[ 585-76-2 ]
[ 49851-36-7 ]
methyl 2-(2-(3-bromobenzamido)phenyl)acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 0.5h;Inert atmosphere;	TEA (0.276 ml_, 1 .984 mmol) was added to a mixture of 3-bromobenzoic acid (199 mg, 0.992 mmol) and HATU (415 mg, 1 .091 mmol) in DMF at 23 C. In a separate vial, methyl 2-(2- aminophenyl)acetate hydrochloride (CAS 49851 -36-7) (200 mg, 0.992 mmol) was stirred with TEA (0.276 ml_, 1 .980 mmol) in DMF (0.5 ml_). After 5 min, the solution of methyl 2-(2- aminophenyl)acetate hydrochloride (200 mg, 0.992 mmol) was added to the 3-bromobenzoic acid (199 mg, 0.992 mmol) mixture and the resulting mixture was stirred at rt for 30 min. The reaction mixture was diluted with EtOAc and washed with water. The aqueous layer was extracted with EtOAc. The combined organics were washed with 5% aq LiCI, dried (Na2S04) and concentrated. The resulting residue was purified by silica gel chromatography (EtOAc- heptanes 0-60%) to provide the title compound. MS (ESI+) m/z 348.0, 350.0 (M+H).
	With triethylamine; HATU; In N,N-dimethyl-formamide; at 23℃; for 0.583333h;	Intermediate 36. Methyl 2-(2-(3-bromobenzamido)phenyl)acetate TEA (0.276 ml_, 1 .984 mmol) was added to a mixture of 3-bromobenzoic acid (199 mg, 0.992 mmol) and HATU (415 mg, 1 .091 mmol) in DMF at 23 C. In a separate vial, methyl 2-(2- aminophenyl)acetate hydrochloride (CAS 49851 -36-7) (200 mg, 0.992 mmol) was stirred with TEA (0.276 ml_, 1 .980 mmol) in DMF (0.5 ml_). After 5 min, the solution of methyl 2-(2- aminophenyl)acetate hydrochloride (200 mg, 0.992 mmol) was added and the resulting mixture was stirred at room temperature for 30 min. The reaction mixture was diluted with EtOAc and washed with water. The aqueous layer was extracted with EtOAc. The combined organics were washed with 5% aq LiCI, dried (Na2S04) and concentrated. The resulting residue was purified by silica gel chromatography (EtOAc- heptanes 0-60%) to provide the title compound. MS (EST) m/z 348.0, 350.0 (M+H).

Reference： [1]Journal of Medicinal Chemistry,2019,vol. 62,p. 4656 - 4668
[2]Patent: WO2015/9977,2015,A1 .Location in patent: Page/Page column 217
[3]Patent: WO2016/88082,2016,A1 .Location in patent: Page/Page column 68-69

10
[ 585-76-2 ]
[ 4467-07-6 ]

Reference： [1]Patent: WO2016/198507,2016,A1

11
[ 1432795-28-2 ]
[ 585-76-2 ]
[ 4467-07-6 ]

Yield	Reaction Conditions	Operation in experiment
91%	With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate; In 1,4-dioxane; water; at 95℃;Inert atmosphere;	General procedure: The halo aryl (1.0 equiv) was dissolved in a mixture of water:dioxane (1:1). The boronic acid or ester(1.5 equiv) and potassium phosphate (5.0 equiv) were added. The solution was degassed byvacuum/argon cycles (10 times) before addition of PdCl2(PPh3)2 (10 mol%) and further degassed (5times). The resulting mixture was stirred at 95 C under argon atmosphere for 16-20 hours. Thereaction mixture was filtered through Celite and diluted with water (approx. 30 mL) before washingwith chloroform (3 x 30 mL). If not stated otherwise, the aqueous phase was concentrated underreduced pressure and applied to a C18 precolumn before purification on a 10g or 60 g C18 column witha gradient of acetonitrile in water (10-100%) to yield the desired product.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 145,p. 634 - 648

12
[ 585-76-2 ]
[ 56836-51-2 ]
[ 376592-93-7 ]

Reference： [1]Patent: CN109485580,2019,A

13
[ 585-76-2 ]
[ 64682-89-9 ]
[ 376592-93-7 ]

Reference： [1]Patent: CN109485580,2019,A

14
[ 585-76-2 ]
[ 49851-36-7 ]
2-(2-(3'-(aminomethyl)-[1,1'-biphenyl]-3-ylcarboxamido)phenyl)acetic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2019,vol. 62,p. 4656 - 4668

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Isomers

Technical Information

? Alkyl Halide Occurrence ? Arndt-Eistert Homologation ? General Reactivity ? Grignard Reaction ? Hiyama Cross-Coupling Reaction ? Hunsdiecker-Borodin Reaction ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Passerini Reaction ? Preparation of Amines ? Preparation of Carboxylic Acids ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reactions of Carboxylic Acids ? Reactions of Dihalides ? Schmidt Reaction ? Specialized Acylation Reagents-Ketenes ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Ugi Reaction

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H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ CAS No. 585-76-2 ] {[proInfo.proName]}

Quality Control of [ 585-76-2 ]

Related Doc. of [ 585-76-2 ]

Product Details of [ 585-76-2 ]

Calculated chemistry of [ 585-76-2 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 585-76-2 ]

Application In Synthesis of [ 585-76-2 ]

[ 585-76-2 ] Synthesis Path-Upstream 1~3

[ 585-76-2 ] Synthesis Path-Downstream 1~14

Technical Information

Related Functional Groups of [ 585-76-2 ]

Aryls

Bromides

Carboxylic Acids

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

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[ 585-76-2 ]