[ CAS No. 1011-40-1 ] {[proInfo.proName]}

Name: 1011-40-1|2-Phenylthiazole-5-carbaldehyde|98%
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2D 3D

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Quality Control of [ 1011-40-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1011-40-1 ]

SDS Specification

Alternatived Products of [ 1011-40-1 ]

Product Details of [ 1011-40-1 ]

CAS No. :	1011-40-1	MDL No. :	MFCD04973719
Formula :	C₁₀H₇NOS	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KKALNCQCDXQTCG-UHFFFAOYSA-N
M.W :	189.23	Pubchem ID :	2763706
Synonyms :

Calculated chemistry of [ 1011-40-1 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	11
Fraction Csp3 :	0.0
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	52.94
TPSA :	58.2 Å²

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) :	-5.74 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.92
Log Po/w (XLOGP3) :	2.41
Log Po/w (WLOGP) :	2.62
Log Po/w (MLOGP) :	1.14
Log Po/w (SILICOS-IT) :	3.83
Consensus Log Po/w :	2.38

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.03
Solubility :	0.178 mg/ml ; 0.000943 mol/l
Class :	Soluble
Log S (Ali) :	-3.27
Solubility :	0.101 mg/ml ; 0.000532 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.76
Solubility :	0.0327 mg/ml ; 0.000173 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.3

Safety of [ 1011-40-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302+H312+H332-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1011-40-1 ]

* 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 [ 1011-40-1 ]
Downstream synthetic route of [ 1011-40-1 ]

[ 1011-40-1 ] Synthesis Path-Upstream 1~2

1
[ 1011-40-1 ]
[ 10058-38-5 ]

Reference： [1] Chemische Berichte, 1964, vol. 97, p. 1684 - 1687

2
[ 36437-19-1 ]
[ 2227-79-4 ]
[ 1011-40-1 ]

Reference： [1] Chemische Berichte, 1964, vol. 97, p. 1684 - 1687
[2] Patent: CN106279132, 2017, A, . Location in patent: Paragraph 0147; 0148
[3] Patent: WO2006/106326, 2006, A1, . Location in patent: Page/Page column 107

[ 1011-40-1 ] Synthesis Path-Downstream 1~39

1
[ 36437-19-1 ]
[ 2227-79-4 ]
[ 1011-40-1 ]

Yield	Reaction Conditions	Operation in experiment
	With 5-bromo-2-thiophencarboxaldehyde; In acetone; for 2h;Reflux;	Thiobenzamide (thiobenzamide) (1.0 equiv),5-bromothiophene-2-carbaldehyde (1.0 equiv) and2-chloromalonedialdehyde (2-chloromalanal) was dissolved in acetone and refluxed for 2 h.After completion of the reaction, the reaction mixture was extracted with water and extracted with ethyl acetate. The combined organic phases were dried over anhydrous sodium sulfate and filtered to give 2-phenylthiazole-5-carbaldehyde (2-phenylthiazole-5-carbaldehyde).
	In acetone; at 20℃;	Example 148; 2-phenyl-4- [(3S)-piperidin-3-ylaminol f 1 ,31 thiazolo [4,5-cl pyridine- 7-carboxamide; 2-phenyl-thiazole-5-carbaldehyde; To a solution of 2-chloromalonaldehyde (500 nig, 4.69 mmol) in 5.00 mL acetone is added thiobenzamide (643 mg, 4.69 mmol). The reaction mixture is stirred at rt until LCMS indicates the reaction is complete. The reaction mixture is concentrated under reduced pressure and the resulting solid is used directly in the next step. 1H NMR delta 7.57 (m, 3H)5 8.09 (d, 2H), 8.78 (s, IH), 10.1 (s, IH). LCMS (ES, M+H=190).

Reference： [1]Chemische Berichte,1964,vol. 97,p. 1684 - 1687
[2]Patent: CN106279132,2017,A .Location in patent: Paragraph 0147; 0148
[3]Patent: WO2006/106326,2006,A1 .Location in patent: Page/Page column 107

2
[ 1011-40-1 ]
[ 10058-38-5 ]

Reference： [1]Chemische Berichte,1964,vol. 97,p. 1684 - 1687

3
[ 532-27-4 ]
[ 1011-40-1 ]
(E)-1-Benzoyl-2-(2-phenyl-thiazolyl-5)-oxiran [ No CAS ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1980,vol. 322,p. 207 - 212

4
[ 616-34-2 ]
[ 1011-40-1 ]
[ 76292-83-6 ]

Reference： [1]Tetrahedron Letters,1980,vol. 21,p. 2197 - 2200

5
[ 67-56-1 ]
[ 760-84-9 ]
[ 1011-40-1 ]
methyl N-(2-phenylthiazol-5-ylmethylene)leucinate [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1987,p. 2285 - 2296

6
[ 67-56-1 ]
[ 71849-99-5 ]
[ 1011-40-1 ]
methyl N-(2-phenylthiazol-5-ylmethylene)phenylglycinate [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1987,p. 2285 - 2296

7
[ 6829-40-9 ]
[ 1011-40-1 ]
[ 76292-83-6 ]

Reference： [1]Tetrahedron,1989,vol. 45,p. 4649 - 4668

8
[ 6829-40-9 ]
[ 1011-40-1 ]
[ 76292-68-7 ]

Reference： [1]Tetrahedron,1989,vol. 45,p. 4649 - 4668
[2]Tetrahedron,1989,vol. 45,p. 4649 - 4668

9
[ 13433-00-6 ]
[ 1011-40-1 ]
[ 76292-75-6 ]

Reference： [1]Tetrahedron Letters,1980,vol. 21,p. 2197 - 2200

10
[ 13433-00-6 ]
[ 1011-40-1 ]
[ 76292-82-5 ]

Reference： [1]Tetrahedron Letters,1980,vol. 21,p. 2197 - 2200

11
[ 13433-00-6 ]
[ 1011-40-1 ]
[ 76292-68-7 ]

Reference： [1]Tetrahedron Letters,1980,vol. 21,p. 2197 - 2200
[2]Tetrahedron Letters,1980,vol. 21,p. 2197 - 2200

12
[ 5680-79-5 ]
[ 1011-40-1 ]
[ 76292-83-6 ]

Reference： [1]Tetrahedron,1989,vol. 45,p. 4649 - 4668

Yield	Reaction Conditions	Operation in experiment
		Stage D: 2-phenyl-5-formyl-thiazol Reduction: A solution of 4.5 g of the product of Stage C in 35 ml of tetrahydrofuran was added over 20 minutes and while maintaining the temperature at 10 C. to a suspension of 1.45 g of lithium-aluminium hydride in 65 ml of tetrahydrofuran cooled to 10 C. The mixture was stirred for 45 minutes at 10 C., then for 2 hours at ambient temperature. Then, 50% tetrahydrofuran in water was added while maintaining the temperature below 20 C. and 15 ml of a solution of potassium sodium tartrate was added. Filtration was carried out followed by rinsing and bringing to dryness under reduced pressure. The residue was impasted in hexane, separated and dried at 40 C. under reduced pressure to obtain 3.6 g of the product melting at 82 C.

14
[ 141-97-9 ]
[ 1011-40-1 ]
3-(2-phenyl-thiazol-5-yl)-pentanedioic acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 845 - 849

15
[ 1011-40-1 ]
[ 877398-87-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 845 - 849

16
[ 1011-40-1 ]
4-chlorocarbonyl-3-(2-phenyl-thiazol-5-yl)-butyric acid ethyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 845 - 849

17
[ 1011-40-1 ]
3-(2-phenyl-thiazol-5-yl)-pentanedioic acid monoethyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 845 - 849

18
[ 1011-40-1 ]
[ 722549-34-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 845 - 849

19
[ 1011-40-1 ]
5-oxo-3-(2-phenyl-thiazol-5-yl)-6-trimethylsilanyl-hexanoic acid ethyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 845 - 849

20
[ 1011-40-1 ]
3-(2-phenyl-1,3-thiazol-5-yl)-4-{2-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl) propyl]-1,3-thiazol-4-yl}butanoic acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 845 - 849

21
[ 1011-40-1 ]
[ 787548-92-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 845 - 849

22
[ 141-82-2 ]
[ 1011-40-1 ]
(2E)-3-(2-phenyl-1,3-thiazol-5-yl)acrylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With piperidine; pyridine; for 6h;Heating / reflux;	r°ip-theta-r°-phenyl-l^-thiazol-S-yDacrylic acid; To <strong>[1011-40-1]2-phenyl-thiazole-5-carbaldehyde</strong> (888 mg, 4.69 mmol) is added malonic acid (684 mg, 6.57 mmol), pyridine (0.859 mL), and piperidine (0.046 mL). The resulting mixture is heated to reflux for six hours followed by cooling to rt. The reaction mixture is poured into water (20 mL) and after stirring for ten minutes, the resultant solid is filtered, rinsed with water, and dried under reduced pressure to afford the title compound (899 mg, 83% yield). 1H NMR delta 6.25 (d, 2H)5 7.53 (m, 3H)5 7.83 (d, IH), 7.95 (m, 2H)5 8.26 (s, IH)5 12.57 (br s, IH). LCMS (ES, M+H=232).
	With piperidine; pyridine; for 6h;Heating / reflux;	<strong>[1011-40-1]2-phenyl-thiazole-5-carbaldehyde</strong> 41 (Silberg A. et al. Chem. Ber. 1964, 97, 1684-1687) (3.1 g, 16.4 mmol) was treated with malonic acid (2.4 g, 23.0 mmol), pyridine (3 mL) and piperidine (0.16 mL) and the mixture was heated at reflux for 6 hours before being cooled to room temperature. The mixture was then poured into water (50 mL) with stirring. The resulted yellow solid 42 was filtered, washed with water and air-dried (2.45 g). 1H NMR (400 MHz, d6-DMSO) delta: 6.25 (d, J=15.7 Hz, 1H), 7.53 (m, 3H), 7.78 (d, J=15.7 Hz, 1H), 7.97 (m, 2H), 8.23 (s, 1H).

Reference： [1]Patent: WO2006/106326,2006,A1 .Location in patent: Page/Page column 107
[2]Patent: US2004/97485,2004,A1 .Location in patent: Page/Page column 30-31

23
[ 81290-20-2 ]
[ 1011-40-1 ]
[ 946501-52-6 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 82.2.2-Trinuoro-l-(2-phenyl-1.3-thiazol-5-vnethanone (H2) Step 1: 2,2,2-Trifluoro-l-(2-phenyl-l,3-thiazol-5-yl)ethanol (Hl)A solution (0.15 M) of 2-phenyl-l,3-thiazole-5-carbaldehyde (1.0 eq.) and CsF (0.2 eq.) in DME was treated with CF3SiMe3 (1.5 eq.) and then stirred for 3 h at RT. The reaction mixture was quenched by adding IN HCl and stirred for 30 min. The mixture was diluted with EtOAc, the organic phase was separated, washed with sat. aq. NaHCO3 solution and dried (Na2SO4). Evaporation of the solvent under reduced pressure afforded the product as an yellow oil. MS (ES+) CnH8F3NOS requires: 259, found: 260 (M+H)+.

Reference： [1]Patent: WO2007/93827,2007,A1 .Location in patent: Page/Page column 48
[2]Journal of Medicinal Chemistry,2009,vol. 52,p. 6782 - 6789

24
[ 3886-69-9 ]
[ 1011-40-1 ]
[ 1195985-33-1 ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 6535 - 6538

25
4-amino-5-cyano-6-ethoxy-N-(piperidin-4-ylmethyl)picolinamide dihydrochloride [ No CAS ]
[ 1011-40-1 ]
[ 1235472-05-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tris(acetoxy)borohydride; triethylamine; In 1,2-dichloro-ethane; at 20℃;	The compound prepared in Example 226 (0.050 g), <strong>[1011-40-1]2-phenylthiazole-5-carbaldehyde</strong> (0.033 g), sodium triacetoxyborohydride (0.141 g) and triethylamine (0.093 mL) were suspended in 1,2-dichloroethane (5 mL) and stirred at room temperature overnight. The reaction mixture was partitioned between saturated aqueous sodium bicarbonate and dichloromethane. The organics were dried, magnesium sulfate and concentrated under reduced pressure to afford the crude material, which was purified by flash column chromatography (eluant: 50 - 100 % ethyl acetate / hexane (0.5 % triethylamine) to furnish the title compound(0.044 g) having the following physical data.1H NMR (CDCl3): delta 7.94-7.90 (m, 2H), 7.83-7.77 (m, IH), 7.61 (s, IH), 7.44-7.40 (m, 3H),7.19 (s, IH)5 5.10 (s, 2H)5 4.43 (q, J = 7.1 Hz5 2H)5 3.74 (s, 2H)5 3.34 (t5 J = 6.5 Hz, 2H)5 3.01-2.93 (m, 2H), 2.10-2.00 (m, 2H), 1.77-1.68 (m, 2H), 1.67-1.57 (m, IH), 1.44 (t, J = 7.1 Hz, 3H)5 1.41-1.31 (m, 2H);Mass data (APCI5 Pos.): m/z 477 (M + H)+.

Reference： [1]Patent: WO2010/80864,2010,A1 .Location in patent: Page/Page column 153-154

26
[ 133095-91-7 ]
[ 1011-40-1 ]
[ 1311195-65-9 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 4678 - 4693
[2]Patent: WO2011/109059,2011,A1

27
[ 133095-91-7 ]
[ 1011-40-1 ]
[ 1311195-97-7 ]

Yield	Reaction Conditions	Operation in experiment
72.9%		To a solution of <strong>[1011-40-1]2-phenylthiazole-5-carbaldehyde</strong> 38e (0.567 g, 3 mmoL) in 15 mL THF was added a THF solution of 3,4,5-trimethoxyphenylmagnesiumbromide (0.5 N, 6.5 mL, 3.25 mmol) at 0 C. The mixture was allowed to stir for 30 min and quenched with satd. NH4C1, extracted with ethyl ether, dried with MgS04. The solvent was removed under reduced pressure to yield a crude product, which was purified by column chromatography to obtain pure compound 40e (72.9 %). 1H NMR (CDCI3) delta 7.90 (m, 2 H), 7.64 (s, 1 H), 7.41 (m, 3 H), 6.69 (s, br, 2 H), 6.04 (s, 1 H), 3.86 (s, 6 H), 3.85 (s, 3 H), 1.57 (d, 1 H, J = 5.5 Hz); MS (ESI) m/z 358.1 (M + Na)+.

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 4678 - 4693
[2]Patent: WO2011/109059,2011,A1 .Location in patent: Paragraph 0035; 00277

28
[ 461-72-3 ]
[ 1011-40-1 ]
C₁₃H₉N₃O₂S [ No CAS ]