[ CAS No. 6436-59-5 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}

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2D 3D

Structure of 6436-59-5 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 6436-59-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 6436-59-5 ]

SDS Specification

Alternatived Products of [ 6436-59-5 ]

Product Details of [ 6436-59-5 ]

CAS No. :	6436-59-5	MDL No. :	MFCD00156148
Formula :	C₇H₉NO₂S	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	QWWPUBQHZFHZSF-UHFFFAOYSA-N
M.W :	171.22	Pubchem ID :	293353
Synonyms :

Calculated chemistry of [ 6436-59-5 ] Expand+

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.43
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	43.17
TPSA :	67.43 ?2

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) :	-5.99 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.85
Log Po/w (XLOGP3) :	1.91
Log Po/w (WLOGP) :	1.63
Log Po/w (MLOGP) :	0.37
Log Po/w (SILICOS-IT) :	2.64
Consensus Log Po/w :	1.68

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.24
Solubility :	0.978 mg/ml ; 0.00571 mol/l
Class :	Soluble
Log S (Ali) :	-2.95
Solubility :	0.192 mg/ml ; 0.00112 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.16
Solubility :	1.19 mg/ml ; 0.00697 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.65

Safety of [ 6436-59-5 ]

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

Application In Synthesis of [ 6436-59-5 ]

* 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.

Upstream synthesis route of [ 6436-59-5 ]
Downstream synthetic route of [ 6436-59-5 ]

[ 6436-59-5 ] Synthesis Path-Upstream 1~1

1
[ 6436-59-5 ]
[ 21917-76-0 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 8, p. 1203 - 1208
[2] Patent: WO2011/106414, 2011, A1,

[ 6436-59-5 ] Synthesis Path-Downstream 1~5

1
[ 6436-59-5 ]
[ 78502-71-3 ]

Yield	Reaction Conditions	Operation in experiment
38%		Ethyl 2-methyl-l,3-thiazole-4-carboxylate (500 mg, 2.92 mmol) was dissolved in CCU (10 rnL) and NBS (624 mg, 3.50 mmol) was added and the reaction heated at 76 0C for 60 min. AIBN (36 mg, 0.21 mmol) was added and heating continued at 76 0C for 4 h. The reaction mixture was allowed to cool to ambient temperature and filtered through Celite. The filter cake was washed with DCM. The combined organic layers were concentrated in vacuo with silica and purified using FCC, eluting with 50 % EtOAc in heptanes, to afford the title compound. Yield: 274 mg, 38 %.
31%	With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane;Heating / reflux;	2-Bromomethyl-thiazole-4-carboxylic acid ethyl ester was prepared according to N. Kindon et al. (U.S. Pat. No. 6,162,808): A mixture of 2-methyl-thiazole-4-carboxylic acid (available from Maybridge pic, Tintagel, UK; 9.8 g, 57.2 mmol), benzoyl peroxide (40 mg, 0.165 mmol) and NBS (10.6 g, 60.0 mmol) in carbon tetrachloride (250 mL) was heated at reflux over the weekend. The reaction mixture was cooled to room temperature and evaporated under reduced pressure. The crude material was partitioned between ethyl acetate and water. The organic layer was dried (magnesium sulfate), filtered, evaporated, and purified by chromatography on flash silica gel, eluting with 20% ethyl acetate/hexane to give 2-bromomethyl-thiazole-4-carboxylic acid ethyl ester (4.4 g, 31%) as an orange oil. 1HNMR (CDCl3): delta 9.23 (s, 1H), 4.77 (s, 2H), 4.44 (q, J=7.0 Hz, 2H), 1.41 (t, J=7.0 Hz, 3H). MS (APCl+): 252 (100), 250 (90).
31%	With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane;Heating / reflux;	2-Bromomethyl-thiazole-4-carboxylic acid ethyl ester was prepared according to Kindon, N et al. (U.S. Pat. No. 6,162,808): A mixture of 2-methyl-thiazole-4-carboxylic acid (available from Maybridge plc, Tintagel, UK; 9.8 g, 57.2 mmol), benzoyl peroxide (40 mg, 0.165 mmol) and NBS (10.6 g, 60.0 mmol) in carbon tetrachloride (250 mL) was heated at reflux over the weekend. The reaction mixture was cooled to room temperature and evaporated under reduced pressure. The crude material was partitioned between ethyl acetate and water. The organic layer was dried (magnesium sulfate), filtered, evaporated, and purified by chromatography on flash silica gel, eluting with 20% ethyl acetate/hexane to give 2-bromomethyl-thiazole-4-carboxylic acid ethyl ester (4.4 g, 31%) as an orange oil. 1HNMR (CDCl3): delta 9.23 (s, 1H), 4.77 (s, 2H), 4.44 (q, J=7.0 Hz, 2H), 1.41 (t, J=7.0 Hz, 3H). MS (APCI+): 252 (100), 250 (90).

	With N-Bromosuccinimide;dibenzoyl peroxide; In 2-Methylpentane; chloroform;	ii 2-Bromomethyl-4-thiazolecarboxylic acid, ethyl ester 2-Methyl-4-thiazolecarboxylic acid ethyl ester (1 g) (Liebigs Ann. Chem. 1981, 623), N-bromosuccinimide (1.04 g) and a catalytic amount of benzoyl peroxide in chloroform (25 ml) was heated at reflux for 20 hours. After cooling, the reaction mixture was washed with saturated aqueous sodium bicarbonate, dried (MgSO4) and evaporated under reduced pressure. Purification was by chromatography eluding with 40% ethyl acetate in isohexane to give the product as an oil. Yield 0.5 g. MS: GC-MS: 249/251 (M+)
	With N-Bromosuccinimide;2,2'-azobis(isobutyronitrile); In tetrachloromethane; for 3h;Heating / reflux;	Reference Example 80; Ethyl 2-dimethylaminomethylthiazole-4-carboxylate; [Show Image] N-Bromosuccinimide (1.14 g) and a catalytic amount of AIBN were added to a carbon tetrachloride solution (20 ml) of ethyl 2-methylthiazole-4-carboxylate (1.00 g), followed by heating under reflux for 3 hours. After cooling the reaction solution to room temperature, the resulting precipitate was removed by filtration, the filtrate was concentrated, and the thus obtained residue was used in the subsequent reaction without purification.
		Preparation Example 22; The following products were prepared with a partial modification of the method of Liu, et al. (Synthesis, 2001 14, 2078-2080). Ethyl (2-methyl-1,3-thiazol-4-yl)carboxylate (25 g) was added to carbon tetrachloride (500 mL), and subsequently, NBS (53 g), and benzoyl peroxide (4.7 g) (wetted with 75% water) were sequentially added thereto, followed by heating to reflux for 100 minutes under close irradiation with a 300 W lamp. The reaction mixture was left to be cooled, then the insoluble material was collected by filtration, and the obtained filtrate was washed with water, followed by extraction with an appropriate amount of CHCl3. The organic layer was sequentially washed with a 5% (W/W) aqueous sodium thiosulfate solution (600 g) and brine, and dried over MgSO4, and then the solvent was evaporated. To the obtained residue was added THF (300 mL), followed by sequential addition dropwise of diethyl phosphite (18.9 mL) and a Hunig's base (25.4 mL) at about 0 C. under an argon atmosphere. Thereafter, the temperature was slowly elevated, and the mixture was stirred at room temperature for about 2 hours. An appropriate amount of ice water was poured into the reaction mixture, followed by extraction with ethyl acetate several times. The organic layer was sequentially washed with 0.3 M hydrochloric acid (1 L) and brine, and dried over MgSO4, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1 to 2:1) to prepare ethyl [2-(bromomethyl)-1,3-thiazol-4-yl]carboxylate (26.82 g).

Reference： [1]Bioorganic and Medicinal Chemistry,2001,vol. 9,p. 1 - 6
[2]Patent: WO2010/20556,2010,A1 .Location in patent: Page/Page column 156
[3]Patent: US2006/122256,2006,A1 .Location in patent: Page/Page column 21
[4]Patent: US2004/266856,2004,A1 .Location in patent: Page/Page column 19
[5]Patent: US2020/123117,2020,A1 .Location in patent: Paragraph 1108; 1109
[6]Liebigs Annalen der Chemie,1981,p. 623 - 632
[7]Bioorganic and medicinal chemistry letters,2002,vol. 12,p. 2443 - 2446
[8]Patent: US6162808,2000,A
[9]Patent: EP1612204,2006,A1 .Location in patent: Page/Page column 47
[10]Patent: US2012/184521,2012,A1 .Location in patent: Page/Page column 23

2
[ 6436-59-5 ]
[ 78502-71-3 ]
[ 78502-72-4 ]
[ 78502-73-5 ]

Reference： [1]Liebigs Annalen der Chemie,1981,p. 623 - 632

3
[ 6436-59-5 ]
[ 78502-71-3 ]
[ 78502-72-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 6142 - 6146

4
[ 6436-59-5 ]
[ 21917-76-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 1203 - 1208
[2]Patent: WO2011/106414,2011,A1

5
[ 6436-59-5 ]
[ 94-36-0 ]
[ 78502-71-3 ]

Yield	Reaction Conditions	Operation in experiment
31%	With N-Bromosuccinimide; In tetrachloromethane;	Preparation of the starting material: A solution of ethyl 2-methyl-4-thiazolecarboxylate [JCS 1946, 87, E. R. H. Jones, F. A. Robinson, M. N. Strachan] (5.0 g, 29.2 mmol) in CCl4 (30 ml) was treated with N-bromosuccinimide (5.2 g, 29.2 mmol) and benzoylperoxide (0.03 g). The reaction was heated to reflux while irradiating with a strong lamp for 21/2 hours. The reaction mixture was allowed to cool to ambient temperature, filtered and evaporated. The residue was purified by chromatography (eluant: CH2 Cl2) to obtain ethyl 2-bromomethyl-4-thiazolecarboxylate (2.27 g, 31%). NMR (250 MH, DMSO-d6): delta8.55 (s, 1H), 5.04 (s, 2H), 4.30 (g, 2H), 1.32 (t, 3H).

Reference： [1]Patent: US5965741,1999,A

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Technical Information

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[ 6436-59-5 ]

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Ghs Precautionary Statements

Precautionary Statements-General
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.
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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.
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P242	Use only non-sparking tools.
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P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
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.
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Code	Phrase
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P330	Rinse mouth.
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P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
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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.
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.
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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.
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H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
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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

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[ CAS No. 6436-59-5 ] {[proInfo.proName]}

Quality Control of [ 6436-59-5 ]

Related Doc. of [ 6436-59-5 ]

Product Details of [ 6436-59-5 ]

Calculated chemistry of [ 6436-59-5 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 6436-59-5 ]

Application In Synthesis of [ 6436-59-5 ]

[ 6436-59-5 ] Synthesis Path-Upstream 1~1

[ 6436-59-5 ] Synthesis Path-Downstream 1~5

Technical Information

Related Functional Groups of [ 6436-59-5 ]

Esters

Related Parent Nucleus of [ 6436-59-5 ]

Thiazoles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 6436-59-5 ]

Related Parent Nucleus of
[ 6436-59-5 ]