[ CAS No. 81569-44-0 ] {[proInfo.proName]}

Name: 81569-44-0|Methyl 4-methylthiazole-5-carboxylate|98%
Brand: Ambeed
SKU: A132435
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Quality Control of [ 81569-44-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 81569-44-0 ]

SDS Specification

Alternatived Products of [ 81569-44-0 ]

Product Details of [ 81569-44-0 ]

CAS No. :	81569-44-0	MDL No. :	MFCD00129998
Formula :	C₆H₇NO₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	RRCLLMUIJYXSGZ-UHFFFAOYSA-N
M.W :	157.19	Pubchem ID :	676432
Synonyms :

Calculated chemistry of [ 81569-44-0 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.33
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	38.36
TPSA :	67.43 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.17 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.88
Log Po/w (XLOGP3) :	1.54
Log Po/w (WLOGP) :	1.24
Log Po/w (MLOGP) :	0.02
Log Po/w (SILICOS-IT) :	2.32
Consensus Log Po/w :	1.4

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.02
Solubility :	1.49 mg/ml ; 0.00949 mol/l
Class :	Soluble
Log S (Ali) :	-2.57
Solubility :	0.428 mg/ml ; 0.00272 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.74
Solubility :	2.83 mg/ml ; 0.018 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.23

Safety of [ 81569-44-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 81569-44-0 ]

* 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 [ 81569-44-0 ]
Downstream synthetic route of [ 81569-44-0 ]

[ 81569-44-0 ] Synthesis Path-Upstream 1~7

1
[ 81569-44-0 ]
[ 82294-70-0 ]

Reference： [1] Journal of Medicinal and Pharmaceutical Chemistry, 1959, vol. 1, p. 577,594
[2] Journal of the American Chemical Society, 1939, vol. 61, p. 891

2
[ 20582-55-2 ]
[ 81569-44-0 ]

Reference： [1] Journal of the American Chemical Society, 1935, vol. 57, p. 1879
[2] Journal of the Chemical Society, 1935, p. 1030

3
[ 105-45-3 ]
[ 81569-44-0 ]

Reference： [1] Journal of Medicinal and Pharmaceutical Chemistry, 1959, vol. 1, p. 577,594
[2] Journal of the American Chemical Society, 1939, vol. 61, p. 891

4
[ 186581-53-3 ]
[ 20485-41-0 ]
[ 81569-44-0 ]

Reference： [1] Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1934, vol. 228, p. 27,31
[2] Journal of the American Chemical Society, 1935, vol. 57, p. 1879

5
[ 115-08-2 ]
[ 4755-81-1 ]
[ 81569-44-0 ]

Reference： [1] Journal of Medicinal and Pharmaceutical Chemistry, 1959, vol. 1, p. 577,594
[2] Journal of the American Chemical Society, 1939, vol. 61, p. 891

6
[ 67-56-1 ]
[ 54237-09-1 ]
[ 81569-44-0 ]

Reference： [1] Patent: WO2012/30990, 2012, A1, . Location in patent: Page/Page column 79-80

7
[ 7647-01-0 ]
[ 20485-41-0 ]
[ 81569-44-0 ]

Reference： [1] Journal of the Chemical Society, 1935, p. 1030

[ 81569-44-0 ] Synthesis Path-Downstream 1~24

1
[ 186581-53-3 ]
[ 20485-41-0 ]
[ 81569-44-0 ]

Reference： [1]Hoppe-Seyler's Zeitschrift fur Physiologische Chemie,1934,vol. 228,p. 27,31

2
[ 81569-44-0 ]
[ 89179-72-6 ]

Reference： [1]Journal of medicinal and pharmaceutical chemistry,1959,vol. 1,p. 577,594

3
[ 115-08-2 ]
[ 4755-81-1 ]
[ 81569-44-0 ]

Reference： [1]Journal of medicinal and pharmaceutical chemistry,1959,vol. 1,p. 577,594

4
(5-methoxycarbonyl-thiazol-4-yl)-acetic acid [ No CAS ]
[ 81569-44-0 ]

Reference： [1]Helvetica Chimica Acta,1948,vol. 31,p. 1342,1348

5
[ 96-48-0 ]
[ 81569-44-0 ]
[ 123039-51-0 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1989,vol. 37,p. 958 - 961

6
[ 7647-01-0 ]
[ 20485-41-0 ]
[ 81569-44-0 ]

Reference： [1]Journal of the Chemical Society,1935,p. 1030

7
[ 81569-44-0 ]
[ 80087-60-1 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1989,vol. 37,p. 958 - 961

8
[ 81569-44-0 ]
[ 123039-52-1 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1989,vol. 37,p. 958 - 961

9
[ 20582-55-2 ]
[ 81569-44-0 ]

Reference： [1]Journal of the American Chemical Society,1935,vol. 57,p. 1879
[2]Journal of the Chemical Society,1935,p. 1030

10
[ 81569-44-0 ]
[ 82294-70-0 ]

Reference： [1]Journal of medicinal and pharmaceutical chemistry,1959,vol. 1,p. 577,594

11
[ 81569-44-0 ]
[ 103987-43-5 ]

Reference： [1]Journal of medicinal and pharmaceutical chemistry,1959,vol. 1,p. 577,594

12
[ 105-45-3 ]
[ 81569-44-0 ]

Reference： [1]Journal of medicinal and pharmaceutical chemistry,1959,vol. 1,p. 577,594

13
[ 81569-44-0 ]
[ 1977-06-6 ]

Yield	Reaction Conditions	Operation in experiment
		To a stirred mixture of lithium aluminum hydride (0.25 g) in THF (100 ml) at 5- 10C was added 4-methyl thiazole-5-caboxylic acid methyl ester (10 g) over a period of 30 minutes. The reaction mixture was stirred at 10- 15C for 2 to 3 hours. Progress of reaction was monitored by TLC. After completion, the reaction was quenched by adding a aqueous solution of sodium sulfate. The resultant inorganic solids were filtered and the cake was washed with ethyl acetate. Filtrate was concentrated under reduced pressure to get a pale yellow solid (7.5 g), providing an HPLC Purity (% area) of more than 99%. ¹H-NMR (300MHz): 2.36 (s, 3H), 3.98 (s broad, 1H), 4.79 (s, 2H), 8.58 (s, 1H).
		EXAMPLE 2 Preparation of 4-methyl-5hydroxymethyl-thiazole (IV) Monoglyme (200 ml) was charged and cooled to -10 C. To this NaBH4 (40.0 g) was charged in one lot at -10 C. and stirred for 15 minutes. AlCl3 (47.0 g) was slowly added for 1 hour at -10 to +5 C., stirred for 30 min at 0 C. Then <strong>[81569-44-0]4-methyl-thiazole-5-carboxylic acid methyl ester</strong> (III) (100.0 g) was added for 1 hour at 0-15 C. The reaction mixture was stirred at 15-25 C. for 4 hours and the progress of reaction was monitored by HPLC. The reaction mixture was poured into mixture of ice (500 g) and conc. HCl (200 ml) and stirred for 30 minutes. The reaction mixture was concentrated at 50-60 C. to remove organic solvents from it and cooled the reaction mixture to 5 C. The pH of the reaction mixture was adjusted with sodium hydroxide solution at 5-15 C. up to 12.5 and heated to 45 C. The reaction mixture was extracted with THF (4*250 ml). Combined THF layers were collected and treated with charcoal at 45 C. THF layer was distilled of at 50 C. to yield the title compound (55-60 g), (purity by HPLC: 97-98%).

Reference： [1]Patent: WO2005/100330,2005,A1 .Location in patent: Page/Page column 11
[2]Patent: US2003/204095,2003,A1 .Location in patent: Page/Page column 2

14
[ 81569-44-0 ]
[ 507-20-0 ]
[ 1361941-36-7 ]

Yield	Reaction Conditions	Operation in experiment
43%		A solution of <strong>[81569-44-0]methyl 3-methylthiophene-2-carboxylate</strong> 109a (33 g, 0.211 mol) in dry CH2CI2 (30 mL) was added dropwise to a mixture of aluminum chloride (40 g, 0.297 mol) and dry CH2CI2 (200 mL) at -78 C, under nitrogen. The reaction mixture was stirred for 10 min at - 78 C, and a solution of ieri-butyl chloride (23 mL, 0.211 mol) in dry CH2C12 (30 mL) was added dropwise at -78 C. The reaction mixture was stirred for 1 h at -78 C, gradually allowed to warm to room temperature and stirred for 16 h at room temperature. It was poured on ice and extracted with CH2CI2 (2 x 200 mL). The organic layer was dried over anhydrous Na2S04 and the solvent evaporated under vacuum. The obtained residue was purified by fractional distillation to yield methyl 5-ieri-butyl-3-methylthiophene-2-carboxylate 109b (19 g, 43%) as a light yellow liquid.

Reference： [1]Patent: WO2012/30990,2012,A1 .Location in patent: Page/Page column 80

15
[ 67-56-1 ]
[ 54237-09-1 ]
[ 81569-44-0 ]

Yield	Reaction Conditions	Operation in experiment
	Reflux;	A 100-mL single-neck round-bottomed flask was charged with 4-methylthiazole-5- carbonyl chloride (13.1 g, 10.0 mmol) in methanol (30 mL). The mixture was reflux overnight. The mixture was cooled to room temperature, and concentrated. The residue was partitioned between diethyl ether (50mL) and water (50mL). The organic layer was washed with brine and dried over sodium sulfate. The drying agent was removed by filtration. The filtrate was concentrated under reduced pressure to afford methyl 3-methylthiophene-2- carboxylate (101a) (12.8 g, 95%) as a colorless oil, which was used in the next step without further purification

Reference： [1]Patent: WO2012/30990,2012,A1 .Location in patent: Page/Page column 79-80

16
[ 81569-44-0 ]
[ 1361941-35-6 ]

Reference： [1]Patent: WO2012/30990,2012,A1

17
[ 81569-44-0 ]
[ 1361386-78-8 ]

Reference： [1]Patent: WO2012/30990,2012,A1

18
[ 81569-44-0 ]
[ 1361386-79-9 ]

Reference： [1]Patent: WO2012/30990,2012,A1

19
[ 81569-44-0 ]
[ 4559-70-0 ]
methyl 2-(diphenylphosphoryl)-4-methylthiazole-5-carboxylate [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 4682 - 4689
[2]Organic Letters,2016,vol. 18,p. 452 - 455

20
[ 81569-44-0 ]
[ 299199-50-1 ]
methyl 4-methyl-2-(2-(quinolin-8-ylcarbamoyl)thiophen-3-yl)thiazole-5-carboxylate [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 10414 - 10418
Angew. Chem.,2016,vol. 128,p. 10570 - 10574,5

21
[ 81569-44-0 ]
[ 135145-81-2 ]
[ 1907-33-1 ]
tert-butyl 2-((2R,3R,4R)-3,4-bis((triisopropylsilyl)oxy)-2-(((triisopropylsilyl)oxy)methyl)-3,4-dihydro-2H-pyran-6-yl)-4-methylthiazole-5-carboxylate [ No CAS ]

Reference： [1]Organic Letters,2017,vol. 19,p. 3608 - 3611

22
[ 3829-80-9 ]
[ 81569-44-0 ]

Yield	Reaction Conditions	Operation in experiment
96%	With tetrahydrofuran; tert.-butylnitrite; dimethyl sulfoxide; at 30℃; for 1h;Green chemistry;	General procedure: A solution of amine 2 (5 mmol) in THF (3 mL) was added dropwise over 20 min to a solution of t-BuONO (7.5 mmol) and DMSO (0.5 mmol) in THF (7 mL) at 30 C. The mixture was stirred at 30 C until the starting materials 2 were consumed (monitored by TLC). The solvent was evaporated, and the yields of the low boiling point products were determined by GC; the high boiling point products were isolated by column chromatography on silica gel (hexane/ethyl acetate).

Reference： [1]Journal of Chemical Research,2018,vol. 42,p. 579 - 583

23
[ 3829-80-9 ]
[ 81569-44-0 ]
2-chloro-4-methyl-thiazole-5-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Journal of Chemical Research,2018,vol. 42,p. 579 - 583

24
[ 81569-44-0 ]
methyl 2-deuterio-4-methylthiazole-5-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With water-d2; silver; In dimethyl sulfoxide; at 25℃; for 12h;	Silver reagent (0.1 mmol), phosphine ligand (0.1 mmol), deuterated water (0.4 g, 20 mmol), <strong>[81569-44-0]methyl 4-methyl-5-thiazolecarboxylate</strong> (0.16 g, 1 mmol) and dimethyl sulfoxide (5 mL) were added to a 10 mL three-necked flask. After reacting for 12 hours at 25 C, the reaction was quenched by the addition of saturated ammonium chloride solution, the mixture was extracted with dichloromethane, the organic phase was combined, the organic solvent was concentrated, and the product was further purified by column chromatography to give deuterated <strong>[81569-44-0]methyl 4-methyl-5-thiazolecarboxylate</strong> was obtained in a yield of 75%. The generation rate is 94%.

Reference： [1]Organic Letters,2019,vol. 21,p. 6745 - 6749
[2]Patent: CN110156766,2019,A .Location in patent: Paragraph 0015

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Ghs Precautionary Statements

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Response
Code	Phrase
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P320
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P321
P322
P330	Rinse mouth.
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P342	If experiencing respiratory symptoms:
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P378
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P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
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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.
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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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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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. 81569-44-0 ] {[proInfo.proName]}

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[ 81569-44-0 ] Synthesis Path-Upstream 1~7

[ 81569-44-0 ] Synthesis Path-Downstream 1~24

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Esters

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Thiazoles

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