[ CAS No. 113602-62-3 ]

Name: Methyl 3-hydroxy-1-methyl-1H-pyrrole-2-carboxylate
Brand: Ambeed
SKU: A144973
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Quality Control of [ 113602-62-3 ]

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COA GC NMR CNMR HPLC/UPLC LC-MS SDS

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SDS

Product Details of [ 113602-62-3 ]

CAS No. :	113602-62-3	MDL No. :	MFCD12924083
Formula :	C₇H₉NO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HJHSYAMEFMNNBD-UHFFFAOYSA-N
M.W :	155.15	Pubchem ID :	54697147
Synonyms :

Computed Properties of [ 113602-62-3 ]

TPSA :Topological Polar Surface Area	51.5	H-Bond Acceptor Count :	3
XLogP3 :	1	H-Bond Donor Count :	1
SP3 :	0.29	Rotatable Bond Count :	2

Safety of [ 113602-62-3 ]

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

Application In Synthesis of [ 113602-62-3 ]

Upstream synthesis route of [ 113602-62-3 ]
Downstream synthetic route of [ 113602-62-3 ]

[ 113602-62-3 ] Synthesis Path-Upstream 1~3

1
[ 80-63-7 ]
[ 5473-12-1 ]
[ 113602-62-3 ]

Reference： [1] Patent: US4748183, 1988, A
[2] Patent: EP249236, 1991, B1

2
[ 150713-74-9 ]
[ 113602-62-3 ]

Reference： [1] Tetrahedron, 1997, vol. 53, # 26, p. 8731 - 8738

3
[ 74-89-5 ]
[ 147624-81-5 ]
[ 113602-62-3 ]

Reference： [1] Tetrahedron, 1997, vol. 53, # 26, p. 8731 - 8738

[ 113602-62-3 ] Synthesis Path-Downstream 1~10

1
[ 74-89-5 ]
[ 147624-81-5 ]
[ 113602-62-3 ]

Reference： [1]Tetrahedron,1997,vol. 53,p. 8731 - 8738

2
[ 113602-62-3 ]
[ 150713-75-0 ]

Yield	Reaction Conditions	Operation in experiment
42%	With N-Bromosuccinimide; In tetrahydrofuran; methanol; at 0 - 20℃; for 4.0h;	General procedure: NBS (63 mg,0.35 mmol) was added to a solution of 1 (100 mg, 0.70 mmol) in 10 mL of THF - CH3OH (1:1, v/v) at 0 C and the mixture was stirred at roomtemperature. After 2 h, NBS (50.4 mg, 0.28 mmol) was added again to the mixture at 0 C, and it was stirred at room temperature for 2 h. The solvent wasremoved in vacuo, and water (15 mL) was added to the residue. The aqueouslayer was extracted three times with EtOAc (30 mL). The organic layers weregathered together, washed with water and brine, dried over MgSO4, filtered,and concentrated in vacuo. Et2O (10 mL) was added to the dry residue todiscard succinimide. The filtrate was concentrated in vacuo, and heptane(10 mL) was added to the dry residue to afford 4 as an orange powder (68.6 mg,44% yield).

Reference： [1]Tetrahedron,1997,vol. 53,p. 8731 - 8738
[2]Tetrahedron Letters,2017,vol. 58,p. 2537 - 2541

3
[ 113602-62-3 ]
methyl 5-chloro-3-hydroxy-1-methyl-1H-pyrrol-2-yl-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
7%	With sulfuryl dichloride; In dichloromethane; at 20℃; for 12.0h;	General procedure: SO2Cl2 (5 M in CH2Cl2, 1.42 mL, 7.09 mmol) was added to a solution of 2 (1 g, 6.44 mmol) in CH2Cl2 (5 mL), and the mixture was stirred during 1 hour at room temperature.The mixture was concentrated in vacuo and the dry residue was purifiedby column chromatography on silica gel (EtOAc - heptane, gradient 1:0 to 7:3,v/v) to afford 8 as a yellowish solid (640 mg, 52% yield).

Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 2537 - 2541

4
[ 113602-62-3 ]
methyl 4,5-dichloro-3-hydroxy-1-methyl-1H-pyrrol-2-yl-carboxylate [ No CAS ]
methyl 5-chloro-3-hydroxy-1-methyl-1H-pyrrol-2-yl-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1%; 52%	With sulfuryl dichloride; In dichloromethane; at 20℃; for 36.0h;	General procedure: SO2Cl2 (5 M in CH2Cl2, 1.42 mL, 7.09 mmol) was added to a solution of 2 (1 g, 6.44 mmol) in CH2Cl2 (5 mL), and the mixture was stirred during 1 hour at room temperature.The mixture was concentrated in vacuo and the dry residue was purifiedby column chromatography on silica gel (EtOAc - heptane, gradient 1:0 to 7:3,v/v) to afford 8 as a yellowish solid (640 mg, 52% yield).

Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 2537 - 2541

5
[ 113602-62-3 ]
methyl 4,5-dichloro-3-hydroxy-1-methyl-1H-pyrrol-2-yl-carboxylate [ No CAS ]
dimethyl 3',4-dichloro-4'-hydroxy-1,1'-dimethyl-3-oxo-2,3-dihydro-1H,1'H-[2,2'-bispyrrole]-2,5'-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
11%	With sulfuryl dichloride; zinc; In dichloromethane; at 20℃; for 24.0h;	General procedure: SO2Cl2 (5 M in CH2Cl2, 1.42 mL, 7.09 mmol) was added to a solution of 2 (1 g, 6.44 mmol) in CH2Cl2 (5 mL), and the mixture was stirred during 1 hour at room temperature.The mixture was concentrated in vacuo and the dry residue was purifiedby column chromatography on silica gel (EtOAc - heptane, gradient 1:0 to 7:3,v/v) to afford 8 as a yellowish solid (640 mg, 52% yield).

Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 2537 - 2541

6
[ 113602-62-3 ]
methyl 4-chloro-3-hydroxy-1-methyl-1H-pyrrol-2-yl-carboxylate [ No CAS ]
methyl 4,5-dichloro-3-hydroxy-1-methyl-1H-pyrrol-2-yl-carboxylate [ No CAS ]
methyl 5-chloro-3-hydroxy-1-methyl-1H-pyrrol-2-yl-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
2%; 4%; 9%	With sulfuryl dichloride; In dichloromethane; at 40℃; for 1.0h;Irradiation;	General procedure: SO2Cl2 (5 M in CH2Cl2, 1.42 mL, 7.09 mmol) was added to a solution of 2 (1 g, 6.44 mmol) in CH2Cl2 (5 mL), and the mixture was stirred during 1 hour at room temperature.The mixture was concentrated in vacuo and the dry residue was purifiedby column chromatography on silica gel (EtOAc - heptane, gradient 1:0 to 7:3,v/v) to afford 8 as a yellowish solid (640 mg, 52% yield).

Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 2537 - 2541

7
[ 113602-62-3 ]
[ 113602-65-6 ]

Yield	Reaction Conditions	Operation in experiment
	With bromine; In water; acetic acid;	EXAMPLE 105 Methyl 4,5-dibromo-3-hydroxy-1-methyl-1H-pyrrole-2-carboxylate Methyl 3-hydroxy-1-methyl-1H-pyrrole-2-carboxylate (5.0 g, 0.032 moles) is dissolved in acetic acid (50 mL) and stirred at room temperature while bromine (3.3 mL, 0.065 moles) is added dropwise. After 1 hour the mixture is stirred into water (250 mL) and the precipitate is collected by filtration, rinsed several times with water and dried to afford the pure product (6.9 g); mp 128-130 C.
	With bromine; In water; acetic acid;	EXAMPLE 105 Methyl 4,5-dibromo-3-hydroxy-1-methyl-1 H -pyrrole-2-carboxylate. Methyl 3-hydroxy-1-methyl-1 H -pyrrole-2-carboxylate (5.0 g, 0.032 moles) is dissolved in acetic acid (50 mL) and stirred at room temperature while bromine (3.3 mL, 0.065 moles) is added dropwise. After 1 hour the mixture is stirred into water (250 mL) and the precipitate is collected by filtration, rinsed several times with water and dried to afford the pure product (6.9 g); mp 128-130C.

Reference： [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 2186 - 2194
[2]Patent: US4748183,1988,A
[3]Patent: EP249236,1991,B1

8
[ 80-63-7 ]
[ 5473-12-1 ]
[ 113602-62-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium; In methanol; water; pentane;	EXAMPLE 101 Methyl 3-hydroxy-1-methyl-1H-pyrrole-2-carboxylate Methyl sarcosinate (14.5 g, 0.14 moles) is added dropwise to methyl alpha-chloroacrylate (16.9 g, 0.14 moles), stirred and cooled in an ice bath. After 15 minutes the mixture is dissolved in methanol (30 mL) and added dropwise to a solution of sodium (9.7 g, 0.42 moles) in methanol (125 mL) under argon. After 18 hours at room temperature, the mixture is stripped of methanol under reduced pressure. The residue is taken up in water (300 mL), acidified with H3 PO4, and extracted with ethyl acetate (5*100 mL). The combined extracts are dried over MgSO4, concentrated under reduced pressure and filtered through a short column of silica gel. The filtrate is stripped of solvent under reduced pressure, leaving the product (16.5 g) as an oil sufficiently pure for further use. An analytically pure sample was obtained by vacuum distillation; bp 61-64 C. (0.5 mm) followed by recrystallization of the distillate from n-pentane to afford the product as shiny white crystals; mp 44-46 C.
	With sodium; In methanol; water; pentane;	EXAMPLE 101 Methyl 3-hydroxy-1-methyl-1 H -pyrrole-2-carboxylate. Methyl sarcosinate (14.5 g, 0.14 moles) is added dropwise to methyl alpha-chloroacrylate (16.9 g, 0.14 moles), stirred and cooled in an ice bath. After 15 minutes the mixture is dissolved in methanol (30 mL) and added dropwise to a solution of sodium (9.7 g, 0.42 moles) in methanol (125 mL) under argon. After 18 hours at room temperature, the mixture is stripped of methanol under reduced pressure. The residue is taken up in water (300 mL), acidified with H3PO4, and extracted with ethyl acetate (5*100 mL). The combined extracts are dried over MgSO4, concentrated under reduced pressure and filtered through a short column of silica gel. The filtrate is stripped of solvent under reduced pressure, leaving the product (16.5 g) as an oil sufficiently pure for further use. An analytically pure sample was obtained by vacuum distillation; bp 61-64C (0.5 mm) followed by recrystallization of the distillate from n-pentane to afford the product as shiny white crystals; mp 44-46C.

Reference： [1]Patent: US4748183,1988,A
[2]Patent: EP249236,1991,B1

9
[ 113602-62-3 ]
[ 113589-14-3 ]

Reference： [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 2186 - 2194

10
[ 113602-62-3 ]
[ 113602-69-0 ]

Reference： [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 2186 - 2194

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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.
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P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
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P337 + P313	IF eye irritation persists: Get medical advice/attention.
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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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H242	Heating may cause a fire
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H311	Toxic in contact with skin
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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
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H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
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H336	May cause drowsiness or dizziness
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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. 113602-62-3 ]

Quality Control of [ 113602-62-3 ]

Related Doc. of [ 113602-62-3 ]

Product Details of [ 113602-62-3 ]

Computed Properties of [ 113602-62-3 ]

Safety of [ 113602-62-3 ]

Application In Synthesis of [ 113602-62-3 ]

[ 113602-62-3 ] Synthesis Path-Upstream 1~3

[ 113602-62-3 ] Synthesis Path-Downstream 1~10

Related Functional Groups of [ 113602-62-3 ]

Phenols

Esters

Alcohols

Related Parent Nucleus of [ 113602-62-3 ]

Aromatic Heterocycles

Pyrroles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

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Related Functional Groups of
[ 113602-62-3 ]

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[ 113602-62-3 ]