[ CAS No. 42087-81-0 ] {[proInfo.proName]}

Name: 42087-81-0|Methyl 3-chloro-2-nitrobenzoate|98%
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Quality Control of [ 42087-81-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 42087-81-0 ]

SDS Specification

Alternatived Products of [ 42087-81-0 ]

Product Details of [ 42087-81-0 ]

CAS No. :	42087-81-0	MDL No. :	MFCD04038813
Formula :	C₈H₆ClNO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VTWUVGLVDQXCJO-UHFFFAOYSA-N
M.W :	215.59	Pubchem ID :	12187125
Synonyms :

Calculated chemistry of [ 42087-81-0 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.12
Num. rotatable bonds :	3
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	51.55
TPSA :	72.12 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.99 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.51
Log Po/w (XLOGP3) :	2.29
Log Po/w (WLOGP) :	2.03
Log Po/w (MLOGP) :	1.43
Log Po/w (SILICOS-IT) :	0.22
Consensus Log Po/w :	1.5

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.74
Solubility :	0.394 mg/ml ; 0.00183 mol/l
Class :	Soluble
Log S (Ali) :	-3.44
Solubility :	0.0779 mg/ml ; 0.000361 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.48
Solubility :	0.717 mg/ml ; 0.00333 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.05

Safety of [ 42087-81-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P301+P312-P302+P352-P304+P340-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 42087-81-0 ]

* 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 [ 42087-81-0 ]
Downstream synthetic route of [ 42087-81-0 ]

[ 42087-81-0 ] Synthesis Path-Upstream 1~4

1
[ 42087-81-0 ]
[ 77820-58-7 ]

Yield	Reaction Conditions	Operation in experiment
79%	With iron; acetic acid In ethanol at 20℃; for 2 h; Heating / reflux	Methyl 2-amino-3-chlorobenzoate. Iron powder (1.94 g, 34.8 mmol) was added to the solution of methyl 3-chloro-2-nitrobenzoate (2.5 g, 111.6 mmol) in EtOH/HOAc (100 mL/100 mL) at room temperature, and then the suspension was refluxed under N₂for 2 hrs. After cooling down to room temperature, partial of the solvents was removed on rotary vacuum, the resulting residue was partitioned between H₂O/EtOAc (200 mL/300 mL). The separated organic phase was washed with aqueous NaOH (1N, 50 mL), brine (50 mL), dried over MgSO₄, and concentrated on rotary vacuum to afford the expected product as a tan oil (1.7 g, 79percent yield) which became wax type solid standing on bench. The crude product was pure enough to be used in next step without further purification; ¹H NMR (400 MHz, CDCl₃) δ ppm 3.86 (s, 3H), 6.25 (s, 2H), 6.57 (t, J=7.93 Hz, 1H), 7.39 (dd, J=7.81, 1.51 Hz, 1H), 7.79 (dd, J=8.06, 1.51 Hz, 1H); Mass spec. 185.95 (MH⁺), Calc. for C₈H₈ClNO₂185.02.
79%	Stage #1: With iron; acetic acid In ethanol at 20℃; for 2 h; Heating / reflux Stage #2: With sodium hydroxide In water; ethyl acetate	Methyl 2-amino-3-chlorobenzoate; Iron powder (1.94 g, 34.8 mmol) was added to the solution of methyl 3-chloro-2-nitrobenzoate (2.5 g, 11.6 mmol) in EtOH/HOAc (100 mL/100 mL) at room temperature, and then the suspension was refluxed under N₂for 2 hrs. After cooling down to room temperature, partial of the solvents was removed on rotary vacuum, the resulting residue was partitioned between H₂O/EtOAc (200 mL/300 mL). The separated organic phase was washed with aqueous NaOH (1N, 50 mL), brine (50 mL), dried over MgSO₄, and concentrated on rotary vacuum to afford the expected product as a tan oil (1.7 g, 79percent yield) which became wax type solid standing on bench. The crude product was pure enough to be used in next step without further purification; ¹H NMR (400 MHz, CDCl₃) δ ppm 3.86 (s, 3 H), 6.25 (s, 2 H), 6.57 (t, J=7.93 Hz, 1 H), 7.39 (dd, J=7.81, 1.51 Hz, 1 H), 7.79 (dd, J=8.06, 1.51 Hz, 1 H); Mass spec. 185.95 (MH⁺), Calc. for C₈H₈ClNO₂185.02.

Reference： [1] Patent: US2006/94707, 2006, A1, . Location in patent: Page/Page column 64
[2] Patent: US2007/259850, 2007, A1, . Location in patent: Page/Page column 99
[3] Bioorganic and Medicinal Chemistry, 1999, vol. 7, # 8, p. 1743 - 1754

2
[ 42087-81-0 ]
[ 22233-52-9 ]

Yield	Reaction Conditions	Operation in experiment
94%	With diisobutylaluminium hydride In dichloromethane at -78℃; for 0.25 h;	Example 116; This example concerns the synthesis of Aldehyde 12: To a stirred solution of 81 (2.91 g, 13.5 mmol) and CH₂Cl₂ (134 mL) at -78°C was added DIBAL-H (16.0 mL, 16.0 mmol, 1.0 M in CH₂Cl₂) over 15 min. After an additional 10 min, the reaction was quenched with MeOH (1.0 mL) and warmed to rt. Next, a solution of aq. sodium potassium tartrate (190 mL, 10percent w/v) was added and vigorously stirred. After 4 h, the reaction mixture was diluted with CH₂Cl₂ (50 mL) and washed with H₂O (3 x 100 mL) and sat. aq. NaCl (100 mL). The dried extract (MgSO₄) was concentrated in vacuo and purified by recrystallization with EtOAc / Hexanes (1 :3) to give known aldehyde 12 (2.32 g, 12.7 mmol, 94percent) as a white crystalline solid. ¹H NMR (400 MHz, CDCl₃) δ 9.90 (s, IH), 7.92 (dd, J= 1.4, 7.7 Hz, IH), 7.80 (dd, J= 1.4, 8.1 Hz, IH), 7.67 (dd, J= 7.7, 8.1 Hz, IH); ¹³C NMR (100 MHz, CDCl₃) δ 186.0, 148.1 136.0, 131.7, 130.1, 128.5, 126.6.

Reference： [1] Journal of Organic Chemistry, 2007, vol. 72, # 26, p. 9857 - 9865
[2] Patent: WO2008/156656, 2008, A2, . Location in patent: Page/Page column 44; 181
[3] Tetrahedron, 2008, vol. 64, # 5, p. 856 - 865

3
[ 42087-81-0 ]
[ 90407-11-7 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 15, p. 5031 - 5034

4
[ 2365-48-2 ]
[ 42087-81-0 ]
[ 33851-23-9 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 7, p. 2162 - 2177
[2] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 15, p. 5031 - 5034

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Yield	Reaction Conditions	Operation in experiment
74%	In methanol; hexanes; acetonitrile; at 0℃; for 0.5h;	Methyl 3-chloro-2-nitrobenzoate. To 3-chloro-2-nitrobenzoic acid (3.15 g, 15.6 mmol) in methanol/acetonitrile (20 mL/20 mL) was dropwise added TMSCHN2 (2N in hexanes, 11.7 mL, and 23.4 mmol) at 0 C. under N2 over 10 min until the yellow color persist. The mixture was continued stirring for 20 min, followed by dropwise addition of HOAc until the yellow color disappeared to kill excessive TMSCHN2. Partial of the solvent was removed on rotary vacuum, the product came out solution as a light yellow solid, which was filtered and washed with Et2O (2×2 mL) to afford the expected product as a white solid (2.5 g, 74% yield); 1H NMR (400 MHz, CDCl3) delta ppm 3.91 (s, 3H), 7.51 (t, J=8.06 Hz, 1H), 7.70 (dd, J=8.06, 1.26 Hz, 1H), 7.97 (dd, J=7.81, 1.26 Hz, 1H); Mass spec. 216.02 (MH+), Calc. for C8H6ClNO4 215.00.
74%	In methanol; hexanes; acetonitrile; at 0℃; for 0.5h;	Methyl 3-chloro-2-nitrobenzoate; To 3-chloro-2-nitrobenzoic acid (3.15 g, 15.6 mmol) in methanol/acetonitrile (20 mL/20 mL) was dropwise added TMSCHN2 (2N in hexanes, 11.7 mL, and 23.4 mmol) at 0 C. under N2 over 10 min until the yellow color persist. The mixture was continued stirring for 20 min, followed by dropwise addition of HOAc until the yellow color disappeared to kill excessive TMSCHN2. Partial of the solvent was removed on rotary vacuum, the product came out solution as a light yellow solid, which was filtered and washed with Et2O (2×2 mL) to afford the expected product as a white solid(2.5 g, 74% yield); 1H NMR (400 MHz, CDCl3) delta ppm 3.91 (s, 3 H), 7.51 (t, J=8.06 Hz, 1 H), 7.70 (dd, J=8.06, 1.26 Hz, 1 H), 7.97 (dd, J=7.81, 1.26 Hz, 1 H); Mass spec. 216.02 (MH+), Calc. for C8H6ClNO4 215.00.

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

Yield	Reaction Conditions	Operation in experiment
79%	With iron; acetic acid; In ethanol; at 20℃; for 2h;Heating / reflux;	Methyl 2-amino-3-chlorobenzoate. Iron powder (1.94 g, 34.8 mmol) was added to the solution of <strong>[42087-81-0]methyl 3-chloro-2-nitrobenzoate</strong> (2.5 g, 111.6 mmol) in EtOH/HOAc (100 mL/100 mL) at room temperature, and then the suspension was refluxed under N2 for 2 hrs. After cooling down to room temperature, partial of the solvents was removed on rotary vacuum, the resulting residue was partitioned between H2O/EtOAc (200 mL/300 mL). The separated organic phase was washed with aqueous NaOH (1N, 50 mL), brine (50 mL), dried over MgSO4, and concentrated on rotary vacuum to afford the expected product as a tan oil (1.7 g, 79% yield) which became wax type solid standing on bench. The crude product was pure enough to be used in next step without further purification; 1H NMR (400 MHz, CDCl3) delta ppm 3.86 (s, 3H), 6.25 (s, 2H), 6.57 (t, J=7.93 Hz, 1H), 7.39 (dd, J=7.81, 1.51 Hz, 1H), 7.79 (dd, J=8.06, 1.51 Hz, 1H); Mass spec. 185.95 (MH+), Calc. for C8H8ClNO2 185.02.
79%		Methyl 2-amino-3-chlorobenzoate; Iron powder (1.94 g, 34.8 mmol) was added to the solution of <strong>[42087-81-0]methyl 3-chloro-2-nitrobenzoate</strong> (2.5 g, 11.6 mmol) in EtOH/HOAc (100 mL/100 mL) at room temperature, and then the suspension was refluxed under N2 for 2 hrs. After cooling down to room temperature, partial of the solvents was removed on rotary vacuum, the resulting residue was partitioned between H2O/EtOAc (200 mL/300 mL). The separated organic phase was washed with aqueous NaOH (1N, 50 mL), brine (50 mL), dried over MgSO4, and concentrated on rotary vacuum to afford the expected product as a tan oil (1.7 g, 79% yield) which became wax type solid standing on bench. The crude product was pure enough to be used in next step without further purification; 1H NMR (400 MHz, CDCl3) delta ppm 3.86 (s, 3 H), 6.25 (s, 2 H), 6.57 (t, J=7.93 Hz, 1 H), 7.39 (dd, J=7.81, 1.51 Hz, 1 H), 7.79 (dd, J=8.06, 1.51 Hz, 1 H); Mass spec. 185.95 (MH+), Calc. for C8H8ClNO2 185.02.

[ CAS No. 42087-81-0 ] {[proInfo.proName]}

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[ 42087-81-0 ] Synthesis Path-Upstream 1~4

[ 42087-81-0 ] Synthesis Path-Downstream 1~74

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