67808-64-4|Methyl 5-formylthiophene-2-carboxylate| Ambeed

CAS No. :	67808-64-4
Formula :	C₇H₆O₃S
M.W :	170.19
SMILES Code :	C(=O)C1=CC=C(S1)C(=O)OC
MDL No. :	MFCD01859942
InChI Key :	APNKWEPRZUSZCJ-UHFFFAOYSA-N
Pubchem ID :	818924

Safety of [ 67808-64-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Computational Chemistry of [ 67808-64-4 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	5
Fraction Csp3	0.14
Num. rotatable bonds	3
Num. H-bond acceptors	3.0
Num. H-bond donors	0.0
Molar Refractivity	40.99
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	71.61 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.57
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.58
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.35
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	0.28
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	2.51
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.46

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.03
Solubility	1.59 mg/ml ; 0.00936 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.69
Solubility	0.344 mg/ml ; 0.00202 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-1.69
Solubility	3.51 mg/ml ; 0.0206 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.22 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	2.32

Application In Synthesis of [ 67808-64-4 ]

* 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.

Downstream synthetic route of [ 67808-64-4 ]

[ 67808-64-4 ] Synthesis Path-Downstream 1~55

1
[ 67808-64-4 ]
[ 50340-79-9 ]

References: [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 17 - 28.
[2]Journal of Medicinal Chemistry,2009,vol. 52,p. 2265 - 2279.
[3]Journal of Medicinal Chemistry,2012,vol. 55,p. 5982 - 5986.
[4]Patent: WO2017/31176,2017,A1 .Location in patent: Page/Page column 85.

2
[ 67808-64-4 ]
[ 133380-60-6 ]

Yield	Reaction Conditions	Operation in experiment
60%	With pyridine; hydroxylamine hydrochloride; In ethanol; for 3h;Reflux;	Hydroxylamine hydrochloride (420 mg, 6.1 mmol) and pyridine (0.5 mL) were added to a solution of <strong>[67808-64-4]methyl 5-formylthiophene-2-carboxylate</strong> (690 mg, 4.1 mmol) in EtOH (25 mL). The reaction mixture was refluxed for 3 h, cooled to room temperature and concentrated under reduced pressure. The residue was dissolved in diethyl ether, the organic layer was washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to get product methyl 5-((hydroxyimino)methyl)thiophene-2-carboxylate (440 mg, yield 60percent), which was carried through without any further purification. 1H NMR (400 MHz, DMSO-d6) delta 12.5 (s, 1 H), 7.98 (s, 1 H), 7.78 (d, J = 4.1 Hz, 1H), 7.51 (d, J = 4.1 Hz, 1 H), 3.82 (s, 3H). MS (ESI) m/z: Calculated for C7H7NO3S: 185.01; found: 186.0 (M+H)+.
	In ethanol;	EXAMPLE 19 Methyl 5-formyl-2-thiophenecarboxylate oxime A solution of <strong>[67808-64-4]methyl 5-formyl-2-thiophenecarboxylate</strong>, prepared according to Example 10, (6.26 g, 36.78 mmoles), hydroxylamine hydrochloride (3.07 g, 44.14 mmoles) and pyridine (3.49 g, 44.14 mmoles) in 200 ml of ethanol was refluxed for 2 hours. The ethanol was removed in vacuo, the residue dissolved in ether and washed with water. The organic layer was dried (magnesium sulfate) and evaporated to a yellow solid. Trituration with a small amount of ether furnished the title compound as a white solid (4.93 g, 72percent), m.p. 164°-7° C. Oxime Z:E ratio:(82:18). Analysis: Calculated for C7 H7 NO3 S: C, 45.39; H, 3.81; N, 7.56percent. Found: C, 45.41; H, 3.69; N,7.48percent. EIMS (m/z): 185 (M+, 97percent), 154 (M+ --CH3 O, base); 1 H-NMR (DMSO-d6) delta, Z isomer:12.52 (1H, br s), 7.99 (1H, s), 7.77 (1H, d, J=4.0 Hz), 7.50 (1H, d, J=4.0 Hz), 3.83 (3H, s); E isomer:11.66 (1H, br s), 8.38 (1H, s), 7.74 (1H, d, J=4.0 Hz), 7.34 (1H, d, J=4.0 Hz), 3.82 (3H, s); ir (potassium bromide): 3400, 1649, 918 cm-1.

References: [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 17 - 28.
[2]Patent: EP2533783,2015,B1 .Location in patent: Paragraph 0261-0262.
[3]Patent: US5047554,1991,A .

3
[ 67808-64-4 ]
[ 119-51-7 ]
[ 133380-55-9 ]

References: [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 17 - 28.

4
[ 67808-64-4 ]
[ 135636-66-7 ]
[ 133380-54-8 ]

References: [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 17 - 28.

5
[ 4565-31-5 ]
[ 74-88-4 ]
[ 67808-64-4 ]

Yield	Reaction Conditions	Operation in experiment
62%	With sodium carbonate; In N,N-dimethyl-formamide; at 25℃; for 20h;	Step 1. Methyl 5-formyl-2-thiophenecarboxylateA mixture of <strong>[4565-31-5]5-formyl-2-thiophene carboxylic acid</strong> (2.34 g, 15 mmol) and sodium carbonate (5.57 g, 52.5 mmol) in DMF (25 ml) at 25 0C was treated with iodomethane (1.15 ml, 18 mmol) and the mixture was stirred for 20 h before being quenched with the addition of water and saturated aqueous NH4Cl. The resulting solid precipitate was collected by filtration to give methyl 5-formyl-2- thiophenecarboxylate as a solid. The filtrate was extracted with EtOAc (3 x 30 ml) and the combined organic extracts were washed with water and brine, dried (Na2SO4), concentrated under reduced pressure, and subjected to flash chromatography to give solid material that was combined with the solid collected by precipitation to give methyl 5-formyl-2-thiophenecarboxylate as a white solid (1.60 g, 62percent): ESI-MS (m/z): 171.2 (M+H+).
	With sodium carbonate; In N,N-dimethyl-formamide;	EXAMPLE 10 Methyl 5-Formyl-2-thiophenecarboxylate The title compound has been described by Gronowitz, S., et al., Arkiv. for Kemi. 21:265 (1963), and was prepared according to the following procedure. Methyliodide (4.36 g, 30.74 mmoles) was added to a stirred suspension of <strong>[4565-31-5]5-formyl-2-thiophenecarboxylic acid</strong> (prepared according to Carpenter, A. J., et al., Tetrahedron 41:3808 (1985)) (4.00 g, 25.61 mmoles) and sodium carbonate (9.50 g, 89.65 mmoles) in 75 ml of N,N-dimethylformamide. After stirring overnight at room temperature the mixture was poured into water (350 ml), saturated with solid sodium chloride and extracted with ethyl acetate. The combined extracts were washed with brine, dried (magnesium sulfate) and concentrated in vacuo to a gray solid (3.83 g, 88percent), m.p. 85°-87° C. EIMS (m/z): 170 (M+, 95percent), 139 (M+ --CH3 O, base), 111 (M+ --CH3 O2 C, 64percent); 1 H-NMR (DMSO-d6) delta, 9.94 (1 H, s), 7.81 (1H, d, J=3.9Hz), 7.71 (1H, d, J=3.9 Hz), 3.91 (3H, s).
	With sodium carbonate; In N,N-dimethyl-formamide; at 20℃; for 11h;	Reference Example 7 methyl 5-formylthiophene-2-carboxylate 5-formylthiophene-2-carboxylic acid (3.13 g, manufactured by Tokyo Chemical Industry Co.) was dissolved in N,N-dimethylformamide (100 mL), and sodium carbonate (8.64 g, manufactured by Wako Pure Chemical Industries, Inc.) and iodomethane (2.49 mL, manufactured by Tokyo Chemical Industry Co.) were sequentially added at room temperature followed by stirring for 11 hours. Insoluble substances were removed from the reaction solution by filtration. Water (200 mL) was added to the filtrate, and the mixed solution was extracted with ethyl acetate. The extract solution was washed with saturated brine and was concentrated after drying over anhydrous magnesium sulfate to obtain the titled compound (3.26 g).

With sodium carbonate; In DMF (N,N-dimethyl-formamide); at 20℃; for 20h;

A mixture of 4.5 g (29 mmol) of <strong>[4565-31-5]5-formyl-2-thiophene carboxylic acid</strong> and 12.6 g (102 mmol, 3.5 eqiv. ) of Na2C03 in 50 mL of DMF was treated with 2.2 mL of iodomethane (35 mmol, 1.2 eqiv. ) at room temperature for 20 h. The mixture was quenched with H20 with some addition of sat. NH4Cl sol. 5-Formyl-thiophene-2-carboxylic acid methyl ester formed as a precipitate and was collected by filtration (quantitative yield), used directly for next step. A mixture of 170 mg (1 mmol) of <strong>[4565-31-5]5-formyl-thiophene-2-carboxylic acid</strong> methyl ester, 197 mg (lmmol) of tosylmethyl isocyanide and 138 mg (lmmol) of K2CO3 in MeOH was refluxed for 0.5 hr. The solvent was evaporated under reduced pressure. The resulting residue was poured into ice-water, and extracted with EtOAc. The extract was washed with saturated aquaous NH4Cl, water, brine and dried over MgS04. The organic solvent was evaporated under reduced pressure and the residue was purified by combiflash to yield 170 mg of 5-oxazol-5-yl-thiophene-2-carboxylic acid methyl ester. Yield 81percent. The above ester (170 mg) was dissolved in 9 mL of THF, 3 mL of MeOH and 3 mL of IN OH solution and stirred overnight. The organic solvent was removed. Acetic acid was added to pH-4-5 and a light yellow precipitate formed. The suspension was diluted with water and the precipitate collected by filtration to yield 105 mg of the title compound. Yield 66percent.

References: [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 17 - 28.
[2]Journal of Medicinal Chemistry,2012,vol. 55,p. 5982 - 5986.
[3]Patent: WO2008/124582,2008,A1 .Location in patent: Page/Page column 130.
[4]Patent: US5047554,1991,A .
[5]Patent: US2006/293343,2006,A1 .Location in patent: Page/Page column 89.
[6]Journal of Medicinal Chemistry,2009,vol. 52,p. 2265 - 2279.
[7]Patent: WO2005/79791,2005,A1 .Location in patent: Page/Page column 125-126.
[8]Patent: WO2006/123639,2006,A1 .Location in patent: Page/Page column 135-136.

6
[ 1001200-44-7 ]
[ 67808-64-4 ]

References: [1]Tetrahedron,2008,vol. 64,p. 688 - 695.

7
[ 67808-64-4 ]
[ 2325-98-6 ]

References: [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 17 - 28.

8
[ 67808-64-4 ]
[ 4192-32-9 ]

References: [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 17 - 28.

9
[ 67808-64-4 ]
[ 125061-05-4 ]

References: [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 17 - 28.

10
[ 67808-64-4 ]
[ 67808-34-8 ]

Yield	Reaction Conditions	Operation in experiment
	With phthalic anhydride; hydroxylamine hydrochloride; triethylamine; In acetonitrile; at 20 - 90℃; for 48h;	Reference Example 8 methyl 5-cyanothiophene-2-carboxylate Hydroxyamine hydrochloride (1.44 g, manufactured by Wako Pure Chemical Co.) was suspended in acetonitrile (80 mL), and triethylamine (2.88 mL, manufactured by Wako Pure Chemical Co.), an acetonitrile solution (100 mL) of the compound (2.93 g) obtained in Reference Example 7 and phthalic anhydride (2.82 g, manufactured by Aldrich Co.) were sequentially added at room temperature, and the solution was stirred at 90° C. for 48 hours in nitrogen atmosphere. After concentrating the reaction solution, ethyl acetate was added to the residue obtained, and the ethyl acetate solution was washed with saturated aqueous sodium hydrogen carbonate solution followed by concentration after drying over anhydrous magnesium sulfate. The residue obtained was purified by column chromatography (hexane/ethyl acetate=6/1) to obtain the titled compound (2.48 g)

References: [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 17 - 28.
[2]Patent: US2006/293343,2006,A1 .Location in patent: Page/Page column 89-90.
[3]Patent: WO2006/123639,2006,A1 .Location in patent: Page/Page column 136.
[4]Journal of Medicinal Chemistry,2012,vol. 55,p. 5982 - 5986.
[5]Patent: EP2533783,2015,B1 .

11
[ 67808-64-4 ]
[ 133380-41-3 ]

References: [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 17 - 28.

12
[ 67808-64-4 ]
[ 133380-46-8 ]

References: [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 17 - 28.

13
[ 67808-64-4 ]
[ 133380-52-6 ]

References: [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 17 - 28.

14
[ 67808-64-4 ]
[ 133380-58-2 ]

References: [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 17 - 28.

15
[ 67808-64-4 ]
[ 133380-61-7 ]

References: [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 17 - 28.
[2]Patent: EP2533783,2015,B1 .

16
[ 67808-64-4 ]
[ 133380-70-8 ]

References: [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 17 - 28.

17
[ 67808-64-4 ]
[ 133380-64-0 ]

References: [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 17 - 28.

18
[ 67808-64-4 ]
[ 133380-68-4 ]

References: [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 17 - 28.

19
[ 67808-64-4 ]
[ 133380-44-6 ]

References: [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 17 - 28.

20
[ 67808-64-4 ]
[ 133380-50-4 ]

References: [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 17 - 28.

21
[ 67808-64-4 ]
[ 133380-56-0 ]

References: [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 17 - 28.

22
[ 67808-64-4 ]
[ 133380-62-8 ]

References: [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 17 - 28.

23
[ 67808-64-4 ]
[ 133380-66-2 ]

References: [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 17 - 28.

24
[ 67808-64-4 ]
[ 133380-74-2 ]

References: [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 17 - 28.

25
[ 67808-64-4 ]
[ 133380-42-4 ]

References: [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 17 - 28.

26
[ 67808-64-4 ]
[ 133380-48-0 ]

References: [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 17 - 28.

27
[ 67808-64-4 ]
[ 133380-53-7 ]

References: [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 17 - 28.

28
[ 67808-64-4 ]
[ 133380-69-5 ]

References: [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 17 - 28.

29
[ 67808-64-4 ]
[ 133380-65-1 ]

References: [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 17 - 28.

30
[ 67808-64-4 ]
[ 133380-59-3 ]

References: [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 17 - 28.

31
[ 67808-64-4 ]
[ 133380-73-1 ]

References: [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 17 - 28.

32
[ 67808-64-4 ]
[ 133380-67-3 ]

References: [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 17 - 28.

33
[ 67808-64-4 ]
[ 133380-45-7 ]

References: [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 17 - 28.

34
[ 67808-64-4 ]
[ 133380-51-5 ]

References: [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 17 - 28.

35
[ 67808-64-4 ]
[ 133405-31-9 ]

References: [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 17 - 28.
[2]Patent: EP2533783,2015,B1 .

36
[ 67808-64-4 ]
[ 133380-93-5 ]

References: [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 17 - 28.

37
[ 67808-64-4 ]
[ 133380-57-1 ]

References: [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 17 - 28.

38
[ 67808-64-4 ]
[ 133380-43-5 ]

References: [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 17 - 28.

39
[ 67808-64-4 ]
[ 133380-49-1 ]

References: [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 17 - 28.

40
[ 67808-64-4 ]
[ 133380-75-3 ]

References: [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 17 - 28.

41
[ 67808-64-4 ]
[ 133380-63-9 ]

References: [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 17 - 28.
[2]Patent: EP2533783,2015,B1 .

42
[ 67808-64-4 ]
methyl 5-(N-benzoyloxy)carboximidamido-2-thiophenecarboxylate [ No CAS ]

References: [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 17 - 28.

43
[ 67808-64-4 ]
[ 2495-15-0 ]

References: [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 17 - 28.

44
[ 67808-64-4 ]
[ 133380-47-9 ]

References: [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 17 - 28.

45
[ 93138-55-7 ]
[ 67808-64-4 ]
N-(5-methoxycarbonyl-2-thenyl)-3-(piperidinomethyl)aniline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With sodium tris(acetoxy)borohydride; In tetrahydrofuran; acetic acid;	Compound AA (0.19 g, 75percent) was obtained as pale yellow crystals using 1-(3-aminobenzyl)piperidine (0.16 g) obtained by the known process (WO99/32100), <strong>[67808-64-4]methyl 5-formyl-2-thiophenecarboxylate</strong> (0.12 g) obtained by the known method (J. Heterocycl. Chem., 28: 17-28 (1991)), sodium triacetoxyborohydride (0.89 g), acetic acid (0.25 mL) and tetrahydrofuran (5.0 mL) as described in Reference Example 6. [0592] 1H NMR (270 MHz, CDCl3) delta7.63 (1H, d), 7.09 (1H, t), 6.96 (1H, brd), 6.72-6.63 (2H, m), 6.52 (1H, m), 4.49 (2H, brs), 4.37 (1H, brs), 3.82 (3H, s), 3.41 (2H, brs), 2.38 (4H, m), 1.57 (4H, m), 1.42 (2H, m).

References: [1]Patent: US2003/225288,2003,A1 .Location in patent: Page 32.

46
[ 67808-64-4 ]
[ 4565-31-5 ]

Yield	Reaction Conditions	Operation in experiment
59%	With potassium hydroxide; water; In tetrahydrofuran;	The compound 25 (2 g, 12.8 mmol) was dissolved in 200 ml of mixture solvent (THF: H20=1 : 1) and HYDROLYZATION was conducted by adding KOH (1.1 g, 19.2 MMOL). After the completion of the reaction, THF was removed under reduced pressure. The water layer was titrated with 1N HC1 solution in pH 1-2 and then extracted with ethyl acetate (200 ml X 5) to obtain the desirable compound 25 (1.2 g, yield 59percent). 1H NMR (300MHZ, CDC13) 10.00 (s, 1H), 7.93-7. 92 (d, J=3.92Hz, 1H), 7.78-7. 77 (d, J=3.9Hz, 1H). I3C NMR (300MHZ, CDC13) 182. 2, 163. 70, 141. 57, 139. 70, 133. 79, 132. 79.

References: [1]Patent: WO2004/37808,2004,A1 .Location in patent: Page 14-15; 93.

47
[ 530145-16-5 ]
[ 67808-64-4 ]

Yield	Reaction Conditions	Operation in experiment
75%	With manganese(IV) oxide; In acetone; for 48h;	The compound 24 (3 g, 17.4 mmol) was dissolved in acetone and an excess of MN02 was added thereto. After 2days of the reaction time, the reaction solution was filtered under reduced pressure with Celite545 and then an exraction process was conducted with acetone sufficiently. The filtrate was concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (hexane: ethyl acetate= 2: 1) to obtain the compound 25 (2.2 g, yield 75percent) 1H NMR (300MHZ, CDC13) 9.98 (s, 1H), 7.85-7. 84 (d, J=3.9Hz, 1H), 7.76-7. 75 (d, J=3.9Hz, 1H). 13C NMR (300MHZ, CDC13) 183.02, 160.99, 139.75, 136.36, 135.09, 132.28, 51.96.

References: [1]Patent: WO2004/37808,2004,A1 .Location in patent: Page 14-15; 93.

Yield	Reaction Conditions	Operation in experiment
		Further examples of compounds of Formula 3 are:...3-carboxy-thiophene-5-carboxaldehyde;3-methoxycarbonyl-thiophene-5-carboxaldehyde;3-ethoxycarbonyl-thiophene-5-carboxaldehyde;2-carboxy-thiophene-5-carboxaldehyde;2-methoxycarbonyl-thiophene-5-carboxaldehyde;2-ethoxycarbonyl-thiophene-5-carboxaldehyde;3-carboxy-furan-5-carboxaldehyde;3-methoxycarbonyl-furan-5-carboxaldehyde;...

49
[ 31108-35-7 ]
[ 67808-64-4 ]
[ 656227-58-6 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium acetate; In acetonitrile; at 150℃; for 0.0833333h;	A mixture of <strong>[67808-64-4]5-formyl-thiophene-2-carboxylic acid methyl ester</strong> [3.37g, 19.8mmol, Reference Example 37 [(A)],] 2,3-dioxo-butyric acid tert-butyl ester (3.4g, 19. [8MMOL),] ammonium acetate (15.25g, [198MMOL)] and acetonitrile [(38ML)] was subjected to microwave irradiation, heating to [150C] for 5 minutes. The reaction mixture was concentrated and the residue was partitioned between 2M sodium carbonate solution and ethyl acetate. The organic layer was separated, dried [(MGS04)] and concentrated to give an orange residue, which was subjected to flash column chromatography on silica using a mixture of pentane and ethyl acetate (gradient, 4: 1 to 1 : [1,] v/v) as eluent, to provide 2-(5-methoxycarbonyl- [THIOPHEN-2-YL)-5-METHYL-1H-IMIDAZOLE-4-CARBOXYLIC] acid tert-butyl ester [(1.] [OG)] as a yellow powder.

References: [1]Patent: WO2004/13130,2004,A1 .Location in patent: Page 202-203.

50
[ 38622-91-2 ]
[ 67808-64-4 ]
[ 863409-10-3 ]

Yield	Reaction Conditions	Operation in experiment
81%	With potassium carbonate; In methanol; for 0.5h;Heating / reflux;	A mixture of 4.5 g (29 mmol) of 5-formyl-2-thiophene carboxylic acid and 12.6 g (102 mmol, 3.5 eqiv. ) of Na2C03 in 50 mL of DMF was treated with 2.2 mL of iodomethane (35 mmol, 1.2 eqiv. ) at room temperature for 20 h. The mixture was quenched with H20 with some addition of sat. NH4Cl sol. 5-Formyl-thiophene-2-carboxylic acid methyl ester formed as a precipitate and was collected by filtration (quantitative yield), used directly for next step. A mixture of 170 mg (1 mmol) of <strong>[67808-64-4]5-formyl-thiophene-2-carboxylic acid methyl ester</strong>, 197 mg (lmmol) of tosylmethyl isocyanide and 138 mg (lmmol) of K2CO3 in MeOH was refluxed for 0.5 hr. The solvent was evaporated under reduced pressure. The resulting residue was poured into ice-water, and extracted with EtOAc. The extract was washed with saturated aquaous NH4Cl, water, brine and dried over MgS04. The organic solvent was evaporated under reduced pressure and the residue was purified by combiflash to yield 170 mg of 5-oxazol-5-yl-thiophene-2-carboxylic acid methyl ester. Yield 81percent. The above ester (170 mg) was dissolved in 9 mL of THF, 3 mL of MeOH and 3 mL of IN OH solution and stirred overnight. The organic solvent was removed. Acetic acid was added to pH-4-5 and a light yellow precipitate formed. The suspension was diluted with water and the precipitate collected by filtration to yield 105 mg of the title compound. Yield 66percent.

References: [1]Patent: WO2005/79791,2005,A1 .Location in patent: Page/Page column 125-126.

51
[ 7732-18-5 ]
[ 154935-51-0 ]
[ 67808-64-4 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; In methanol;	Methyl 5-formylthiophene-2-carboxylate (7) To a solution of 6 (500 mg, 2.5 mmol) in 10 mL of dry methanol was added 2 mL of SOCl2 at 0° C. The reaction mixture was stirred for 18 h at room temperature, monitoring the reaction by TLC. After the starting material was consumed, 5 mL of dist. H2 O was added to the mixture and let stir for 3 to 4 h at room temperature. The reaction mixture was concentrated at 50° C. using a rotary evaporator and extracted with CH2 Cl2. The CH2 Cl2 layer was dried over Na2 SO4 and filtered through a silica gel column. Removal of the solvent gave cream crystals of 7. Yield 400 mg (95percent) mp 79° C.; MS m/z, 171 (MH+); calcd for (C7 H6 O3 S), 170. Anal. C,H,S. NMR (CDCl3) delta7.89 (c,2H, thiophene 2H, thiophene 3-H) 4.05 (s,3H COOCH3).

References: [1]Patent: US5260296,1993,A .

52
methyl 5-(difluoromethyl)thiophene-2-carboxylate [ No CAS ]
diethylaminosulfur trifluoride [DAST] [ No CAS ]
[ 144-55-8 ]
[ 67808-64-4 ]
5-(difluoromethyl)thiophene-2-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In methanol; dichloromethane; water;	Reference Example 125 5-Difluoromethyl-2-thiophenecarboxylic Acid <strong>[67808-64-4]5-Formyl-2-thiophenecarboxylic acid methyl ester</strong> (1.7 g) (synthesised in accordance with the method described in J. Heterocyclic Chem., 28, 17 (1991)) in methylene chloride (10 ml) was slowly added dropwise to diethylaminosulfur trifluoride (DAST) (1.6 g) in methylene chloride (20 ml). The mixture was stirred at room temperature for 2 hours, and then diethylaminosulfur trifluoride (DAST) (0.5 g) was further added. The resulting mixture was stirred at room temperature for 1 hour, and water (10 ml) and saturated aqueous sodium bicarbonate (10 ml) were added. The resulting mixture was allowed to stand overnight. The organic layer was collected, washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give 5-difluoromethyl-2-thiophenecarboxylic acid methyl ester (0.81 g). 5-Difluoromethyl-2-thiophenecarboxylic acid methyl ester (2.58 g) synthesised in this manner was dissolved in methanol (50 ml), and 1N sodium hydroxide (30 ml) was added. The mixture was stirred at room temperature for 2 hours and washed with diethyl ether. The aqueous layer was acidified with 1N hydrochloric acid and extracted with diethyl ether. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 5-difluoromethyl-2-thiophenecarboxylic acid (2.13 g) as crystals. mp 111°-112° C.

References: [1]Patent: US5840917,1998,A .

53
jones' reagent [ No CAS ]
[ 67808-64-4 ]
[ 50340-79-9 ]

Yield	Reaction Conditions	Operation in experiment
	In ethyl acetate; acetone;	EXAMPLE 11 5-Methoxycarbonyl-2-thiophenecarboxylic acid The title compound has been described by Benkeser, R. A., et al., J.O.C. 38, 3660 (1973) and in British Patent 705950, and was prepared according to the following procedure. A stirred solution of <strong>[67808-64-4]methyl 5-formyl-2-thiophenecarboxylate</strong> (2.00 g, 11.75 mmoles) in 100 ml of acetone was treated dropwise with Jones' reagent (9 ml). Once addition was complete the mixture was stirred at room temperature for 1 hours, the excess oxidant decomposed with isopropanol and the mixture filtered through diatomaceous earth. The acetone was removed in vacuo, the residue dissolved in ethyl acetate (75 ml) and the solution dried over magnesium sulfate. Filtration and concentration furnished a yellow solid (1.60 g, 73percent). An analytical sample was obtained by trituration with warm ethyl acetate, m.p. 186°-189° C. Analysis: Calcualted for C7 H6 O4 S: C, 45.15; H, 3.25percent. Found C, 45.12percent; H, 3.09percent. EIMS (m/z): 186 (M+, 70percent), 169 (M+ --OH, 7percent), 155 (M+ --CH3 O, base); 1 H-NMR (DMSO-d6) delta, 7.78 (1H, d, J=4.0 Hz), 7.72 (1H, d, J=4.0 Hz), 3.85 (3H, s); ir (potassium bromide): 3416, 1712, 1666, 1258 cm-1.

References: [1]Patent: US5047554,1991,A .

54
[ 67808-64-4 ]
[ 431-67-4 ]
[ 656227-16-6 ]

Yield	Reaction Conditions	Operation in experiment
16%		To a solution of sodium acetate (1.2g, 13. [9MMOL)] in water (15ml) was added [1,] [1-DIBROMO-] 3,3, 3-trifluoroacetone (0. [80ML,] 5.37mmol) and the resulting mixture was heated to [80C] for 45 minutes. The solution was cooled to [0C] and [5-FORMYL-TLIIOPHENE-2-CARBOXYLIC] acid methyl ester (0.84g, 4. [92MMOL)] in methanol [(20ML)] was added followed by conc. ammonium hydroxide solution [(25ML)] and the solution was allowed to warm to room temperature overnight. The reaction mixture was concentrated and the aqueous residue was extracted three times with ethyl acetate. The combined organic phase was evaporated and the crude product was purified by column chromatography on silica eluting with 10percent [V/V] ethyl acetate in dichloromethane to yield [5-(4-TRIFLUOROMETHYL-LH-IMIDAZOL-2-YL !-] [THIOPHENE-2-CARBOXYLIC] acid methyl ester (0.22g, 16percent) as a pale yellow powder. LCMS (Method A): RT = 7.55 minutes; 277 (M+H) +.

References: [1]Patent: WO2004/13130,2004,A1 .Location in patent: Page 148-149.

55
[ 52157-62-7 ]
[ 79-22-1 ]
[ 67808-64-4 ]

Yield	Reaction Conditions	Operation in experiment
		To a cooled [(-78C)] solution of [2- (5-BROMO-THIOPHEN-2-YL)- [1,] 3] dioxolane [(5.] 0g, [21. 3MMOL)] in tetrahydrofuran [(150ML)] was added n-butyl lithium (8. [52ML,] 21.3mmol, 2. 5M in hexanes) whilst keeping the temperature below [70C.] After 45 minutes [METHYLCHLOROFORMATE] (1. [65ML,] 21. [3MMOL)] in tetrahydrofuran [(5ML)] was added, and the reaction mixture was stirred for a further 4 hours. [1M] hydrochloric acid [(500ML)] was added and the resultant mixture was extracted with diethyl ether (2x [250ML).] The organic layers were combined, dried [(MGS04)] and concentrated to give an oil which was subjected to flash column chromatography on silica using a mixture of cyclohexane and ethyl acetate (4: 1, v/v) as eluent. The resulting fractions were concentrated and dissolved in 1,2- dimethoxyethane and water, to which concentrated sulphuric acid was added. After 1 hour the mixture was concentrated, to provide [5-FORMYL-THIOPHENE-2-CARBOXVLIC] acid methyl ester as a black solid, which was used in the next reaction without further purification.

References: [1]Patent: WO2004/13130,2004,A1 .Location in patent: Page 203.

Historical Records

Technical Information

• Acyl Group Substitution • Barbier Coupling Reaction • Baylis-Hillman Reaction • Bouveault-Blanc Reduction • Bucherer-Bergs Reaction • Catalytic Hydrogenation • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Chaykovsky Reaction • Corey-Fuchs Reaction • Ester Cleavage • Fischer Indole Synthesis • Grignard Reaction • Hantzsch Dihydropyridine Synthesis • Henry Nitroaldol Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Julia-Kocienski Olefination • Knoevenagel Condensation • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mukaiyama Aldol Reaction • Nozaki-Hiyama-Kishi Reaction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Amines • Reactions with Organometallic Reagents • Reformatsky Reaction • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Stetter Reaction • Stobbe Condensation • Tebbe Olefination • Ugi Reaction • Wittig Reaction • Wolff-Kishner Reduction

Related Functional Groups of
[ 67808-64-4 ]

Aldehydes

A263847 [4565-31-5]

5-Formylthiophene-2-carboxylic acid

Similarity: 0.89

A270093 [13679-70-4]

5-Methylthiophene-2-carbaldehyde

Similarity: 0.68

A161612 [98-03-3]

Thiophene-2-carbaldehyde

Similarity: 0.66

A434996 [67808-70-2]

Ethyl 2-formylthiophene-3-carboxylate

Similarity: 0.66

A168740 [211235-87-9]

2,3-Dihydrothieno[3,4-b][1,4]dioxine-5,7-dicarbaldehyde

Similarity: 0.63

Esters

A114742 [50340-79-9]

5-(Methoxycarbonyl)thiophene-2-carboxylic acid

Similarity: 1.00

A120099 [5751-81-5]

Ethyl 5-methylthiophene-2-carboxylate

Similarity: 0.96

A150394 [81452-54-2]

Methyl 3-methylthiophene-2-carboxylate

Similarity: 0.87

A428602 [160744-13-8]

Methyl 5-(2-hydroxyethyl)thiophene-2-carboxylate

Similarity: 0.85

A185351 [5556-22-9]

Methyl 3-hydroxy-5-methyl-2-thiophenecarboxylate

Similarity: 0.81

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.
P202	Do not handle until all safety precautions have been read and understood.
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.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
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.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
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:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
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.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
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.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
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:
P370 + P380	In case of fire: Evacuate area.
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.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
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

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

{[proInfo.proName]}

CAS No.: 67808-64-4

{[proInfo.proName]}

CAS No.: 67808-64-4

Alternative Products

Product Details of [ 67808-64-4 ]

Safety of [ 67808-64-4 ]

Computational Chemistry of [ 67808-64-4 ] Show Less

Physicochemical Properties

Lipophilicity

Water Solubility

Pharmacokinetics

Druglikeness

Medicinal Chemistry

Application In Synthesis of [ 67808-64-4 ]

[ 67808-64-4 ] Synthesis Path-Downstream 1~55

Related Products

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 67808-64-4 ]

Aldehydes

Esters

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Molarity Calculator

Total Compounds Calculator

Dissolution Calculator

{[proInfo.proName]}

CAS No.: 67808-64-4

{[proInfo.proName]}

CAS No.: 67808-64-4

Alternative Products

Product Details of [ 67808-64-4 ]

Safety of [ 67808-64-4 ]

Computational Chemistry of [ 67808-64-4 ] Show Less

Physicochemical Properties

Lipophilicity

Water Solubility

Pharmacokinetics

Druglikeness

Medicinal Chemistry

Application In Synthesis of [ 67808-64-4 ]

[ 67808-64-4 ] Synthesis Path-Downstream 1~55

Related Products

Historical Records

Technical Information

Categories

Related Functional Groups of [ 67808-64-4 ]

Aldehydes

Esters

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Molarity Calculator

Total Compounds Calculator

Dissolution Calculator

Related Functional Groups of
[ 67808-64-4 ]