[ CAS No. 51939-71-0 ] {[proInfo.proName]}

Name: 51939-71-0|Chromane-2-carboxylic acid|97%
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Quality Control of [ 51939-71-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 51939-71-0 ]

Product Details of [ 51939-71-0 ]

CAS No. :	51939-71-0	MDL No. :	MFCD00044719
Formula :	C₁₀H₁₀O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SFLFCQJQOIZMHF-UHFFFAOYSA-N
M.W :	178.18	Pubchem ID :	2723665
Synonyms :

Calculated chemistry of [ 51939-71-0 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.3
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	47.17
TPSA :	46.53 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) :	-6.04 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.6
Log Po/w (XLOGP3) :	1.9
Log Po/w (WLOGP) :	1.46
Log Po/w (MLOGP) :	1.28
Log Po/w (SILICOS-IT) :	1.67
Consensus Log Po/w :	1.58

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.42
Solubility :	0.682 mg/ml ; 0.00383 mol/l
Class :	Soluble
Log S (Ali) :	-2.5
Solubility :	0.564 mg/ml ; 0.00316 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.11
Solubility :	1.39 mg/ml ; 0.00778 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.49

Safety of [ 51939-71-0 ]

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

Application In Synthesis of [ 51939-71-0 ]

* 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 [ 51939-71-0 ]
Downstream synthetic route of [ 51939-71-0 ]

[ 51939-71-0 ] Synthesis Path-Upstream 1~6

1
[ 4940-39-0 ]
[ 51939-71-0 ]

Yield	Reaction Conditions	Operation in experiment
96%	Stage #1: With hydrogen; acetic acid In ethyl acetate for 22.5 h; Stage #2: With water; sodium hydrogencarbonate In ethyl acetate	EXAMPLE 20 (+-)-Chroman-2-carboxylic acid A mixture of the compound from Example 19 (20.0 g, 105 mmol), and palladium on activated carbon (Pd 10percent, 2.0 g) in acetic acid (200 mL) was placed under hydrogen pressure (60 psig) in a Parr hydrogenation apparatus. After 22.5 hours the mixture was removed from the hydrogen atmosphere and filtered through a pad of Celite. The Celite pad was washed with ethyl acetate (800 mL), and the combined filtrate concentrated to give a brown oil. The oil was dissolved in ethyl acetate (500 mL) and extracted with saturated aqueous NaHCO₃ solution (4 x 125 mL). The aqueous phase was acidified to pH = 2 with concentrated HCl and extracted with ethyl acetate (4 x 100 mL). The combined organic phase was washed with saturated aqueous sodium chloride solution (100 mL), dried (MgSO₄), and concentrated to give a colorless solid (18.0 g, 96percent). Mp 97.5-99°C; ¹H NMR (DMSO-d₆, 300 MHz) δ 12.96 (br s, 1 H), 7.03 (m, 2 H), 6.78 (m, 2 H), 4.74 (dd, J = 6.4 Hz, 3.9 Hz, 1 H), 2.73 (m, 1 H), 2.63 (m, 1 H), 2.03 (m, 2 H).
95%	With palladium 10% on activated carbon; hydrogen In methanol; water at 20℃; for 2 h; Inert atmosphere	Intermediate- 1 Chromane -2-carboxylic acid To a suspension of commercially available chromone-2-carboxylic acid (50g, 281mmol) in methanol (500mL), slurry of (10percent Pd/C wet, 5g) in water (lOmL) was added under nitrogen atmosphere. The mixture was hydrogenated at 60 psi at room temperature (RT) and further maintained hydrogen reservoir up to 60 psi for 2h. The progress of reaction was monitored by TLC. Reaction mixture was filtered through celite and the filtrate was concentrated under reduced pressure to yield chromane -2-carboxylic acid as off-white solid (44.7 g, 95percent). m/z-178.02.
95%	With palladium 10% on activated carbon; hydrogen In methanol; water at 20℃; for 2 h; Inert atmosphere	Intermediate-1 Chromane-2-carboxylic Acid [0355] chromone-2-carboxylic acid (50 g, 281 mmol) in methanol (500 mL), slurry of (10percent Pd/C wet, 5 g) in water (10 mL) was added under nitrogen atmosphere. The mixture was hydrogenated at 60 psi at room temperature (RT) and further maintained hydrogen reservoir up to 60 psi for 2 h. The progress of reaction was monitored by TLC. Reaction mixture was filtered through celite and the filtrate was concentrated under reduced pressure to yield chromane-2-carboxylic acid as off-white solid (44.7 g, 95percent). m/z-178.02.

80%

at 20℃; for 16 h;

4-Oxo-4H-chromene-2-carboxylic acid (4.0 g, 21.03 mmol) was dissolved in 20 mL of acetic acid. 10percent Pd/C(0.4 g) was added thereto and stirred at room temperature for 16 hours under 60 psi of hydrogen. The reaction solutionwas filtered through Celite, diluted with EtOAc, and extracted with sodium bicarbonate aqueous solution. The water layerwas again acidified with 6N HCl and extracted with EtOAc. The organic layer was dried with MgSO4 and concentratedunder reduced pressure to obtain the title compound (3.0 g, 80 percent).1H-NMR (CDCl3) δ 7.13 (1H, t), 7.05 (1H, d), 6.95∼6.85 (2H, m), 4.75 (1H, m), 3.00∼2.80 (2H, m), 2.40 (1H, m), 2.20 (1H, m)

Reference： [1] Patent: EP1054881, 2008, B1, . Location in patent: Page/Page column 31
[2] Patent: US6469031, 2002, B1,
[3] Patent: WO2013/124828, 2013, A1, . Location in patent: Page/Page column 48
[4] Patent: US2015/38546, 2015, A1, . Location in patent: Paragraph 0355-0356
[5] Patent: EP3239143, 2017, A2, . Location in patent: Paragraph 0071
[6] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1981, vol. 20, # 12, p. 1063 - 1067
[7] European Journal of Medicinal Chemistry, 1987, vol. 22, p. 539 - 544
[8] Patent: US2008/153871, 2008, A1, . Location in patent: Page/Page column 20
[9] Journal of Heterocyclic Chemistry, 2010, vol. 47, # 3, p. 582 - 588
[10] Patent: US2015/111885, 2015, A1, . Location in patent: Paragraph 1476; 1477
[11] Patent: WO2007/123941, 2007, A2, . Location in patent: Page/Page column 70
[12] Patent: WO2007/123941, 2007, A2,

2
[ 66598-81-0 ]
[ 51939-71-0 ]

Reference： [1] Tetrahedron Asymmetry, 2015, vol. 26, # 17, p. 912 - 917
[2] Patent: WO2007/123941, 2007, A2, . Location in patent: Page/Page column 59-61

3
[ 24698-77-9 ]
[ 51939-71-0 ]

Reference： [1] Organic Letters, 2018, vol. 20, # 13, p. 3928 - 3932

4
[ 118-93-4 ]
[ 51939-71-0 ]

Reference： [1] Patent: US6469031, 2002, B1,
[2] Organic Letters, 2018, vol. 20, # 13, p. 3928 - 3932

5
[ 14736-31-3 ]
[ 51939-71-0 ]

Reference： [1] Organic Letters, 2018, vol. 20, # 13, p. 3928 - 3932

6
[ 118-93-4 ]
[ 95-92-1 ]
[ 51939-71-0 ]

Reference： [1] Journal of Heterocyclic Chemistry, 1992, vol. 29, # 2, p. 431 - 438

[ 51939-71-0 ] Synthesis Path-Downstream 1~88

1
[ 4940-39-0 ]
[ 51939-71-0 ]

Yield	Reaction Conditions	Operation in experiment
96%		EXAMPLE 20 (+-)-Chroman-2-carboxylic acid A mixture of the compound from Example 19 (20.0 g, 105 mmol), and palladium on activated carbon (Pd 10%, 2.0 g) in acetic acid (200 mL) was placed under hydrogen pressure (60 psig) in a Parr hydrogenation apparatus. After 22.5 hours the mixture was removed from the hydrogen atmosphere and filtered through a pad of Celite. The Celite pad was washed with ethyl acetate (800 mL), and the combined filtrate concentrated to give a brown oil. The oil was dissolved in ethyl acetate (500 mL) and extracted with saturated aqueous NaHCO3 solution (4 x 125 mL). The aqueous phase was acidified to pH = 2 with concentrated HCl and extracted with ethyl acetate (4 x 100 mL). The combined organic phase was washed with saturated aqueous sodium chloride solution (100 mL), dried (MgSO4), and concentrated to give a colorless solid (18.0 g, 96%). Mp 97.5-99C; 1H NMR (DMSO-d6, 300 MHz) delta 12.96 (br s, 1 H), 7.03 (m, 2 H), 6.78 (m, 2 H), 4.74 (dd, J = 6.4 Hz, 3.9 Hz, 1 H), 2.73 (m, 1 H), 2.63 (m, 1 H), 2.03 (m, 2 H).
96%	palladium on activated carbon; In acetic acid; ethyl acetate;	EXAMPLE 9 (+-)-Chroman-2-carboxylic acid A mixture of the compound from Example 8 (20.0 g, 105 mmol), and 10% palladium on activated carbon (2.0 g) in acetic acid (200 mL) was placed under hydrogen pressure (60 psig) in a Parr hydrogenation apparatus. After 22.5 hours the mixture was removed from the hydrogen atmosphere and filtered through a pad of Celite. The Celite pad was washed with ethyl acetate (800 mL), and the combined filtrate concentrated to give a brown oil. The oil was dissolved in ethyl acetate (500 mL) and extracted with saturated NaHCO3 (4125 mL). The aqueous phase was acidified to pH=2 with concentrated HCl and extracted with ethyl acetate (4100 mL). The combined organic phase was washed with saturated aqueous sodium chloride solution (100 mL), dried (MgSO4), and concentrated to give a colorless solid (18.0 g, 96%). Mp 97.5-99 C.; 1H NMR (300 MHz, DMSO-d6) delta12.96 (br s, 1H), 7.03 (m, 2H), 6.78 (m, 2H), 4.74 (dd, J=6.4 Hz, J=3.9 Hz, 1H), 2.73 (m, 1H), 2.63 (m, 1H), 2.03 (m, 2H).
95%	With palladium 10% on activated carbon; hydrogen; In methanol; water; at 20℃; under 3102.97 Torr; for 2h;Inert atmosphere;	Intermediate- 1 Chromane -2-carboxylic acid To a suspension of commercially available chromone-2-carboxylic acid (50g, 281mmol) in methanol (500mL), slurry of (10% Pd/C wet, 5g) in water (lOmL) was added under nitrogen atmosphere. The mixture was hydrogenated at 60 psi at room temperature (RT) and further maintained hydrogen reservoir up to 60 psi for 2h. The progress of reaction was monitored by TLC. Reaction mixture was filtered through celite and the filtrate was concentrated under reduced pressure to yield chromane -2-carboxylic acid as off-white solid (44.7 g, 95%). m/z-178.02.

95%	With palladium 10% on activated carbon; hydrogen; In methanol; water; at 20℃; under 3102.97 Torr; for 2h;Inert atmosphere;	Intermediate-1 Chromane-2-carboxylic Acid [0355] chromone-2-carboxylic acid (50 g, 281 mmol) in methanol (500 mL), slurry of (10% Pd/C wet, 5 g) in water (10 mL) was added under nitrogen atmosphere. The mixture was hydrogenated at 60 psi at room temperature (RT) and further maintained hydrogen reservoir up to 60 psi for 2 h. The progress of reaction was monitored by TLC. Reaction mixture was filtered through celite and the filtrate was concentrated under reduced pressure to yield chromane-2-carboxylic acid as off-white solid (44.7 g, 95%). m/z-178.02.
80%	With palladium 10% on activated carbon; hydrogen; acetic acid; at 20℃; under 3102.97 Torr; for 16h;	4-Oxo-4H-chromene-2-carboxylic acid (4.0 g, 21.03 mmol) was dissolved in 20 mL of acetic acid. 10% Pd/C(0.4 g) was added thereto and stirred at room temperature for 16 hours under 60 psi of hydrogen. The reaction solutionwas filtered through Celite, diluted with EtOAc, and extracted with sodium bicarbonate aqueous solution. The water layerwas again acidified with 6N HCl and extracted with EtOAc. The organic layer was dried with MgSO4 and concentratedunder reduced pressure to obtain the title compound (3.0 g, 80 %).1H-NMR (CDCl3) delta 7.13 (1H, t), 7.05 (1H, d), 6.95?6.85 (2H, m), 4.75 (1H, m), 3.00?2.80 (2H, m), 2.40 (1H, m), 2.20 (1H, m)
	With hydrogen; acetic acid;palladium 10% on activated carbon; at 70℃; under 3102.97 Torr; for 2.5h;glass reactor sealed;	4-Oxo-4H-chromene-2-carboxylic acid (Aldrich, 3.0 g, 15.8 mmol) was added to a mixture of acetic acid (30 mL) and 10% palladium on carbon (0.3 g) in a Parr shaker. The glass reactor was sealed and flushed with nitrogen, and it was pressurized with hydrogen (60 psi). The mixture was shaken at 70 C. for 2.5 hours. The mixture was filtered and the solids were rinsed with methanol. The filtrate was concentrated under reduced pressure and chromatographed on silica gel eluding with 0-to-10% methanol in ethyl acetate to afford the title compound. 1H NMR (300 MHz, DMSO-d6) delta ppm 2.04 (m, 1H), 2.14 (m, 1H), 2.63 (dt, 1H), 2.78 (dt, 1H), 4.76 (dd, 1H), 6.80 (m, 2H), 7.05 (m, 2H). MS (ESI) m/z 177.09 (M-H)-.
	With palladium on activated charcoal; hydrogen; acetic acid; In water; at 20℃; under 2585.81 Torr; for 25h;	A mixture of 4-oxochromene-2-carboxylic acid (20.0 g, 105 mmol) and Pd/C (3.0 g, w/w=10%) in AcOH (200 mL) was placed in Parr hydrogenation apparatus under H2 (50 psi) and stirred for 25 h at rt. It was then filtered and concentrated. The residue was suspended in water (300 mL), stirred for 10 min, filtered and dried to give 3,4-dihydro-2H-chromene-2-carboxylic acid (13.5 g, 72%) as a white solid.13H3 (57 mE, 114 mmol, 2.0 M in THF) was added slowly to a solution of this carboxylic acid in THF (120 mE) at 0 C. The reaction mixture was then warmed to rt and stirred for 5 hat this temperature. THF/H20 (30 mE, 1:1) was added drop wise while keeping the temperature between 0-5 C. and stirred for 20 mi K2C03 (26.0 g, 189 mmol) was added and the reaction was vigorously stirred for 30 mm. The THF layer was separated and concentrated to give the title compound (11.0 g, 89%) as a brown oil. ?H NMR (400 MHz, CDC13): oe 7.10-7.03 (m, 2H), 6.86-6.81 (m, 2H), 4.14-4.08 (m, 1H),3.85-3.68 (m, 2H), 2.92-2.84 (m, 1H), 2.80-2.73 (m, 1H),1.98-1.92 (m, 1H), 1.90-1.79 (m, 1H). ECMS: 165 (M+17
	With sulfuric acid; hydrogen;5% palladium over charcoal; In acetic acid; at 50℃; under 2068.65 - 2585.81 Torr; for 12h;Product distribution / selectivity;	Example 3; [00189] Cleavage of the 4-carbonyl moiety by hydrogenolysis (racemic model).1 2 3[00190] The 4-carbonyl moiety of 4-oxo- 4H-l-benzopyran-2-carboxylic acid did not reduce under the homogenous catalysis conditions, only the double bond. The moiety was cleaved in the presence of palladium on carbon under acidic conditions. When methanol was used as the solvent, methyl ester was the main product (e.g. 1). This ester can be elaborated to the amide without intermediary hydrolysis. When acetic acid was used, the chroman-2- carboxylic acid (e.g. 2) was the sole product.[00191] Experiments per formed in a manner similar to that described in Example 1 (50 0C, 500 rpm, 12 hours, 2 drops of an acid per each vessel), using 5% Pd/C (Degussa type E1002 XU/W, 50% wet).

Reference： [1]Patent: EP1054881,2008,B1 .Location in patent: Page/Page column 31
[2]Patent: US6469031,2002,B1
[3]Patent: WO2013/124828,2013,A1 .Location in patent: Page/Page column 48
[4]Patent: US2015/38546,2015,A1 .Location in patent: Paragraph 0355-0356
[5]Patent: EP3239143,2017,A2 .Location in patent: Paragraph 0071
[6]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1981,vol. 20,p. 1063 - 1067
[7]European Journal of Medicinal Chemistry,1987,vol. 22,p. 539 - 544
[8]Patent: US2008/153871,2008,A1 .Location in patent: Page/Page column 20
[9]Journal of Heterocyclic Chemistry,2010,vol. 47,p. 582 - 588
[10]Patent: US2015/111885,2015,A1 .Location in patent: Paragraph 1476; 1477
[11]Patent: WO2007/123941,2007,A2 .Location in patent: Page/Page column 70
[12]Patent: WO2007/123941,2007,A2

2
[ 51939-71-0 ]
[ 64-17-5 ]
[ 24698-77-9 ]

Reference： [1]Journal of Heterocyclic Chemistry,1992,vol. 29,p. 431 - 438
[2]Journal of Heterocyclic Chemistry,2010,vol. 47,p. 582 - 588

3
[ 51939-71-0 ]
[ 40515-98-8 ]
[ 116635-85-9 ]

Reference： [1]Journal of Medicinal Chemistry,1988,vol. 31,p. 2300 - 2304

4
[ 51939-71-0 ]
[ 77039-78-2 ]

Yield	Reaction Conditions	Operation in experiment
	In thionyl chloride;	Stage I A solution of 3,4-dihydro-1-benzopyran-2-carboxylic acid (0.59 g 3.3 mmol) in thionyl chloride (15 ml) was stirred at 20 C. for 16 hours. Excess thionyl chloride was evaporated, azeotroping with dry toluene, to give 3,4-dihydro-1-benzopyran-2-carboxylic acid chloride as a yellow oil (numax (film) 1805 cm-1) which was used immediately.
	With oxalyl dichloride;N,N-dimethyl-formamide; In dichloromethane; at 20℃; for 1h;	Example 10A (2.796 g, 15.7 mmol) was dissolved in dichloromethane (60 mL), and oxalyl chloride (4.1 mL, 47.1 mmol) was added with a few drops of dimethylformamide. The mixture stirred for one hour at ambient temperature and was concentrated under reduced pressure to an orange oil. The residue was dissolved in dichloromethane (20 mL), and added to 0.5M ammonia in dioxane (200 mL). After stirring overnight, and filtering off the salts, the filtrate was concentrated under reduced pressure and chromatographed on silica gel eluding with 50-to-100% ethyl acetate in hexane to afford the title compound. 1H NMR (300 MHz, DMSO-d6) delta ppm 1.89 (m, 1H), 2.15 (m, 1H), 2.68 (dt, 1H), 2.80 (ddd, 1H), 4.45 (dd, 1H), 6.83 (m, 2H), 7.07 (m, 2H), 7.35 (d, 2H). MS (DCI) m/z 195.08 (M+NH4)+.
	With oxalyl dichloride;N,N-dimethyl-formamide; In tetrahydrofuran; at 0 - 20℃;	EXAMPLE 21 (+-)-<strong>[51939-71-0]Chroman-2-carboxylic acid</strong> amide Oxalyl chloride (11.0 mL, 126 mmol) was added dropwise to a cooled (0 C) solution of the compound from Example 20 (15 g, 84.3 mmol) and N,N-dimethylformamide (1 mL) in tetrahydrofuran (250 mL). Upon completion of gas evolution the mixture was warmed to room temperature and concentrated in vacuo. The residue was dissolved in tetrahydrofuran (450 mL). The solution was cooled to -78C and ammonia condensed onto the mixture. After 30 minutes the mixture was warmed to room temperature, diluted with water, and extracted with ethyl acetate (2x). The combined organic phase was washed with saturated aqueous sodium chloride solution (2x), dried (MgSO4), and concentrated to give a solid. The solid was triturated with 1:1 diethyl ether/hexanes and dried at 50C in vacuo to give a colorless solid (14.5 g, 97%). Mp 125-127C; 1H NMR (acetone-d6, 300 MHz) delta 7.08 (m, 3 H), 6.86 (m, 2 H), 6.75 (br s, 1 H), 4.47 (dd, 9.2 Hz, 2.9 Hz, 1 H), 2.76 (m, 2 H), 2.28 (m, 1 H), 0.96 (m, 1 H).

Reference： [1]Journal of Medicinal Chemistry,1984,vol. 27,p. 570 - 576
[2]European Journal of Medicinal Chemistry,1987,vol. 22,p. 539 - 544
[3]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1981,vol. 20,p. 1063 - 1067
[4]Patent: US4745114,1988,A
[5]Patent: US2008/153871,2008,A1 .Location in patent: Page/Page column 20
[6]Patent: EP1054881,2008,B1 .Location in patent: Page/Page column 32

5
[ 51939-71-0 ]
[ 83278-86-8 ]

Yield	Reaction Conditions	Operation in experiment
89%	With diborane; In tetrahydrofuran; at 0 - 20℃; for 5h;	A mixture of 4-oxochromene-2-carboxylic acid (20.0 g, 105 mmol) and Pd/C (3.0 g, w/w=10%) in AcOH (200 mE) was placed in Parr hydrogenation apparatus under H2 (50 psi) and stirred for 25 h at rt. It was then filtered and concentrated. The residue was suspended in water (300 mE), stirred for 10 mm, filtered and dried to give 3,4-dihydro-2H- chromene-2-carboxylic acid (13.5 g, 72%) as a white solid. 13H3 (57 mE, 114 mmol, 2.0 M in THF) was added slowly to a solution of this carboxylic acid in THF (120 mE) at 0 C. The reaction mixture was then warmed to rt and stirred for 5 hat this temperature. THF/H20 (30 mE, 1:1) was added drop wise while keeping the temperature between 0-5 C. and stirred for 20 mi K2C03 (26.0 g, 189 mmol) was added and the reaction was vigorously stirred for 30 mm. The THF layer was separated and concentrated to give the title compound (11.0 g, 89%) as a brown oil. ?H NMR (400 MHz, CDC13): oe 7.10-7.03 (m, 2H), 6.86-6.81 (m, 2H), 4.14-4.08 (m, 1H),3.85-3.68 (m, 2H), 2.92-2.84 (m, 1H), 2.80-2.73 (m, 1H),1.98-1.92 (m, 1H), 1.90-1.79 (m, 1H). ECMS: 165 (M+17
		Example 9; Chroman-2-vlmethylsulfamate (Compound No.11); <strong>[51939-71-0]Chroman-2-carboxylic acid</strong> (4.3 g, 24 mmol) in THF (70 mL) was combined with 1M LAH in THF (30 mL, 30 mmol) and stirred at room temperature for 2h. The reaction mixture was quenched with water and then stirred for 2 hours. The THF solution was decanted from the solid, which was washed with fresh THF. The combined THF solution was dried (Na2S04) and evaporated in vacuo to yield chroman-2-yl-methanol as an oil.
		EXAMPLE 9 Chroman-2-ylmethylsulfamate (Compound #11) <strong>[51939-71-0]Chroman-2-carboxylic acid</strong> (4.3 g, 24 mmol) in THF (70 mL) was combined with 1M LAH in THF (30 mL, 30 mmol) and stirred at room temperature for 2 h. The reaction mixture was quenched with water and then stirred for 2 hours. The THF solution was decanted from the solid, which was washed with fresh THF. The combined THF solution was dried (Na2SO4) and evaporated in vacuo to yield chroman-2-yl-methanol as an oil.

Reference： [1]Patent: US2015/111885,2015,A1 .Location in patent: Paragraph 1476; 1477
[2]European Journal of Medicinal Chemistry,1985,vol. 20,p. 117 - 120
[3]Farmaco, Edizione Pratica,1987,vol. 42,p. 805 - 813
[4]Journal of Medicinal Chemistry,2005,vol. 48,p. 1941 - 1947
[5]Tetrahedron Letters,2005,vol. 46,p. 987 - 990
[6]Patent: WO2006/7435,2006,A1 .Location in patent: Page/Page column 44
[7]Patent: US2005/282887,2005,A1 .Location in patent: Page/Page column 19

6
[ 51939-71-0 ]
[ 83780-47-6 ]

Reference： [1]Journal of Medicinal Chemistry,1983,vol. 26,p. 328 - 334

7
[ 51939-71-0 ]
[ 83780-46-5 ]

Reference： [1]Journal of Medicinal Chemistry,1983,vol. 26,p. 328 - 334

8
[ 67-56-1 ]
[ 51939-71-0 ]
[ 66598-81-0 ]

Yield	Reaction Conditions	Operation in experiment
95%	With diazomethyl-trimethyl-silane; In diethyl ether; dichloromethane; at 0℃; for 1h;	Trimethylsilyldiazomethane (10% in ethyl ether, 10.5 mL, 6.17 mmol) is added dropwise to 2-chromanecarboxylic acid (1 g, 5.61 mmol) in dry DCM (8 mL) and MeOH (0.8 mL) cooled to 0C. Stirring is continued for 60 mm, then the solvents are evaporated under reduced pressure to furnish the title compound (1 g, 95%).U PLC-MS (Method 2): R = 1 .06 mmMS (ESI pos): mlz = 193 (M+H)
93%	With hydrogenchloride; In 1,4-dioxane; at 20℃;	a) (R,S)-<strong>[51939-71-0]Chroman-2-carboxylic acid</strong> methyl ester (29a) To a stirred solution of compound 14a (15 g, 84.2 mmol) in dry methanol (250 mL) was added hydrogen chloride (4.0 M solution in dioxane, 60 mL) and the mixture was stirred overnight at room temperature. The solvents were removed under reduced pressure, the residue was dissolved in ether (300 mL) and washed with IN sodium bicarbonate (2100 mL), brine (1100 mL), dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and dried in vacuo to afford the title compound (15.05 g, 93%). 1H NMR (400 MHz, CDCl3) delta 7.15-6.83 (m, 4H), 4.76 (dd, 1H), 3.79 (s, 3H), 2.8 (m, 2H), 2.25 (m, 2H).

Reference： [1]Patent: WO2014/184275,2014,A1 .Location in patent: Page/Page column 143
[2]Patent: US2005/54630,2005,A1 .Location in patent: Page/Page column 39
[3]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5114 - 5119
[4]Journal of the American Chemical Society,2019,vol. 141,p. 14870 - 14877

9
[ 51939-71-0 ]
[ 99199-63-0 ]

Yield	Reaction Conditions	Operation in experiment
70.4%	With nitric acid; In water; at 0℃; for 1h;	EXAMPLE 60 (+-)-6-Nitro-<strong>[51939-71-0]chroman-2-carboxylic acid</strong> To a solution of concentrated nitric acid (70%, 166 mL), at 0C, was added the chroman acid, from Example 20, (10.0 g, 56.0 mmol) portionwise. The reaction mixture was stirred until all solids were dissolved (1 h) and was then poured onto ice (400 g). The fine precipitate was collected via filtration through a medium porosity sintered glass funnel. The crude precipitate was washed with water (2 * 100 mL) followed by brine (1 * 50 mL) and finally dried under vacuum at 60C for 24 h to afford (8.85 g, 70.4%) pure product. Rf = 0.2 (methylene chloride: methanol 9:1); mp 110-111C; MS (FAB) m/z 224 (MH+).
61.5%	With nitric acid; In water; at 0℃; for 1h;	a) (R,S)-6-Nitro-<strong>[51939-71-0]chroman-2-carboxylic acid</strong> (20a) (R,S)-<strong>[51939-71-0]Chroman-2-carboxylic acid</strong> 14a was nitrated using the literature procedure (WO 99/32475). To a solution of nitric acid (70%, 250 mL) at 0 C. was added portionwise <strong>[51939-71-0]chroman-2-carboxylic acid</strong> (15 g, 84.3 mmol). The reaction mixture was stirred for 1 hours and poured into ice (600 g). the solid was collected by filtration, washed with cold water (2*100 mL), and dried under vacuum to give the title acid (11.56 g, 61.5%). 1H NMR (400 MHz, DMSO-d6) delta: 13.25 (brs, 1H), 8.02 (m, 2H), 7.02 (d, 1H), 5.01 (t, 1H), 2.92 (m, 1H), 2.75 (m, 1H), 2.20 (m, 2H).

Reference： [1]Patent: EP1054881,2008,B1 .Location in patent: Page/Page column 41
[2]Patent: US2005/54630,2005,A1 .Location in patent: Page/Page column 37-38
[3]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5114 - 5119

10
[ 51939-71-0 ]
[ 83780-46-5 ]
[ 83780-47-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5114 - 5119

11
[ 66598-81-0 ]
[ 51939-71-0 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium hydroxide; In tetrahydrofuran; methanol; water; at 20℃; for 2h;	General procedure: To a stirred solution of 2a-f in THF (2 mL) and MeOH (1 mL),0.25 M aqueous LiOH (1.05 equiv) was added dropwise at roomtemperature and stirred for 2 h. The reaction mixture was concentratedunder reduced pressure and then acidified with dil HCl. Thecrude product was extracted with ethyl acetate and concentrated.This organic layer was dried over anhydrous MgSO4, filtered, andevaporated under reduced pressure. The concentrate was furtherpurified by crystallization with n-hexane to afford 6a-f.
		rac- Chroman- 2- carboxylic acid; [00139] A 2.5 L Parr shaker vessel was charged with chromone-2- carboxylic acid (150.0 g, 0.789 mol), a slurry of palladium on carbon (10% wet, Aldrich, 8.36 g, 3.9 mmol Pd, 0.5 mol%) in methanol (20 mL). Concentrated sulfuric acid (46 mL, 0.83 mol) was dissolved in 1.00 L of methanol (Very exothermic.) and the solution was added to the mixture in the Parr vessel.[00140] The mixture was hydrogenated on a Parr shaker at 50 psi hydrogen pressure and room temperature. Hydrogen reservoir was refilled to 50 psi whenever pressure dropped below 40 psi. The reaction was monitored by HPLC. Hydrogenation was continued until the starting material became undetectable (< 0.1% at 215 ran), usually overnight. [00141] The catalyst was removed by filtering the reaction mixture through a pad of Celite. The filtrate containing methyl chromane- 2-carboxylate was transferred into a 4- liter Erlenmeyer flask equipped with a mechanical stirrer. Water (0.50 L) and 10 M aqueous solution of NaOH (300 mL, 3.0 mol) were added (mild exotherm, 42 0C, precipitate of sodium sulfate separated) and the mixture was stirred for 10 min at room temperature at <n="62"/>which point HPLC analysis showed complete hydrolysis of the ester (< 0.1% at 215 nm). The inorganic precipitate was filtered off and methanol was removed from the solution on rotary evaporator. The residue after evaporation was mixed with MTBE (250 mL)and the mixture was acidified with 6 M aq. HCl until pH of the aqueous layer fell below 3 (ca. 300 mL). The aqueous layer was separated and extracted with MTBE (2 x 300 mL). The extracts, combined with the organic layer, were washed with brine (200 mL) and dried with MgSO4. The drying agent was filtered off and the filtrate was evaporated to a thick oil (180 g). This residue was triturated with heptane (50 mL) which caused rapid crystallization of the acid. The mixture was chilled in ice, filtered and the solid on the filter was washed with cold heptane and dried on the filter in a stream of air. Yield of the chromane- 2- carboxylic acid 117.6 g (85%) as colorless crystals. Purity 99% (HPLC, 215 nm).A second crop of crystals was obtained by evaporation of the filtrate to 30 mL and filtration of the separated crystals: 10.7 g (8%). Purity 94% (HPLC, 215 nm, 2 major impurities 2.8 and 3.4%).

Reference： [1]Tetrahedron Asymmetry,2015,vol. 26,p. 912 - 917
[2]Patent: WO2007/123941,2007,A2 .Location in patent: Page/Page column 59-61

12
[ 51939-71-0 ]
[ 2941-20-0 ]
[ 955124-58-0 ]

Yield	Reaction Conditions	Operation in experiment
42%	In tert-butyl methyl ether; acetonitrile; at 20℃; for 6.08h;Resolution of racemate;Purification / work up;	(R)- (- )- Chromane- 2- carboxylic acid (chemical resolution).; [00147] A 1- L Erlenmeyer flask equipped with a magnetic stirrer was charged with racemic chromane-2-carboxylic acid (60.9 g, 0.342 mol) and acetonitrile (300 mL). In a separate flask, (R)-(+)-l-phenylpropylamine (30.0 g, 0.222 mol, 0.65 eq.) was mixed with 40 mL of MTBE and this solution was added portionwise to the solution of the acid via pipette. After about half of the total amount of the amine solution was added, the reaction mixture was seeded with a few crystals of (R)-(+)-l- phenylpropylammonium (R)-(- )- chromane-2- carboxylate. When precipitation of the salt began, the remainder of the amine solution was added over about 5 min. The thick slurry of crystalline salt was diluted with 260 mL of MTBE (total volume of MTBE added was 300 mL) and the mixture was stirred gently for 6 hr at room temperature.[00148] The salt was filtered, washed with MTBE and dried in air. Yield 45.2 g (acid content 25.7 g, 42%). Ratio of the acid enantiomers 98:2 (see note below for analytical determination).[00149] The salt (45.13 g, 0.144 mol) was placed into a 1- L Erlenmeyer flask equipped with a magnetic stirrer and was suspended in MTBE (250 mL). Aqueous 1 M HCl solution (290 mL, 0.290 mol) was added and the mixture was stirred at room temperature until all solid dissolved and 2 clear phases formed (about 10 min). The layers were separated. The aq. layer was extracted with MTBE (2 x 100 mL). The extracts were combined with the organic <n="64"/>layer and the solution was washed with 0.5 M aq. HCl (100 mL), then brine (2 x 100 mL).The solution was then dried with MgS O4, the drying agent was filtered and the filtrate was concentrated in vacuum to ca. 50 mL. Heptane (50 mL) was mixed with the residue and crystallization of the product was induced by seeding it a few crystals of the optically pure acid. The solvents were then removed in vacuum. Yield 25.58 g (42% from the racemic acid,99% from the salt) as white crystals. M.p. 81-83 0C.[00150] 1H NMR (400 MHz, CDCl3), delta: 9.23 (br s, IH)5 7.13 (X, J= 7.8 Hz, IH), 7.06 (d, J= 1.6 Hz, IH)5 6.95-6.87 (m, 2H), 4.76 (dd, J = 3.5, 8.1 Hz5 IH), 2.93-2.76 (m, 2H), 2.41-2.32 (m, IH), 2.25-2.14 (m, IH).[00151] 13C NMR (100 MHz, CDCl3), delta: 175.43, 152.85, 129.53, 127.73, 121.29, 121.18,116.85, 73.29, 24.49, 23.40.[00152] HRMS (ESI), m/z: 177.05519 (M-H)"; calc'd for Ci0H9O3: 177.05572. [00153] Enantiomeric purity determination. HPLC method: Chiralcel ODH, 0.46 x 25 cm column, isocratic 75% heptane/TFA, 25% Ethanol, distomer 4.4 min, eutomer 6.7 min.

Reference： [1]Patent: WO2007/123941,2007,A2 .Location in patent: Page/Page column 59; 62-63

13
[ 51939-71-0 ]
[ 847948-85-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5114 - 5119

14
[ 51939-71-0 ]
(S)-6-Amino-chroman-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5114 - 5119

15
[ 51939-71-0 ]
(R)-6-Amino-chroman-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5114 - 5119

16
[ 51939-71-0 ]
(S)-6-Nitro-chroman-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5114 - 5119

17
[ 51939-71-0 ]
(R)-6-Nitro-chroman-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5114 - 5119

18
[ 51939-71-0 ]
[ 847948-84-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5114 - 5119

19
[ 51939-71-0 ]
(S)-6-Cyano-chroman-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5114 - 5119

20
[ 51939-71-0 ]
(R)-6-Cyano-chroman-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5114 - 5119

21
[ 51939-71-0 ]
(S)-6-Iodo-chroman-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5114 - 5119

22
[ 51939-71-0 ]
(R)-6-Iodo-chroman-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5114 - 5119

23
[ 51939-71-0 ]
(S)-6-Aminomethyl-chroman-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5114 - 5119

24
[ 51939-71-0 ]
(R)-6-Aminomethyl-chroman-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5114 - 5119

25
[ 51939-71-0 ]
6-nitrochroman-2(S)-carboxylic acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5114 - 5119

26
[ 51939-71-0 ]
[ 474112-72-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5114 - 5119

27
[ 51939-71-0 ]
[ 600166-79-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5114 - 5119

28
[ 51939-71-0 ]
[ 847948-86-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5114 - 5119

29
[ 51939-71-0 ]
6-methanesulfonylamino-chroman-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5114 - 5119

30
[ 51939-71-0 ]
[ 847948-87-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5114 - 5119

31
[ 51939-71-0 ]
6-sulfamoyl-chroman-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5114 - 5119

32
[ 51939-71-0 ]
6-methylsulfamoyl-chroman-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5114 - 5119

33
[ 51939-71-0 ]
[ 871213-61-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5114 - 5119

34
[ 51939-71-0 ]
[ 871213-62-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5114 - 5119

35
[ 51939-71-0 ]
[ 871213-63-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5114 - 5119

36
[ 51939-71-0 ]
[ 871213-67-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5114 - 5119

37
[ 51939-71-0 ]
[ 871213-66-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5114 - 5119

38
[ 51939-71-0 ]
[ 871213-65-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5114 - 5119

39
[ 51939-71-0 ]
[ 871213-64-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5114 - 5119

40
[ 51939-71-0 ]
(S)-6-(Methoxycarbonylamino-methyl)-chroman-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5114 - 5119

41
[ 51939-71-0 ]
(R)-6-(Methoxycarbonylamino-methyl)-chroman-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5114 - 5119

42
[ 51939-71-0 ]
(S)-6-(Methanesulfonylamino-methyl)-chroman-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5114 - 5119

43
[ 51939-71-0 ]
(R)-6-(Methanesulfonylamino-methyl)-chroman-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5114 - 5119

44
[ 51939-71-0 ]
[ 847948-89-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5114 - 5119

45
[ 51939-71-0 ]
[ 847948-88-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5114 - 5119

46
[ 51939-71-0 ]
(S)-6-(Propane-1-sulfonylamino)-chroman-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5114 - 5119

47
[ 51939-71-0 ]
(R)-6-(Propane-1-sulfonylamino)-chroman-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5114 - 5119

48
[ 51939-71-0 ]
(S)-chroman-2-carboxylic acid {2-[(S)-3-hydroxy-pyrrolidin-1-yl]-(S)-1-phenyl-ethyl}-methyl-amide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5114 - 5119

49
[ 51939-71-0 ]
(R)-chroman-2-carboxylic acid {2-[(S)-3-hydroxy-pyrrolidin-1-yl]-(S)-1-phenyl-ethyl}-methyl-amide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5114 - 5119

50
[ 51939-71-0 ]
(R,S)-6-sulfamoyl-chroman-2-carboxylic acid {2-[(S)-3-hydroxy-pyrrolidin-1-yl]-(S)-1-phenyl-ethyl}-methyl-amide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5114 - 5119

51
[ 51939-71-0 ]
6-Acetylamino-chroman-2-carboxylic acid [(S)-2-((S)-3-hydroxy-pyrrolidin-1-yl)-1-phenyl-ethyl]-methyl-amide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5114 - 5119

52
[ 51939-71-0 ]
6-Methanesulfonylamino-chroman-2-carboxylic acid [(S)-2-((S)-3-hydroxy-pyrrolidin-1-yl)-1-phenyl-ethyl]-methyl-amide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5114 - 5119

53
[ 51939-71-0 ]
(R,S)-6-methylsulfamoyl-chroman-2-carboxylic acid {2-[(S)-3-hydroxy-pyrrolidin-1-yl]-(S)-1-phenyl-ethyl}-methyl-amide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5114 - 5119

54
[ 51939-71-0 ]
(S)-6-(methane sulfonylamino-methyl)-chroman-2-carboxylic acid {2-[(S)-3-hydroxy-pyrrolidin-1-yl]-(S)-1-phenyl-ethyl}-methyl-amide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5114 - 5119

55
[ 51939-71-0 ]
(R)-6-(methane sulfonylamino-methyl)-chroman-2-carboxylic acid {2-[(S)-3-hydroxy-pyrrolidin-1-yl]-(S)-1-phenyl-ethyl}-methyl-amide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5114 - 5119

56
[ 51939-71-0 ]
(2-[2-({S}-3-hydroxy-pyrrolidin-1-yl)-{S}-1-phenyl-ethyl]-(S)-methyl-carbamoyl}-chroman-6-ylmethyl)-carbamic acid methyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5114 - 5119

57
[ 51939-71-0 ]
(2-[2-({S}-3-hydroxy-pyrrolidin-1-yl)-{S}-1-phenyl-ethyl]-(R)-methyl-carbamoyl}-chroman-6-ylmethyl)-carbamic acid methyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5114 - 5119

58
[ 51939-71-0 ]
6-(propane-1-sulfonylamino)-(S)-chroman-2-carboxylic acid {2-[(S)-3-hydroxy-pyrrolidin-1-yl]-(S)-1-phenyl-ethyl}-methyl-amide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5114 - 5119

59
[ 51939-71-0 ]
6-(propane-1-sulfonylamino)-(R)-chroman-2-carboxylic acid {2-[(S)-3-hydroxy-pyrrolidin-1-yl]-(S)-1-phenyl-ethyl}-methyl-amide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5114 - 5119

60
[ 51939-71-0 ]
[ 474111-17-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5114 - 5119

61
[ 51939-71-0 ]
[ 437763-84-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5114 - 5119

62
[ 51939-71-0 ]
chroman-2-ylmethylsulfamate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 1941 - 1947

63
[ 51939-71-0 ]
N-(chroman-2-ylmethyl)sulfamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 1941 - 1947
[2]Journal of Medicinal Chemistry,2013,vol. 56,p. 9019 - 9030

64
[ 51939-71-0 ]
[ 3990-59-8 ]

Yield	Reaction Conditions	Operation in experiment
		<strong>[51939-71-0]Chroman-2-carboxylic acid</strong> (4.5 g, 25 mmol) and HOBT (3.86 g, 25 mmol) were combined in DCM (40 mL) and DMF (10 mL). Dimethylaminopropyl ethylcarbodiimide (EDC, 4.84 g, 25 mmol) was added at room temperature and the reaction mixture was stirred for 30 min. Ammonium hydroxide (2.26 mL, 33.4 mmol) was added and the reaction mixture was stirred for 16h. The reaction mixture was diluted with DCM (50 mL) and water (50 mL) and the pH of the mixture was adjusted to about pH=3.0 with 1N HCl. The DCM was separated and the aqueous phase extracted twice with DCM. The combined DCM phase was dried (Na2SO4) and evaporated in vacuo to yield an oil, which was purified with flash column chromatography (ethyl acetate) to yield an oil.
		<strong>[51939-71-0]Chroman-2-carboxylic acid</strong> (4.5 g, 25 mmol) and HOBT (3.86 g, 25 mmol) were combined in DCM (40 mL) and DMF (10 mL). Dimethylaminopropyl ethylcarbodiimide (EDC, 4.84 g, 25 mmol) was added at room temperature and the reaction mixture was stirred for 30 min. Ammonium hydroxide (2.26 mL, 33.4 mmol) was added and the reaction mixture was stirred for 16h. The reaction mixture was diluted with DCM (50 mL) and water (50 mL) and the pH of the mixture was adjusted to about pH=3.0 with 1 N HCl. The DCM was separated and the aqueous phase extracted twice with DCM. The combined DCM phase was dried (Na2SO4) and evaporated in vacuo to yield an oil, which was purified with flash column chromatography (ethyl acetate) to yield an oil.
		<strong>[51939-71-0]Chroman-2-carboxylic acid</strong> (4.5 g, 25 mmol) and HOBT (3.86 g, 25 mmol) were combined in DCM (40 mL) and DMF (10 mL). Dimethylaminopropyl ethylcarbodiimide (EDC, 4.84 g, 25 mmol) was added at room temperature and the reaction mixture was stirred for 30 min. Ammonium hydroxide (2.26 mL, 33.4 mmol) was added and the reaction mixture was stirred for 16 h. The reaction mixture was diluted with DCM (50 mL) and water (50 mL) and the pH of the mixture was adjusted to about pH=3.0 with 1N HCl. The DCM was separated and the aqueous phase extracted twice with DCM. The combined DCM phase was dried (Na2SO4) and evaporated in vacuo to yield an oil, which was purified with flash column chromatography (ethyl acetate) to yield an oil. The oil (5.35 g, 30 mmol) in THF (90 mL) was stirred as 1M LAH in THF (36 mL, 36 mmol) was added and the reaction mixture was then stirred at room temperature for 20 h. The reaction was quenched with water, stirred for 2 hours, the solution decanted, dried (Na2SO4) and evaporated in vacuo to yield C-chroman-2-yl-methylamine as an oily amine.

		<strong>[51939-71-0]Chroman-2-carboxylic acid</strong> (4.5 g, 25 mmol) and HOBT (3.86 g, 25 mmol) were combined in DCM (40 mL) and DMF (10 mL). Dimethylaminopropyl ethylcarbodiimide (EDC, 4.84 g, 25 mmol) was added at room temperature and the reaction mixture was stirred for 30 min. Ammonium hydroxide (2.26 mL, 33.4 mmol) was added and the reaction mixture was stirred for 16 h. The reaction mixture was diluted with DCM (50 mL) and water (50 mL) and the pH of the mixture was adjusted to about pH=3.0 with 1N HCl. The DCM was separated and the aqueous phase extracted twice with DCM. The combined DCM phase was dried (Na2SO4) and evaporated in vacuo to yield an oil, which was purified with flash column chromatography (ethyl acetate) to yield an oil. The oil (5.35 g, 30 mmol) in THF (90 mL) was stirred as 1M LAH in THF (36 mL, 36 mmol) was added and the reaction mixture was then stirred at room temperature for 20 h. The reaction was quenched with water, stirred for 2 hours, the solution decanted, dried (Na2SO4) and evaporated in vacuo to yield C-chroman-2-yl-methylamine as an oily amine.
		<strong>[51939-71-0]Chroman-2-carboxylic acid</strong> (4.5 g, 25 mmol) and HOBT (3.86 g, 25 mmol) were combined in DCM (40 mL) and DMF (10 mL). Dimethylaminopropyl ethylcarbodiimide (EDC, 4.84 g, 25 mmol) was added at room temperature and the reaction mixture was stirred for 30 min. Ammonium hydroxide (2.26 mL, 33.4 mmol) was added and the reaction mixture was stirred for 16 h. The reaction mixture was diluted with DCM (50 mL) and water (50 mL) and the pH of the mixture was adjusted to about pH=3.0 with 1N HCl. The DCM was separated and the aqueous phase extracted twice with DCM. The combined DCM phase was dried (Na2SO4) and evaporated in vacuo to yield an oil, which was purified with flash column chromatography (ethyl acetate) to yield an oil.The oil (5.35 g, 30 mmol) in THF (90 mL) was stirred as 1M LAH in THF (36 mL, 36 mmol) was added and the reaction mixture was then stirred at room temperature for 20 h. The reaction was quenched with water, stirred for 2 hours, the solution decanted, dried (Na2SO4) and evaporated in vacuo to yield C-chroman-2-yl-methylamine as an oily amine.

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 1941 - 1947
[2]Patent: US2007/155822,2007,A1 .Location in patent: Page/Page column 16
[3]Patent: US2007/155821,2007,A1 .Location in patent: Page/Page column 17
[4]Patent: US2007/155823,2007,A1 .Location in patent: Page/Page column 15
[5]Patent: US2007/155827,2007,A1 .Location in patent: Page/Page column 16
[6]Patent: US2007/191474,2007,A1 .Location in patent: Page/Page column 17
[7]Journal of Medicinal Chemistry,2013,vol. 56,p. 9019 - 9030

65
[ 51939-71-0 ]
[ 68118-01-4 ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 987 - 990

66
[ 51939-71-0 ]
[ 99199-77-6 ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 987 - 990

67
[ 51939-71-0 ]
[ 40515-95-5 ]

Reference： [1]Farmaco, Edizione Pratica,1987,vol. 42,p. 805 - 813

68
[ 51939-71-0 ]
acide (chromannyl-2) methane phosphonique [ No CAS ]

Reference： [1]Farmaco, Edizione Pratica,1987,vol. 42,p. 805 - 813

69
[ 51939-71-0 ]
[ 116877-00-0 ]

Reference： [1]Farmaco, Edizione Pratica,1987,vol. 42,p. 805 - 813

70
[ 51939-71-0 ]
[ 40516-01-6 ]

Reference： [1]Journal of Medicinal Chemistry,1988,vol. 31,p. 2300 - 2304

71
[ 51939-71-0 ]
(3aR,4R,5R,6aS)-4-[(E)-(R)-3-Chroman-2-yl-3-(tetrahydro-pyran-2-yloxy)-propenyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-ol [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1983,vol. 26,p. 328 - 334
[2]Journal of Medicinal Chemistry,1983,vol. 26,p. 328 - 334

72
[ 51939-71-0 ]
[ 66598-88-7 ]

Reference： [1]Journal of Medicinal Chemistry,1983,vol. 26,p. 328 - 334
[2]Journal of Medicinal Chemistry,1983,vol. 26,p. 328 - 334

73
[ 51939-71-0 ]
[(1R,3R,5S)-2-[(E)-(S)-3-Chroman-2-yl-3-(tetrahydro-pyran-2-yloxy)-propenyl]-5-hydroxy-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-acetaldehyde [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1983,vol. 26,p. 328 - 334
[2]Journal of Medicinal Chemistry,1983,vol. 26,p. 328 - 334

74
[ 51939-71-0 ]
[ 66598-82-1 ]

Reference： [1]Journal of Medicinal Chemistry,1983,vol. 26,p. 328 - 334

75
[ 51939-71-0 ]
[ 66598-81-0 ]

Reference： [1]Journal of Medicinal Chemistry,1983,vol. 26,p. 328 - 334

76
[ 51939-71-0 ]
[ 66598-87-6 ]

Reference： [1]Journal of Medicinal Chemistry,1983,vol. 26,p. 328 - 334

77
[ 51939-71-0 ]
[ 66598-86-5 ]

Reference： [1]Journal of Medicinal Chemistry,1983,vol. 26,p. 328 - 334

78
[ 51939-71-0 ]
[ 66598-90-1 ]

Reference： [1]Journal of Medicinal Chemistry,1983,vol. 26,p. 328 - 334
[2]Journal of Medicinal Chemistry,1983,vol. 26,p. 328 - 334

79
[ 51939-71-0 ]
[ 66598-90-1 ]

Reference： [1]Journal of Medicinal Chemistry,1983,vol. 26,p. 328 - 334
[2]Journal of Medicinal Chemistry,1983,vol. 26,p. 328 - 334

80
[ 51939-71-0 ]
[ 66598-97-8 ]

Reference： [1]Journal of Medicinal Chemistry,1983,vol. 26,p. 328 - 334
[2]Journal of Medicinal Chemistry,1983,vol. 26,p. 328 - 334

81
[ 51939-71-0 ]
[ 66598-97-8 ]

Reference： [1]Journal of Medicinal Chemistry,1983,vol. 26,p. 328 - 334
[2]Journal of Medicinal Chemistry,1983,vol. 26,p. 328 - 334

82
[ 51939-71-0 ]
[ 66598-93-4 ]

Reference： [1]Journal of Medicinal Chemistry,1983,vol. 26,p. 328 - 334
[2]Journal of Medicinal Chemistry,1983,vol. 26,p. 328 - 334

83
[ 51939-71-0 ]
[ 66598-93-4 ]

Reference： [1]Journal of Medicinal Chemistry,1983,vol. 26,p. 328 - 334
[2]Journal of Medicinal Chemistry,1983,vol. 26,p. 328 - 334

84
[ 51939-71-0 ]
[ 66598-91-2 ]

Reference： [1]Journal of Medicinal Chemistry,1983,vol. 26,p. 328 - 334
[2]Journal of Medicinal Chemistry,1983,vol. 26,p. 328 - 334

85
[ 51939-71-0 ]
[ 66598-91-2 ]

Reference： [1]Journal of Medicinal Chemistry,1983,vol. 26,p. 328 - 334
[2]Journal of Medicinal Chemistry,1983,vol. 26,p. 328 - 334

86
[ 51939-71-0 ]
[ 66598-89-8 ]

Reference： [1]Journal of Medicinal Chemistry,1983,vol. 26,p. 328 - 334
[2]Journal of Medicinal Chemistry,1983,vol. 26,p. 328 - 334

87
[ 51939-71-0 ]
[ 66598-89-8 ]

Reference： [1]Journal of Medicinal Chemistry,1983,vol. 26,p. 328 - 334
[2]Journal of Medicinal Chemistry,1983,vol. 26,p. 328 - 334

88
[ 51939-71-0 ]
[ 66598-92-3 ]

Reference： [1]Journal of Medicinal Chemistry,1983,vol. 26,p. 328 - 334
[2]Journal of Medicinal Chemistry,1983,vol. 26,p. 328 - 334

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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

[ CAS No. 51939-71-0 ] {[proInfo.proName]}

Quality Control of [ 51939-71-0 ]

Related Doc. of [ 51939-71-0 ]

Product Details of [ 51939-71-0 ]

Calculated chemistry of [ 51939-71-0 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 51939-71-0 ]

Application In Synthesis of [ 51939-71-0 ]

[ 51939-71-0 ] Synthesis Path-Upstream 1~6

[ 51939-71-0 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 51939-71-0 ]

Carboxylic Acids

Related Parent Nucleus of [ 51939-71-0 ]

Other Aromatic Heterocycles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 51939-71-0 ]

Related Parent Nucleus of
[ 51939-71-0 ]