23681-89-2|2,3-Dihydrobenzofuran-6-ol| Ambeed

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Quality Control of [ 23681-89-2 ] Purity: 98% SDS Specification

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Product Details of [ 23681-89-2 ]

CAS No. :	23681-89-2
Formula :	C₈H₈O₂
M.W :	136.15
SMILES Code :	OC1=CC=C2CCOC2=C1
MDL No. :	MFCD18378253
InChI Key :	IAFNMXBIRZBSFU-UHFFFAOYSA-N
Pubchem ID :	12236540

Safety of [ 23681-89-2 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P280-P305+P351+P338-P310

Computational Chemistry of [ 23681-89-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	6
Fraction Csp3	0.25
Num. rotatable bonds	0
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	37.81
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	29.46 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.59
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	1.78
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.33
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.	1.09
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	2.06
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.57

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.25
Solubility	0.766 mg/ml ; 0.00563 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.	-2.02
Solubility	1.31 mg/ml ; 0.00962 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	-2.08
Solubility	1.13 mg/ml ; 0.00828 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	Yes
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	No
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.	-5.87 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	0.0 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)	1.71

Application In Synthesis of [ 23681-89-2 ]

* 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 [ 23681-89-2 ]

[ 23681-89-2 ] Synthesis Path-Downstream 1~35

1
[ 13196-11-7 ]
[ 23681-89-2 ]

References: [1]Chemische Berichte,1936,vol. 69,p. 1087,1089.
[2]Bulletin of the Chemical Society of Japan,1938,vol. 13,p. 653.

2
[ 23681-89-2 ]
[ 74-90-8 ]
[ 24416-63-5 ]

References: [1]Journal of the Chemical Society,1948,p. 2254,2258.

3
[ 23681-89-2 ]
[ 107-93-7 ]
[ 107058-03-7 ]

References: [1]Justus Liebigs Annalen der Chemie,1957,vol. 605,p. 146,153.

4
[ 23681-89-2 ]
[ 6213-90-7 ]
[ 100062-28-0 ]

References: [1]Justus Liebigs Annalen der Chemie,1957,vol. 605,p. 146,153.

5
[ 23681-89-2 ]
[ 6214-25-1 ]
[ 107625-47-8 ]

References: [1]Justus Liebigs Annalen der Chemie,1957,vol. 605,p. 146,153.

6
[ 23681-89-2 ]
[ 617-48-1 ]
[ 7535-48-0 ]

References: [1]Bulletin of the Chemical Society of Japan,1938,vol. 13,p. 653.

7
[ 23681-89-2 ]
[ 1738-36-9 ]
[ 30434-16-3 ]

References: [1]Journal Of Scientific and Industrial Research,1955,vol. 14 B,p. 157,159.

8
[ 23681-89-2 ]
[ 7035-03-2 ]
[ 110394-05-3 ]

References: [1]Current Science,1957,vol. 26,p. 145.

9
[ 23681-89-2 ]
[ 412022-22-1 ]
[ 30153-23-2 ]
[ 30153-27-6 ]

References: [1]Current Science,1957,vol. 26,p. 145.

10
[ 23681-89-2 ]
[ 140-29-4 ]
[ 93011-93-9 ]

References: [1]Journal Of Scientific and Industrial Research,1956,vol. 15 B,p. 495.

11
[ 23681-89-2 ]
[ 122-04-3 ]
4-nitro-benzoic acid-(2,3-dihydro-benzofuran-6-yl ester) [ No CAS ]

References: [1]Bulletin of the Chemical Society of Japan,1938,vol. 13,p. 653.

12
[ 23681-89-2 ]
[ 75-05-8 ]
[ 23681-90-5 ]

References: [1]Journal of the Chemical Society,1950,p. 3206,3212.

13
[ 6272-26-0 ]
[ 23681-89-2 ]

References: [1]Journal of the Chemical Society,1950,p. 3206,3212.
[2]Journal of the Chemical Society,1950,p. 3206,3212.

14
[ 85878-59-7 ]
[ 23681-89-2 ]

Yield	Reaction Conditions	Operation in experiment
99%	With water; potassium carbonate; In tetrahydrofuran; at 20℃; for 3h;	Add a saturated solution of potassium carbonated (3.5 mL) to a solution of acetic acid 2,3-dihydrobenzofuran-6-yl ester (0.250, 1.403 mmol) in tetrahydrofuran (7.0 mL) and stir at room temperature for 3 h. Dilute with ethyl acetate (100 mL) and wash with water (2 x 100 mL), saturated aqueous sodium chloride (100 mL), dry (sodium sulfate), filte, concentrate and purify (HPLC, eluting with 8: 2 hexanes: ethyl acetate) to give the title compound as pale yellow oil (189.0 mg, 99percent). HRMS m/z Calculated: 137.0602; Found: 137.0575

References: [1]Patent: WO2005/100301,2005,A1 .Location in patent: Page/Page column 64.
[2]Journal of the American Chemical Society,1948,vol. 70,p. 3619.
Organic Syntheses,1950,vol. 30,p. 22.

15
[ 320350-81-0 ]
[ 23681-89-2 ]

References: [1]Journal of the Chemical Society,1948,p. 2254,2258.

16
[ 109-01-3 ]
[ 23681-89-2 ]
[ 50-00-0 ]
5-(4-methyl-piperazin-1-ylmethyl)-2,3-dihydro-benzofuran-6-ol [ No CAS ]

References: [1]Heterocycles,2000,vol. 53,p. 197 - 204.

Yield	Reaction Conditions	Operation in experiment
41%		The resultig acetylated product (3.0 g) was stirred together with 0.3 g of 10percent palladium-carbon and 50 ml of ethanol at 60° C. for 4 hours in an atmosphere of hydrogen to give 2.0 g of white crystals. The crystals were hydrolyzed in a customary manner to give 1.0 g (total yield 41percent) of the desired product as a brown liquid.
		Representative compounds of formula (I) include5-hydroxybenzofuran,6-hydroxybenzofuran,2,3-dihydro-6-hydroxybenzofuran,3-methyl-6-hydroxybenzofuran,2,3-dimethyl-6-hydroxybenzofuran,2,3-dihydro-3-methyl-6-hydroxybenzofuran and2-methyl-5-hydroxybenzofuran.

19
6-oxy-coumarone [ No CAS ]
[ 23681-89-2 ]

References: [1]Chemische Berichte,1925,vol. 58,p. 97.

20
[ 23681-89-2 ]
zinc cyanide [ No CAS ]
[ 24416-63-5 ]

References: [1]Journal of the Chemical Society,1950,p. 3206,3212.

21
[ 23681-89-2 ]
[ 7647-01-0 ]
2,3-dihydro-furo[3,2-g]chromene-5,7-dione [ No CAS ]

References: [1]Journal of the American Chemical Society,1950,vol. 72,p. 1514,1516.

22
[ 23681-89-2 ]
[ 73097-13-9 ]

References: [1]Journal of the American Chemical Society,1948,vol. 70,p. 3619.
Organic Syntheses,1950,vol. 30,p. 22.

23
[ 90921-05-4 ]
[ 23681-89-2 ]

References: [1]Journal of the American Chemical Society,1948,vol. 70,p. 3619.
Organic Syntheses,1950,vol. 30,p. 22.

24
[ 23681-89-2 ]
[ 858249-45-3 ]

References: [1]Journal Of Scientific and Industrial Research,1955,vol. 14 B,p. 157,159.
[2]Journal Of Scientific and Industrial Research,1955,vol. 14 B,p. 157,159.

25
[ 23681-89-2 ]
7-phenyl-2,3-dihydro-furo[3,2-g]chromene-5,6-dione [ No CAS ]

References: [1]Journal Of Scientific and Industrial Research,1955,vol. 14 B,p. 157,159.

26
[ 23681-89-2 ]
[ 30153-23-2 ]

References: [1]Current Science,1957,vol. 26,p. 145.

27
[ 23681-89-2 ]
[ 30153-31-2 ]

References: [1]Current Science,1957,vol. 26,p. 145.
[2]Current Science,1957,vol. 26,p. 145.

28
[ 23681-89-2 ]
1-(6-hydroxy-2,3-dihydro-benzofuran-5-yl)-2-methoxy-ethanone-(2,4-dinitro-phenylhydrazone) [ No CAS ]

References: [1]Journal Of Scientific and Industrial Research,1955,vol. 14 B,p. 157,159.

29
[ 23681-89-2 ]
[ 858792-27-5 ]

References: [1]Journal of the Chemical Society,1948,p. 2254,2258.

30
[ 23681-89-2 ]
5-ethyl-2,3-dihydro-benzofuran-6-ol [ No CAS ]

References: [1]Journal of the Chemical Society,1950,p. 3206,3212.

31
[ 23681-89-2 ]
2,3-dihydro-furo[3,2-g]chromen-5-one [ No CAS ]

References: [1]Journal of the Chemical Society,1950,p. 3206,3212.

32
[ 23681-89-2 ]
[ 1627-20-9 ]

References: [1]Journal of the Chemical Society,1950,p. 3206,3212.

33
[ 23681-89-2 ]
[ 66-97-7 ]

References: [1]Bulletin of the Chemical Society of Japan,1938,vol. 13,p. 653.
[2]Journal of the Chemical Society,1948,p. 2254,2258.

34
[ 23681-89-2 ]
[ 7535-48-0 ]

References: [1]Journal of the Chemical Society,1950,p. 3206,3212.
[2]Journal of the Chemical Society,1948,p. 2254,2258.

35
[ 23681-89-2 ]
[ 7674-93-3 ]

References: [1]Journal of the Chemical Society,1950,p. 3206,3212.

Historical Records

Technical Information

• Appel Reaction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chugaev Reaction • Corey-Kim Oxidation • Dess-Martin Oxidation • Hydride Reductions • Jones Oxidation • Martin's Sulfurane Dehydrating Reagent • Mitsunobu Reaction • Moffatt Oxidation • Oxidation of Alcohols by DMSO • Preparation of Alcohols • Preparation of Amines • Reactions of Alcohols • Reactions with Organometallic Reagents • Ritter Reaction • Sharpless Olefin Synthesis • Swern Oxidation

Related Functional Groups of
[ 23681-89-2 ]

Alcohols

A104660 [40492-52-2]

2,3-Dihydrobenzofuran-5-ol

Similarity: 0.97

A136197 [1083168-69-7]

(2,3-Dihydrobenzofuran-6-yl)methanol

Similarity: 0.95

A161972 [61439-59-6]

2-(4-(Benzyloxy)phenyl)ethanol

Similarity: 0.92

A451063 [177259-98-2]

2-(3-(Benzyloxy)phenyl)ethanol

Similarity: 0.90

A233314 [7417-18-7]

2-(2-Methoxyphenyl)ethanol

Similarity: 0.90

Related Parent Nucleus of
[ 23681-89-2 ]

Benzofurans

A104660 [40492-52-2]

2,3-Dihydrobenzofuran-5-ol

Similarity: 0.97

A113217 [230642-84-9]

4-Vinyl-2,3-dihydrobenzofuran

Similarity: 0.95

A136197 [1083168-69-7]

(2,3-Dihydrobenzofuran-6-yl)methanol

Similarity: 0.95

A154248 [127264-14-6]

5-(2-Bromoethyl)-2,3-dihydrobenzofuran

Similarity: 0.84

A267964 [66158-96-1]

(2,3-Dihydrobenzofuran-2-yl)methanol

Similarity: 0.84

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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

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CAS No.: 23681-89-2

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