[ CAS No. 135533-78-7 ] {[proInfo.proName]}

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Quality Control of [ 135533-78-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 135533-78-7 ]

Product Details of [ 135533-78-7 ]

CAS No. :	135533-78-7	MDL No. :	MFCD11890748
Formula :	C₇H₃ClFNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QFKHKBJLBBASAZ-UHFFFAOYSA-N
M.W :	171.56	Pubchem ID :	14169817
Synonyms :

Safety of [ 135533-78-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H320-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 135533-78-7 ]

* 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 [ 135533-78-7 ]
Downstream synthetic route of [ 135533-78-7 ]

[ 135533-78-7 ] Synthesis Path-Upstream 1~5

1
[ 13451-78-0 ]
[ 135533-78-7 ]

Yield	Reaction Conditions	Operation in experiment
81%	Stage #1: With phosphorus pentachloride; trichlorophosphate In dichloromethane at 20℃; for 24 h; Stage #2: With sodium hydroxide In waterCooling	Step 2. 2-Chloro-5-fluoro-benzoxazole; To a suspension of 5-fluoro-2-mercapto-benzoxazole (5.0 g) in POCl₃ (8.8 eq) at room temperature, was added PCl₅ (1.2 eq) along with 20 mL DCM. After 24 hr of stirring at room temperature, the mixture was concentrated to remove excessPOCl₃. The residue was neutralized with cool aqueous NaOH mixed with CH₂Cl₂.The organic layer was washed with brine and the crude product was purified by silica gel chromatography to obtain 2-chloro-5-fluoro-benzoxazole (4.1 g, 81percent).

Reference： [1] Patent: WO2009/151744, 2009, A1, . Location in patent: Page/Page column 118
[2] Journal of Medicinal Chemistry, 1988, vol. 31, # 9, p. 1719 - 1728
[3] Journal of Medicinal Chemistry, 1994, vol. 37, # 7, p. 913 - 923
[4] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 7, p. 1975 - 1980
[5] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 16, p. 4689 - 4693
[6] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 9, p. 3044 - 3049
[7] Patent: WO2016/25669, 2016, A1, . Location in patent: Page/Page column 68; 69
[8] Patent: WO2017/88759, 2017, A1, . Location in patent: Paragraph 00200

2
[ 399-97-3 ]
[ 135533-78-7 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 16, p. 4689 - 4693
[2] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 7, p. 1975 - 1980
[3] Journal of Medicinal Chemistry, 1994, vol. 37, # 7, p. 913 - 923
[4] Journal of Medicinal Chemistry, 1988, vol. 31, # 9, p. 1719 - 1728
[5] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 9, p. 3044 - 3049
[6] ACS Medicinal Chemistry Letters, 2015, vol. 6, # 7, p. 798 - 803
[7] Patent: WO2016/25669, 2016, A1,
[8] Patent: WO2009/151744, 2009, A1,

3
[ 144-55-8 ]
[ 13451-78-0 ]
[ 135533-78-7 ]

Reference： [1] Patent: EP883611, 2002, B1,

4
[ 75-09-2 ]
[ 144-55-8 ]
[ 13451-78-0 ]
[ 135533-78-7 ]

Reference： [1] Patent: US5736545, 1998, A,

5
[ 13451-78-0 ]
[ 135533-78-7 ]

Reference： [1] ACS Medicinal Chemistry Letters, 2015, vol. 6, # 7, p. 798 - 803

[ 135533-78-7 ] Synthesis Path-Downstream 1~5

1
[ 13451-78-0 ]
[ 135533-78-7 ]

Yield	Reaction Conditions	Operation in experiment
81%		Step 2. 2-Chloro-5-fluoro-benzoxazole; To a suspension of 5-fluoro-2-mercapto-benzoxazole (5.0 g) in POCl3 (8.8 eq) at room temperature, was added PCl5 (1.2 eq) along with 20 mL DCM. After 24 hr of stirring at room temperature, the mixture was concentrated to remove excessPOCl3. The residue was neutralized with cool aqueous NaOH mixed with CH2Cl2.The organic layer was washed with brine and the crude product was purified by silica gel chromatography to obtain 2-chloro-5-fluoro-benzoxazole (4.1 g, 81%).
	With phosphorus pentachloride; In toluene; for 2h;Reflux;	General procedure: The substituted 2-aminophenol (1eq.) in water and 95% ethanol was added potassium carbonate (1eq.) and CS2 (1eq.).The mixture was heated under reflux for 3 hours. After cooling, the solution was neutralized with 15 mL of acetic acid in 30 mL water. The precipitate was collected to give 2-thiolbenzoxazoles. Then, the substituted 2-thiolbenzoxazoles (1eq.) dissolved in toluene, PCl5 (1.5eq) was added dropwise. The mixture was heated to reflux for 2 hours. After the solvent was evaporated, the crude product was purified by silica gel column chromatography using PE-EA as an eluent.
	With thionyl chloride; N,N-dimethyl-formamide; at 70℃; for 3h;	Step 2. A mixture of <strong>[13451-78-0]5-fluorobenzo[d]oxazole-2-thiol</strong> (300 mg, 1.7 mmol) in thionyl chloride (6 mL) and 2 drops of DMF were heated at 70 C for 3 h. The mixture was cooled to rt and concentrated in vacuo. The crude was dissolved in EtOAc and filtered through silica gel. The filtrate was concentrated to obtain the title compound, which was used without further purification. 1H NMR (CDC13, 400 MHz) delta 7.44 (dd, J= 4.3, 8.6 Hz, 1H), 7.37 (dd, J= 2.8, 8.08 Hz, 1H), 7.09 (dt, J= 2.5, 9.09 Hz, 1H).

With thionyl chloride; N,N-dimethyl-formamide; for 3h;Reflux;

Step 2) Synthesis of 2-chloro-5-fluorobenzo [d] oxazole A mixture of 5-fluorobenzo [d] oxazole-2-thiol (2.538 g, 15.0 mmol) , sulfoxide chloride (20 mL, 272.6 mmol) and N, N-dimethylformamide (0.05 mL, 0.65 mmol) was heated to reflux and stirred for 3 hours, and then cooled, and the solvent was removed in vacuo. The resulting product was used directly in the next step.

Reference： [1]Patent: WO2009/151744,2009,A1 .Location in patent: Page/Page column 118
[2]Journal of Medicinal Chemistry,1988,vol. 31,p. 1719 - 1728
[3]Journal of Medicinal Chemistry,1994,vol. 37,p. 913 - 923
[4]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 1975 - 1980
[5]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4689 - 4693
[6]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3044 - 3049
[7]Patent: WO2016/25669,2016,A1 .Location in patent: Page/Page column 68; 69
[8]Patent: WO2017/88759,2017,A1 .Location in patent: Paragraph 00200

2
[ 17193-39-4 ]
[ 135533-78-7 ]
(S)-3-Cyclohexyl-2-(5-fluoro-benzooxazol-2-ylamino)-propionic acid methyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 1975 - 1980

3
[ 75-09-2 ]
[ 144-55-8 ]
[ 13451-78-0 ]
[ 135533-78-7 ]

Yield	Reaction Conditions	Operation in experiment
	With phosphorus pentachloride; In trichlorophosphate;	Step 2 The <strong>[13451-78-0]2-mercapto-5-fluorobenzoxazole</strong> (2.0 g, 11.8 mmol) is slurried into POCl3 (9.7 mL, 104 mmol). The slurry is treated with PCl5 (3.0 g, 14.2 mmol) and 5.0 mL of anhydrous CH2 Cl2. The mixture is stirred at room temperature for 5.5 hours. After this time excess POCl3 is removed under reduced pressure. The residue is treated with saturated aqueous NaHCO3 and the mixture is poured into a separatory funnel. The mixture is extracted with EtOAc and the combined extracts are washed with brine and dried over anhydrous Na2 SO4. Filtration and concentration gives 1.76 g of 2-chloro-5-fluorobenzoxazole as a waxy solid. The crude chloride is used in the piperazine displacement reaction.

Reference： [1]Patent: US5736545,1998,A

4
[ 144-55-8 ]
[ 13451-78-0 ]
[ 135533-78-7 ]

Yield	Reaction Conditions	Operation in experiment
	With phosphorus pentachloride; In dichloromethane; trichlorophosphate;	Step 2 The <strong>[13451-78-0]2-mercapto-5-fluorobenzoxazole</strong> (2.0 g, 11.8 mmol) is slurried into POCl3 (9.7 mL, 104 mmol). The slurry is treated with PCl5 (3.0 g, 14.2 mmol) and 5.0 mL of anhydrous CH2Cl2. The mixture is stirred at room temperature for 5.5 hours. After this time excess POCl3 is removed under reduced pressure. The residue is treated with saturated aqueous NaHCO3 and the mixture is poured into a separatory funnel. The mixture is extracted with EtOAc and the combined extracts are washed with brine and dried over anhydrous Na2SO4. Filtration and concentration gives 1.76 g of 2-chloro-5-fluorobenzoxazole as a waxy solid. The crude chloride is used in the piperazine displacement reaction.

Reference： [1]Patent: EP883611,2002,B1

5
[ 141449-85-6 ]
[ 135533-78-7 ]
5-(5-fluorobenzo[d]oxazol-2-yl)hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With potassium carbonate In acetonitrile at 95℃;	1.2 Step 2) 5- (5-fluoro - benzo [d] oxazol-2-yl) hexahydro-pyrrolo [3,4-c] pyrrole -2 (1H) - carboxylatesynthesized Potassium carbonate (2.10 g, 15.0 mmol), hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylic acid tert-butyl ester (1.06 g, 4.99 mmol), 2-chloro-5-fluorobenzene And [d] oxazole (1 g, 5.9 mmol) was placed in a 100 mL single-necked flask, acetonitrile (20 mL) was added, and reflux was started at 95 ° C overnight, and the material was almost disappeared by TLC. Add water (100 mL) to quench the reaction, ethyl acetate (3*30 mL) was extracted, dried over anhydrous sodium sulfate and concentrated and purified by column chromatography ( petroleum ether/ethyl acetate (v/v) = 3/1)The title compound was a pale red solid (1.09 g, 63%).

Reference： [1]Current Patent Assignee: SHENZHEN DONGYANGGUANG INDUSTRIAL DEVELOPMENT CO LTD - CN109988169, 2019, A Location in patent: Paragraph 0196; 0202-0205

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P101	If medical advice is needed,have product container or label at hand.
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Code	Phrase
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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.
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P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
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P272	Contaminated work clothing should not be allowed out of the workplace.
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P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
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P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
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P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
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.
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P334	Immerse in cool water/wrap n wet bandages.
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P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
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.
P351	Rinse cautiously with water for several minutes.
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.
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P370	In case of fire:
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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:
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H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 135533-78-7 ] {[proInfo.proName]}

Quality Control of [ 135533-78-7 ]

Related Doc. of [ 135533-78-7 ]

Product Details of [ 135533-78-7 ]

Safety of [ 135533-78-7 ]

Application In Synthesis of [ 135533-78-7 ]

[ 135533-78-7 ] Synthesis Path-Upstream 1~5

[ 135533-78-7 ] Synthesis Path-Downstream 1~5

Precautionary Statements-General

Prevention

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