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[ CAS No. 88071-90-3 ] {[proInfo.proName]}

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Chemical Structure| 88071-90-3
Chemical Structure| 88071-90-3
Structure of 88071-90-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 88071-90-3 ]

CAS No. :88071-90-3 MDL No. :MFCD25968335
Formula : C9H8BrNO4 Boiling Point : -
Linear Structure Formula :- InChI Key :FMYMKUZFDVJUIQ-UHFFFAOYSA-N
M.W : 274.07 Pubchem ID :10683691
Synonyms :

Calculated chemistry of [ 88071-90-3 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 4
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 59.38
TPSA : 72.12 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.44 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.78
Log Po/w (XLOGP3) : 2.16
Log Po/w (WLOGP) : 2.12
Log Po/w (MLOGP) : 1.61
Log Po/w (SILICOS-IT) : 0.6
Consensus Log Po/w : 1.66

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.93
Solubility : 0.321 mg/ml ; 0.00117 mol/l
Class : Soluble
Log S (Ali) : -3.31
Solubility : 0.135 mg/ml ; 0.000493 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.11
Solubility : 0.213 mg/ml ; 0.000776 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 3.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.2

Safety of [ 88071-90-3 ]

Signal Word:Danger Class:8
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338-P310-P332+P313-P362-P403+P233-P405-P501 UN#:1759
Hazard Statements:H315-H318-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 88071-90-3 ]

* 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 [ 88071-90-3 ]

[ 88071-90-3 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 24078-21-5 ]
  • [ 88071-90-3 ]
YieldReaction ConditionsOperation in experiment
With bromine; dibenzoyl peroxide; In tetrachloromethane; b) Preparation of methyl 3-bromomethyl-4-nitrobenzoate In a 5-liter three-necked round-bottomed flask equipped with a reflux condenser, overhead stirrer, addition funnel and nitrogen inlet, was placed 220 g of <strong>[24078-21-5]methyl 3-methyl-4-nitrobenzoate</strong>, 2 l of anhydrous carbon tetrachloride and 4 g of benzoyl peroxide. To the resulting solution, irradiated with a 275 watt UV light, was added 198 g of bromine dropwise over a period of 2 hours at reflux. After the addition was complete the reaction mixture was refluxed for an additional 60 hours. The reaction mixture was cooled to room temperature. The solid which formed was separated by suction filtration. This solid (159.1 g) consisted of the expected methyl 3-bromomethyl-4-nitrobenzoate with minor amounts of the starting material. The mother liquors together with another 220 g of <strong>[24078-21-5]methyl 3-methyl-4-nitrobenzoate</strong> and 4 g of benzoyl peroxide were returned to the flask and treated with 198 g of bromine as described above. After the addition was complete the reaction mixture was refluxed another 96 hours, cooled to room temperature and the resulting solid separated by filtration yielding another 252 g of methyl 3-bromomethyl-4-nitrobenzoate.
With bromine; dibenzoyl peroxide; In tetrachloromethane; b) Preparation of methyl 3-bromomethyl-4-nitrobenzoate. In a 5-liter three-necked round-bottomed flask equipped with a reflux condenser, overhead stirrer, addition funnel and nitrogen inlet, was placed 220 g of <strong>[24078-21-5]methyl 3-methyl-4-nitrobenzoate</strong>, 2 l of anhydrous carbon tetrachloride and 4 g of benzoyl peroxide. To the resulting solution, irradiated with a 275 watt UV light, was added 198 g of bromine dropwise over a period of 2 hours at reflux. After the addition was complete the reaction mixture was refluxed for an additional 60 hours. The reaction mixture was cooled to room temperature. The solid which formed was separated by suction filtration. This solid (159.1 g) consisted of the expected methyl 3-bromomethyl-4-nitrobenzoate with minor amounts of the starting material. The mother liquors together with another 220 g of <strong>[24078-21-5]methyl 3-methyl-4-nitrobenzoate</strong> and 4 g of benzoyl peroxide were returned to the flask and treated with 198 g of bromine as described above. After the addition was complete the reaction mixture was refluxed another 96 hours, cooled to room temperature and the resulting solid separated by filtration yielding another 252 g of methyl 3-bromomethyl-4-nitrobenzoate.
The solids were combined yielding a total of 411.1 g of methyl 3-bromomethyl-4-nitrobenzoate with minor amounts of the starting <strong>[24078-21-5]methyl 3-methyl-4-nitrobenzoate</strong> and methyl 3-dibromomethyl-4-nitrobenzoate. This solid was used as such in the next step.
The solids were combined yielding a total of 411.1 g of methyl 3-bromomethyl-4-nitrobenzoate with minor amounts of the starting <strong>[24078-21-5]methyl 3-methyl-4-nitrobenzoate</strong> and methyl 3-dibromomethyl-4-nitrobenzoate. This solid was used as such in the next step.
With bromine; dibenzoyl peroxide; In tetrachloromethane; b) Preparation of methyl 3-bromomethyl-4-nitrobenzoate In a 5-liter three-necked round-bottomed flask equipped with a reflux condenser, overhead stirrer, addition funnel and nitrogen inlet, was placed 220 g of <strong>[24078-21-5]methyl 3-methyl-4-nitrobenzoate</strong>, 2 l of anhydrous carbon tetrachloride and 4 g of benzoyl peroxide. To the resulting solution, irradiated with a 275 watt UV light, was added 198 g of bromine dropwise over a period of 2 hours at reflux. After the addition was complete the reaction mixture was refluxed for an additional 60 hours. The reaction mixture was cooled to room temperature. The solid which formed was separated by suction filtration. This solid (159.1 g) consisted of the expected methyl 3-bromomethyl-4-nitrobenzoate with minor amounts of the starting material. The mother liquors together with another 220 g of <strong>[24078-21-5]methyl 3-methyl-4-nitrobenzoate</strong> and 4 g of benzoyl peroxide were returned to the flask and treated with 198 g of bromine as described above. After the addition was complete the reaction mixture was refluxed another 96 hours, cooled to room temperature and the resulting solid separated by filtration yielding another 252 g of methyl 3-bromomethyl-4-nitrobenzoate.
With bromine; dibenzoyl peroxide; In tetrachloromethane; b) Preparation of methyl 3-bromomethyl-4-nitrobenzoate. In a 5-liter three-necked round-bottomed flask equipped with a reflux condenser, overhead stirrer, addition funnel and nitrogen inlet, was placed 220 g of <strong>[24078-21-5]methyl 3-methyl-4-nitrobenzoate</strong>, 2 l of anhydrous carbon tetrachloride and 4 g of benzoyl peroxide. To the resulting solution, irradiated with a 275 watt UV light, was added 198 g of bromine dropwise over a period of 2 hours at reflux. After the addition was complete the reaction mixture was refluxed for an additional 60 hours. The reaction mixture was cooled to room temperature. The solid which formed was separated by suction filtration. This solid (159.1 g) consisted of the expected methyl 3-bromomethyl-4-nitrobenzoate with minor amounts of the starting material. The mother liquors together with another 220 g of <strong>[24078-21-5]methyl 3-methyl-4-nitrobenzoate</strong> and 4 g of benzoyl peroxide were returned to the flask and treated with 198 g of bromine as described above. After the addition was complete the reaction mixture was refluxed another 96 hours, cooled to room temperature and the resulting solid separated by filtration yielding another 252 g of methyl 3-bromomethyl-4-nitrobenzoate.
The solids were combined yielding a total of 411.1 g of methyl 3-bromomethyl-4-nitrobenzoate with minor amounts of the starting <strong>[24078-21-5]methyl 3-methyl-4-nitrobenzoate</strong> and methyl 3-dibromomethyl-4-nitrobenzoate. This solid was used as such in the next step.
With bromine; dibenzoyl peroxide; In tetrachloromethane; b) Preparation of methyl 3-bromomethyl-4-nitrobenzoate. In a 5-liter three-necked round-bottomed flask equipped with a reflux condenser, overhead stirrer, addition funnel and nitrogen inlet, was placed 220 g of <strong>[24078-21-5]methyl 3-methyl-4-nitrobenzoate</strong>, 2 l of anhydrous carbon tetrachloride and 4 g of benzoyl peroxide. To the resulting solution, irradiated with a 275 watt UV light, was added 198 g of bromine dropwise over a period of 2 hours at reflux. After the addition was complete the reaction mixture was refluxed for an additional 60 hours. The reaction mixture was cooled to room temperature. The solid which formed was separated by suction filtration. This solid (159.1 g) consisted of the expected methyl 3-bromomethyl-4-nitrobenzoate with minor amounts of the starting material. The mother liquors together with another 220 g of <strong>[24078-21-5]methyl 3-methyl-4-nitrobenzoate</strong> and 4 g of benzoyl peroxide were returned to the flask and treated with 198 g of bromine as described above. After the addition was complete the reaction mixture was refluxed another 96 hours, cooled to room temperature and the resulting solid separated by filtration yielding another 252 g of methyl 3-bromomethyl-4-nitrobenzoate.
The solids were combined yielding a total of 411.1 g of methyl 3-bromomethyl-4-nitrobenzoate with minor amounts of the starting <strong>[24078-21-5]methyl 3-methyl-4-nitrobenzoate</strong> and methyl 3-dibromomethyl-4-nitrobenzoate. This solid was used as such in the next step.
The solids were combined yielding a total of 411.1 g of methyl 3-bromomethyl-4-nitrobenzoate with minor amounts of the starting <strong>[24078-21-5]methyl 3-methyl-4-nitrobenzoate</strong> and methyl 3-dibromomethyl-4-nitrobenzoate. This solid was used as such in the next step.
With bromine; dibenzoyl peroxide; b) Preparation of methyl 3-bromomethyl-4-nitrobenzoate. In a 5-liter three-necked round-bottomed flask equipped with a reflux condenser, overhead stirrer, addition funnel and nitrogen inlet, was placed 220 g of <strong>[24078-21-5]methyl 3-methyl-4-nitrobenzoate</strong>, 2 1 of anhydrous carbon tetrachloride and 4 g of benzoyl peroxide. To the resulting solution, irradiated with a 275 watt UV light, was added 198 g of bromine dropwise over a period of 2 hours at reflux. After the addition was complete the reaction mixture was refluxed for an additional 60 hours. The reaction mixture was cooled to room temperature. The solid which formed was separated by suction filtration. This solid (159.1 g) consisted of the expected methyl 3-bromomethyl-4-nitrobenzoate with minor amounts of the starting material. The mother liquors together with another 220 g of <strong>[24078-21-5]methyl 3-methyl-4-nitrobenzoate</strong> and 4 g of benzoyl peroxide were returned to the flask and treated with 198 g of bromine as described above. After the addition was complete the reaction mixture was refluxed another 96 hours, cooled to room temperature and the resulting solid separated by filtration yielding another 252 g of methyl 3-bromomethyl-4-nitrobenzoate.
With bromine; dibenzoyl peroxide; In tetrachloromethane; b) Preparation of methyl 3-bromomethyl-4-nitrobenzoate. In a 5-liter three-necked round-bottomed flask equipped with a reflux condenser, overhead stirrer, addition funnel and nitrogen inlet, was placed 220 g of <strong>[24078-21-5]methyl 3-methyl-4-nitrobenzoate</strong>, 2 l of anhydrous carbon tetrachloride and 4 g of benzoyl peroxide. To the resulting solution, irradiated with a 275 watt UV light, was added 198 g of bromine dropwise over a period of 2 hours at reflux. After the addition was complete the reaction mixture was refluxed for an additional 60 hours. The reaction mixture was cooled to room temperature. The solid which formed was separated by suction filtration. This solid (159.1 g) consisted of the expected methyl 3-bromomethyl-4-nitrobenzoate with minor amounts of the starting material. The mother liquors together with another 220 g of <strong>[24078-21-5]methyl 3-methyl-4-nitrobenzoate</strong> and 4 g of benzoyl peroxide were returned to the flask and treated with 198 g of bromine as described above. After the addition was complete the reaction mixture was refluxed another 96 hours, cooled to room temperature and the resulting solid separated by filtration yielding another 252 g of methyl 3-bromomethyl-4-nitrobenzoate.
With tetrachloromethane; N-Bromosuccinimide; at 80℃;Inert atmosphere; Into a 2000-mL oven-dried round-bottom flask, were placed a solution of <strong>[24078-21-5]methyl 3-methyl-4-nitrobenzoate</strong> (199.6 g, 1.02 mol) in CCU (1500 mL) and NBS (199.4 g, 1.12 mol), BPO (24.7 g, 96.39 mmol). The resulting mixture was stirred overnight at 80C under nitrogen in an oil bath. After the precipitate was filtered out, the filtrate was concentrated under vacuum. The residue was purified on a silica gel column eluted with ethyl acetate/petroleum ether (1 :20) to yield methyl 3-(bromomethyl)-4-nitrobenzoate as a light yellow solid.
Methyl 3-methyl-4-nitrobenzoate (5.00 g, 25.6 mmol), benzoyl peroxide (91.0 mg, 0.376 mmol) was dissolved in carbon tetrachloride (50 mL) and stirred at room temperature for 5 min. After adding N-bromosuccinimide (6.83 g, 38.4 mmol) at 85 C for 2 hours, the reaction mixture was diluted with water (150 mL), dichloromethane (200 mL×3) Title compound.

  • 2
  • [ 24078-21-5 ]
  • [ 207862-97-3 ]
  • [ 88071-90-3 ]
YieldReaction ConditionsOperation in experiment
34%; 48% With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 16h;Reflux; To a solution of 3 (1.33 g, 7.43 mmol) in anhydrous CCl4 (34 m:) were added benzoyl peroxide (200 mg, 0.83 mmol) and NBS (1.98 g, 11.14 mmol) at room temperature. The reaction mixture was heated at reflux for 16 h and then it was cooled to room temperature. After filtration and washing with hexane, the filtrate was concentrated in vacuo and the obtained residue was column chromatographed on silica gel to give both 4 (0.98 g, 48 %) as a white solid, and a byproduct, 3-dibromomethyl-4-nitrobenzoic acid methylester (0.89 g, 34 %) as a white solid. Rf: 0.4 (EtOAc:Hex = 1:10); m.p. 117.0-117.5 C; IR (film, cm-1) 3124 and 3053 (=C-H), 3002 and 2952 (-C-H), 1722 (C=O), 1586 (Ar), 1529 (N=O), 1442 (Ar), 1356 (N=O), 1277 (CH2-Br, bending), 624 (C-Br); 1H NMR (in CDCl3, delta) 3.99 (s, 3H, OCH3), 4.83 (s, 2H, CH2Br), 8.06 (d, 1H, J = 8.43 Hz), 8.13 (dd, 1H, J = 8.49 and 1.77 Hz), 8.24 (d, 1H, J = 1.59 Hz) [aromatic protons]; 13C NMR (in CDCl3, delta) 28.09 (CBr), 53.17 (OCH3), 125.80, 130.83, 133.28, 133.95, 134.80, 150.72 (aromatic carbons), 164.85 (C=O); HR-FABMS [M+H]+ calcd for C9H9BrNO4 m/z 273.9715, found 273.9711.
34%; 48% With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; at 20℃; for 16h; Benzoyl peroxide (200 mg, 0.83 mmol) and n-bromosuccinimide (1.98 g, 11.14 mmol) are added to a solution containing the compound 3 (1.33 g, 7.43 mmol) dissolved in anhydrous CC14 (34 ml) at the room temperature. The reactant mixture is subjected to a 16-hour reflux under agitation and then cooled down to the room temperature. The mixture is filtered and washed with hexane. The filtrate is concentrated under vacuum, and the residue is purified by colunm chromatography to yield a compound 4 (0.98 g, 48%) as a white solid and 3-dibromomethyl-4-nitrobenzoic acid methylester (0.89 g, 34%) as a white solid by-product.
  • 4
  • [ 201932-92-5 ]
  • [ 88071-90-3 ]
YieldReaction ConditionsOperation in experiment
30% With phosphorus tribromide; In diethyl ether; for 1.0h; ( RS-3-53) Benzylic alcohol MRS-3-49 (1.06 g, 5.35 mmol) was dissolved in Et20 (15 mL) and cooled to 0 C. Phosphorus tribromide (0.254 mL, 2.67 mmol) was carefully added dropwise. After 1 hour, the reaction mixture was poured into ice water (50 mL) and extracted with Et20 (3 chi 20 mL) . The ethereal phases were washed with sat. NaHC03 (20 mL) , water (10 mL) and sat. aqueous NaCl (10 mL) , and dried over Na2S04. Evaporation of the Et20 revealed 440 mg (30%) of the primary alkyl bromide.
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