[ CAS No. 101935-40-4 ] {[proInfo.proName]}

Name: 101935-40-4|2-Bromo-3-nitrophenol|98%
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Quality Control of [ 101935-40-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 101935-40-4 ]

CAS No. :	101935-40-4	MDL No. :	MFCD08704555
Formula :	C₆H₄BrNO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HRVRWIBVVHOHNN-UHFFFAOYSA-N
M.W :	218.01	Pubchem ID :	8167254
Synonyms :

Calculated chemistry of [ 101935-40-4 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	44.99
TPSA :	66.05 Å²

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) :	-6.15 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.31
Log Po/w (XLOGP3) :	2.09
Log Po/w (WLOGP) :	2.06
Log Po/w (MLOGP) :	1.05
Log Po/w (SILICOS-IT) :	-0.1
Consensus Log Po/w :	1.28

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.85
Solubility :	0.311 mg/ml ; 0.00143 mol/l
Class :	Soluble
Log S (Ali) :	-3.11
Solubility :	0.17 mg/ml ; 0.000782 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.06
Solubility :	1.89 mg/ml ; 0.00867 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.92

Safety of [ 101935-40-4 ]

Signal Word:	Danger	Class:	9
Precautionary Statements:	P261-P264-P270-P272-P273-P280-P301+P312+P330-P302+P352-P305+P351+P338+P310-P333+P313-P391-P501	UN#:	3077
Hazard Statements:	H302-H315-H317-H318-H410	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 101935-40-4 ]

* 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 [ 101935-40-4 ]
Downstream synthetic route of [ 101935-40-4 ]

[ 101935-40-4 ] Synthesis Path-Upstream 1~15

1
[ 101935-40-4 ]
[ 74-88-4 ]
[ 67853-37-6 ]

Yield	Reaction Conditions	Operation in experiment
94%	With caesium carbonate In DMF (N,N-dimethyl-formamide) at 18 - 22℃;	The nitrophenol starting material B2 (3.1 g; 14.2 MMOL) was dissolved in DMF (20 mL) and to the solution was added ground cesium carbonate (5. 58 G ; 17.1 MMOL) followed by Mel (2.6 mL; 42.5 MMOL). The mixture was stirred at room temperature overnight. The DMF was evaporated, the residue taken up in ether (1X 200 mL), washed with water (1X 200 ML), brine (4x 100 mL), dried (MGS04), filtered and evaporated to afford the crude 2-bromo-3-nitroanisole B3 (94percent; 3.1 g) as an orange solid. MS 234 (M+2H) + ; Homogeneity by HPLC (TFA) 220 nm: 98percent.
94%	With caesium carbonate In N,N-dimethyl-formamide at 20℃;	Step B:; The nitrophenol starting material 1b2 (3.1 g; 14.2 mmol) was dissolved inDMF (20 mL) and to the solution was added ground cesium carbonate (5.58 g; 17.1mmol) followed by Mel (2.6 mL; 42.5 mmol). The mixture was stirred at roomtemperature overnight. The DMF was evaporated, the residue taken up in ether (1 X200 mL), washed with water (1 X 200 mL), brine (4 X 100 mL), dried (MgSO₄), filteredand evaporated to afford the crude 2-bromo-3-nitroanisole 1b3 (94percent; 3.1 g) as anorange solid.MS 234 (M+2H)⁺; Homogeneity by HPLC (TFA) (at) 220nm: 98percent
94%	With caesium carbonate In DMF (N,N-dimethyl-formamide) at 20℃;	The nitrophenol starting material 1b2 (3.1 g; 14.2 mmol) was dissolved in DMF (20 mL) and to the solution was added ground cesium carbonate (5.58 g; 17.1 mmol) followed by Mel (2.6 mL; 42.5 mmol). The mixture was stirred at room temperature overnight. The DMF was evaporated, the residue taken up in ether (1200 mL), washed with water (1200 mL), brine (4*100 mL), dried (MgSO4), filtered and evaporated to afford the crude 2-bromo-3-nitroanisole 1b3 (94percent; 3.1 g) as an orange solid.MS 234 (M+2H)+; Homogeneity by HPLC (TFA)at;220 nm: 98percent

94%	With caesium carbonate In N,N-dimethyl-formamide at 20℃;	The nitrophenol starting material 2b2 (3.1 g; 14.2 mmol) was dissolved inDMF (20 mL) and to the solution was added ground cesium carbonate (5.58 g; 17.1mmol) followed by Mel (2.6 mL; 42.5 mmol). The mixture was stirred at roomtemperature overnight. The DMF was evaporated, the residue taken up in ether (1 X200 mL), washed with water (1 X 200 mL), brine (4 X 100 mL), dried ( MgSO₄),filtered and evaporated to afford the crude 2-bromo-3-nitroanisole 2b3 (94percent; 3.1 g)as an orange solid.MS 234 (M+2H)⁺; Homogeneity by HPLC (TFA) (at) 220nm: 98percent
94%	With caesium carbonate In N,N-dimethyl-formamide at 18 - 22℃;	Step B; The nitrophenol starting material 2B2 (3.1 g; 14.2 mmol) was dissolved in DMF (20 mL) and to the solution was added ground cesium carbonate (5.58 g; 17.1 mmol) followed by MeI (2.6 mL; 42.5 mmol). The mixture was stirred at room temperature overnight. The DMF was evaporated, the residue taken up in ether (1 X 200 mL), washed with water (1 X 200 mL), brine (4 X 100 mL), dried (MgSO₄), filtered and evaporated to afford the crude 2-bromo-3-nitroanisole 2B3 (94percent; 3.1 g) as an orange solid. MS 234 (M+2H)⁺; Homogeneity by HPLC (TFA) (at) 220nm: 98percent

Reference： [1] Patent: WO2004/103996, 2004, A1, . Location in patent: Page 40-41
[2] Patent: WO2006/7700, 2006, A1, . Location in patent: Page/Page column 62
[3] Patent: US2006/19905, 2006, A1, . Location in patent: Page/Page column 24
[4] Patent: WO2006/85, 2006, A1, . Location in patent: Page/Page column 75-76
[5] Patent: WO2007/9227, 2007, A1, . Location in patent: Page/Page column 35

2
[ 101935-40-4 ]
[ 77-78-1 ]
[ 67853-37-6 ]

Reference： [1] Journal of Organic Chemistry, 1988, vol. 53, # 6, p. 1170 - 1176

3
[ 101935-40-4 ]
[ 112970-44-2 ]

Reference： [1] Journal of Organic Chemistry, 1988, vol. 53, # 6, p. 1170 - 1176

4
[ 603-85-0 ]
[ 101935-40-4 ]

Yield	Reaction Conditions	Operation in experiment
56%	Stage #1: With hydrogen bromide In 1,4-dioxane; water at 80℃; for 0.5 h; Stage #2: With sodium nitrite In 1,4-dioxane; water at 0℃; Stage #3: With hydrogen bromide; copper(I) bromide In 1,4-dioxane; water at 0 - 60℃;	Example 11 : Preparation of 2-Bromo-3-nitro-phenol; 2-Amino-3-nitrophenol (commercially available) (24.6g, 160 mmol) is suspended in mixture of water (150 ml) and dioxane (75 ml). At 80⁰C hydrobromic acid (48percent, 85 ml) is added dropwise. This mixture is stirred at reflux temperature for 30 minutes and then cooled to 0⁰C. A solution of sodium nitrite (11.04 g, 160 mmol) in Water (100ml) is added dropwise and the reaction mixture is stirred at 0⁰C for 1 hour. The reaction mixture is added dropwise to a solution of CuBr (26.4g, 184 mmol) in Water (150 ml) and hydrobromic acid (48percent, 85 ml). The resulting suspension is stirred at 0⁰C for 30 minutes and at 60°C for 1 hour. The reaction mixture is cooled to room temperature, diluted with Water and extracted three times with ethyl acetate. <n="71"/>The combined organic phases are dried over sodium sulfate and concentrated. The residue is purified by column chromatography on silica gel (eluent: dichloromethane / cyclohexane 7:3) to give 2-Bromo-3-nitro-phenol (19.5g, 56 percent yield) as a yellow solid. ¹H-NMR (CDCI₃, 400 MHz): 7.50 (d, 1 H), 7.35 (t, 1 H), 7.25 (d, 1 H), 6.05 (s, 1 H) ppm.
56%	Stage #1: With hydrogen bromide In 1,4-dioxane; water at 80℃; Reflux Stage #2: With sodium nitrite In 1,4-dioxane; water at 0℃; Stage #3: With hydrogen bromide In 1,4-dioxane; water at 0 - 60℃;	2-Amino-3-nitrophenol (24.6g, 160 mmol) is suspended in mixture of water (150 ml) and dioxane (75 ml). At 80⁰C hydrobromic acid (48percent, 85 ml) is added dropwise. This mixture is stirred at reflux temperature for 30 minutes and then cooled to 0⁰C. A solution of sodium nitrite (1 1.04 g, 160 mmol) in water (100ml) is added dropwise and the reaction mixture is stirred at 0°C for 1 hour. The reaction mixture is added dropwise to a solution of CuBr (26.4g, 184 mmol) in water (150 ml) and hydrobromic acid (48percent, 85 ml). The resulting suspension is stirred at 0⁰C for 30 minutes and at 60⁰C for 1 hour. The reaction mixture is cooled to room temperature, diluted with water and extracted three times with ethyl acetate. The combined organic phases are dried over sodium sulfate and concentrated. The residue is purified by column <n="67"/>chromatography on silica gel (eluent: dichloromethane / cyclohexane 7:3) to give 2-Bromo-3- nitro-phenol (19.5g, 56 percent yield) as a yellow solid. ¹H-NMR (CDCI₃, 400 MHz): 7.50 (d, 1 H), 7.35 (t, 1 H), 7.25 (d, 1 H), 6.05 (s, 1 H) ppm.
45%	Stage #1: With hydrogen bromide In 1,4-dioxane; water for 0.25 h; Heating / reflux Stage #2: With sodium nitrite In 1,4-dioxane; water at 0℃; for 0.25 h; Stage #3: With copper(I) bromide In 1,4-dioxane; water at 0 - 60℃; for 0.5 h;	2-Amino-3-nitrophenol B1 (5 g; 32.4 MMOL) was dissolved in H20 (29.5 ML) and 1,4- dioxane (14.7 mL). The mixture was heated to reflux and hydrobromic acid (48percent; 16.7 mL; 147 MMOL) was added dropwise over a period of 20 min. Upon completion of the addition, the reflux was maintained an additional 15 min. The reaction was cooled to 0 C (ice bath), and sodium nitrite (2.23 g; 32.3 MMOL) in H20 (20 mL) was added over a period of 30 min. The stirring was continued for 15 min at 0 C, then the mixture was transferred to a jacketed dropping FUNNEL (0 C) and added dropwise to a stirred mixture of Cu (I) Br (5.34 g; 37.2 MMOL) in H20 (29.5 mL) and HBr (48percent; 16.7 mL; 147 MMOL) at 0°C. The reaction was stirred for 15 min at 0°C, warmed to 60 C, stirred for an additional 15 min, cooled to room temperature, and left to stir overnight. The reaction mixture was transferred to a separatory funnel and extracted with ether (3x 150 mL). The organic layers were combined, washed with brine (1X), dried (Na2SO), filtered and concentrated to afford the crude product (7. 99 g) as a red-brown oil. The crude material was purified by flash column chromatography (1: 25 ultra pure silica gel, 230-400 mesh, 40-60 mm, 60 angstroms; CH2CL2AS the solvent) to afford pure 2-bromo-3-nitrophenol B2 (45percent; 3.16 g) as an orange-brown solid. MS 217. 8 (MH) . Homogeneity by HPLC (TFA) 220 nm: 97percent.

45%	Stage #1: With hydrogen bromide In 1,4-dioxane; water for 0.583333 h; Heating / reflux Stage #2: With sodium nitrite In 1,4-dioxane; water at 0℃; for 0.75 h; Stage #3: With hydrogen bromide; copper(I) bromide In 1,4-dioxane; water at 0 - 60℃; for 0.5 h;	Step A:; 2-Amino-3-nitrophenol 1b1 (5 g; 32.4 mmol) was dissolved in H₂O (29.5 ml)and 1,4-dioxane (14.7 mL). The mixture was heated to reflux and hydrobromic acid(48percent; 16.7 mL; 147 mmol) was added dropwise over a period of 20 min. Uponcompletion of the addition, the reflux was maintained an additional 15 min. Thereaction was cooled to 0°C (ice bath), and sodium nitrite (2.23 g; 32.3 mmol) in H₂O(20 mL) was added over a period of 30 min. The stirring was continued for 15 min. at0°C, the mixture transferred to a jacketed dropping funnel (0°C) and added dropwiseto a stirred mixture of Cu(l)Br (5.34 g; 37.2 mmol) in H₂O (29.5 mL) and HBr (48percent;16.7 mL; 147 mmol) at 0°C. The reaction was stirred for 15 min. at 0°C, warmed to60°C, stirred for an additional 15 min., cooled to room temperature, and left to stirovernight. The reaction mixture was transferred to a separatory funnel and extractedwith ether (3 X 150 mL). The organic layers were combined, washed with brine (1 X),dried (Na₂SO₄), filtered and concentrated to afford the crude product (7.99 g) as a red-brown oil. The crude material was purified by flash column chromatography (1:25 ultrapure silica gel, 230-400 mesh, 40-60mm, 60 angstroms; CH₂CI₂ as the solvent) toafford pure 2-bromo-3-nitrophenol 1b2 (45percent; 3.16 g) as an orange-brown solid. MS217.8 (MM)'. Homogeneity by HPLC (TFA) (at) 220 nm: 97percent.
45%	Stage #1: With hydrogen bromide In 1,4-dioxane; water for 0.583333 h; Heating / reflux Stage #2: With sodium nitrite In 1,4-dioxane; water at 0℃; for 0.75 h; Stage #3: With hydrogen bromide; copper(I) bromide In 1,4-dioxane; water at 0 - 60℃;	2-Amino-3-nitrophenol 1b1 (5 g; 32.4 mmol) was dissolved in H2O (29.5 mL) and 1,4-dioxane (14.7 mL). The mixture was heated to reflux and hydrobromic acid (48percent; 16.7 mL; 147 mmol) was added dropwise over a period of 20 min. Upon completion of the addition, the reflux was maintained an additional 15 min. The reaction was cooled to 0° C. (ice bath), and sodium nitrite (2.23 g; 32.3 mmol) in H2O (20 mL) was added over a period of 30 min. The stirring was continued for 15 min. at 0° C., the mixture transferred to a jacketed dropping funnel (0° C.) and added dropwise to a stirred mixture of Cu(I)Br (5.34 g; 37.2 mmol) in H2O (29.5 mL) and HBr (48percent; 16.7 mL; 147 mmol) at 0° C. The reaction was stirred for 15 min. at 0° C., warmed to 60° C., stirred for an additional 15 min., cooled to room temperature, and left to stir overnight. The reaction mixture was transferred to a separatory funnel and extracted with ether (3150 mL). The organic layers were combined, washed with brine (1), dried (Na2SO4), filtered and concentrated to afford the crude product (7.99 g) as a red-brown oil. The crude material was purified by flash column chromatography (1:25 ultra pure silica gel, 230-400 mesh, 40-60mm, 60 angstroms; CH2Cl2as the solvent) to afford pure 2-bromo-3-nitrophenol 1b2 (45percent; 3.16 g) as an orange-brown solid. MS 217.8 (MH)-. Homogeneity by HPLC (TFA)at;220 nm: 97percent.
45%	Stage #1: With hydrogen bromide In 1,4-dioxane; water for 0.583333 h; Heating / reflux Stage #2: With sodium nitrite In 1,4-dioxane; water at 0℃; for 0.75 h; Stage #3: With copper(I) bromide In 1,4-dioxane; water at 0 - 60℃;	2-Amino-3-nitrophenol 2b1 (5 g; 32.4 mmol) was dissolved in H₂O (29.5 ml)and 1,4-dioxane (14.7 ml). The mixture was heated to reflux and hydrobromic acid(48percent; 16.7 ml 147 mmol) was added dropwise over a period of 20 min. Uponcompletion of the addition, the reflux was maintained an additional 15 min. Thereaction was cooled to 0°C (ice bath), and sodium nitrite (2.23 g; 32.3 mmol) in H₂O(20 mL) was added over a period of 30 min. The stirring was continued for 15 min. at0°C, the mixture transferred to a jacketed dropping funnel (0°C) and added dropwiseto a stirred mixture of Cu(l)Br (5.34 g; 37.2 mmol) in H₂O( 29.5 mL) and HBr (48percent;16.7 mL; 147 mmol) at 0°C. The reaction was stirred for 15 min. at 0°C, warmed to60°C, stirred for an additional 15 min., cooled to room temperature, and left to stirovernight. The reaction mixture was transferred to a separatory funnel and extractedwith ether (3 X 150 mL). The organic layers were combined, washed with brine (1 X),dried (Na₂SO₄), filtered and concentrated to afford the crude product (7.99 g ) as ared-brown oil. The crude material was purified by flash column chromatpgraphy (1:25ultra pure silica gel, 230-400 mesh, 40-60mm, 60 angstroms; CH₂CI₂as the solvent)to afford pure 2-bromo-3-nitrophenol 2b2 (45percent; 3.16 g ) as an orange-brown solid.MS 217.8 (MH)'. Homogeneity by HPLC (TFA) (at) 220 nm: 97percent.
45%	Stage #1: With hydrogen bromide In 1,4-dioxane; water for 0.583333 h; Heating / reflux Stage #2: With sodium nitrite In 1,4-dioxane; water at 0℃; for 0.75 h; Stage #3: With hydrogen bromide; copper(I) bromide In 1,4-dioxane; water at 0 - 60℃;	EXAMPLE 2B; Synthesis of 2-bromo-3-methoxy aniline (2B4); Step A; 2-Amino-3-nitrophenol 2B1 (5 g; 32.4 mmol) was dissolved in H₂O (29.5 mL) and 1 ,4-dioxane (14.7 mL). The mixture was heated to reflux and hydrobromic acid (48percent; 16.7 mL; 147 mmol) was added dropwise over a period of 20 min. Upon completion of the addition, the reflux was maintained an additional 15 min. The reaction was cooled to 0⁰C (ice bath), and sodium nitrite (2.23 g; 32.3 mmol) in H₂O (20 mL) was added over a period of 30 min. The stirring was continued for 15 min. at 0⁰C, the mixture EPO <DP n="36"/>transferred to a jacketed dropping funnel (0⁰C) and added dropwise to a stirred mixture of Cu(I)Br (5.34 g; 37.2 mmol) in H₂O (29.5 mL) and HBr (48percent; 16.7 ml 147 mmol) at 0⁰C. The reaction was stirred for 15 min. at O⁰C, warmed to 60°C, stirred for an additional 15 min., cooled to room temperature, and left to stir overnight. The reaction mixture was transferred to a separatory funnel and extracted with ether (3 X 150 mL). The organic layers were combined, washed with brine (1 X), dried (Na₂SO₄), filtered and concentrated to afford the crude product (7.99 g) as a red-brown oil. The crude material was purified by flash column chromatography (1 :25 ultra pure silica gel, 230-400 mesh, 40-60mm, 60 angstroms; CH₂CI₂ as the solvent) to afford pure 2-bromo-3-nitro-phenol 2B2 (45percent; 3.16 g) as an orange-brown solid. MS 217.8 (MH)-. Homogeneity by HPLC (TFA) (at) 220 nm: 97percent.

Reference： [1] Chemistry - A European Journal, 2017, vol. 23, # 42, p. 9996 - 10000
[2] Patent: JP2005/522501, 2005, A, . Location in patent: Page/Page column 18
[3] Patent: WO2009/92590, 2009, A2, . Location in patent: Page/Page column 69-70
[4] Patent: WO2009/109539, 2009, A2, . Location in patent: Page/Page column 65; 66
[5] Patent: WO2004/103996, 2004, A1, . Location in patent: Page 40
[6] Patent: WO2006/7700, 2006, A1, . Location in patent: Page/Page column 61-62
[7] Patent: US2006/19905, 2006, A1, . Location in patent: Page/Page column 24
[8] Patent: WO2006/85, 2006, A1, . Location in patent: Page/Page column 75-76
[9] Patent: WO2007/9227, 2007, A1, . Location in patent: Page/Page column 34-35
[10] Journal of Organic Chemistry, 1988, vol. 53, # 6, p. 1170 - 1176

5
[ 67853-37-6 ]
[ 101935-40-4 ]

Yield	Reaction Conditions	Operation in experiment
98%	With boron tribromide In dichloromethane at -70 - 20℃; for 26 h; Inert atmosphere	SSynthesis of 2-f2'-Nitro-6'-pyridin-4-yl-biphenyl-4-yloxymethyl)-αuinoline (Example 384)2-Bromo-3-nitrophenol Error. Objects cannot be created from editing field codes.BBr₃ (1.0M in CH₂Cl₂, 88 mL, 88 mmol) was added dropwise over 1 h to a stirred solution of 2-bromo-3-nitroanisole in CH₂Cl₂ (35 mL) under argon at -70 ⁰C. The resulting deep burgundy-colored reaction mixture was allowed to warm up to RT slowly (over 2 h) and stirred at RT for 23 h. The reaction mixture was poured onto 35O g crushed ice and extracted with EtOAc (300 mL). The organic phase was separated, washed with brine (75 mL), and dried over MgSO₄. Concentration and purification by chromatography (5-70percent EtO Ac/heptane) gave the title compound 2-bromo-3-nitrophenol (5.36 g, 98percent) as a yellow solid. ¹H NMR (300 MHz, CDCI3/TMS) δ 7.48 (d, J= 8.1 Hz, IH), 7.37 (t, J = 8.1 Hz, IH), 7.27 (d, J= 8.4 Hz, IH), 6.13 (br s, IH); ¹³C NMR (75 MHz, CDCI3/TMS) δ 153.7, 128.7, 119.8, 117.5, 102.9.

Reference： [1] Patent: WO2009/158467, 2009, A2, . Location in patent: Page/Page column 59-60; 91

6
[ 5344-78-5 ]
[ 205187-37-7 ]
[ 101935-40-4 ]

Yield	Reaction Conditions	Operation in experiment
79%	With boron tribromide In dichloromethane; ethyl acetate	Example 48 2-Bromo-3-isopropoxynitrobenzene BBr₃ (1 M in CH₂ Cl₂, 77 mL, 77 mmol) was added dropwise, over 1 h, to a stirred solution of 4-bromo-3-nitroanisole (5.0 g, 22 mmol) in 30 mL CH₂ Cl₂ at -70° C. under nitrogen. The resulting deep burgundy-colored reaction was stirred overnight (23 h) and then poured onto 300 g crushed ice. EtOAc (250 mL) was added and the organic fraction washed with brine (250 mL), dried (MgSO₄) and concentrated in vacuo to 5.06 g of a yellow-brown solid. Purification by column chromatography (EtOAc/hexane, gradient elution 5:95 to 15:85) afforded 3.77 g (79percent) of 2-bromo-3-nitrophenol as a yellow solid: TLC (EtOAc/hesane 20:80) R_f =0.12; HPLC (T_r =12.2); ¹ H-NMR (CDCl₃) δ 5.57 (s, 1H, --OH), δ 6.95 (dd, J=8 Hz, J=3 Hz, 1H), δ 7.36 (d, J=3 Hz, 1H), δ 7.58 (d, J=8 Hz, 1H); MS m/z (relative intensity) 218 (MH⁺, 100), 220 (MH⁺ +2.56). Anal. Calcd. for C₆ H₄ BrNO₃: C, 33.06; H, 1.85; N, 6.42; Br, 36.65 Found: C, 33.14; H, 1.86; N, 6.38; Br, 36.57.

Reference： [1] Patent: US6110961, 2000, A,

7
[ 7486-35-3 ]
[ 101935-40-4 ]
[ 90481-68-8 ]

Reference： [1] Tetrahedron, 2018, vol. 74, # 21, p. 2547 - 2560

8
[ 7486-35-3 ]
[ 112970-61-3 ]
[ 101935-40-4 ]
[ 112970-62-4 ]

Reference： [1] Tetrahedron, 2018, vol. 74, # 21, p. 2547 - 2560

9
[ 7486-35-3 ]
[ 112970-61-3 ]
[ 101935-40-4 ]
[ 112970-62-4 ]

Reference： [1] Tetrahedron, 2018, vol. 74, # 21, p. 2547 - 2560

10
[ 7486-35-3 ]
[ 101935-40-4 ]

Reference： [1] Tetrahedron, 2018, vol. 74, # 21, p. 2547 - 2560

11
[ 13073-25-1 ]
[ 101935-40-4 ]

Reference： [1] Tetrahedron, 2018, vol. 74, # 21, p. 2547 - 2560

12
[ 13073-25-1 ]
[ 101935-40-4 ]

Reference： [1] Tetrahedron, 2018, vol. 74, # 21, p. 2547 - 2560

13
[ 554-84-7 ]
[ 7726-95-6 ]
[ 101935-40-4 ]

Reference： [1] Chemische Berichte, 1892, vol. 25, p. 552

14
[ 101935-40-4 ]
[ 100367-36-0 ]

Yield	Reaction Conditions	Operation in experiment
43.9%	With iron; acetic acid In ethanolReflux	[00408] 2-Bromo-3-nitro-phenol (3.35 g, 15.4 mmol), acetic acid (35 mL) and iron powder(4.5 g, 77.2 mmol) were stirred in ethanol (50 mL) under reflux overnight. The mixture was diluted with 1 00m1 of water and neutralised with potassium carbonate before extraction with DCM. The organics were dried with sodium sulfate and concentrated in vacuo to leave the crude product as a brown oil. This was dry-packed on to silica and purified by columnchromatography using a 0-50percent gradient of ethyl acetate in isohexane. The resulting fragments were concentrated in vacuo to give 3-amino-2-bromo-phenol (1 .27 g, 6.75 mmol, 43.9percent) as a pale yellow solid.[00409] 1H NMR (DMSO-d6): O 7.02 (t, J = 8.0 Hz, 1H), 6.45 (dd, J= 1.6 and 8.0 Hz,1 H), 6.38 (dd, J = 1 .6 and 8.0 Hz, 1 H) 5.44 (bs, 1 H), 4.89 (bs, 2H).

Reference： [1] Journal of Organic Chemistry, 1988, vol. 53, # 6, p. 1170 - 1176
[2] Chemistry - A European Journal, 2017, vol. 23, # 42, p. 9996 - 10000
[3] Patent: WO2015/79251, 2015, A1, . Location in patent: Paragraph 00408; 00409

15
[ 101935-40-4 ]
[ 170729-16-5 ]

Reference： [1] Tetrahedron Letters, 2007, vol. 48, # 17, p. 3039 - 3041

[ 101935-40-4 ] Synthesis Path-Downstream 1~77

1
[ 358-23-6 ]
[ 101935-40-4 ]
[ 112970-61-3 ]

Reference： [1]Journal of Organic Chemistry,1988,vol. 53,p. 1170 - 1176

2
[ 603-85-0 ]
[ 101935-40-4 ]

Yield	Reaction Conditions	Operation in experiment
56%		Example 11 : Preparation of 2-Bromo-3-nitro-phenol; 2-Amino-3-nitrophenol (commercially available) (24.6g, 160 mmol) is suspended in mixture of water (150 ml) and dioxane (75 ml). At 800C hydrobromic acid (48%, 85 ml) is added dropwise. This mixture is stirred at reflux temperature for 30 minutes and then cooled to 00C. A solution of sodium nitrite (11.04 g, 160 mmol) in Water (100ml) is added dropwise and the reaction mixture is stirred at 00C for 1 hour. The reaction mixture is added dropwise to a solution of CuBr (26.4g, 184 mmol) in Water (150 ml) and hydrobromic acid (48%, 85 ml). The resulting suspension is stirred at 00C for 30 minutes and at 60C for 1 hour. The reaction mixture is cooled to room temperature, diluted with Water and extracted three times with ethyl acetate. <n="71"/>The combined organic phases are dried over sodium sulfate and concentrated. The residue is purified by column chromatography on silica gel (eluent: dichloromethane / cyclohexane 7:3) to give 2-Bromo-3-nitro-phenol (19.5g, 56 % yield) as a yellow solid. 1H-NMR (CDCI3, 400 MHz): 7.50 (d, 1 H), 7.35 (t, 1 H), 7.25 (d, 1 H), 6.05 (s, 1 H) ppm.
56%		2-Amino-3-nitrophenol (24.6g, 160 mmol) is suspended in mixture of water (150 ml) and dioxane (75 ml). At 800C hydrobromic acid (48%, 85 ml) is added dropwise. This mixture is stirred at reflux temperature for 30 minutes and then cooled to 00C. A solution of sodium nitrite (1 1.04 g, 160 mmol) in water (100ml) is added dropwise and the reaction mixture is stirred at 0C for 1 hour. The reaction mixture is added dropwise to a solution of CuBr (26.4g, 184 mmol) in water (150 ml) and hydrobromic acid (48%, 85 ml). The resulting suspension is stirred at 00C for 30 minutes and at 600C for 1 hour. The reaction mixture is cooled to room temperature, diluted with water and extracted three times with ethyl acetate. The combined organic phases are dried over sodium sulfate and concentrated. The residue is purified by column <n="67"/>chromatography on silica gel (eluent: dichloromethane / cyclohexane 7:3) to give 2-Bromo-3- nitro-phenol (19.5g, 56 % yield) as a yellow solid. 1H-NMR (CDCI3, 400 MHz): 7.50 (d, 1 H), 7.35 (t, 1 H), 7.25 (d, 1 H), 6.05 (s, 1 H) ppm.
45%		2-Amino-3-nitrophenol B1 (5 g; 32.4 MMOL) was dissolved in H20 (29.5 ML) and 1,4- dioxane (14.7 mL). The mixture was heated to reflux and hydrobromic acid (48%; 16.7 mL; 147 MMOL) was added dropwise over a period of 20 min. Upon completion of the addition, the reflux was maintained an additional 15 min. The reaction was cooled to 0 C (ice bath), and sodium nitrite (2.23 g; 32.3 MMOL) in H20 (20 mL) was added over a period of 30 min. The stirring was continued for 15 min at 0 C, then the mixture was transferred to a jacketed dropping FUNNEL (0 C) and added dropwise to a stirred mixture of Cu (I) Br (5.34 g; 37.2 MMOL) in H20 (29.5 mL) and HBr (48%; 16.7 mL; 147 MMOL) at 0C. The reaction was stirred for 15 min at 0C, warmed to 60 C, stirred for an additional 15 min, cooled to room temperature, and left to stir overnight. The reaction mixture was transferred to a separatory funnel and extracted with ether (3x 150 mL). The organic layers were combined, washed with brine (1X), dried (Na2SO), filtered and concentrated to afford the crude product (7. 99 g) as a red-brown oil. The crude material was purified by flash column chromatography (1: 25 ultra pure silica gel, 230-400 mesh, 40-60 mm, 60 angstroms; CH2CL2AS the solvent) to afford pure 2-bromo-3-nitrophenol B2 (45%; 3.16 g) as an orange-brown solid. MS 217. 8 (MH) . Homogeneity by HPLC (TFA) 220 nm: 97%.

45%		Step A:; 2-Amino-3-nitrophenol 1b1 (5 g; 32.4 mmol) was dissolved in H2O (29.5 ml)and 1,4-dioxane (14.7 mL). The mixture was heated to reflux and hydrobromic acid(48%; 16.7 mL; 147 mmol) was added dropwise over a period of 20 min. Uponcompletion of the addition, the reflux was maintained an additional 15 min. Thereaction was cooled to 0C (ice bath), and sodium nitrite (2.23 g; 32.3 mmol) in H2O(20 mL) was added over a period of 30 min. The stirring was continued for 15 min. at0C, the mixture transferred to a jacketed dropping funnel (0C) and added dropwiseto a stirred mixture of Cu(l)Br (5.34 g; 37.2 mmol) in H2O (29.5 mL) and HBr (48%;16.7 mL; 147 mmol) at 0C. The reaction was stirred for 15 min. at 0C, warmed to60C, stirred for an additional 15 min., cooled to room temperature, and left to stirovernight. The reaction mixture was transferred to a separatory funnel and extractedwith ether (3 X 150 mL). The organic layers were combined, washed with brine (1 X),dried (Na2SO4), filtered and concentrated to afford the crude product (7.99 g) as a red-brown oil. The crude material was purified by flash column chromatography (1:25 ultrapure silica gel, 230-400 mesh, 40-60mm, 60 angstroms; CH2CI2 as the solvent) toafford pure 2-bromo-3-nitrophenol 1b2 (45%; 3.16 g) as an orange-brown solid. MS217.8 (MM)'. Homogeneity by HPLC (TFA) (at) 220 nm: 97%.
45%		2-Amino-3-nitrophenol 1b1 (5 g; 32.4 mmol) was dissolved in H2O (29.5 mL) and 1,4-dioxane (14.7 mL). The mixture was heated to reflux and hydrobromic acid (48%; 16.7 mL; 147 mmol) was added dropwise over a period of 20 min. Upon completion of the addition, the reflux was maintained an additional 15 min. The reaction was cooled to 0 C. (ice bath), and sodium nitrite (2.23 g; 32.3 mmol) in H2O (20 mL) was added over a period of 30 min. The stirring was continued for 15 min. at 0 C., the mixture transferred to a jacketed dropping funnel (0 C.) and added dropwise to a stirred mixture of Cu(I)Br (5.34 g; 37.2 mmol) in H2O (29.5 mL) and HBr (48%; 16.7 mL; 147 mmol) at 0 C. The reaction was stirred for 15 min. at 0 C., warmed to 60 C., stirred for an additional 15 min., cooled to room temperature, and left to stir overnight. The reaction mixture was transferred to a separatory funnel and extracted with ether (3150 mL). The organic layers were combined, washed with brine (1), dried (Na2SO4), filtered and concentrated to afford the crude product (7.99 g) as a red-brown oil. The crude material was purified by flash column chromatography (1:25 ultra pure silica gel, 230-400 mesh, 40-60mm, 60 angstroms; CH2Cl2as the solvent) to afford pure 2-bromo-3-nitrophenol 1b2 (45%; 3.16 g) as an orange-brown solid. MS 217.8 (MH)-. Homogeneity by HPLC (TFA)a220 nm: 97%.
45%		2-Amino-3-nitrophenol 2b1 (5 g; 32.4 mmol) was dissolved in H2O (29.5 ml)and 1,4-dioxane (14.7 ml). The mixture was heated to reflux and hydrobromic acid(48%; 16.7 ml 147 mmol) was added dropwise over a period of 20 min. Uponcompletion of the addition, the reflux was maintained an additional 15 min. Thereaction was cooled to 0C (ice bath), and sodium nitrite (2.23 g; 32.3 mmol) in H2O(20 mL) was added over a period of 30 min. The stirring was continued for 15 min. at0C, the mixture transferred to a jacketed dropping funnel (0C) and added dropwiseto a stirred mixture of Cu(l)Br (5.34 g; 37.2 mmol) in H2O( 29.5 mL) and HBr (48%;16.7 mL; 147 mmol) at 0C. The reaction was stirred for 15 min. at 0C, warmed to60C, stirred for an additional 15 min., cooled to room temperature, and left to stirovernight. The reaction mixture was transferred to a separatory funnel and extractedwith ether (3 X 150 mL). The organic layers were combined, washed with brine (1 X),dried (Na2SO4), filtered and concentrated to afford the crude product (7.99 g ) as ared-brown oil. The crude material was purified by flash column chromatpgraphy (1:25ultra pure silica gel, 230-400 mesh, 40-60mm, 60 angstroms; CH2CI2as the solvent)to afford pure 2-bromo-3-nitrophenol 2b2 (45%; 3.16 g ) as an orange-brown solid.MS 217.8 (MH)'. Homogeneity by HPLC (TFA) (at) 220 nm: 97%.
45%		EXAMPLE 2B; Synthesis of 2-bromo-3-methoxy aniline (2B4); Step A; 2-Amino-3-nitrophenol 2B1 (5 g; 32.4 mmol) was dissolved in H2O (29.5 mL) and 1 ,4-dioxane (14.7 mL). The mixture was heated to reflux and hydrobromic acid (48%; 16.7 mL; 147 mmol) was added dropwise over a period of 20 min. Upon completion of the addition, the reflux was maintained an additional 15 min. The reaction was cooled to 00C (ice bath), and sodium nitrite (2.23 g; 32.3 mmol) in H2O (20 mL) was added over a period of 30 min. The stirring was continued for 15 min. at 00C, the mixture EPO <DP n="36"/>transferred to a jacketed dropping funnel (00C) and added dropwise to a stirred mixture of Cu(I)Br (5.34 g; 37.2 mmol) in H2O (29.5 mL) and HBr (48%; 16.7 ml 147 mmol) at 00C. The reaction was stirred for 15 min. at O0C, warmed to 60C, stirred for an additional 15 min., cooled to room temperature, and left to stir overnight. The reaction mixture was transferred to a separatory funnel and extracted with ether (3 X 150 mL). The organic layers were combined, washed with brine (1 X), dried (Na2SO4), filtered and concentrated to afford the crude product (7.99 g) as a red-brown oil. The crude material was purified by flash column chromatography (1 :25 ultra pure silica gel, 230-400 mesh, 40-60mm, 60 angstroms; CH2CI2 as the solvent) to afford pure 2-bromo-3-nitro-phenol 2B2 (45%; 3.16 g) as an orange-brown solid. MS 217.8 (MH)-. Homogeneity by HPLC (TFA) (at) 220 nm: 97%.

Reference： [1]Chemistry - A European Journal,2017,vol. 23,p. 9996 - 10000
[2]Patent: JP2005/522501,2005,A .Location in patent: Page/Page column 18
[3]Patent: WO2009/92590,2009,A2 .Location in patent: Page/Page column 69-70
[4]Patent: WO2009/109539,2009,A2 .Location in patent: Page/Page column 65; 66
[5]Patent: WO2004/103996,2004,A1 .Location in patent: Page 40
[6]Patent: WO2006/7700,2006,A1 .Location in patent: Page/Page column 61-62
[7]Patent: US2006/19905,2006,A1 .Location in patent: Page/Page column 24
[8]Patent: WO2006/85,2006,A1 .Location in patent: Page/Page column 75-76
[9]Patent: WO2007/9227,2007,A1 .Location in patent: Page/Page column 34-35
[10]Journal of Organic Chemistry,1988,vol. 53,p. 1170 - 1176

3
[ 101935-40-4 ]
[ 100367-36-0 ]

Yield	Reaction Conditions	Operation in experiment
43.9%	With iron; acetic acid; In ethanol;Reflux;	[00408] 2-Bromo-3-nitro-phenol (3.35 g, 15.4 mmol), acetic acid (35 mL) and iron powder(4.5 g, 77.2 mmol) were stirred in ethanol (50 mL) under reflux overnight. The mixture was diluted with 1 00m1 of water and neutralised with potassium carbonate before extraction with DCM. The organics were dried with sodium sulfate and concentrated in vacuo to leave the crude product as a brown oil. This was dry-packed on to silica and purified by columnchromatography using a 0-50% gradient of ethyl acetate in isohexane. The resulting fragments were concentrated in vacuo to give 3-amino-2-bromo-phenol (1 .27 g, 6.75 mmol, 43.9%) as a pale yellow solid.[00409] 1H NMR (DMSO-d6): O 7.02 (t, J = 8.0 Hz, 1H), 6.45 (dd, J= 1.6 and 8.0 Hz,1 H), 6.38 (dd, J = 1 .6 and 8.0 Hz, 1 H) 5.44 (bs, 1 H), 4.89 (bs, 2H).

Reference： [1]Journal of Organic Chemistry,1988,vol. 53,p. 1170 - 1176
[2]Chemistry - A European Journal,2017,vol. 23,p. 9996 - 10000
[3]Patent: WO2015/79251,2015,A1 .Location in patent: Paragraph 00408; 00409

4
[ 101935-40-4 ]
[ 108-24-7 ]
[ 112970-42-0 ]

Reference： [1]Journal of Organic Chemistry,1988,vol. 53,p. 1170 - 1176

5
[ 101935-40-4 ]
[ 77-78-1 ]
[ 67853-37-6 ]

Reference： [1]Journal of Organic Chemistry,1988,vol. 53,p. 1170 - 1176

6
[ 101935-40-4 ]
[ 7486-35-3 ]
[ 195992-07-5 ]

Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 3039 - 3041
[2]Journal of Organic Chemistry,1997,vol. 62,p. 5838 - 5845

7
[ 5162-44-7 ]
[ 101935-40-4 ]
[ 226895-32-5 ]

Reference： [1]Tetrahedron Letters,1999,vol. 40,p. 3657 - 3660
[2]Tetrahedron,2005,vol. 61,p. 3637 - 3649

8
[ 554-84-7 ]
[ 7726-95-6 ]
[ 101935-40-4 ]

Reference： [1]Chemische Berichte,1892,vol. 25,p. 552

9
[ 101935-40-4 ]
[ 105685-39-0 ]

Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 3039 - 3041

10
[ 101935-40-4 ]
[ 846037-68-1 ]

Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 3039 - 3041

11
[ 101935-40-4 ]
[ 170729-16-5 ]

Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 3039 - 3041

12
[ 101935-40-4 ]
[ 846037-69-2 ]

Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 3039 - 3041

13
[ 101935-40-4 ]
3,5-dihydro-2H-pyrano<4,3,2-cd>indole [ No CAS ]

Reference： [1]Tetrahedron Letters,1999,vol. 40,p. 3657 - 3660
[2]Tetrahedron Letters,1999,vol. 40,p. 3657 - 3660

14
[ 101935-40-4 ]
2-bromo-3-but-3-enyloxy-phenylamine [ No CAS ]

Reference： [1]Tetrahedron Letters,1999,vol. 40,p. 3657 - 3660

15
[ 101935-40-4 ]
[ 226895-33-6 ]

Reference： [1]Tetrahedron Letters,1999,vol. 40,p. 3657 - 3660

16
[ 101935-40-4 ]
[ 2380-94-1 ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 5838 - 5845
[2]Journal of Organic Chemistry,1988,vol. 53,p. 1170 - 1176

17
[ 101935-40-4 ]
[ 4837-90-5 ]

Reference： [1]Journal of Organic Chemistry,1988,vol. 53,p. 1170 - 1176

18
[ 101935-40-4 ]
[ 112970-44-2 ]

Reference： [1]Journal of Organic Chemistry,1988,vol. 53,p. 1170 - 1176

19
[ 101935-40-4 ]
[ 112970-73-7 ]

Reference： [1]Journal of Organic Chemistry,1988,vol. 53,p. 1170 - 1176

20
[ 101935-40-4 ]
[ 112970-71-5 ]

Reference： [1]Journal of Organic Chemistry,1988,vol. 53,p. 1170 - 1176

21
[ 101935-40-4 ]
[ 112970-45-3 ]

Reference： [1]Journal of Organic Chemistry,1988,vol. 53,p. 1170 - 1176

22
[ 101935-40-4 ]
[ 112970-63-5 ]

Reference： [1]Journal of Organic Chemistry,1988,vol. 53,p. 1170 - 1176

23
[ 101935-40-4 ]
[ 68900-04-9 ]

Reference： [1]Journal of Organic Chemistry,1988,vol. 53,p. 1170 - 1176

24
[ 101935-40-4 ]
[ 112970-67-9 ]

Reference： [1]Journal of Organic Chemistry,1988,vol. 53,p. 1170 - 1176

25
[ 101935-40-4 ]
[ 112970-46-4 ]

Reference： [1]Journal of Organic Chemistry,1988,vol. 53,p. 1170 - 1176

26
[ 101935-40-4 ]
[ 112970-49-7 ]

Reference： [1]Journal of Organic Chemistry,1988,vol. 53,p. 1170 - 1176

27
[ 101935-40-4 ]
[ 112970-54-4 ]

Reference： [1]Journal of Organic Chemistry,1988,vol. 53,p. 1170 - 1176

28
[ 101935-40-4 ]
[ 112970-62-4 ]

Reference： [1]Journal of Organic Chemistry,1988,vol. 53,p. 1170 - 1176

29
[ 101935-40-4 ]
[ 112970-55-5 ]

Reference： [1]Journal of Organic Chemistry,1988,vol. 53,p. 1170 - 1176

30
[ 101935-40-4 ]
[ 112970-50-0 ]

Reference： [1]Journal of Organic Chemistry,1988,vol. 53,p. 1170 - 1176

31
[ 101935-40-4 ]
[ 112970-68-0 ]

Reference： [1]Journal of Organic Chemistry,1988,vol. 53,p. 1170 - 1176

32
[ 101935-40-4 ]
[ 112970-72-6 ]

Reference： [1]Journal of Organic Chemistry,1988,vol. 53,p. 1170 - 1176

33
[ 101935-40-4 ]
[ 112970-64-6 ]

Reference： [1]Journal of Organic Chemistry,1988,vol. 53,p. 1170 - 1176

34
[ 101935-40-4 ]
[ 74-88-4 ]
[ 67853-37-6 ]

Yield	Reaction Conditions	Operation in experiment
94%	With caesium carbonate; In DMF (N,N-dimethyl-formamide); at 18 - 22℃;	The nitrophenol starting material B2 (3.1 g; 14.2 MMOL) was dissolved in DMF (20 mL) and to the solution was added ground cesium carbonate (5. 58 G ; 17.1 MMOL) followed by Mel (2.6 mL; 42.5 MMOL). The mixture was stirred at room temperature overnight. The DMF was evaporated, the residue taken up in ether (1X 200 mL), washed with water (1X 200 ML), brine (4x 100 mL), dried (MGS04), filtered and evaporated to afford the crude 2-bromo-3-nitroanisole B3 (94%; 3.1 g) as an orange solid. MS 234 (M+2H) + ; Homogeneity by HPLC (TFA) 220 nm: 98%.
94%	With caesium carbonate; In N,N-dimethyl-formamide; at 20℃;	Step B:; The nitrophenol starting material 1b2 (3.1 g; 14.2 mmol) was dissolved inDMF (20 mL) and to the solution was added ground cesium carbonate (5.58 g; 17.1mmol) followed by Mel (2.6 mL; 42.5 mmol). The mixture was stirred at roomtemperature overnight. The DMF was evaporated, the residue taken up in ether (1 X200 mL), washed with water (1 X 200 mL), brine (4 X 100 mL), dried (MgSO4), filteredand evaporated to afford the crude 2-bromo-3-nitroanisole 1b3 (94%; 3.1 g) as anorange solid.MS 234 (M+2H)+; Homogeneity by HPLC (TFA) (at) 220nm: 98%
94%	With caesium carbonate; In DMF (N,N-dimethyl-formamide); at 20℃;	The nitrophenol starting material 1b2 (3.1 g; 14.2 mmol) was dissolved in DMF (20 mL) and to the solution was added ground cesium carbonate (5.58 g; 17.1 mmol) followed by Mel (2.6 mL; 42.5 mmol). The mixture was stirred at room temperature overnight. The DMF was evaporated, the residue taken up in ether (1200 mL), washed with water (1200 mL), brine (4*100 mL), dried (MgSO4), filtered and evaporated to afford the crude 2-bromo-3-nitroanisole 1b3 (94%; 3.1 g) as an orange solid.MS 234 (M+2H)+; Homogeneity by HPLC (TFA)a220 nm: 98%

94%	With caesium carbonate; In N,N-dimethyl-formamide; at 20℃;	The nitrophenol starting material 2b2 (3.1 g; 14.2 mmol) was dissolved inDMF (20 mL) and to the solution was added ground cesium carbonate (5.58 g; 17.1mmol) followed by Mel (2.6 mL; 42.5 mmol). The mixture was stirred at roomtemperature overnight. The DMF was evaporated, the residue taken up in ether (1 X200 mL), washed with water (1 X 200 mL), brine (4 X 100 mL), dried ( MgSO4),filtered and evaporated to afford the crude 2-bromo-3-nitroanisole 2b3 (94%; 3.1 g)as an orange solid.MS 234 (M+2H)+; Homogeneity by HPLC (TFA) (at) 220nm: 98%
94%	With caesium carbonate; In N,N-dimethyl-formamide; at 18 - 22℃;	Step B; The nitrophenol starting material 2B2 (3.1 g; 14.2 mmol) was dissolved in DMF (20 mL) and to the solution was added ground cesium carbonate (5.58 g; 17.1 mmol) followed by MeI (2.6 mL; 42.5 mmol). The mixture was stirred at room temperature overnight. The DMF was evaporated, the residue taken up in ether (1 X 200 mL), washed with water (1 X 200 mL), brine (4 X 100 mL), dried (MgSO4), filtered and evaporated to afford the crude 2-bromo-3-nitroanisole 2B3 (94%; 3.1 g) as an orange solid. MS 234 (M+2H)+; Homogeneity by HPLC (TFA) (at) 220nm: 98%

Reference： [1]Patent: WO2004/103996,2004,A1 .Location in patent: Page 40-41
[2]Patent: WO2006/7700,2006,A1 .Location in patent: Page/Page column 62
[3]Patent: US2006/19905,2006,A1 .Location in patent: Page/Page column 24
[4]Patent: WO2006/85,2006,A1 .Location in patent: Page/Page column 75-76
[5]Patent: WO2007/9227,2007,A1 .Location in patent: Page/Page column 35

35
[ 101935-40-4 ]
[ 107-30-2 ]
[ 615267-06-6 ]

Reference： [1]Patent: JP2005/522501,2005,A .Location in patent: Page/Page column 18-19

36
[ 101935-40-4 ]
[ 6163-58-2 ]
[ 140-88-5 ]
[ 153136-82-4 ]

Yield	Reaction Conditions	Operation in experiment
70%	With triethylamine;palladium diacetate;	Example 206 Ethyl (2E)-3-(2-hydroxy-6-nitrophenyl)prop-2-enoate To a thick-walled vessel was charged with <strong>[101935-40-4]2-bromo-3-nitrophenol</strong> (1.16 g, 5.32 mmol), ethyl acrylate (666 mg, 0.72 mmol), tri-(o-tolyl)phosphine (65 mg, 0.21 mmol), palladium acetate (12 mg, 0.05 mmol), and triethylamine(10 mL). The vessel was then sealed and the resulting mixture was heated to 100 C. overnight. In the morning, the vessel was cooled to rt and the mixture was poured into water. The mixture was acidified with hydrochloric acid and extracted with ethyl acetate (2*50 mL). The combined organic layer was washed with water, brine and dried over anhydrous sodium sulfate. The residue was purified with silica gel flash chromatography by using hexane/ethyl acetate (2/1) as the eluant to give ethyl (2E)-3-(2-hydroxy-6-nitrophenyl)prop-2-enoate (883 mg, 70%): Rf 0.16 (3/1 hexane/ethyl acetate); 1H NMR (CDCl3) delta7.6(d, J=16.1 Hz, 1H), 7.05-7.23 (m, 3H), 6.71 (dd, J=16.1, 0.8 Hz, 1H), 4.18 (q, J=7.1 Hz, 2H), 1.26 (t, J=7.1 Hz, 2H).

Reference： [1]Patent: US2003/87902,2003,A1

37
[ 75-30-9 ]
Cs₂ CO₃ [ No CAS ]
[ 101935-40-4 ]
[ 205187-37-7 ]

Yield	Reaction Conditions	Operation in experiment
3.49 g (97%)	In ethyl acetate;	Cs2 CO3 was added in 3 portions over 15 min to a stirred solution of 2-bromo-3 nitrophenol (3.00 g, 13.8 mmol) and 2-iodopropane (4.79 g, 27.6 mmol) in 50 ml anhydrous DMF cooled to 0 C. under N2. The reaction was allowed to warm to ambient temperature (2 h) and stirred overnight (17 h). EtOAc (250 ml) was added, the reaction mixture washed with water (2*250 ml) and brine (250 ml), dried (Na2 SO4) and concentrated in vacuo to an orange oil (3.78 g). Purification by column chromatography (EtOAc/hexane, 5:95) afforded 3.49 g (97%) of 2-bromo-3-isopropoxynitrobenzene as a yellow oil. TLC (EtOAc/hexane 20:80)Rf =0.12; HPLC (Tr =16.1); 1 H-NMR (CDCl3) d 1.35 (d, J=6 Hz, 6H), delta 4.56 (m, J=6 Hz, 1H), delta 6.95 (dd, J=8 Hz, J=3 Hz, 1H), delta 7.34 (d, J=3 Hz, 1H), delta 7.57 (d, J=8 Hz, 1H): MS m/z (relative intensity) 260 (MH+, 100), 262 (MH+ +2, 72). Anal. Calcd. for C9 H10 BrNO3: C, 41.56; H, 3.88; N, 5.39; Br, 30.72. Found: C, 42.47; H, 3.98; N, 5.24; Br, 30.04.

Reference： [1]Patent: US6110961,2000,A

38
[ 5344-78-5 ]
[ 205187-37-7 ]
[ 101935-40-4 ]

Yield	Reaction Conditions	Operation in experiment
3.77 g (79%)	With boron tribromide; In dichloromethane; ethyl acetate;	Example 48 2-Bromo-3-isopropoxynitrobenzene BBr3 (1 M in CH2 Cl2, 77 mL, 77 mmol) was added dropwise, over 1 h, to a stirred solution of 4-bromo-3-nitroanisole (5.0 g, 22 mmol) in 30 mL CH2 Cl2 at -70 C. under nitrogen. The resulting deep burgundy-colored reaction was stirred overnight (23 h) and then poured onto 300 g crushed ice. EtOAc (250 mL) was added and the organic fraction washed with brine (250 mL), dried (MgSO4) and concentrated in vacuo to 5.06 g of a yellow-brown solid. Purification by column chromatography (EtOAc/hexane, gradient elution 5:95 to 15:85) afforded 3.77 g (79%) of 2-bromo-3-nitrophenol as a yellow solid: TLC (EtOAc/hesane 20:80) Rf =0.12; HPLC (Tr =12.2); 1 H-NMR (CDCl3) delta 5.57 (s, 1H, --OH), delta 6.95 (dd, J=8 Hz, J=3 Hz, 1H), delta 7.36 (d, J=3 Hz, 1H), delta 7.58 (d, J=8 Hz, 1H); MS m/z (relative intensity) 218 (MH+, 100), 220 (MH+ +2.56). Anal. Calcd. for C6 H4 BrNO3: C, 33.06; H, 1.85; N, 6.42; Br, 36.65 Found: C, 33.14; H, 1.86; N, 6.38; Br, 36.57.

Reference： [1]Patent: US6110961,2000,A

39
[ 101935-40-4 ]
[ 1895-39-2 ]
[ 1174315-54-8 ]

Yield	Reaction Conditions	Operation in experiment
91%	With potassium carbonate; In water; N,N-dimethyl-formamide; at 100℃; for 2h;Inert atmosphere;	Example I2: Preparation of 2-Bromo-1-difluoromethoxy-3-nitro-benzene; To a mixture of sodium chlorodifluoro acetate (1.29g, 8.5 mmol) and K2CO3 Jn DMF (5 ml) and Water (1.3 ml) is added 2-Bromo-3-nitro-phenol (0.5 g, 2.3 mmol) dissolved in DMF (5 ml) then heated to 1000C under an Argon atmosphere and stirred for 2 hours. The reaction mixture is cooled to room temperature, diluted with Water and extracted three times with ethyl acetate. The combined organic phases are dried over sodium sulfate and concentrated to yield 2-Bromo- 1-difluoromethoxy-3-nitro-benzene (0.56 g, 91% yield) in pure form. 1H-NMR (CDCI3, 400 MHz): 7.65 (m, 1 H), 7.45 (m, 2H), 6.60 (t, 1 H) ppm.
91%	With potassium carbonate; In water; N,N-dimethyl-formamide; at 100℃; for 2h;	To a mixture of sodium chlorodifluoro acetate (1.29g, 8.5 mmol) and K2CO3 in DMF (5 ml) and water (1.3 ml) is added 2-Bromo-3-nitro-phenol (0.5 g, 2.3 mmol) dissolved in DMF (5 ml) then heated to 1000C under an argon atmosphere and stirred for 2 hours. The reaction mixture is cooled to room temperature, diluted with water and extracted three times with ethyl acetate. The combined organic phases are dried over sodium sulfate and concentrated to yield 2-Bromo- 1-difluoromethoxy-3-nitro-benzene (0.56 g, 91% yield) in pure form. 1H-NMR (CDCI3, 400 MHz): 7.65 (m, 1 H), 7.45 (m, 2H), 6.60 (t, 1 H) ppm.

Reference： [1]Patent: WO2009/92590,2009,A2 .Location in patent: Page/Page column 70
[2]Patent: WO2009/109539,2009,A2 .Location in patent: Page/Page column 66

40
[ 101935-40-4 ]
[ 146631-00-7 ]
[ 1202677-59-5 ]

Yield	Reaction Conditions	Operation in experiment
80%		4'-Benzyloxy-6-nitro-biphenyl-2-ol Error. Objects cannot be created from editing field codes.To a solution of <strong>[101935-40-4]2-bromo-3-nitrophenol</strong> (5.36 g) and 4-benzyloxyphenyl boronic acid (6.73 g) in dioxane (220 mL) was added 2 M aqueous Na2COs solution (55.4 mL) and the mixture was purged with argon. Pd(PPh3 )4 (1.42 g) was added and the mixture was purged again with argon. The reaction mixture was heated to reflux for 24 h. The mixture was cooled to room temperature and the organic solvent was removed under reduced pressure. The residue was diluted with water (150 mL), neutralized with 2 N HCl, filtered through a Celite plug, and washed with EtOAc. The filtrate was extracted with EtOAc (3 x 100 mL). The combined organic phases were washed with brine (50 mL) and dried over MgSO4. Concentration and purification by silica gel chromatography eluting with 5-40% EtO Ac/heptane provided 4'-benzyloxy-6-nitro-biphenyl-2-ol (6.35 g, 80 %) as yellow solid. 1H NMR (300 MHz, CDCI3/TMS) delta 7.52-7.30 (m, 7H), 7.27-7.15 (m, 3H), 7.09 (d, J= 7.8 Hz, 2H), 5.73 (s, IH), 5.09 (s, 2H); 13C NMR (75 MHz, CDCI3/TMS) delta 159.1, 154.1, 149.9, 136.3, 130.4, 128.7, 128.4, 127.9, 127.3, 122.7, 121.8, 119.4, 115.7, 115.5, 70.0.

Reference： [1]Patent: WO2009/158467,2009,A2 .Location in patent: Page/Page column 60; 91-92

41
[ 67853-37-6 ]
[ 101935-40-4 ]

Yield	Reaction Conditions	Operation in experiment
98%	With boron tribromide; In dichloromethane; at -70 - 20℃; for 26h;Inert atmosphere;Product distribution / selectivity;	SSynthesis of 2-f2'-Nitro-6'-pyridin-4-yl-biphenyl-4-yloxymethyl)-alphauinoline (Example 384)2-Bromo-3-nitrophenol Error. Objects cannot be created from editing field codes.BBr3 (1.0M in CH2Cl2, 88 mL, 88 mmol) was added dropwise over 1 h to a stirred solution of 2-bromo-3-nitroanisole in CH2Cl2 (35 mL) under argon at -70 0C. The resulting deep burgundy-colored reaction mixture was allowed to warm up to RT slowly (over 2 h) and stirred at RT for 23 h. The reaction mixture was poured onto 35O g crushed ice and extracted with EtOAc (300 mL). The organic phase was separated, washed with brine (75 mL), and dried over MgSO4. Concentration and purification by chromatography (5-70% EtO Ac/heptane) gave the title compound 2-bromo-3-nitrophenol (5.36 g, 98%) as a yellow solid. 1H NMR (300 MHz, CDCI3/TMS) delta 7.48 (d, J= 8.1 Hz, IH), 7.37 (t, J = 8.1 Hz, IH), 7.27 (d, J= 8.4 Hz, IH), 6.13 (br s, IH); 13C NMR (75 MHz, CDCI3/TMS) delta 153.7, 128.7, 119.8, 117.5, 102.9.

Reference： [1]Patent: WO2009/158467,2009,A2 .Location in patent: Page/Page column 59-60; 91

42
2-(2-bromo-2-propen-1-yl)-3(R)-hydroxy-1-(methoxycarbonyl)-5(R)-methylpyrrolidine [ No CAS ]
[ 101935-40-4 ]
3-(2-bromo-3-nitrophenoxy)-2(R)-(2-bromo-2-propen-1-yl)-1-(methoxycarbonyl)-5(R)-methylpyrrolidine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2015,vol. 80,p. 4783 - 4790

43
1-(t-butoxycarbonyl)-3(R)-hydroxy-5(R)-methyl-2(R)-(2-propen-1-yl)pyrrolidine [ No CAS ]
[ 101935-40-4 ]
2(R)-(2-propen-1-yl)-1-(t-butoxycarbonyl)-3(S)-(2-bromo-3-nitrophenoxy)-5(R)-methylpyrrolidine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2015,vol. 80,p. 4783 - 4790

44
2(R)-(2-bromo-2-propen-1-yl)-3(R)-hydroxy-1-(methoxycarbonyl)pyrrolidine [ No CAS ]
[ 101935-40-4 ]
3(S)-(2-bromo-3-nitrophenyloxy)-2(R)-(2-bromo-2-propen-1-yl)-1-(methoxycarbonyl)pyrrolidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20℃; for 17h;Inert atmosphere;	To a solution of 6 (422 mg, 1.60 mmol) in THF (25 mL) was added triphenylphosphine (1.46 g, 5.58mmol) and <strong>[101935-40-4]2-bromo-3-nitrophenol</strong> (8)[i] (525 mg, 2.41 mmol). The solution was cooled to 0 C, and diisopropylazodicarboxylate (1.26 mL, 6.40 mmol) was added dropwise. The mixture was stirred at ambient temperature for 17h, brine (50 mL) was added, and the resulting mixture was extracted with EtOAc(3x50 mL). The combined organic phases were dried (MgSO4), filtered,and the solvent was removed. The crude product was purified by chromatography on silica gel (CH2Cl2/hexanes, 1:1, then CH2Cl2) to give 9 (530 mg, 1.14 mmol, 71 %) as a pale yellow oil.1HNMR (600 MHz, CDCl3, 65 oC) delta 7.39 (t, J = 8.2 Hz, 1H), 7.34 (dd, J = 8.0, 1.3 Hz, 1H), 7.17 (dd, J = 8.2, 1.1 Hz, 1H), 5.72 (s, 1H), 5.58(d, J = 1.6 Hz, 1H), 4.93 (s, 1H),4.26-4.35 (m, 1H), 3.69-3.79 (m, 1H), 3.72 (s, 3H), 3.57-3.64 (m, 1H), 3.01 (brs, 1H), 2.50 (dd, J = 14.6, 9.7 Hz,1H), 2.22-2.29 (m, 2H); 13C NMR (150 MHz, CDCl3, 65 oC)d 155.2, 154.8, 151.9, 128.9, 128.4, 120.0,118.2, 117.4, 106.4, 81.7, 61.9, 52.2, 44.4, 43.8, 29.1; IR (ATR) 2955, 1693,1533, 1449, 1386, 1357, 1270, 1196, 1121, 1010, 903, 773 cm-1; HRMS (ESI) calcd for C15H16Br2N2NaO5(M+Na+) 484.9324, found 484.9322; [alpha]25D = 30.6± 0.1 (c = 1.0, CHCl3);[i] Krolski, M. E.; Renaldo,A. F.; Rudisill, D. E.; Stille, J. K. J.Org. Chem. 1988, 53, 1170-1176.

Reference： [1]Tetrahedron Letters,2016,vol. 57,p. 2865 - 2867

45
[ 121-43-7 ]
[ 101935-40-4 ]
2-bromo-3-nitrophenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%		In compound <strong>[101935-40-4]2-bromo-3-nitro-phenol</strong> (10g, 45.8mmol) in the dissolved in THF, at -78 C to wherein the slowly dropping 2.5M n-BuLi of (21.9 ml, 54 . 9mmol). Furthermore, the obtained reaction product is stirring 30 minutes. In adding trimethoxy-after (14.2 ml, 137mmol), raising the temperature to room temperature and the resulting reaction product stirring 1 hour. After the reaction is finished, and HCl to the stirring 1 hour, then the resulting reaction product with distilled water and EA extraction. Organic layer using an anhydrous MgSO4drying, and the post for rotary evaporimeter to remove the solvent, the use of methylene chloride and methanol as the solvent through a column chromatography purification of the resulting reaction product, to obtain a target compound 40-6 (5.9g, 59%).

Reference： [1]Patent: CN105358533,2016,A .Location in patent: Paragraph 0410; 0411; 0412; 0413

46
[ 101935-40-4 ]
C₁₆H₁₁NO₃ [ No CAS ]

Reference： [1]Patent: CN105358533,2016,A

47
[ 101935-40-4 ]
C₁₆H₁₃NO [ No CAS ]

Reference： [1]Patent: CN105358533,2016,A

48
[ 101935-40-4 ]
C₂₇H₁₉NO₂ [ No CAS ]

Reference： [1]Patent: CN105358533,2016,A

49
[ 101935-40-4 ]
C₂₇H₁₇NO [ No CAS ]

Reference： [1]Patent: CN105358533,2016,A

50
[ 101935-40-4 ]
C₂₈H₁₆F₃NO₃S [ No CAS ]

Reference： [1]Patent: CN105358533,2016,A

51
[ 101935-40-4 ]
C₄₂H₂₉N [ No CAS ]

Reference： [1]Patent: CN105358533,2016,A

52
[ 101935-40-4 ]
[ 863870-88-6 ]

Reference： [1]Chemistry - A European Journal,2017,vol. 23,p. 9996 - 10000

53
[ 101935-40-4 ]
2,4,6-tribromo-3-(quinolin-8-yl)phenol [ No CAS ]
2,4,6-tribromo-3-(quinolin-8-yl)phenol [ No CAS ]

Reference： [1]Chemistry - A European Journal,2017,vol. 23,p. 9996 - 10000

54
[ 101935-40-4 ]
2-bromo-3-(quinolin-8-yl)phenol [ No CAS ]

Reference： [1]Chemistry - A European Journal,2017,vol. 23,p. 9996 - 10000

55
2-bromo-6-nitrophenyl trifluoromethanesulfonate [ No CAS ]
[ 7486-35-3 ]
[ 101935-40-4 ]
6-ethenyl-2-nitrophenyl trifluoromethanesulfonate [ No CAS ]

Reference： [1]Tetrahedron,2018,vol. 74,p. 2547 - 2560

56
2-bromo-6-nitrophenyl trifluoromethanesulfonate [ No CAS ]
[ 7486-35-3 ]
[ 101935-40-4 ]
[ 90481-68-8 ]

Reference： [1]Tetrahedron,2018,vol. 74,p. 2547 - 2560

57
[ 13073-25-1 ]
[ 101935-40-4 ]
6-ethenyl-2-nitrophenyl trifluoromethanesulfonate [ No CAS ]

Reference： [1]Tetrahedron,2018,vol. 74,p. 2547 - 2560

58
[ 13073-25-1 ]
[ 101935-40-4 ]

Reference： [1]Tetrahedron,2018,vol. 74,p. 2547 - 2560

59
[ 7486-35-3 ]
[ 112970-61-3 ]
o-Bromo-nitrostyrene [ No CAS ]
[ 101935-40-4 ]
[ 112970-62-4 ]

Reference： [1]Tetrahedron,2018,vol. 74,p. 2547 - 2560

60
[ 7486-35-3 ]
[ 112970-61-3 ]
[ 101935-40-4 ]
[ 112970-62-4 ]

Reference： [1]Tetrahedron,2018,vol. 74,p. 2547 - 2560

61
[ 101935-40-4 ]
[ 889097-54-5 ]

Reference： [1]Patent: WO2009/109539,2009,A2

62
[ 101935-40-4 ]
[ 1174315-56-0 ]

Reference： [1]Patent: WO2009/109539,2009,A2

63
[ 101935-40-4 ]
[ 1174315-55-9 ]

Reference： [1]Patent: WO2009/109539,2009,A2

64
[ 101935-40-4 ]
[ 1186383-30-1 ]

Reference： [1]Patent: WO2009/109539,2009,A2

65
[ 101935-40-4 ]
[ 1202677-62-0 ]

Reference： [1]Patent: WO2009/158467,2009,A2

66
[ 101935-40-4 ]
[ 1202677-97-1 ]

Reference： [1]Patent: WO2009/158467,2009,A2

67
[ 101935-40-4 ]
[ 1202677-95-9 ]

Reference： [1]Patent: WO2009/158467,2009,A2

68
[ 101935-40-4 ]
[ 1202677-61-9 ]

Reference： [1]Patent: WO2009/158467,2009,A2

69
[ 101935-40-4 ]
[ 1202677-94-8 ]

Reference： [1]Patent: WO2009/158467,2009,A2

70
[ 101935-40-4 ]
[ 1202677-96-0 ]

Reference： [1]Patent: WO2009/158467,2009,A2

71
[ 101935-40-4 ]
[ 1202677-60-8 ]

Reference： [1]Patent: WO2009/158467,2009,A2

72
[ 101935-40-4 ]
[ 1202661-19-5 ]

Reference： [1]Patent: WO2009/158467,2009,A2

73
[ 101935-40-4 ]
[ 1202676-60-5 ]

Reference： [1]Patent: WO2009/158467,2009,A2

74
[ 101935-40-4 ]
[ 1202661-27-5 ]

Reference： [1]Patent: WO2009/158467,2009,A2

75
[ 101935-40-4 ]
[ 41355-44-6 ]
(2R,3R,4R,5R,6S)-5-acetamido-2-(acetoxymethyl)-6-(2-bromo-3-nitrophenoxy)tetrahydro-2H-pyran-3,4-diyl diacetate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2019,vol. 62,p. 467 - 479

76
[ 101935-40-4 ]
(2R,3R,4R,5R,6S)-5-acetamido-2-(acetoxymethyl)-6-((3'-(methylsulfonamido)-6-nitro-[1,1'-biphenyl]-2-yl)oxy)tetrahydro-2H-pyran-3,4-diyl diacetate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2019,vol. 62,p. 467 - 479

77
[ 101935-40-4 ]
N-((2S,3R,4R,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-((3′-(methylsulfonamido)-6-nitro-[1,1′-biphenyl]-2-yl)oxy)tetrahydro-2H-pyran-3-yl)acetamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2019,vol. 62,p. 467 - 479

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P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
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

[ CAS No. 101935-40-4 ] {[proInfo.proName]}

Quality Control of [ 101935-40-4 ]

Related Doc. of [ 101935-40-4 ]

Product Details of [ 101935-40-4 ]

Calculated chemistry of [ 101935-40-4 ]

Physicochemical Properties

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Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

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Application In Synthesis of [ 101935-40-4 ]

[ 101935-40-4 ] Synthesis Path-Upstream 1~15

[ 101935-40-4 ] Synthesis Path-Downstream 1~77

Pharmaceutical Intermediates of [ 101935-40-4 ]

Faldaprevir Intermediates

Related Functional Groups of [ 101935-40-4 ]

Aryls

Bromides

Nitroes

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Health hazards

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[ 101935-40-4 ]

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[ 101935-40-4 ]