[ CAS No. 77242-30-9 ] {[proInfo.proName]}

Name: 77242-30-9|(2-Amino-5-nitrophenyl)methanol|97%
Brand: Ambeed
SKU: A395135
Price: 18.0 USD
Availability: InStock
Rating: 90 (30 reviews)

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

HazMat Fee +

There will be a HazMat fee per item when shipping a dangerous goods. The HazMat fee will be charged to your UPS/DHL/FedEx collect account or added to the invoice unless the package is shipped via Ground service. Ship by air in Excepted Quantity (each bottle), which is up to 1g/1mL for class 6.1 packing group I or II, and up to 25g/25ml for all other HazMat items.

Type	HazMat fee for 500 gram (Estimated)
Excepted Quantity	USD 0.00
Limited Quantity	USD 15-60
Inaccessible (Haz class 6.1), Domestic	USD 80+
Inaccessible (Haz class 6.1), International	USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic	USD 100+
Accessible (Haz class 3, 4, 5 or 8), International	USD 200+

2D 3D

Structure of 77242-30-9 * Storage: {[proInfo.prStorage]}

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 110K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 77242-30-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 77242-30-9 ]

SDS Specification

Alternatived Products of [ 77242-30-9 ]

Product Details of [ 77242-30-9 ]

CAS No. :	77242-30-9	MDL No. :	MFCD09834918
Formula :	C₇H₈N₂O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XEALBFKUNCXFTO-UHFFFAOYSA-N
M.W :	168.15	Pubchem ID :	3018706
Synonyms :

Calculated chemistry of [ 77242-30-9 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	45.8
TPSA :	92.07 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) :	-6.8 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.93
Log Po/w (XLOGP3) :	0.74
Log Po/w (WLOGP) :	0.53
Log Po/w (MLOGP) :	0.59
Log Po/w (SILICOS-IT) :	-1.19
Consensus Log Po/w :	0.32

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.59
Solubility :	4.35 mg/ml ; 0.0259 mol/l
Class :	Very soluble
Log S (Ali) :	-2.25
Solubility :	0.94 mg/ml ; 0.00559 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.24
Solubility :	9.61 mg/ml ; 0.0571 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	3.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.69

Safety of [ 77242-30-9 ]

Signal Word:	Danger	Class:	9
Precautionary Statements:	P501-P273-P260-P270-P264-P280-P391-P314-P337+P313-P305+P351+P338-P301+P312+P330	UN#:	3077
Hazard Statements:	H302-H319-H372-H410	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 77242-30-9 ]

* 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 [ 77242-30-9 ]
Downstream synthetic route of [ 77242-30-9 ]

[ 77242-30-9 ] Synthesis Path-Upstream 1~8

1
[ 616-79-5 ]
[ 77242-30-9 ]

Yield	Reaction Conditions	Operation in experiment
98%	With borane-THF In tetrahydrofuran at 0 - 30℃; for 23 h; Inert atmosphere	5.1.123 6,7-Didehydro-17-methyl-6'-nitroquinolino[2',3':6,7]morphinan-3,14β-diol (29b) Compound 29b was prepared from compound 23b according to the procedure used to prepare compound 24a. Yield, 92percent; a yellow oil. IR (neat): 3365, 2918, 1612, 1528, 1345, 1239, 1051, 755 cm^-1. ¹H NMR (400 MHz, CDCl₃) δ: 1.27-1.35 (1H, m), 2.11 (1H, dt, J = 5.3, 12.8 Hz), 2.25 (1H, dt, J = 2.8, 12.0 Hz), 2.36-2.48 (1H, m), 2.43 (3H, s), 2.90-3.00 (2H, m), 2.96 (1H, d, J = 18.0 Hz), 3.10 (1H, d, J = 18.0 Hz), 3.27 (1H, d, J = 18.0 Hz), 3.52 (1H, d, J = 17.6 Hz), 3.65 (1H, d, J = 17.6 Hz), 6.63 (1H, dd, J = 2.4, 8.4 Hz), 6.93 (1H, d, J = 2.4 Hz), 7.01 (1H, d, J = 8.4 Hz), 7.34 (1H, d, J = 9.6 Hz), 7.61 (1H, dd, J = 2.0, 9.6 Hz), 7.67 (1H, s), 8.29 (1H, d, J = 2.0 Hz), two protons (OH) were not observed. ¹³C NMR (100 MHz, CDCl₃) δ: 23.9, 35.8, 36.1, 39.1, 40.4, 42.9, 45.3, 61.4, 69.2, 112.6, 115.0, 121.7, 123.3, 125.6, 127.0, 128.3, 129.2, 131.0, 137.2, 140.3, 144.4, 147.0, 155.2, 162.0. HRMS (ESI) Calcd for C₂₄H₂₄N₃O₄ [M+H]⁺: 418.1767. Found: 418.1748.
98%	Stage #1: With borane-THF In tetrahydrofuran for 1 h; Reflux Stage #2: With hydrogenchloride In ethyl acetate	5-Nitroanthranilic acid (5.0 g, 27.45 mmol) is dissolved in THF (100 mL) and 1 M borane/THF complex (55 mL, 54.9 mmol) is added. The mixture is heated to reflux for 1 h. Analysis by TLC indicates complete consumption of starting material. The volatiles are removed in vacuo and the residue is dissolved in ethyl acetate (150 mL). The organic phase is washed with 1 N HCl, saturated NaHCO₃, and saturated NaCl. Evaporation provides 10.8 g (98percent) of a dark brown oil product which is used directly in the next reaction; ¹H-NMR (500 MHz, CDCl₃); δ 4.61 (s, 2 H), 6.62 (s, 1 H), 8.01 (m, 2 H).
73%	With borane-THF In tetrahydrofuran at 0 - 23℃;	EXAMPLE A1 (2-Amino-5-nitro-phenyl)-methanol CAS-No. [77242-30-9] To a solution of commercially available 5-nitroanthranilic acid (28.37 g, 156 mmol; HPLC 1.428 min) in tetrahydrofuran (900 mL) at 0° C. was cannulated a 1 M sol. of borane.tetrahydrofuran complex (500 mL, 500 mmol) [gas[evolution], but almost no exothermic reaction]. The cooling bath was removed and the mixture was stirred at 23° C. for 16 h. Then water (142 mL) was added [strong gas evolution upon addition of the first ca. 30[mL]] followed by 1 M HCl (71 mL) and the resulting yellow mixture was stirred at 23° C. for 1 h. Then a 1 M solution of potassium carbonate in water (35 mL) was added and the entire reaction mixture was concentrated in vacuum on a rotary evaporator to remove all tetrahydrofuran, the resulting yellow precipitate was diluted with ice water (-100 mL), the precipitate was filtered off, washed with ice water and dried in vacuum to give a yellow solid (19.0 g, 73percent; HPLC 0.998 min 100percent). ¹H NMR (300 MHz, DMSO-d₆) δ=4.39 (d, ³J(H,H)=5.4 Hz, 2H, C₂OH), 5.32 (t, ³J(H,H)=5.4 Hz, 1H, O), 6.46 (bs, 2H, N₂), 6.65 (d, ⁴J(H,H)=9.0 Hz, 1H, H3), 7.89 (dd, ^4,5J(H,H)=8.7, 2,7 Hz, 1H, H4), 8.05 (d, ⁵J(H,H)=2.7 Hz, H6); MS (ISN) m/e=167.1 [(M-H)^-].

Reference： [1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 19, p. 5810 - 5831
[2] Patent: US2014/121415, 2014, A1, . Location in patent: Paragraph 0050
[3] Patent: US2010/63037, 2010, A1, . Location in patent: Page/Page column 20
[4] Journal of Organic Chemistry, 2010, vol. 75, # 20, p. 7033 - 7036
[5] Patent: WO2015/164308, 2015, A1,

2
[ 3816-62-4 ]
[ 77242-30-9 ]

Reference： [1] Synlett, 2011, # 6, p. 844 - 848
[2] Patent: WO2015/164308, 2015, A1, . Location in patent: Page/Page column 97; 98

3
[ 4693-02-1 ]
[ 77242-30-9 ]

Reference： [1] Patent: US2014/121414, 2014, A1, . Location in patent: Paragraph 0045

4
[ 56008-61-8 ]
[ 77242-30-9 ]

Reference： [1] Patent: US4268510, 1981, A,

5
[ 83326-80-1 ]
[ 77242-30-9 ]

Reference： [1] Bulletin de la Societe Chimique de France, 1933, vol. <4> 53, p. 330,332

6
[ 118-48-9 ]
[ 77242-30-9 ]

Reference： [1] Patent: US2014/121414, 2014, A1,

7
[ 91538-60-2 ]
[ 77242-30-9 ]
[ 616-79-5 ]

Reference： [1] Journal of the Indian Chemical Society, 1931, vol. 8, p. 59,65

8
[ 5344-90-1 ]
[ 77242-30-9 ]

Reference： [1] Bulletin de la Societe Chimique de France, 1933, vol. <4> 53, p. 330,332

[ 77242-30-9 ] Synthesis Path-Downstream 1~45

1
[ 91538-60-2 ]
[ 77242-30-9 ]
[ 616-79-5 ]

Reference： [1]Journal of the Indian Chemical Society,1931,vol. 8,p. 59,65

2
[ 77242-30-9 ]
[ 39224-61-8 ]

Reference： [1]Bulletin de la Societe Chimique de France,1933,vol. <4> 53,p. 330,332

3
[ 77242-30-9 ]
[ 73793-80-3 ]

Reference： [1]Bulletin de la Societe Chimique de France,1933,vol. <4> 53,p. 330,332

4
[ 83326-80-1 ]
[ 77242-30-9 ]

Reference： [1]Bulletin de la Societe Chimique de France,1933,vol. <4> 53,p. 330,332

5
[ 77242-30-9 ]
[ 108-24-7 ]
[ 861222-14-2 ]

Reference： [1]Journal of the Indian Chemical Society,1931,vol. 8,p. 59,65

6
[ 5344-90-1 ]
[ 77242-30-9 ]

Reference： [1]Bulletin de la Societe Chimique de France,1933,vol. <4> 53,p. 330,332

Yield	Reaction Conditions	Operation in experiment
		a) 2-Amino-5-nitrobenzyl alcohol To a suspension of 676 mg (17.9 mmol) of lithium aluminum hydride in 35 ml of dry tetrahydrofuran was dropwise added under stirring and chilling with ice (below 10 C.) a solution of 3.5 g (17.9 mmol) of methyl 5-nitroanthranylate in 50 ml of dry tetrahydrofuran for 15 min. The mixture was further stirred for 30 min. To the solution was dropwise added saturated aqueous sodium sulfate. Insolubles were removed by filtration. The filtrate was then placed under reduced pressure to distill off the solvent. There was obtained 2.76 g of the desired compound as a yellow crystalline product. 1 H--NMR (CDCl3):delta 4.57 (s, 2H), 0.68 (d, 1H, J=9Hz), 7.8-8.1 (m, 2H)

8
[ 56008-61-8 ]
[ 77242-30-9 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium borohydrid; In ethanol;	The 2-amino-5-nitrobenzyl alcohol used as the starting material in the preparation of this compound may be obtained as follows: A suspension of 2-amino-5-nitrobenzaldehyde (6.0 g.) in ethanol (250 ml.) was stirred at ambient temperature while sodium borohydride (1.6 g.) was added in small portions, and the reaction mixture was stirred for 1 hour. The reaction mixture was made acid with 2 N hydrochloric acid to destroy the excess of sodium borohydride, and then basified to pH 8 to 9 with solid sodium carbonate and extracted with diethyl ether (3*200 ml.). The extracts were combined and dried, the solvent was evaporated and the residue was crystallized from water (about 200 ml.) to give the required 2-amino-5-nitrobenzyl alcohol, m.p. 141-142 C.;

Reference： [1]Patent: US4268510,1981,A

9
[ 77242-30-9 ]
[ 530-62-1 ]
[ 94107-60-5 ]

Yield	Reaction Conditions	Operation in experiment
	In 1,4-dioxane; at 20℃;	Example 4 Preparation of (R)-3-(l-methyl-2-oxo-2,4-dihydro-lH-benzo[d][l,3]oxazin-6-yl)-2-oxooxazolidine-5-carboxamideStep 1: Preparation of 6-nitro-lH-benzo[d][l,3]oxazin-2(4H)-one.; 1 , 1 '-Carbonyldiimidazole (2.78 g, 17.02 mmol) is added in one portion to a suspension of <strong>[77242-30-9](2-amino-5-nitro-phenyl)-methanol</strong> (2.60 g, 15.4 mmol) in dioxane (20 mL) and the mixture stirred overnight at room temperature. The reaction is quenched with 0.1 N HCl (25 mL) followed by extraction with ethyl acetate (50 mL X 3). The combined organic phases are washed with water (50 mL), sat. Na2CO3 (50 mL), brine (50 mL), dried (Na2SO4) and concentrated under reduced pressure. The residue is purified by flash column chromatography (ethyl acetate) to obtain the title compound.

Reference： [1]Patent: WO2007/93904,2007,A1 .Location in patent: Page/Page column 24

10
[ 616-79-5 ]
[ 77242-30-9 ]

Yield	Reaction Conditions	Operation in experiment
98%	With borane-THF; In tetrahydrofuran; at 0 - 30℃; for 23.0h;Inert atmosphere;	5.1.123 6,7-Didehydro-17-methyl-6'-nitroquinolino[2',3':6,7]morphinan-3,14beta-diol (29b) Compound 29b was prepared from compound 23b according to the procedure used to prepare compound 24a. Yield, 92%; a yellow oil. IR (neat): 3365, 2918, 1612, 1528, 1345, 1239, 1051, 755 cm-1. 1H NMR (400 MHz, CDCl3) delta: 1.27-1.35 (1H, m), 2.11 (1H, dt, J = 5.3, 12.8 Hz), 2.25 (1H, dt, J = 2.8, 12.0 Hz), 2.36-2.48 (1H, m), 2.43 (3H, s), 2.90-3.00 (2H, m), 2.96 (1H, d, J = 18.0 Hz), 3.10 (1H, d, J = 18.0 Hz), 3.27 (1H, d, J = 18.0 Hz), 3.52 (1H, d, J = 17.6 Hz), 3.65 (1H, d, J = 17.6 Hz), 6.63 (1H, dd, J = 2.4, 8.4 Hz), 6.93 (1H, d, J = 2.4 Hz), 7.01 (1H, d, J = 8.4 Hz), 7.34 (1H, d, J = 9.6 Hz), 7.61 (1H, dd, J = 2.0, 9.6 Hz), 7.67 (1H, s), 8.29 (1H, d, J = 2.0 Hz), two protons (OH) were not observed. 13C NMR (100 MHz, CDCl3) delta: 23.9, 35.8, 36.1, 39.1, 40.4, 42.9, 45.3, 61.4, 69.2, 112.6, 115.0, 121.7, 123.3, 125.6, 127.0, 128.3, 129.2, 131.0, 137.2, 140.3, 144.4, 147.0, 155.2, 162.0. HRMS (ESI) Calcd for C24H24N3O4 [M+H]+: 418.1767. Found: 418.1748.
98%		5-Nitroanthranilic acid (5.0 g, 27.45 mmol) is dissolved in THF (100 mL) and 1 M borane/THF complex (55 mL, 54.9 mmol) is added. The mixture is heated to reflux for 1 h. Analysis by TLC indicates complete consumption of starting material. The volatiles are removed in vacuo and the residue is dissolved in ethyl acetate (150 mL). The organic phase is washed with 1 N HCl, saturated NaHCO3, and saturated NaCl. Evaporation provides 10.8 g (98%) of a dark brown oil product which is used directly in the next reaction; 1H-NMR (500 MHz, CDCl3); delta 4.61 (s, 2 H), 6.62 (s, 1 H), 8.01 (m, 2 H).
73%	With borane-THF; In tetrahydrofuran; at 0 - 23℃;	EXAMPLE A1 (2-Amino-5-nitro-phenyl)-methanol CAS-No. [77242-30-9] To a solution of commercially available 5-nitroanthranilic acid (28.37 g, 156 mmol; HPLC 1.428 min) in tetrahydrofuran (900 mL) at 0 C. was cannulated a 1 M sol. of borane.tetrahydrofuran complex (500 mL, 500 mmol) [gas[evolution], but almost no exothermic reaction]. The cooling bath was removed and the mixture was stirred at 23 C. for 16 h. Then water (142 mL) was added [strong gas evolution upon addition of the first ca. 30[mL]] followed by 1 M HCl (71 mL) and the resulting yellow mixture was stirred at 23 C. for 1 h. Then a 1 M solution of potassium carbonate in water (35 mL) was added and the entire reaction mixture was concentrated in vacuum on a rotary evaporator to remove all tetrahydrofuran, the resulting yellow precipitate was diluted with ice water (-100 mL), the precipitate was filtered off, washed with ice water and dried in vacuum to give a yellow solid (19.0 g, 73%; HPLC 0.998 min 100%). 1H NMR (300 MHz, DMSO-d6) delta=4.39 (d, 3J(H,H)=5.4 Hz, 2H, C2OH), 5.32 (t, 3J(H,H)=5.4 Hz, 1H, O), 6.46 (bs, 2H, N2), 6.65 (d, 4J(H,H)=9.0 Hz, 1H, H3), 7.89 (dd, 4,5J(H,H)=8.7, 2,7 Hz, 1H, H4), 8.05 (d, 5J(H,H)=2.7 Hz, H6); MS (ISN) m/e=167.1 [(M-H)-].

Reference： [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 5810 - 5831
[2]Patent: US2014/121415,2014,A1 .Location in patent: Paragraph 0050
[3]Patent: US2010/63037,2010,A1 .Location in patent: Page/Page column 20
[4]Journal of Organic Chemistry,2010,vol. 75,p. 7033 - 7036
[5]Patent: WO2015/164308,2015,A1

11
[ 77242-30-9 ]
[ 18162-48-6 ]
[ 1214247-96-7 ]

Yield	Reaction Conditions	Operation in experiment
99%	With 1H-imidazole; In N,N-dimethyl-formamide; at 23℃;	EXAMPLE B1 2-(tert-Butyl-dimethyl-silanyloxymethyl)-4-nitro-phenylamine To a mixture of <strong>[77242-30-9](2-amino-5-nitro-phenyl)-methanol</strong> (Example A1) (22.7 g, 135 mmol; HPLC 0.998 min) and imidazole (28.5 g, 419 mmol) in N,N-dimethylformamide (68 mL) at 0 C. was added tert-butyl(chloro)dimethylsilane (33.6 g, 223 mmol) and the mixture was stirred and allowed to reach 23 C. overnight. Poured onto water (plus little NaH2PO4-buffer, pH 4), extracted twice with tert-butylmethyl ether, washed with sat. NaCl-sol., dried over sodium sulfate, filtered off and evaporated to give a brown liquid, which was purified by a silica gel column chromatography with heptane/ethyl acetate 1:4 to give a yellow solid (38.02 g, 99%; HPLC 3.200 min 100%). 1H NMR (300 MHz, CDCl3) delta=0.10 (s, 6H, 2*C3), 0.92 (s, 9H, C(C3)3), 4.72 (s, 2H, C2), 5.03 (bs, 2H, N2), 6.62 (d, 4J(H,H)=9.0 Hz, 1H, H3), 7.97 (d, 5J(H,H)=2.7 Hz, H6), 8.03 (dd, 4,5J(H,H)=8.7, 2,7 Hz, 1H, H4); MS (ISN) m/e=281.2 [(M-H)-].

Reference： [1]Patent: US2010/63037,2010,A1 .Location in patent: Page/Page column 20

12
[ 77242-30-9 ]
[ 100-52-7 ]
C₁₄H₁₂N₂O₃ [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 7033 - 7036

13
[ 3816-62-4 ]
[ 77242-30-9 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium borohydride; In tetrahydrofuran; at 0 - 10℃; for 21h;	Step 2: (2-amino-S -nitrophenyl)methanolTo a solution of methyl 2-amino-S-nitrobenzoate (14 g, 71.4 mmol) in THF (200 mL) was added LiBH4 (2.35 g, 112 mmol) at 0C and the reaction mixture was sitrred at 10C for S h. Another batch of LiBH4 (2 g, 88 mmol) was added at 0C. The mixture was further stirred at 10 C for 16 h. TLC (PE/EtOAc=2/1) showed the reaction was complete. The reaction was quenched with sat. aq. NH4C1 (55 mL) and extracted with EtOAc (150 mL x 3). The combined organic layers werewashed with brine (100 x 3 mL), dried over Na2SO4, filtered and concentrated to give the title compound, which was used for the next step without further purification.MS (ESI) m/z 169.0 (M+H).

Reference： [1]Synlett,2011,p. 844 - 848
[2]Patent: WO2015/164308,2015,A1 .Location in patent: Page/Page column 97; 98

14
[ 6587-24-2 ]
[ 77242-30-9 ]
[ 129490-16-0 ]

Reference： [1]Synlett,2011,p. 844 - 848

15
[ 6587-24-2 ]
[ 77242-30-9 ]
[ 67199-66-0 ]

Reference： [1]Synlett,2011,p. 844 - 848

16
[ 120-07-0 ]
[ 77242-30-9 ]
[ 1371596-68-7 ]