[ CAS No. 61161-83-9 ]

Name: 61161-83-9|5-(Hydroxymethyl)-2-nitrophenol|98%
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Quality Control of [ 61161-83-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 61161-83-9 ]

SDS Specification

Alternatived Products of [ 61161-83-9 ]

Product Details of [ 61161-83-9 ]

CAS No. :	61161-83-9	MDL No. :	MFCD00086342
Formula :	C₇H₇NO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YDFRYKXELURVHE-UHFFFAOYSA-N
M.W :	169.13	Pubchem ID :	14520114
Synonyms :

Calculated chemistry of [ 61161-83-9 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	2
Num. H-bond acceptors :	4.0
Num. H-bond donors :	2.0
Molar Refractivity :	43.41
TPSA :	86.28 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.58 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.13
Log Po/w (XLOGP3) :	1.06
Log Po/w (WLOGP) :	0.64
Log Po/w (MLOGP) :	-0.22
Log Po/w (SILICOS-IT) :	-0.95
Consensus Log Po/w :	0.13

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.79
Solubility :	2.72 mg/ml ; 0.0161 mol/l
Class :	Very soluble
Log S (Ali) :	-2.46
Solubility :	0.582 mg/ml ; 0.00344 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.03
Solubility :	15.9 mg/ml ; 0.094 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.59

Safety of [ 61161-83-9 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P310-P330-P332+P313-P362-P403+P233-P405-P501	UN#:	1759
Hazard Statements:	H302-H315-H318-H335	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 61161-83-9 ]

* 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 [ 61161-83-9 ]
Downstream synthetic route of [ 61161-83-9 ]

[ 61161-83-9 ] Synthesis Path-Upstream 1~1

1
[ 61161-83-9 ]
[ 704-13-2 ]

Reference： [1] Journal of Organic Chemistry, 1994, vol. 59, # 15, p. 4285 - 4296

[ 61161-83-9 ] Synthesis Path-Downstream 1~68

1
[ 619-14-7 ]
[ 61161-83-9 ]

Yield	Reaction Conditions	Operation in experiment
98%		Step A-5-(Hydroxymethyl)-2-nitrophenol To a mixture of 3-hydroxy-4-nitrobenzoic acid (5.0 g, 27 mmol) in 1,2-dichloroethane (100 mL) was added trimethyl borate (4.9 mL, 44 mmol), followed by boron trifluoride diethyl etherate (5.5 mL. 44 mmol). Borane-pyridine complex (4.1 mL, 41 mmol) was then slowly added drop wise. The reaction was stirred 4 h at rt, then cooled to 0 C. and quenched with MeOH (10 mL). The mixture was concentrated under vacuum and the residue taken up in toluene (200 mL), then extracted with aqueous 1 N NaOH (3×100 mL). The combined aqueous layers were adjusted to pH 1.0 by addition of 12 N HCl, then extracted with EtOAc (3×250 mL). The combined organic layers were washed with water, brine, dried over MgSO4 and concentrated under vacuum to give 4.55 g (98%) of the title compound as a light yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 10.87 (s, 1H), 7.85 (d, 1H, J=8.6 Hz), 7.08 (s, 1H), 6.88 (dd, 1H, J=1.19, 8.51 Hz), 5.43 (s, 1H), 3.33 (s, 2H).
98%	With borane pyridine; Trimethyl borate; boron trifluoride diethyl etherate; In 1,2-dichloro-ethane; at 20℃; for 4h;	To a mixture of 3-hydroxy-4-nitrobenzoic acid (5.0 g, 27.3 mmol) in 1,2- dichloroethane (100 ml_) was added trimethyl borate (4.9 nriL, 43.7 mmol), followed by boron trifluoride diethyl etherate (5.5 ml_, 43.7 mmol). Borane- pyridine complex (4.1 ml_, 41.0 mmol) was then slowly added drop wise. The reaction was stirred 4 h at room temperature, then cooled to 00C and quenched with MeOH (10 ml_). The mixture was concentrated under vacuum and the residue taken up in toluene (200 mL), then extracted with aqueous 1 N sodium hydroxide (3 x 100 mL). The combined aqueous layers were adjusted to pH 1.0 by addition of 12 N HCI1 then extracted with EtOAc (3 x 250 mL). The combined organic layers were washed with water, brine, dried over MgSO4 and concentrated under vacuum to give 4.55 g (98%) of the title compound as a light yellow solid. 1H NMR (400 MHz, DMSO-ofe): δ 10.87 (s, 1H), 7.85 (d, 1H, J= 8.6 Hz), 7.08 (s, 1H), 6.88 (dd, 1H, J= 1.19, 8.51 Hz)1 5.43 (s, 1 H)1 3.33 (S1 2H).
98%		To a mixture of 3-hydroxy-4-nitrobenzoic acid (5.0 g, 27.3 mmol) in 1 ,2- dichloroethane (100 ml_) was added trimethyl borate (4.9 ml_, 43.7 mmol), followed by boron trifluoride diethyl etherate (5.5 mL, 43.7 mmol). Borane- pyridine complex (4.1 mL, 41.0 mmol) was then slowly added dropwise. The reaction was stirred 4 hrs at room temperature, then cooled to 0 0C and quenched with methanol (10 mL). The mixture was concentrated under vacuum and the residue taken up in toluene (200 mL), then extracted with aqueous 1 N sodium hydroxide (3 x 100 mL). The combined aqueous layers were adjusted to pH 1.0 by addition of 12 N HCI, then extracted with ethyl acetate (3 x 250 mL). The combined organic layers were washed with water, brine, dried over magnesium sulfate and concentrated under vacuum to give 4.55 g (98%) of the title compound as a light yellow solid. 1H NMR (400 MHz, DMSO-Cf6): δ 10.87 (s, 1 H), 7.85 (d, 1 H, J= 8.6 Hz), 7.08 (s, 1 H), 6.88 (dd, 1 H1 J= 1.19, 8.51 Hz), 5.43 (s, 1 H), 3.33 (s, 2H).

98%		Intermediate 31 : Methyl 5-[6-(hydroxymeihyl)-1 Mbenzimidazol-1 -yi]-3-({(1 Rl- 1-f2-ftrifiuoromethyl)phenvllethviK)xv)thiQpheϖβ-2-c6it»oxvl3teStep A - 5-(Hydroxymethyl}-2~ϖitfx>phenoiTo a mixture of 3-hydroxy-4-nitnobenzoic acid (5,0 g, 27 mmoi) in 1 ,2- dichioroethane (100 mL) was added trimethy. borate (4.9 ml, 44 mmol), followed by boron trifluorlde diethyl etherate (5.5 mL, 44 mmol). Borane- pyridine complex (4.1 mL, 41 mmo.) was then siowiy added drop wise. The reaction was stirred 4 h at rt, then cooled to 0 0C and quenched with MeOH {10 ml). The mixture was concentrated under vacuum and the residue taken up in toluene (200 rut), then extracted with aqueous 1 N NaOH (3 x 100 ml). The combined aqueous layers were adjusted to pH 1.0 by addition of 12 N HCI, then extracted with EtOAc (3 x 250 ml). The combined organic layers were washed with water, brine, dried over MgSO4 and concentrated under vacuum to give 4.55 g (98%) of the tie compound as a light yellow solid, 1H NMR (400 MHz, DMSO-ofe): δ 10.87 (s, 1H)1 7.85 (d, 1H1 J= 8.6 Hz), 7,08 (s5 1 H), 8,88 (eld, 1 H, J= 1.19, S.51 Hz), 5.43 (s, IH), 3.33 (s, 2H).
4.3 g	With borane pyridine; Trimethyl borate; boron trifluoride diethyl etherate; In methanol; dichloromethane; at 35℃; for 4h;Cooling with ice;	A) 5-(hydroxymethyl)-2-nitrophenol (0921) To a mixture of 180 3-hydroxy-4-nitrobenzoic acid (5 g) and 110 dichloromethane (54.6 ml) were added 181 trimethyl borate (5.18 ml) and boron trifluoride diethyl ether complex (5.88 ml) under ice-cooling. To the reaction mixture was added dropwise borane pyridine complex (4.41 ml) under ice-cooling. The reaction mixture was stirred at room temperature for 4 hr, and 39 methanol (15 ml) was added under ice-cooling. The obtained mixture was concentrated under reduced pressure, and 54 toluene (200 ml) was added. The obtained mixture was extracted 3 times with 1N aqueous sodium hydroxide solution (100 ml), and the combined aqueous layer was acidified with 6N hydrochloric acid. The obtained mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the 182 title compound (4.3 g). 1H NMR (400 MHz, DMSO-d6) δ 4.48 (2H, s), 6.85 (1H, dd, J = 8.4, 1.6 Hz), 7.05-7.06 (1H, m), 7.83 (1H, d, J = 8.4 Hz), 10.87 (1H, brs). * The peak of OH of -CH2OH was not observed.

Reference： [1]Journal of Photochemistry and Photobiology A: Chemistry,2014,vol. 281,p. 18 - 26
[2]Patent: US2008/300247,2008,A1 .Location in patent: Page/Page column 54
[3]Tetrahedron Letters,2008,vol. 49,p. 6348 - 6351
[4]Patent: WO2007/30361,2007,A2 .Location in patent: Page/Page column 43
[5]Patent: WO2007/30366,2007,A1 .Location in patent: Page/Page column 70-71
[6]Patent: WO2007/143456,2007,A2 .Location in patent: Page/Page column 125
[7]Journal of Medicinal Chemistry,2003,vol. 46,p. 691 - 701
[8]Organic Preparations and Procedures International,2002,vol. 34,p. 665 - 670
[9]Journal of Organic Chemistry,1994,vol. 59,p. 4285 - 4296
[10]Russian Journal of Organic Chemistry,1996,vol. 32,p. 394 - 400
[11]Russian Journal of Organic Chemistry,1996,vol. 32,p. 394 - 400
[12]Patent: EP3225618,2017,A1 .Location in patent: Paragraph 0921

2
[ 61161-83-9 ]
[ 144371-59-5 ]
1⁵,3⁵,5⁵,7⁵-tetra-tert-butyl-1²-(3-hydroxy-4-nitrobenzyloxycarbonylmethoxy)-3²,5²,7²-tri(ethoxycarbonylmethoxy)-1,3,5,7-tetra<1,3>benzenacyclooctaphane [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin transactions II,1993,p. 1963 - 1968
[2]Journal of the Chemical Society. Chemical communications,1992,p. 1287 - 1289

3
[ 61161-83-9 ]
5,11,17,23-tetra-tert-butyl-25,26,27,28-tetrakis(chlorocarbonylmethoxy)calix[4]arene [ No CAS ]
1⁵,3⁵,5⁵,7⁵-tetra-tert-butyl-1²,3²,5²,7²-tetra(3-hydroxy-4-nitrobenzyloxycarbonylmethoxy)-1,3,5,7-tetra<1,3>benzenacyclooctaphane [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin transactions II,1993,p. 1963 - 1968
[2]Journal of the Chemical Society. Chemical communications,1992,p. 1287 - 1289

4
[ 61161-83-9 ]
[ 704-13-2 ]

Reference： [1]Journal of Organic Chemistry,1994,vol. 59,p. 4285 - 4296

5
[ 61161-83-9 ]
[ 42533-61-9 ]

Reference： [1]Journal of the Chemical Society,1961,p. 221 - 222

6
[ 704-13-2 ]
[ 61161-83-9 ]

Reference： [1]Journal of the American Chemical Society,1997,vol. 119,p. 7676 - 7684
[2]Journal of Organic Chemistry,2017,vol. 82,p. 1796 - 1802
[3]Journal of the Chemical Society,1961,p. 221 - 222
[4]Bioorganic and Medicinal Chemistry Letters,1998,vol. 8,p. 2945 - 2948
[5]Journal of the American Chemical Society,2014,vol. 136,p. 3673 - 3679

7
[ 61161-83-9 ]
[ 26386-82-3 ]

Yield	Reaction Conditions	Operation in experiment
92%	With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 0 - 20℃; for 16h;	Carbon tetrabromide (4.05 g, 12.18 mmol, (0899) 2.0 equiv) was added in 4 portions to a solution of compound 40-2 (1.0 g, 6.09 mmol, 1.0 equiv) and triphenylphosphine (3.19 g, 12.18 mmol, 2.0 equiv) in dichloromethane (50 mL) at 0C. The resulting solution was stirred at room temperature for 16 hours. (0900) The reaction mixture was quenched by the addition of 1M HC1 (40 mL). The layers were separated and the aqueous layer was extracted with dichloromethane (2 × 20 mL). The combined organic layers were dried over sodium sulfate and evaporated under reduced pressure. The residue was purified on a Reveleris automated chromatography system (Sorbtech 40 g column), eluting with a gradient of 0 to 40% ethyl acetate in heptanes to give compound 40-3 (1.5 g, 92% yield) as a yellow solid (NRK-6-23).

Reference： [1]Patent: WO2021/127743,2021,A1 .Location in patent: Page/Page column 170-171
[2]Journal of the American Chemical Society,1997,vol. 119,p. 7676 - 7684
[3]Journal of Photochemistry and Photobiology A: Chemistry,2014,vol. 281,p. 18 - 26
[4]Journal of Medicinal Chemistry,1997,vol. 40,p. 1049 - 1062

8
[ 61161-83-9 ]
[ 188907-48-4 ]
[ 193957-49-2 ]

Reference： [1]Journal of the American Chemical Society,1997,vol. 119,p. 7676 - 7684

9
[ 36852-58-1 ]
[ 61161-83-9 ]

Reference： [1]Russian Journal of Organic Chemistry,1996,vol. 32,p. 394 - 400

10
[ 713-52-0 ]
[ 61161-83-9 ]

Reference： [1]Russian Journal of Organic Chemistry,1996,vol. 32,p. 394 - 400

11
[ 61161-83-9 ]
[ 108-24-7 ]
[ 182913-52-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1998,vol. 8,p. 2945 - 2948

12
4-nitro-3-oxy-benzaldehyde [ No CAS ]
[ 619-14-7 ]
[ 61161-83-9 ]

Reference： [1]Chemische Berichte,1929,vol. 62,p. 1182
Chemische Berichte,1933,vol. 66,p. 1761,1762

13
[ 704-13-2 ]
KOH-solution [ No CAS ]
[ 619-14-7 ]
[ 61161-83-9 ]

Reference： [1]Chemische Berichte,1929,vol. 62,p. 1182
Chemische Berichte,1933,vol. 66,p. 1761,1762

14
[ 61161-83-9 ]
[ 474010-01-0 ]
[ 502481-62-1 ]