[ CAS No. 618-30-4 ] {[proInfo.proName]}

Name: 618-30-4|5-Chlorofuran-2-carboxylic acid|97%
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Quality Control of [ 618-30-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 618-30-4 ]

CAS No. :	618-30-4	MDL No. :	MFCD00093272
Formula :	C₅H₃ClO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NNTBDUTXMIMRKK-UHFFFAOYSA-N
M.W :	146.53	Pubchem ID :	234853
Synonyms :

Calculated chemistry of [ 618-30-4 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	30.68
TPSA :	50.44 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) :	-5.91 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.05
Log Po/w (XLOGP3) :	1.81
Log Po/w (WLOGP) :	1.63
Log Po/w (MLOGP) :	0.29
Log Po/w (SILICOS-IT) :	1.34
Consensus Log Po/w :	1.22

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-2.23
Solubility :	0.855 mg/ml ; 0.00584 mol/l
Class :	Soluble
Log S (Ali) :	-2.49
Solubility :	0.476 mg/ml ; 0.00325 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.58
Solubility :	3.86 mg/ml ; 0.0264 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.1

Safety of [ 618-30-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 618-30-4 ]

* 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.

Upstream synthesis route of [ 618-30-4 ]
Downstream synthetic route of [ 618-30-4 ]

[ 618-30-4 ] Synthesis Path-Upstream 1~8

1
[ 618-30-4 ]
[ 21508-19-0 ]

Reference： [1] Nippon Kagaku Zasshi, 1958, vol. 79, p. 1366,1369[2] Chem.Abstr., 1960, p. 24633

2
[ 21508-19-0 ]
[ 618-30-4 ]

Yield	Reaction Conditions	Operation in experiment
95%	With sodium hydroxide; ammonia; water; silver nitrate In methanol at 20℃; for 0.5 h;	Example 7: Synthesis of N-(5-chlorofuran-2-ylcarbonyl)-3,7- diazabicyclo [3.3.0] octane trifluoroacetate Example 7 relates to the synthesis of 5-chlorofuran-2- yl(hexahydropyrrolo[3,4-c]pyrrol-2-yl)methanone trifluoroacetate (or N-(5- chlorofuran-2-ylcarbonyl)-3,7-diazabicyclo[3.3.0]octane trofluoroacetate), which was prepared according to the following techniques, illustrative of the coupling reaction used to make heteroaromatic amides of 3,7-diazabicyclo[3.3.0]octane: S-Chlorofuran-l-carboxylic acid; Aqueous sodium hydroxide (80 mL of 10percent) was added to a solution of silver nitrate (8.0 g, 47 mmol) in water (20 mL). This suspension was stirred and slowly treated with 30percent aqueous ammonium hydroxide until it became clear. A solution of S-chlorofuran^-carboxaldehyde (3.0 g, 23 mmol) (Aldrich Chemical) in methanol (5 mL) was added, and the resulting mixture was stirred at ambient temperature for 30 min. The reaction mixture was filtered, and the filtrate was washed with ether (100 mL). The aqueous filtrate was then made acidic (~pH 3) by the addition of cold 20percent sulfuric acid. The resulting mixture was extracted with ethyl acetate (3 x 100 mL). The extracts were washed with saturated aqueous sodium chloride solution (100 mL), dried (anhydrous sodium sulfate) and concentrated under vacuum to give 3.2 g (95percent yield) of white solid (mp 178- 179⁰C). This reaction was easily scalable and was run multiple times at >10 g scale.

Reference： [1] Patent: WO2008/57938, 2008, A1, . Location in patent: Page/Page column 32
[2] Patent: WO2008/67644, 2008, A1, . Location in patent: Page/Page column 36

3
[ 4301-39-7 ]
[ 618-30-4 ]

Reference： [1] Patent: US5840917, 1998, A,

4
[ 88-14-2 ]
[ 618-30-4 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 19, p. 5213 - 5224

5
[ 21508-19-0 ]
[ 27230-59-7 ]
[ 618-30-4 ]

Reference： [1] Journal of the American Chemical Society, 1949, vol. 71, p. 2257

6
[ 614-99-3 ]
[ 618-30-4 ]

Reference： [1] American Chemical Journal, 1890, vol. 12, p. 38

7
[ 527-69-5 ]
[ 618-30-4 ]

Reference： [1] Nippon Kagaku Zasshi, 1958, vol. 79, p. 1366,1369[2] Chem.Abstr., 1960, p. 24633
[3] Iowa State College Journal of Science, 1932, vol. 6, p. 137,139

8
[ 24078-79-3 ]
[ 618-30-4 ]

Reference： [1] Iowa State College Journal of Science, 1932, vol. 6, p. 137,139

[ 618-30-4 ] Synthesis Path-Downstream 1~53

1
[ 21508-19-0 ]
[ 27230-59-7 ]
[ 618-30-4 ]

Reference： [1]Journal of the American Chemical Society,1949,vol. 71,p. 2257

2
[ 527-69-5 ]
[ 618-30-4 ]

Reference： [1]Nippon Kagaku Zasshi,1958,vol. 79,p. 1366,1369
Chem.Abstr.,1960,p. 24633
[2]Iowa State College Journal of Science,1932,vol. 6,p. 137,139

3
[ 618-30-4 ]
[ 3187-94-8 ]

Reference： [1]Journal of the American Chemical Society,1930,vol. 52,p. 2083,2086
[2]Bulletin de la Societe Chimique de France,1946,p. 669,672

4
[ 618-30-4 ]
[ 24078-79-3 ]

Yield	Reaction Conditions	Operation in experiment
	With oxalyl dichloride;N,N-dimethyl-formamide; In dichloromethane; at 0 - 20℃; for 3h;	To a mixture of compound 1 b2 (3.0 g, 1.0 eq.) and CH2CI2 (30 mL) at O0C is added DMF (0.1 mL) and (COCI)2 (6.7 g, 2.5 eq.). The mixture is allowed to stir at room temperature for 3 h, then concentrated under reduced pressure to give compound 1b3.

Reference： [1]Bulletin de la Societe Chimique de France,1946,p. 669,672
[2]Nippon Kagaku Zasshi,1958,vol. 79,p. 1366,1369
Chem.Abstr.,1960,p. 24633
[3]Organic Letters,2003,vol. 5,p. 3337 - 3340
[4]Journal of the Chemical Society. Perkin Transactions 2 (2001),2001,p. 2211 - 2218
[5]Patent: WO2008/67644,2008,A1 .Location in patent: Page/Page column 36

5
[ 24078-79-3 ]
[ 618-30-4 ]

Reference： [1]Iowa State College Journal of Science,1932,vol. 6,p. 137,139

6
[ 614-99-3 ]
[ 618-30-4 ]

Reference： [1]American Chemical Journal,1890,vol. 12,p. 38

7
[ 618-30-4 ]
[ 52744-72-6 ]
2-(5-Chloro-furan-2-yl)-4,4-diphenyl-4H-benzo[d][1,3]oxazine; compound with perchloric acid [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,1993,vol. 29,p. 465 - 468
Khimiya Geterotsiklicheskikh Soedinenii,1993,p. 542 - 546

8
[ 618-30-4 ]
[ 120759-30-0 ]
2-(5-Chloro-furan-2-yl)-4,4-diphenyl-4H-benzo[d][1,3]oxazine; compound with perchloric acid [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,1993,vol. 29,p. 465 - 468
Khimiya Geterotsiklicheskikh Soedinenii,1993,p. 542 - 546

9
[ 618-30-4 ]
[ 113984-17-1 ]
[ 113984-16-0 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1987,vol. 23,p. 753 - 758
Zhurnal Organicheskoi Khimii,1987,vol. 23,p. 833 - 838
[2]Bulletin de la Societe Chimique de France,1986,p. 974 - 979

10
[ 618-30-4 ]
[ 67101-89-7 ]

13
[ 618-30-4 ]
[ 7697-37-2 ]
[ 110-17-8 ]

Reference： [1]American Chemical Journal,1890,vol. 12,p. 38

14
[ 618-30-4 ]
bromine water [ No CAS ]
[ 110-17-8 ]

Reference： [1]American Chemical Journal,1890,vol. 12,p. 38

15
[ 88-14-2 ]
[ 618-30-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 5213 - 5224

16
[ 618-30-4 ]
[ 192191-46-1 ]
C₂₆H₂₆ClFO₇ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 5213 - 5224

17
[ 618-30-4 ]
C₂₇H₂₈ClFO₇ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 5213 - 5224

18
[ 618-30-4 ]
9α-chloro-17α-[(5-chloro-2-furanylcarbonyl)oxy]-6α-fluoro-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 5213 - 5224

19
[ 618-30-4 ]
[ 583052-89-5 ]

Reference： [1]Organic Letters,2003,vol. 5,p. 3337 - 3340

20
[ 618-30-4 ]
3-benzyl-7-chloro-10-oxa-3-azatricyclo[5.2.1.0^1,5]dec-8-en-2-one [ No CAS ]

Reference： [1]Organic Letters,2003,vol. 5,p. 3337 - 3340

21
[ 618-30-4 ]
[ 82366-66-3 ]

Reference： [1]Journal of the Chemical Society. Perkin Transactions 2 (2001),2001,p. 2211 - 2218

22
[ 618-30-4 ]
[ 21508-19-0 ]

Reference： [1]Nippon Kagaku Zasshi,1958,vol. 79,p. 1366,1369
Chem.Abstr.,1960,p. 24633

23
[ 618-30-4 ]
[ 3216-65-7 ]

Reference： [1]Nippon Kagaku Zasshi,1958,vol. 79,p. 1366,1369
Chem.Abstr.,1960,p. 24633

24
[ 618-30-4 ]
[ 103987-69-5 ]

Reference： [1]Nippon Kagaku Zasshi,1958,vol. 79,p. 1366,1369
Chem.Abstr.,1960,p. 24633

25
[ 618-30-4 ]
[ 91498-60-1 ]

Reference： [1]Nippon Kagaku Zasshi,1958,vol. 79,p. 1366,1369
Chem.Abstr.,1960,p. 24633

26
[ 618-30-4 ]
[ 111252-98-3 ]

Reference： [1]Nippon Kagaku Zasshi,1958,vol. 79,p. 1366,1369
Chem.Abstr.,1960,p. 24633

27
[ 4301-39-7 ]
[ 618-30-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In ethanol; water;	Reference Example 151 5-Chloro-2-furancarboxylic Acid 5-Chloro-2-furancarboxylic acid ethyl ester (8 g) (synthesised in accordance with the method described in Chem. Pharm. Bull., 40, 1966 (1992)) was dissolved in ethanol (50 ml), and 1N aqueous sodium hydroxide (50 ml) was added. The mixture was stirred at room temperature for 1 hour and concentrated under reduced pressure. The residue was dissolved in water and washed with diethyl ether. The aqueous layer was acidified with 1N hydrochloric acid and extracted with ethyl acetate. The extract was washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Precipitated crystals were collected by filtration and washed with diethyl etherhexane to give 5-chloro-2-furancarboxylic acid (5.3 g) as crystals. mp 182-183 C.

Reference： [1]Patent: US5840917,1998,A

28
[ 618-30-4 ]
[ 34010-15-6 ]
cis-5-(11-tetradecenyloxy)furan-2-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In N,N,N,N,N,N-hexamethylphosphoric triamide; toluene;	(A) 8.8 g (0.0414 mole) of cis-11-tetradecen-1-ol was combined with 4.0 g (0.0829 mole) of sodium hydroxide (50% in oil) in 200 ml of dry toluene and heated to reflux with stirring for 3 hours. 6.1 g (0.414 mole) of 5-chloro-2furoic acid was added, followed by 25 ml of hexamethylphosphoric triamide (HMPA), and the reaction mixture refluxed with stirring for 20 hours, cooled, and acidified with acetic acid. The mixture was extracted into ether and the organic layer washed with water and with brine and evaporated to yield cis-5-(11-tetradecenyloxy)furan-2-carboxylic acid, M.P. 89-90 C.
	With sodium hydroxide; In N,N,N,N,N,N-hexamethylphosphoric triamide; toluene;	(A) 8.8 g (0.0414 mole) of cis-11-tetradecen-1-ol was combined with 4.0 g (0.0829 mole) of sodium hydroxide (50% in oil) in 200 ml of dry toluene and heated to reflux with stirring for 3 hours. 6.1 g (0.414 mole) of <strong>[618-30-4]5-chloro-2-furoic acid</strong> was added, followed by 25 ml of hexamethylphosphoric triamide (HMPA), and the reaction mixture refluxed with stirring for 20 hours, cooled, and acidified with acetic acid. The mixture was extracted into ether and the organic layer washed with water and with brine and evaporated to yield cis-5-(11-tetradecenyloxy)furan-2-carboxylic acid, M.P. 89-90 C.

Reference： [1]Patent: US4980371,1990,A
[2]Patent: US4602099,1986,A

29
[ 618-30-4 ]
[ 79-37-8 ]
[ 24078-79-3 ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane; at 0 - 20℃; for 1h;	N-(5-chIorofuran-2-ylcarbonyl)-3,7-diazabicyclo [3.3.0] octane trifluoroacetate; Oxalyl chloride (12.2 g, 95.8 mmol) containing a drop of DMF was added drop-wise to an ice-cooled solution of <strong>[618-30-4]5-chlorofuran-2-carboxylic acid</strong> (6.25 g, 47.9 mmol) in 200 mL of dichloromethane. After complete addition, the ice bath was removed and the reaction was warmed to ambient temperature over a 1 h period. The volatiles were then removed under vacuum, and the residue was dissolved in THF (50 mL). This solution of the acid chloride was then added to an stirred, ice-cooled solution of hexahydropyrrolo[3,4-c]pyrrole-2-carboxylic acid tert-butyl ester (10.2 g, 47.9 mmol) and diisopropylethylamine (25 g, ~4 EPO <DP n="34"/>equivalents) in THF (200 mL). This mixture was stirred at ambient temperature for 16 h. The volatiles were then removed under vacuum, and the residue was partitioned between water (100 mL) and ether (300 mL). The ether layer and two ether extracts (100 mL) of the aqueous layer were concentrated on the rotary evaporator. The residue was column chromatographed on silica gel, eluting with a 0-60% ethyl acetate in hexane gradient. Concentration of selected fractions gave 13.9 g (85.3% yield) of pale yellow syrup. A portion of this material (12.9 g, 37.9 mmol) was dissolved in a mixture of dichloromethane and trifluoroacetic acid (100 mL each). This mixture was stirred at ambient temperature for 2 h and then concentrated under vacuum. The residue was partitioned between chloroform (200 mL) and 50% aqueous potassium carbonate (200 mL), and the aqueous layer was extracted with chloroform (3 x 200 mL). The combined chloroform layers were dried over anhydrous sodium sulfate and concentrated under vacuum, leaving 8.66 g (95% yield) of pale yellow solid (1H NMR (^-methanol, 300 MHz) 3.15-3.35 (m, 4H), 3.50-4.20 (m, 6H), 6.51 (d, IH), 7.17 (d, IH); MS m/z 241 (M+H)).

Reference： [1]Patent: WO2008/57938,2008,A1 .Location in patent: Page/Page column 32-33

30
[ 21508-19-0 ]
[ 618-30-4 ]

Yield	Reaction Conditions	Operation in experiment
95%	With sodium hydroxide; ammonia; water; silver nitrate; In methanol; at 20℃; for 0.5h;	Example 7: Synthesis of N-(5-chlorofuran-2-ylcarbonyl)-3,7- diazabicyclo [3.3.0] octane trifluoroacetate Example 7 relates to the synthesis of 5-chlorofuran-2- yl(hexahydropyrrolo[3,4-c]pyrrol-2-yl)methanone trifluoroacetate (or N-(5- chlorofuran-2-ylcarbonyl)-3,7-diazabicyclo[3.3.0]octane trofluoroacetate), which was prepared according to the following techniques, illustrative of the coupling reaction used to make heteroaromatic amides of 3,7-diazabicyclo[3.3.0]octane: S-Chlorofuran-l-carboxylic acid; Aqueous sodium hydroxide (80 mL of 10%) was added to a solution of silver nitrate (8.0 g, 47 mmol) in water (20 mL). This suspension was stirred and slowly treated with 30% aqueous ammonium hydroxide until it became clear. A solution of S-chlorofuran^-carboxaldehyde (3.0 g, 23 mmol) (Aldrich Chemical) in methanol (5 mL) was added, and the resulting mixture was stirred at ambient temperature for 30 min. The reaction mixture was filtered, and the filtrate was washed with ether (100 mL). The aqueous filtrate was then made acidic (~pH 3) by the addition of cold 20% sulfuric acid. The resulting mixture was extracted with ethyl acetate (3 x 100 mL). The extracts were washed with saturated aqueous sodium chloride solution (100 mL), dried (anhydrous sodium sulfate) and concentrated under vacuum to give 3.2 g (95% yield) of white solid (mp 178- 1790C). This reaction was easily scalable and was run multiple times at >10 g scale.
	With sodium chlorate; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In water; tert-butyl alcohol; at 20℃; for 3h;	To a mixture of compound 1 b1 (5.0 g, 1.0 eq.) and terf-butanol (30 mL) is added 2- methyl-2-butene (13.5 g, 5.0 eq.), aqueous NaH2PO4 (150 mL containing 29.8 g of NaH2PO4, 5.0 eq.) and NaCIO3 (13.8 g, 4.0 eq.). The mixture is allowed to stir at room temperature for 3 h, then is extracted with EtOAc (6 x 150 mL). The combined organic extract is dried (Na2SO4), filtered and concentrated under reduced pressure to provide compound 1b2

Reference： [1]Patent: WO2008/57938,2008,A1 .Location in patent: Page/Page column 32
[2]Patent: WO2008/67644,2008,A1 .Location in patent: Page/Page column 36

31
[ 618-30-4 ]
[ 227940-72-9 ]
[ 1025008-23-4 ]