[ CAS No. 130200-01-0 ] {[proInfo.proName]}

Name: 130200-01-0|7-Bromo-2,2-dimethylchroman-4-one|97%
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Product Details of [ 130200-01-0 ]

CAS No. :	130200-01-0	MDL No. :	MFCD13190381
Formula :	C₁₁H₁₁BrO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QCVDUIIUXMKXQC-UHFFFAOYSA-N
M.W :	255.11	Pubchem ID :	14755365
Synonyms :

Safety of [ 130200-01-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 130200-01-0 ]

* 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.

Upstream synthesis route of [ 130200-01-0 ]
Downstream synthetic route of [ 130200-01-0 ]

[ 130200-01-0 ] Synthesis Path-Upstream 1~4

1
[ 30186-18-6 ]
[ 67-64-1 ]
[ 130200-01-0 ]

Reference： [1] Journal of Medicinal Chemistry, 1990, vol. 33, # 11, p. 3028 - 3034
[2] Patent: WO2015/65937, 2015, A1, . Location in patent: Paragraph 000645
[3] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 11, p. 2594 - 2601

2
[ 591-20-8 ]
[ 130200-01-0 ]

Yield	Reaction Conditions	Operation in experiment
22%	With PPA In water	7-bromo-2,2-dimethyl-chroman-4-one (Compound 65) Approximately 15 g of polyphosphoric acid was added to a mixture of 3,3-dimethylarylic acid (5.0 g, 54.9 mmol) and 3-bromophenol (10.4 g, 60.4 mmol). The mixture was stirred at 95° C. under argon for 4 hours. After cooling to 0° C. with an ice bath, the slurry was dissolved in 200 mL of ice/water and extracted with diethyl ether (3*100 mL). The organic phase was separated, washed with KOH aqueous solution (5N, 50 mL) and brine (50 mL). The extract was then dried (Mg₂SO₄), filtered, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (5percent EtOAc:hexane) to yield the title compound as a brown solid: (2.80 g, 22percent yield), ¹H-NMR (300 MHz, CDCl₃): δ 1.45 (s, 6H), 2.71 (s, 2H), 7.13 (m, 2H), 7.72 (d, 1H, J=8.3 Hz).

Reference： [1] Patent: US6403638, 2002, B1,

3
[ 112090-04-7 ]
[ 130200-01-0 ]

Reference： [1] Patent: US2005/148590, 2005, A1, . Location in patent: Page/Page column 29

4
[ 544-92-3 ]
[ 130200-01-0 ]
[ 130200-02-1 ]

Reference： [1] Journal of Medicinal Chemistry, 1990, vol. 33, # 11, p. 3028 - 3034

[ 130200-01-0 ] Synthesis Path-Downstream 1~21

1
[ 544-92-3 ]
[ 130200-01-0 ]
[ 130200-02-1 ]

Reference： [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 3028 - 3034

2
[ 30186-18-6 ]
[ 67-64-1 ]
[ 130200-01-0 ]

Yield	Reaction Conditions	Operation in experiment
	With pyrrolidine; In toluene; at 80℃; for 16h;	[0006451 A solution of Compound 71A (4.50 g, 20.93 mmol), acetone (12.14 g, 0.209 mol), and pyrrolidine (1.51 g, 20.93 mmol) intoluene (50 mL)was stirred at 80C for 16 h. It was purified with flash colunm chromatography on silica gel (ethyl acetate in petroleum ether, from 0% to 8% v/v) to furnish Compound 71B. ?H-NMR (CDC13, 400 MHz) 5 (ppm) 1.46 (s, 6H), 2.71 (s, 2H), 7.10-7.14 (m, 2H), 27.72 (d, J 8.4 Hz, 1H).
		General procedure: To the solution of 1-(2-hydroxy-4-iodophenyl)ethanone 1c (3.0 g, 11.4 mmol) in MeOH (25 mL) was added pyrrolidine (10 mL) and stirred further for 20-30 min at 0-5 C. Acetone (0.992 g, 17.10 mmol) was then added slowly at room temperature and stirred for 30 min. The reaction mixture was further heated to reflux for 4-6 h, then quenched with water and extracted with ethyl acetate (2 x 50 mL). The combined organic portion was dried over sodium sulfate and concentrated to afford 7-iodo-2,2-dimethylchroman-4-one 2c (2.1 g) in 61% yield.
	With pyrrolidine; In toluene; at 80℃;	A solution of 1-(4-bromo-2-hydroxyphenyl)ethanone (1.00 g, 4.649 mmol, 1.00 equiv.), acetone (2.70 g, 46.488 mmol, 10.00 equiv.), and pyrrolidine (330 mg, 4.640 mmol, 1.00 equiv.) in toluene (20 mL) was stirred overnight at 80 C. The reaction was monitored by LCMS. The resulting mixture was purified with flash column chromategraphy on silica gel (ethyl acetate in petroleum ether, from 0 percent to 8 percent v/v) to yield 7-bromo-2,2-dimethylchroman-4-one. Mass spectrum (ESI, m/z): Calculated for C11H11BrO2, 255.0[M+H], found 256.9.

	With pyrrolidine; In toluene; at 80℃;	A solution of 1-(4-bromo-2-hydroxyphenyl)ethanone (1.00 g, 4.649 mmol, 1.00 equiv.), acetone (2.70 g, 46.488 mmol, 10.00 equiv.), and pyrrolidine (330 mg, 4.640 mmol, 1.00 equiv.) in toluene (20 mL) was stirred overnight at 80 C. The reaction was monitored by LCMS. The resulting mixture was purified with flash column chromategraphy on silica gel (ethyl acetate in petroleum ether, from 0 percent to 8 percent v/v) to yield 7-bromo-2,2-dimethylchroman-4-one. Mass spectrum (ESI, m/z): Calculated for C11H11BrO2, 255.0[M+H], found 256.9.
	With pyrrolidine; In toluene; at 80℃;	A solution of 1-(4-bromo-2-hydroxyphenyl)ethanone (1.00 g, 4.649 mmol, 1.00 equiv.), acetone (2.70 g, 46.488 mmol, 10.00 equiv.), and pyrrolidine (330 mg, 4.640 mmol, 1.00 equiv.) in toluene (20 mL) was stirred overnight at 80 C. The reaction was monitored by LCMS. The resulting mixture was purified with flash column chromategraphy on silica gel (ethyl acetate in petroleum ether, from 0 percent to 8 percent v/v) to yield 7-bromo-2,2-dimethylchroman-4-one. Mass spectrum (ESI, m/z): Calculated for C11H11BrO2, 255.0[M+H], found 256.9.

Reference： [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 3028 - 3034
[2]Patent: WO2015/65937,2015,A1 .Location in patent: Paragraph 000645
[3]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 2594 - 2601
[4]Patent: US2019/47960,2019,A1 .Location in patent: Paragraph 0724; 0725; 0726
[5]Patent: US2019/47959,2019,A1 .Location in patent: Paragraph 0720-0721
[6]Patent: US2019/47961,2019,A1 .Location in patent: Paragraph 0723-0724

3
[ 130200-01-0 ]
7-bromo-2,2-dimethyl-chroman-4-ol [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin Transactions 2 (2001),2000,p. 263 - 269

4
[ 130200-01-0 ]
[ 101911-39-1 ]

Yield	Reaction Conditions	Operation in experiment
	With methanol; sodium tetrahydroborate; for 2.0h;	Into a 50 ml flask were placed a solution of <strong>[130200-01-0]7-bromo-2,2-dimethylchroman-4-one</strong> (815 mg, 3.195 mmol, 1.00 equiv.) in MeOH (20 ml). NaBH4 (488 mg, 12.899 mmol, 4.00 equiv.) was added. The mixture was stirred for 2 h. The reaction was monitored by LCMS. The mixture was concentrated under vacuum. The residue was applied on a silica gel column and eluted with PE/EA (6/1) to yield 7-bromo-2,2-dimethyl-2H-chromene as white solid. Mass spectrum (ESI, m/z): Calculated for C11H11O2, 239.0 [M+H], found 238.8.
	With methanol; sodium tetrahydroborate; for 2.0h;	Into a 50 ml flask were placed a solution of <strong>[130200-01-0]7-bromo-2,2-dimethylchroman-4-one</strong> (815 mg, 3.195 mmol, 1.00 equiv.) in MeOH (20 ml). NaBH4 (488 mg, 12.899 mmol, 4.00 equiv.) was added. The mixture was stirred for 2 h. The reaction was monitored by LCMS. The mixture was concentrated under vacuum. The residue was applied on a silica gel column and eluted with PE/EA (6/1) to yield 7-bromo-2,2-dimethyl-2H-chromene as white solid. Mass spectrum (ESI, m/z): Calculated for C11H11O2, 239.0 [M+H], found 238.8.
	With methanol; sodium tetrahydroborate; for 2.0h;	Into a 50 ml flask were placed a solution of <strong>[130200-01-0]7-bromo-2,2-dimethylchroman-4-one</strong> (815 mg, 3.195 mmol, 1.00 equiv.) in MeOH (20 ml). NaBH4 (488 mg, 12.899 mmol, 4.00 equiv.) was added. The mixture was stirred for 2 h. The reaction was monitored by LCMS. The mixture was concentrated under vacuum. The residue was applied on a silica gel column and eluted with PE/EA (6/1) to yield 7-bromo-2,2-dimethyl-2H-chromene as white solid. Mass spectrum (ESI, m/z): Calculated for C11H11O2, 239.0 [M+H], found 238.8.

Reference： [1]Journal of the Chemical Society. Perkin Transactions 2 (2001),2000,p. 263 - 269
[2]Patent: US2019/47960,2019,A1 .Location in patent: Paragraph 0724; 0727; 0728
[3]Patent: US2019/47959,2019,A1 .Location in patent: Paragraph 0722-0723
[4]Patent: US2019/47961,2019,A1 .Location in patent: Paragraph 0725-0726

5
[ 130200-01-0 ]
[ 264265-10-3 ]

Reference： [1]Journal of the Chemical Society. Perkin Transactions 2 (2001),2000,p. 263 - 269

6
[ 130200-01-0 ]
{4-[(4-dimethylamino-phenyl)-(2,2-dimethyl-2<i>H</i>-chromen-7-yl)-methylene]-cyclohexa-2,5-dienylidene}-dimethyl-ammonium [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin Transactions 2 (2001),2000,p. 263 - 269

7
[ 130200-01-0 ]
[ 82305-04-2 ]

Reference： [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 3028 - 3034

8
[ 130200-01-0 ]
[ 86824-81-9 ]

Reference： [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 3028 - 3034

9
[ 130200-01-0 ]
[ 86824-80-8 ]

Reference： [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 3028 - 3034

10
[ 130200-01-0 ]
[ 130200-05-4 ]

Reference： [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 3028 - 3034

11
[ 130200-01-0 ]
[ 86824-73-9 ]

Reference： [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 3028 - 3034

12
[ 130200-01-0 ]
[ 130199-96-1 ]

Reference： [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 3028 - 3034

13
[ 130200-01-0 ]
[ 130199-85-8 ]

Reference： [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 3028 - 3034

14
[ 112090-04-7 ]
[ 130200-01-0 ]

Reference： [1]Patent: US2005/148590,2005,A1 .Location in patent: Page/Page column 29

Yield	Reaction Conditions	Operation in experiment
		Example 25 7-Bromo-2,2-dimethyl-2,3-dihydro-4H-chromen-4-one 7.02 g (8.89 ml, 120.90 mmol) of acetone and 1.98 g (2.33 ml, 27.90 mmol) of pyrrolidine are added to a solution of 20.00 g (93.00 mmol) of the compound from Example 3 in 100 ml of toluene. The mixture is boiled with a water trap for 20 hours. The solvent is removed by distillation and the product is isolated by chromatography on silica gel (cyclohexane/ethyl acetate 20:1). Recovered precursor is stirred in 100 ml of benzene and 50 ml of acetone in the presence of 5.00 ml of piperidine under reflux for 16 h. After removal of the solvent by distillation, the product is purified by column chromatography on silica gel (V 20:1). Yellow crystals are obtained from the combined oils from ethyl acetate/petroleum ether and are filtered off with suction and washed with diethyl ether. Yield: 5.95 g (25.08%). 1H-NMR (200 MHz, CDCl3, delta/ppm): 1.45 (s, 6H), 2.70 (s, 2H), 7.10 (dd, 1H), 7.25 (s, 1H), 7.70 (d, 1H). MS (DCI/NH3): 255 [M+H]+, 272 [M+NH4]+.

16
[ 591-20-8 ]
[ 130200-01-0 ]

Yield	Reaction Conditions	Operation in experiment
22%	With PPA; In water;	7-bromo-2,2-dimethyl-chroman-4-one (Compound 65) Approximately 15 g of polyphosphoric acid was added to a mixture of 3,3-dimethylarylic acid (5.0 g, 54.9 mmol) and 3-bromophenol (10.4 g, 60.4 mmol). The mixture was stirred at 95 C. under argon for 4 hours. After cooling to 0 C. with an ice bath, the slurry was dissolved in 200 mL of ice/water and extracted with diethyl ether (3*100 mL). The organic phase was separated, washed with KOH aqueous solution (5N, 50 mL) and brine (50 mL). The extract was then dried (Mg2SO4), filtered, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (5% EtOAc:hexane) to yield the title compound as a brown solid: (2.80 g, 22% yield), 1H-NMR (300 MHz, CDCl3): delta 1.45 (s, 6H), 2.71 (s, 2H), 7.13 (m, 2H), 7.72 (d, 1H, J=8.3 Hz).

Reference： [1]Patent: US6403638,2002,B1

17
(1H) pyrimidone (DMPU) [ No CAS ]
[ 130200-01-0 ]
[ 361177-51-7 ]

Yield	Reaction Conditions	Operation in experiment
	With isopropylmagnesium chloride; potassium carbonate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; diethyl ether;	7-Bromo-4-isopropyl-2,2-dimethyl-2H-chromene (Compound 66) A 2.0 M solution of isopropyl magnesium chloride in diethyl ether (15.5 mL, 31 mmol) was added slowly to a solution of <strong>[130200-01-0]7-bromo-2,2-dimethyl-chroman-4-one</strong> (Compound 65, 1.58 g, 6.2 mmol) and 1,3-dimethyl-3,4,5,6-tetrahydro 2(1H) pyrimidone (DMPU) (7.5 mL, 30 mmol) in 30 mL THF at -30 C. The reaction mixture was warmed to room temperature and stirred for 15 hours. The reaction was then quenched with water (20 mL), saturated NH4Cl (aq) (15 mL) and 10% HCl (20 mL) at -78 C. The mixture was warmed to room temperature, was extracted with ethyl acetate (330 mL), the combined extracts were washed with water and brine, dried (MgSO4), filtered, and concentrated in vacuo. The residue was then refluxed in 40 mL methanol with p-toluenesulfonic acid (160 mg) for 20 hours. The reaction mixture was made basic by addition of solid K2CO3, the solvent was removed and the residue was dissolved in diethyl ether (50 mL). The ether solution was washed with water (250 mL) and brine (50 mL), dried (MgSO4), filtered, and concentrated in vacuo. The resulting crude product was purified by column chromatography on silica gel (hexane) to give the title compound as a clear oil: (650 mg, 37%). 1H-NMR (300 MHz, CDCl3): delta 1.12 (d, 6H, J=6.7 Hz), 1.40 (s, 6H), 2.80 (m, 1H, J=1.1 Hz), 5.40 (s, 1H), 7.0 (m, 3H).

Reference： [1]Patent: US6403638,2002,B1

18
[ 130200-01-0 ]
7-bromo-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylsilane; trifluoroacetic acid; at 30℃; for 16.0h;	[000646j A mixture of Compound 71B (3.80 g, 5.90 mmol) and TES (5 mL) in TFA (5 mL) was stirred at 30 C for 16 h. It was purified with flash column chromatography on silica gel (ethyl acetate in petroleum ether, from 0% to 5% v/v) to furnish Compound 71C. ?HNMR (CDC13, 400 MHz) 5 (ppm) 1.32 (s, 6H), 1.79 (t, J= 6.8 Hz, 2H), 2.71 (t, J= 6.8 Hz, 2H), 6.91-6.95 (m, 3H).

Reference： [1]Patent: WO2015/65937,2015,A1 .Location in patent: Paragraph 000646

19
[ 130200-01-0 ]
[ 1393843-31-6 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; isopentyl nitrite; In ethanol; at 20℃;	General procedure: To the solution of 7-iodo-2,2-dimethyl-2,3-dihydro-4H-chromen-4-one 2c (2.5 g, 8.28 mmol) in ethanol (50 mL) was added isoamylnitrite (0.290 g, 2.48 mmol), HCl (3.0 mL) and the reaction mixture was stirred at room temperature for 12-16 h. The reaction mixture was quenched with water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated to afford 1.5 g (57%) of crude product 3c, which was used in the next step as such.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 2594 - 2601

20
[ 130200-01-0 ]
C₁₈H₁₃Br₃N₂O [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 2594 - 2601

21
[ 130200-01-0 ]
7-bromo-2-(2-chloro-6-fluorophenyl)-4,4-dimethyl-1,4-dihydrochromeno[3,4-d]imidazole [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 2594 - 2601

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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

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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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. 130200-01-0 ] {[proInfo.proName]}

Quality Control of [ 130200-01-0 ]

Related Doc. of [ 130200-01-0 ]

Product Details of [ 130200-01-0 ]

Safety of [ 130200-01-0 ]

Application In Synthesis of [ 130200-01-0 ]

[ 130200-01-0 ] Synthesis Path-Upstream 1~4

[ 130200-01-0 ] Synthesis Path-Downstream 1~21

Related Functional Groups of [ 130200-01-0 ]

Bromides

Ketones

Related Parent Nucleus of [ 130200-01-0 ]

Other Aromatic Heterocycles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 130200-01-0 ]

Related Parent Nucleus of
[ 130200-01-0 ]