[ CAS No. 848499-31-0 ] {[proInfo.proName]}

Name: 848499-31-0|2-Bromo-thiazole-5-carboxamide|97%
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SKU: A240216
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Quality Control of [ 848499-31-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 848499-31-0 ]

Product Details of [ 848499-31-0 ]

CAS No. :	848499-31-0	MDL No. :	MFCD09998942
Formula :	C₄H₃BrN₂OS	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	RXTGRIUBDYHCKY-UHFFFAOYSA-N
M.W :	207.05	Pubchem ID :	20328604
Synonyms :

Calculated chemistry of [ 848499-31-0 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	37.91
TPSA :	84.22 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.72 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.1
Log Po/w (XLOGP3) :	1.19
Log Po/w (WLOGP) :	1.0
Log Po/w (MLOGP) :	-0.31
Log Po/w (SILICOS-IT) :	2.03
Consensus Log Po/w :	1.0

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.22
Solubility :	1.25 mg/ml ; 0.00605 mol/l
Class :	Soluble
Log S (Ali) :	-2.55
Solubility :	0.577 mg/ml ; 0.00279 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.74
Solubility :	3.75 mg/ml ; 0.0181 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.51

Safety of [ 848499-31-0 ]

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 [ 848499-31-0 ]

* 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 [ 848499-31-0 ]
Downstream synthetic route of [ 848499-31-0 ]

[ 848499-31-0 ] Synthesis Path-Upstream 1~3

1
[ 848499-31-0 ]
[ 440100-94-7 ]

Reference： [1] Patent: WO2010/94126, 2010, A1, . Location in patent: Page/Page column 68
[2] Patent: WO2010/94120, 2010, A1, . Location in patent: Page/Page column 60
[3] Patent: WO2010/108268, 2010, A1, . Location in patent: Page/Page column 51
[4] Patent: WO2011/11872, 2011, A1, . Location in patent: Page/Page column 47; 50
[5] Patent: US2011/301143, 2011, A1, . Location in patent: Page/Page column 43
[6] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 2, p. 980 - 984

2
[ 41731-83-3 ]
[ 848499-31-0 ]

Reference： [1] Patent: WO2010/94126, 2010, A1, . Location in patent: Page/Page column 67-68
[2] Patent: WO2010/108268, 2010, A1, . Location in patent: Page/Page column 50-51
[3] Patent: WO2011/11872, 2011, A1, . Location in patent: Page/Page column 47; 50
[4] Patent: US2011/301143, 2011, A1, . Location in patent: Page/Page column 43
[5] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 2, p. 980 - 984

3
[ 54045-76-0 ]
[ 848499-31-0 ]

Reference： [1] Patent: WO2010/94120, 2010, A1, . Location in patent: Page/Page column 60

[ 848499-31-0 ] Synthesis Path-Downstream 1~6

2
[ 848499-31-0 ]
[ 1073319-94-4 ]
[ 1073319-64-8 ]

Yield	Reaction Conditions	Operation in experiment
		Step 1 2-[3-(2-Chloro-5-iodophenoxy)propoxy)-l ,3-thiazole-5-carboxamideTo a stirred solution of 3-(2-chloro-5-iodophenoxy)propan-l -ol (1 59 g, 5 09 mmol) in DMF (14 mL) cooled to -78 0C was added 60% NaH in oil (495 mg, 12 38 mmol) The reaction mixture was warmed to room temperature for 5-10 mm and cooled again to -78 0C 2- Bromo-l,3-thiazole-5-carboxamide (1 00 g, 4 84 mmol) was then added and the reaction mixture was allowed to warm to room temperature and heated to 60 0C for 45 mm The suspension was <n="80"/>cooled to room temperature and poured into 1 N HCl, extracted with EtOAc, washed with 1 N HCl and bnne, dried (Na2SC»4) and filtered The organic layer was concentrated to dryness to afford a solid which was used in Step 2 without further purification

Reference： [1]Patent: WO2008/128335,2008,A1 .Location in patent: Page/Page column 78-79

3
[ 41731-83-3 ]
[ 848499-31-0 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium hydroxide; In tetrahydrofuran; methanol; water; at 20℃; for 4h;	INTERMEDIATE 1; Ethyl [5-(2-bromo-l,3-thiazol-5-yl)-2//-tetrazol-2-yl]acetate; Step 1 : 2-Bromo-l,3-thiazole-5-carboxamide; Into a 2 L round-bottom flask was added ethyl 2-bromothiazole-5-carboxylate (50.0 g, 212 mmol), THF (500 mL) and MeOH (250 mL). To this was added concentrated ammonium hydroxide in water (590 mL) and the reaction mixture was stirred at room temperature for 4 h. The solvents were removed under reduced pressure and the crude mixture poured into a separatory funnel containing brine (1 L). The aqueous layer was extracted with EtOAc (4 x 500 mL) and the combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure.
	With ammonium hydroxide; In tetrahydrofuran; methanol; water; at 20℃; for 4h;	INTERMEDIATE 1; Ethyl [5-(2-bromo-l ,3-thiazol-5-ylV2//-tetrazol-2-yl]acetate; Step 1 2-Bromo-L3-fhiazole-5-carboxarmde; Into a 2 L round-bottom flask was added ethyl 2-bromothiazole-5-carboxylate (50 O g, 212 mmol), THF (500 mL) and MeOH (250 mL) To this was added concentrated 5 ammonium hydroxide m water (590 mL) and the reaction mixture was stirred at room temperature for 4 h The solvents were removed under reduced pressure and the crude mixture poured into a separatory funnel containing brine (1 L) The aqueous layer was extracted with EtOAc (4 x 500 mL) and the combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure
	With ammonium hydroxide; In tetrahydrofuran; methanol; water; at 20℃; for 4h;	Into a 2 L round-bottom flask was added ethyl 2-bromothiazole-5-carboxylate (50.0 g, 212 mmol), THF (500 mL) and MeOH (250 mL). To this mixture was added concentrated ammonium hydroxide in water (590 mL) and the reaction mixture was stirred at room temperature for 4 h. The solvents were removed under reduced pressure, and the resulting crude mixture poured into a separatory funnel containing brine (1 L). The aqueous layer was extracted with EtOAc (4 x 500 mL) and the combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to give the title compound.

With ammonium hydroxide; In tetrahydrofuran; methanol; water; at 20℃; for 4h;

Step 1: 2-Bromo-1,3-thiazole-5-carboxamide Into a 2 L round-bottom flask was added ethyl 2-bromothiazole-5-carboxylate (50.0 g, 212 mmol), THF (500 mL) and MeOH (250 mL). To this was added concentrated ammonium hydroxide in water (590 mL) and the reaction mixture was stirred at room temperature for 4 h. The solvents were removed under reduced pressure and the crude mixture poured into a separatory funnel containing brine (1 L). The aqueous layer was extracted with EtOAc (4*500 mL) and the combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure.

Reference： [1]Patent: WO2010/94126,2010,A1 .Location in patent: Page/Page column 67-68
[2]Patent: WO2010/108268,2010,A1 .Location in patent: Page/Page column 50-51
[3]Patent: WO2011/11872,2011,A1 .Location in patent: Page/Page column 47; 50
[4]Patent: US2011/301143,2011,A1 .Location in patent: Page/Page column 43
[5]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 980 - 984

4
[ 848499-31-0 ]
[ 440100-94-7 ]

Yield	Reaction Conditions	Operation in experiment
		Step 2: 2-Bromo- 1 ,3-thiazole-5-carbonitrile; Into a 2 L round-bottom flask containing 2-bromo-l,3-thiazole-5-carboxamide (41.5 g, 201 mmol) in CH2Cl2 (1.3 L) was added triethylamine (70 mL, 502 mmol). The resulting solution was cooled to 0 0C and TFAA (34 mL, 241 mmol) was added slowly over 15 min. The reaction mixture was allowed to warm to room temperature and stirred for 2 h. The reaction mixture was poured into a 3 L separatory funnel containing saturated aqueous NaHCO3 solution (500 mL). The aqueous layer was extracted with CH2Cl2 (2 x 1.2 L) and the combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The crude reaction mixture was filtered through a short plug of silica gel on a sintered glass funnel, washing with copious quantities of EtOAc. The filtrate was concentrated under reduced pressure to provide the title compound.
	With triethylamine; trifluoroacetic anhydride; In dichloromethane; at 0 - 20℃;	Into a 2 L round-bottom flask containing 2-bromo- l,3-thiazole-5-carboxamide (41.5 g, 201 mmol) in CH2Cl2 (1.3 L) was added triethylamine (70 mL, 502 mmol). The resulting solution was cooled to 0 C and trifluoroacetic anhydride (34 mL, 241 mmol) was added slowly over 15 minutes. The reaction mixture was allowed to warm to room temperature and stirred for 2 h. The reaction mixture was poured into a 3 L separatory funnel containing saturated aqueous NaHCO3 solution (500 mL). The aqueous layer was extracted with dichloromethane (2 x 1.2 L) and the combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The resulting crude reaction mixture was filtered through a short plug of silica gel on a sintered glass funnel, washing with copious quantities of EtOAc. The filtrate was concentrated under reduced pressure to provide the title compound.
	With triethylamine; trifluoroacetic anhydride; In dichloromethane; at 0 - 20℃;	Step 2 2-Bromo- 1 ,3-thiazole-5-carbonit?le; Into a 2 L round-bottom flask containing 2-bromo-l,3-thiazole-5-carboxamide (41 5 g, 201 mmol) in CH2Cl2 (1 3 L) was added t?ethylamme (70 mL, 502 mmol) The15 resulting solution was cooled to 0 0C and TFAA (34 mL, 241 mmol) was added slowly over 15 mm The reaction mixture was allowed to warm to room temperature and stirred for 2 h The reaction mixture was poured into a 3 L separatory funnel containing saturated aqueous NaHCO3 solution (500 mL) The aqueous layer was extracted with CH2Cl2 (2 x 1 2 L) and the combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under20 reduced pressure The crude reaction mixture was filtered through a short plug of silica gel on a sintered glass funnel, washing with copious quantities of EtOAc The filtrate was concentrated under reduced pressure to provide the title compound

		Into a 2 L round-bottom flask containing 2- bromo-l,3-thiazole-5-carboxamide (41.5 g, 201 mmol) in CH2Cl2 (1.3 L) was addedtriethylamine (70 mL, 502 mmol). The resulting solution was cooled to 0 C and trifluoroacetic anhydride (34 mL, 241 mmol) was added slowly over 15 minutes. The reaction mixture was allowed to warm to room temperature and stirred for 2 h. Then the reaction mixture was poured into a 3 L separatory funnel containing saturated aqueous NaHCO3 solution (500 mL). The aqueous layer was extracted with dichloromethane (2 x 1.2 L) and the combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The resulting crude reaction mixture was filtered through a short plug of silica gel on a sintered glass funnel, and washed with copious quantities of EtOAc. The resulting filtrate was concentrated under reduced pressure to provide the title compound.
	With triethylamine; trifluoroacetic anhydride; In dichloromethane; at 0 - 20℃; for 2.25h;	Step 2: 2-Bromo-1,3-thiazole-5-carbonitrile Into a 2 L round-bottom flask containing <strong>[848499-31-0]2-bromo-1,3-thiazole-5-carboxamide</strong> (41.5 g, 201 mmol) in CH2Cl2 (1.3 L) was added triethylamine (70 mL, 502 mmol). The resulting solution was cooled to 0 C. and TFAA (34 mL, 241 mmol) was added slowly over 15 min. The reaction mixture was allowed to warm to room temperature and stirred for 2 h. The reaction mixture was poured into a 3 L separatory funnel containing saturated aqueous NaHCO3 solution (500 mL). The aqueous layer was extracted with CH2Cl2 (2*1.2 L) and the combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The crude reaction mixture was filtered through a short plug of silica gel on a sintered glass funnel, washing with copious quantities of EtOAc. The filtrate was concentrated under reduced pressure to provide the title compound.

Reference： [1]Patent: WO2010/94126,2010,A1 .Location in patent: Page/Page column 68
[2]Patent: WO2010/94120,2010,A1 .Location in patent: Page/Page column 60
[3]Patent: WO2010/108268,2010,A1 .Location in patent: Page/Page column 51
[4]Patent: WO2011/11872,2011,A1 .Location in patent: Page/Page column 47; 50
[5]Patent: US2011/301143,2011,A1 .Location in patent: Page/Page column 43
[6]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 980 - 984

5
[ 54045-76-0 ]
[ 848499-31-0 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium hydroxide; In tetrahydrofuran; methanol; water; at 20℃; for 4h;	Into a 2 L round-bottom flask was added ethyl 2- bromothiazole-5-carboxylate (50.0 g, 212 mmol), THF (500 niL) and MeOH (250 mL). To this was added concentrated ammonium hydroxide in water (590 mL) and the reaction mixture was stirred at room temperature for 4 h. The solvents were removed under reduced pressure, and the crude mixture poured into a separatory funnel containing brine (1 L). The aqueous layer was extracted with EtOAc (4 x 500 mL) and the combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to give the title compound.

Reference： [1]Patent: WO2010/94120,2010,A1 .Location in patent: Page/Page column 60

6
[ 848499-31-0 ]
(S)-3-(1-aminoethyl)-6-chloroquinolin-2(1H)-one monohydrochloride [ No CAS ]
2-[(1S)-1-(6-chloro-2-oxo-1,2-dihydroquinolin-3-yl) ethyl]amino}-1,3-thiazole-5-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
10%	With dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In water; at 140℃; for 2.5h;	A mixture of (S)-3-(1-aminoethyl)-6-chloroquino- lin-2(1H)-one HC1, 11-1 (450 mg, 1.7 mmol, 1 eq.), 2-bro- mothiazole-5-carboxamide (425 mg, 2.05 mmol, 1.2 eq.) and DIEA (482 mg, 3.7 mmol, 2.2 eq.) in 10 mE DM50 in a sealed tube was heated at 140 C. for 2.5 hours. The reaction was then poured into water and extracted with EtOAc (x2). The combined organic extracts were washed with brine and dried over Na2SO4. After rotary evaporation, trituration with DCM afforded 184 mg crude product as a solid. Chromatography over 6.5 g silica gel, eluting with a 0 to 15% EtOH/DCM gradient, provided 100 mg of crude product as a gold solid still containing DIEA. Trituration with DCM, followed by evaporation of a MeOR solution of the solid afforded 70 mg 1-10 as a yellow-orange solid (10%). H-NMR (300 MHz, d6DMSO) oe ppm: 12.0 (s, 0.75H), 8.54 (d, J=6.87, 1H), 7.79 (d, J=2.19, 1H), 7.73 (s, 1H), 7.61 (s, 1H), 7.61 (broad s, 1H), 7.48 (dd, J=2.19, 8.79, 1H), 7.29 (d, J=8.79, 1H), 7.06 (broad s, 1H), 4.89 (m, 1H),1.40 (d, J=6.60, 3H). ECMS (Method 3): Rt 3.85 mi mlz349 [M+H]

Reference： [1]Patent: US2016/311818,2016,A1 .Location in patent: Paragraph 0599; 0600

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Ghs Precautionary Statements

Precautionary Statements-General
Code	Phrase
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Code	Phrase
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P342	If experiencing respiratory symptoms:
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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.
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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.
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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.
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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. 848499-31-0 ] {[proInfo.proName]}

Quality Control of [ 848499-31-0 ]

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Application In Synthesis of [ 848499-31-0 ]

[ 848499-31-0 ] Synthesis Path-Upstream 1~3

[ 848499-31-0 ] Synthesis Path-Downstream 1~6

Related Functional Groups of [ 848499-31-0 ]

Bromides

Amides

Amines

Related Parent Nucleus of [ 848499-31-0 ]

Thiazoles

Precautionary Statements-General

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Physical hazards

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[ 848499-31-0 ]

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[ 848499-31-0 ]