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[ CAS No. 22721-16-0 ]

{[proInfo.proName]} ,{[proInfo.pro_purity]}

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DV 2D 3D

3d Animation Molecule Structure of 22721-16-0

Chemical Structure| 22721-16-0

Chemical Structure| 22721-16-0

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Quality Control of [ 22721-16-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 22721-16-0 ]

SDS

Alternatived Products of [ 22721-16-0 ]

Product Details of [ 22721-16-0 ]

CAS No. :	22721-16-0	MDL No. :	MFCD07439747
Formula :	C₈H₈BrNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	230.06 g/mol	Pubchem ID :	-
Synonyms :

Calculated chemistry of of [ 22721-16-0 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.12
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	50.41
TPSA :	49.33 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) :	-5.17 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.54
Log Po/w (XLOGP3) :	3.57
Log Po/w (WLOGP) :	2.0
Log Po/w (MLOGP) :	0.95
Log Po/w (SILICOS-IT) :	1.57
Consensus Log Po/w :	1.93

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.75
Solubility :	0.0406 mg/ml ; 0.000176 mol/l
Class :	Soluble
Log S (Ali) :	-4.29
Solubility :	0.0118 mg/ml ; 0.0000511 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-3.07
Solubility :	0.196 mg/ml ; 0.000851 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	1.43

Safety of [ 22721-16-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501	UN#:	N/A
Hazard Statements:	H302-H312-H332	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 22721-16-0 ]

* 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 [ 22721-16-0 ]

[ 22721-16-0 ] Synthesis Path-Downstream 1~12

1
[ 119-68-6 ]
[ 22721-16-0 ]

Yield	Reaction Conditions	Operation in experiment
	With chloroform; bromine
	With bromine; acetic acid

Reference： [1]Heilbron; Holt; Kitchen [Journal of the Chemical Society, 1928, p. 936,939]
[2]Heilbron; Holt; Kitchen [Journal of the Chemical Society, 1928, p. 936,939]

2
[ 22721-16-0 ]
[ 108-24-7 ]
[ 860732-60-1 ]

Yield	Reaction Conditions	Operation in experiment
	With (R)-10-camphorsulfonic acid; acetic acid

Reference： [1]Heilbron; Holt; Kitchen [Journal of the Chemical Society, 1928, p. 936,939]

3
[ 22721-16-0 ]
[ 541-41-3 ]
[ 22721-17-1 ]

Yield	Reaction Conditions	Operation in experiment
	for 20h; Heating;

Reference： [1]Doleschall,G.; Lempert,K. [Tetrahedron, 1969, vol. 25, p. 2539 - 2547]

Yield	Reaction Conditions	Operation in experiment
	Rk. mit NH3 -> 5-Brom-2-methylamino-benzoesaeureamid;
	Rk. mit Chlorameisensaeureethylester -> 6-Brom-1,2-dihydro-1-methyl-4H-3,1-benzoxazindion-(2,4);

Yield	Reaction Conditions	Operation in experiment
	N-Methyl-anthranilsaeure, Br2 (Eisessig);
	(yield)57percent;
	2-Methylamino-benzoesaeure, Brom, Nitrobenzol;

6
[ 22721-16-0 ]
[ 108-24-7 ]
[ 64-19-7 ]
[ 860732-60-1 ]

Reference： [1]Heilbron; Holt; Kitchen [Journal of the Chemical Society, 1928, p. 936,939]

7
[ 717866-13-2 ]
[ 22721-16-0 ]
[ 717866-09-6 ]

Yield	Reaction Conditions	Operation in experiment
	With HATU; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 18h;	22.e (E). N- {1-ACETYL-2, 2, 4-trimethyl-4-[4-(3-morpholin-4-yl-propoxy)-phenyl]-1,2,3, 4- tetrahydro-quinolin-6-yl}-5-bromo-2-methylamino-benzamide; General procedure C To a solution of the compound described in example 22d (132 mg), 5-bromo-2-methylamino benzoic acid (101 mg) and DIPEA (255 PI) in CH2Cl2 (3 ML) was added HATU (166 mg) at room temperature. The reaction mixture was stirred for 18 h at room temperature. Ethyl acetate (15 ml) and 2 M aqueous NAOH (15 ml) were added. The organic layer was separated and washed with 2 M aqueous NAOH (10 ml) and water (15 ml), dried and concentrated in vacuo. The title compound was purified by preparative HPLC (method A). Yield: 69.8 mg; MS-ESI: [M+H] += 663.4 ; HPLC : Rt = 14. 65 min (method 3).

Reference： [1]Current Patent Assignee: MERCK & CO INC; ORGANON & CO - WO2004/56779, 2004, A2 Location in patent: Page 32

8
[ 371-71-1 ]
[ 22721-16-0 ]
[ 50736-90-8 ]

Yield	Reaction Conditions	Operation in experiment
50-70	In acetonitrile in presence of NaF, 20°C, 20 min;
50-70	In acetonitrile in presence of NaF, 20°C, 20 min;

Reference： [1][Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: F: PerFHalOrg.9, 8, page 125 - 158]
[2]Current Patent Assignee: BAYER AG - DE2218302, 1973, A1 [Chem.Abstr., vol. 80, # 14938][Chem.Abstr., vol. 80, # 14938]

9
[ 22721-16-0 ]
[ 98-59-9 ]
[ 1207101-82-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate In water

Reference： [1]Location in patent: scheme or table Chen, Jack J.; Cole, Derek C.; Ciszewski, Greg; Crouse, Kimberly; Ellingboe, John W.; Nowak, Pawel; Tawa, Gregory J.; Berstein, Gabriel; Li, Wei [Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 2, p. 662 - 664]

10
[ 610-71-9 ]
[ 593-51-1 ]
[ 22721-16-0 ]

Reference： [1]Advanced Synthesis and Catalysis,2009,vol. 351,p. 1671 - 1676

11
[ 22721-16-0 ]
[ 917-61-3 ]
6-bromo-1-methylquinazoline-2,4(1H,3H)-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
16%	Stage #1: 2-(methylamino)-5-bromobenzoic acid; sodium isocyanate With acetic acid In water at 40℃; for 0.5h; Stage #2: With sodium hydroxide In water at 40 - 70℃; for 1.16667h;	31.2; 49.2 Step 2: 2-(cyanomethyl)-5-hydroxybenzonitrile. To a stirred mixture of 5-bromo-2- (methylamino) benzoic acid (280.00 mg, 1.217 mmol, 1.00 equiv) in AcOH/H2O (16.00 mL, 1/50) at room temperature under air atmosphere was added NaOCN (112.00 mg, 1.723 mmol, 1.42 equiv) at room temperature. The resulting mixture was stirred for additional 30 min at 40 oC. To the above mixture was added NaOH (1.38 g, 0.035 mmol, 0.03 equiv) in portions over 10 min at 40 oC. The resulting mixture was stirred for additional 1 h at 70 oC. The reaction was monitored by LCMS. The resulting mixture was cooled down to room temperature and was diluted with water (50 mL). The mixture was acidified to pH 6 with aq. HCl (1 M). The resulting mixture was extracted with EtOAc (30 mL), dried over anhydrous Na2SO4. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by reverse phase Flash chromatography with the following conditions: Column: WelFlash TM C18-I, 20-40 um, 120 g; Eluent A: water (plus 10 mmol/L NH4HCO3); Eluent B: ACN; Gradient: 30% - 50% B in 30 min; Flow rate: 60 mL/min; Detector: 220/254 nm; desired fractions were collected at 42% B and concentrated under reduced pressure to afford 6-bromo-1-methyl-3H-quinazoline-2,4-dione (50 mg, 16%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) d 11.71 (s, 1H), 8.05 (d, J = 2.5 Hz, 1H), 7.92 (dd, J = 8.9, 2.5 Hz, 1H), 7.41 (d, J = 9.0 Hz, 1H), 3.43 (s, 3H). LC/MS (ESI, m/z): [(M + 18)]+ = 254.75, 256.75.

Reference： [1]Current Patent Assignee: KYMERA THERAPEUTICS INC - WO2021/11631, 2021, A1 Location in patent: Paragraph 00400-00401; 00452; 00455-00456

12
[ 50-00-0 ]
[ 5794-88-7 ]
[ 22721-16-0 ]

Yield	Reaction Conditions	Operation in experiment
85%	With sodium cyanoborohydride; acetic acid In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	31.1; 49.1 Step 1: 5-Bromo-2-(methylamino)benzoic acid To a stirred mixture of 5-bromoanthranilic acid (2.00 g, 9.258 mmol, 1.00 equiv) and (HCHO)n (0.83 g, 27.667 mmol, 2.99 equiv) in DMF (20.00 mL) were added HOAc (5.58 g, 92.919 mmol, 10.04 equiv) and NaBH3CN (1.76 g, 28.007 mmol, 3.03 equiv) at room temperature. The resulting mixture was stirred for 6 h at room temperature. The resulting mixture was diluted with water (60 mL) and extracted with EtOAc (3 x 50 mL). The combined organic phase was dried over anhydrous Na2SO4. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by reverse phase Flash chromatography with the following conditions: Column: WelFlash TM C18-I, 20-40 mm, 330 g; Eluent A: water (plus 10 mmol/L FA); Eluent B: ACN; Gradient: 30% - 50% B in 25 min; Flow rate: 80 mL/min; Detector: 220/254 nm; desired fractions were collected at 42% B and concentrated under reduced pressure to afford 5-bromo-2- (methylamino)benzoic acid (1.8 g, 85%) as a white solid. LC/MS (ESI, m/z): [(M + 1)]+ = 230.00, 232.00.

Reference： [1]Current Patent Assignee: KYMERA THERAPEUTICS INC - WO2021/11631, 2021, A1 Location in patent: Paragraph 00337; 00400; 00452-00454

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Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
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P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
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P270	Do not eat, drink or smoke when using this product.
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P285	In case of inadequate ventilation wear respiratory protection.
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P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
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P308	IF exposed or concerned:
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P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
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P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
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P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
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P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
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P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
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:
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.
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P401
P402	Store in a dry place.
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P410 + P403	Protect from sunlight. Store in a well-ventilated place.
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Physical hazards
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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
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H240	Heating may cause an explosion
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H242	Heating may cause a fire
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H310	Fatal in contact with skin
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H320	Causes eye irritation
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Code	Phrase
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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