[ CAS No. 19932-85-5 ] {[proInfo.proName]}

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2D 3D

Structure of 19932-85-5 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 19932-85-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 19932-85-5 ]

SDS Specification

Alternatived Products of [ 19932-85-5 ]

Product Details of [ 19932-85-5 ]

CAS No. :	19932-85-5	MDL No. :	MFCD00694727
Formula :	C₇H₄BrNO₂	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	DDNKJFBQMQOIKI-UHFFFAOYSA-N
M.W :	214.02	Pubchem ID :	29859
Synonyms :

Calculated chemistry of [ 19932-85-5 ] Expand+

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	44.53
TPSA :	46.0 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) :	-6.29 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.65
Log Po/w (XLOGP3) :	1.85
Log Po/w (WLOGP) :	1.88
Log Po/w (MLOGP) :	1.59
Log Po/w (SILICOS-IT) :	2.72
Consensus Log Po/w :	1.94

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.94
Solubility :	0.247 mg/ml ; 0.00115 mol/l
Class :	Soluble
Log S (Ali) :	-2.44
Solubility :	0.783 mg/ml ; 0.00366 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.68
Solubility :	0.0446 mg/ml ; 0.000208 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.44

Safety of [ 19932-85-5 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P305+P351+P338	UN#:
Hazard Statements:	H302-H319	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 19932-85-5 ]

* 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 [ 19932-85-5 ]

[ 19932-85-5 ] Synthesis Path-Downstream 1~14

1
[ 59-49-4 ]
[ 19932-85-5 ]

Yield	Reaction Conditions	Operation in experiment
94%	With bromine; acetic acid; at 20℃; for 4h;	3H-1,3-Benzoxazol-2-one (5.00 g, 37.00 mmol) was dissolved in acetic acid (50 mL) and bromine (1.9 mL, 37.0 mmol) was added dropwise. The reaction mixture was stirred at 20 C for 4 h.The reaction mixture was poured onto ice and the precipitate was collected by filtration, washed with water and air-dried to give a pink powder (7.48 g, 34.8 mmol, 94%). Mp 191.6-192.3 C. 1H NMR (300 MHz, DMSOd6): δ 11.81 (s, 1H), 7.57 (dd, J = 1.9 Hz, J = 0.3 Hz, 1H), 7.30 (dd, J = 8.3 Hz, J = 1.9 Hz, 1H), 7.04 (dd, J = 8.3 Hz, J = 0.3 Hz, 1H). 13C NMR (75 MHz, DMSOd6): δ 154.5, 144.5, 130.3, 126.9, 113.5, 113.2, 111.7. LCMS m/z calc for [M - H]+: 211.9, 213.9, found: 211.8, 213.8.
94%		3H-1,3-Benzoxazol-2-one (5.00 g, 37.00 mmol) was dissolved in acetic acid (50 mL) and bromine (1.9 mL, 37.0 mmol) was added dropwise. The reaction mixture was stirred at20C for 4 h. The reaction mixture was poured onto ice and the precipitate was collected by filtration, washed with water and air-dried to give 1 as a pink powder (7.48 g, 94%). Mp 191.6C. 1H NMR (300 MHz), (5(ppm, DMSO-d6): 11.81 (s, 1H), 7.57 (dd, J= 1.9 Hz, J0.3 Hz, 1H), 7.30 (dd, J= 8.3 Hz, J= 1.9 Hz, 1H), 7.04 (dd, J 8.3 Hz, J 0.3 Hz, 1H).13C NMR (75 MHz), (5(ppm, DMSO-d6): 154.5, 144.5, 130.3, 126.9, 113.5, 113.2, 111.7.LCMS m/zcalc for [M-H]: 211.9, 213.9, found: 211.8, 213.8.
84%	With bromine; In dichloromethane; at 20℃; for 19.5h;	To a mixture of 3H-benzooxazol-2-one (20 g, 0.15 mol) in DCM (500 mL) was added bromine (8.34 mL, 0.16 mol). After stirring at room temperature for 19.5 h, the orange precipitate that had formed was filtered off and washed with DCM until the orange color was washed out. The filtrate was concentrated to approximately 33% of its original volume and filtered and washed as before. The combined solids weighed 28.36 g. 1H NMR indicated the product was clean albeit contained ca. 8-9% starting material meaning the true yield of product was 26.72 g, 84%.

70%	With N-Bromosuccinimide; In acetic acid; at 20℃; for 72h;	Step 1: N-Bromosuccinimide (26.6 g, 0.15 mol) was added to a stirred solution of 2-benzoxazolinone (20.0 g, 0.15 mol) in glacial acetic acid (220 mL), and the mixture was stirred at room temperature for 3 days. The reaction mixture was poured into H2O (1.2 L), and the white solid that formed was collected. Recrystallization from hot EtOH (300 mL) gave bromide 1 (22.1 g, 70%) as an off-white solid: mp 190-195 C.; IR (KBr): 3278, 1779, 1736, 1623 cm?1; 1H NMR (300 MHz, CD3OD): ?7.41 (d, J=2 Hz, 1H), 7.32 (dd, J=5, 2 Hz, 1H), 6.99 (d, J=5 Hz, 1H); CI MS (methane) (m/z): 215 [M+H]+.
31%	With N-Bromosuccinimide; In acetonitrile; at -15 - 20℃;	Preparation of 6-Bromo-3H-benzoxazol-2-one. To a stirred suspension of 3H-benzoxazol-2-one (1.35 g, 10 mmol) in acetonitrile (23 ML) at -15 C. was added portionwise NBS (2.00 g, 11.0 mmol).Following complete addition of NBS the mixture was stirred at -15 to 0 C. for 3 h then allowed to warm to ambient temperature and stirred overnight.The solvent was evaporated in vacuo and the residue was partitioned between CH2Cl2/H2O precipitating the intermediate title compound, 6-bromo-3H-benzoxazol-2-one, (0.67 g, 31%) as a brown solid. 1HNMR(CDCl3) δ 7.0 (1H, d), 7.15 (1H.,d), 7.3 (1H, s), 11.9 (1H, s).
	With bromine; In dichloromethane; at 20℃; for 19.5h;	To a mixture of 3H-benzooxazol-2-one (20 g, 0.15 mol) in DCM (500 mL) was added bromine (8.34 mL, 0.16 mol). After stirring at room temperature for 19.5 h, the orange precipitate that had formed was filtered off and washed with DCM until the orange color was washed out. The filtrate was concentrated to approximately 33% of its original volume and filtered and washed as before. The combined solids weighed 28.36 g and contained ca. 8-9% starting material.
	With N-Bromosuccinimide; In water; acetic acid;	Step 1: To a solution of benzoxazolinone (20 g, 0.148 mol) in 220 mL glacial acetic acid was added N-bromosuccinimide (NBS, 26.36 g, 0.148 mol), and the reaction mixture was stirred at room temperature for 63 hours before pouring into 1500 mL water. The precipitated product was washed thoroughly with water upon collection and recrystallized from EtOH to give 6-bromo-3H-benzoxazol-2-one (9) (25.09 g, 79%): Theory: C, 39.28; H, 1.88; N, 6.54; Br, 37.33. Found: C, 39.36; H, 2.02; N, 6.36; Br, 37.43. MP 192-194 C.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 159,p. 104 - 125
[2]Patent: WO2020/11848,2020,A1 .Location in patent: Page/Page column 38; 41-42
[3]Patent: US6372933,2002,B1 .Location in patent: Page column 5 - 6
[4]Patent: US2008/138413,2008,A1 .Location in patent: Page/Page column 22
[5]Monatshefte fur Chemie,2011,vol. 142,p. 67 - 80
[6]Patent: EP1251128,2002,A1 .Location in patent: Page 38
[7]Patent: US2003/236252,2003,A1 .Location in patent: Page 14
[8]Monatshefte fur Chemie,1993,vol. 124,p. 367 - 380
[9]Patent: US2003/225127,2003,A1 .Location in patent: Page 10
[10]Journal fur praktische Chemie (Leipzig 1954),1888,vol. <2> 37,p. 28 Anm. 1, 31, 38, 46
[11]Journal of the Chemical Society,1934,p. 1186,1190
[12]Collection of Czechoslovak Chemical Communications,1979,vol. 44,p. 1790 - 1798
[13]Patent: WO2006/86705,2006,A1 .Location in patent: Page/Page column 84
[14]Acta poloniae pharmaceutica,2013,vol. 70,p. 245 - 253
[15]European Journal of Medicinal Chemistry,2015,vol. 92,p. 575 - 582
[16]Patent: US2003/18021,2003,A1
[17]ChemMedChem,2018,vol. 13,p. 2522 - 2529

2
[ 52112-66-0 ]
[ 19932-85-5 ]

Reference： [1]Patent: US2895877,1956,A

3
[ 19932-85-5 ]
[ 77-78-1 ]
[ 67927-44-0 ]

Reference： [1]Journal of the Chemical Society,1938,p. 321,326

4
[ 19932-85-5 ]
[ 38191-34-3 ]

Reference： [1]Journal of the Chemical Society,1938,p. 321,326

5
[ 6322-49-2 ]
[ 19932-85-5 ]
[ 13604-03-0 ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1966,vol. 33,p. 144 - 148

6
[ 19932-85-5 ]
[ 50277-65-1 ]
[ 59676-68-5 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1976,vol. 12,p. 366
Khimiya Geterotsiklicheskikh Soedinenii,1976,vol. 12,p. 429

7
[ 19932-85-5 ]
[ 4554-16-9 ]
[ 13610-68-9 ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1966,vol. 33,p. 130 - 138

8
[ 19932-85-5 ]
[ 107-13-1 ]
[ 13610-57-6 ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1966,vol. 33,p. 130 - 138

9
[ 19932-85-5 ]
[ 598-31-2 ]
[ 13603-99-1 ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1966,vol. 33,p. 144 - 148

10
[ 19932-85-5 ]
[ 99-81-0 ]
[ 554-68-7 ]
[ 120007-58-1 ]

Reference： [1]Chemistry of Natural Compounds,1987,vol. 23,p. 340 - 344
Khimiya Prirodnykh Soedinenii,1987,p. 411 - 415

11
[ 19932-85-5 ]
[ 532-27-4 ]
[ 120007-47-8 ]

Reference： [1]Chemistry of Natural Compounds,1987,vol. 23,p. 340 - 344
Khimiya Prirodnykh Soedinenii,1987,p. 411 - 415

12
[ 19932-85-5 ]
[ 816-40-0 ]
[ 93232-04-3 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1987,vol. 23,p. 1024 - 1026
Khimiya Geterotsiklicheskikh Soedinenii,1987,p. 1277 - 1279

13
[ 19932-85-5 ]
[ 814-75-5 ]
[ 113922-38-6 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1987,vol. 23,p. 1024 - 1026
Khimiya Geterotsiklicheskikh Soedinenii,1987,p. 1277 - 1279

14
[ 19932-85-5 ]
[ 24316-84-5 ]

Reference： [1]Synthesis,1983,p. 936 - 937

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Technical Information

• Acyl Group Substitution • Alkyl Halide Occurrence • Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Baylis-Hillman Reaction • Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Bucherer-Bergs Reaction • Chan-Lam Coupling Reaction • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Fischer Indole Synthesis • Friedel-Crafts Reaction • General Reactivity • Grignard Reaction • Henry Nitroaldol Reaction • Hiyama Cross-Coupling Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Hydrogenolysis of Benzyl Ether • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Lawesson's Reagent • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Peterson Olefination • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Alkylbenzene • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions of Dihalides • Reformatsky Reaction • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Ketenes • Stille Coupling • Stobbe Condensation • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Tebbe Olefination • Ugi Reaction • Vilsmeier-Haack Reaction • Wittig Reaction • Wolff-Kishner Reduction

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Ghs Precautionary Statements

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Code	Phrase
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Code	Phrase
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P378
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P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
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:
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P401
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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. 19932-85-5 ] {[proInfo.proName]}

Quality Control of [ 19932-85-5 ]

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Product Details of [ 19932-85-5 ]

Calculated chemistry of [ 19932-85-5 ] Expand+

Physicochemical Properties

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Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 19932-85-5 ]

Application In Synthesis of [ 19932-85-5 ]

[ 19932-85-5 ] Synthesis Path-Downstream 1~14

Technical Information

Related Functional Groups of [ 19932-85-5 ]

Bromides

Amides

Related Parent Nucleus of [ 19932-85-5 ]

Benzoxazoles

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[ 19932-85-5 ]

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[ 19932-85-5 ]