[ CAS No. 74598-03-1 ] {[proInfo.proName]}

Name: 74598-03-1|5-Chloro-4-methylthiophene carboxylic acid|98%
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SKU: A1243530
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3d Animation Molecule Structure of 74598-03-1

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Quality Control of [ 74598-03-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 74598-03-1 ]

SDS Specification

Alternatived Products of [ 74598-03-1 ]

Product Details of [ 74598-03-1 ]

CAS No. :	74598-03-1	MDL No. :	MFCD01830083
Formula :	C₆H₅ClO₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DFFITKIQYSTVPF-UHFFFAOYSA-N
M.W :	176.62	Pubchem ID :	12605957
Synonyms :

Calculated chemistry of [ 74598-03-1 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.17
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	41.25
TPSA :	65.54 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) :	-5.4 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.61
Log Po/w (XLOGP3) :	2.79
Log Po/w (WLOGP) :	2.41
Log Po/w (MLOGP) :	1.52
Log Po/w (SILICOS-IT) :	2.99
Consensus Log Po/w :	2.26

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.85

Water Solubility

Log S (ESOL) :	-3.0
Solubility :	0.178 mg/ml ; 0.00101 mol/l
Class :	Soluble
Log S (Ali) :	-3.82
Solubility :	0.0266 mg/ml ; 0.00015 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.04
Solubility :	1.61 mg/ml ; 0.0091 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.33

Safety of [ 74598-03-1 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P330-P362-P403+P233-P501	UN#:
Hazard Statements:	H302-H312-H332	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 74598-03-1 ]

* 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.

Downstream synthetic route of [ 74598-03-1 ]

[ 74598-03-1 ] Synthesis Path-Downstream 1~22

1
[ 14345-97-2 ]
[ 124-38-9 ]
[ 74598-03-1 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1980,p. 1029 - 1037

2
[ 74598-03-1 ]
[ 91505-29-2 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride

Reference： [1]Clarke, Kenneth; Fox, William Richard; Scrowston, Richard M. [Journal of the Chemical Society. Perkin transactions I, 1980, p. 1029 - 1037]

3
[ 74598-03-1 ]
5-Chlor-4-methyl-thiophen-2-carbonsaeureazid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium azide; chloroformic acid ethyl ester; triethylamine 1) acetone, 5 deg C, 2) H₂O, 0 - 10 deg C, 1h; Yield given. Multistep reaction;

Reference： [1]Stanetty, Peter; Puschautz, Erhard [Monatshefte fur Chemie, 1989, vol. 120, p. 65 - 72]

4
[ 74598-03-1 ]
[ 74598-04-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: SOCl₂

Reference： [1]Clarke, Kenneth; Fox, William Richard; Scrowston, Richard M. [Journal of the Chemical Society. Perkin transactions I, 1980, p. 1029 - 1037]

5
[ 74598-03-1 ]
[ 74598-12-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1: SOCl₂ 3: 94 percent / bromine / CCl₄ / 5 h / Heating; Irradiation 4: 90 percent / H₂SO₄ / 4 h 5: 92 percent / NH₂OH / ethanol / 2 h / 0 °C 6: 79 percent / NaHS, DMSO / acetone / 2 h / Heating 7: 74 percent / dimethylsulfoxide / 0.08 h / 170 °C / other 2,3-disubstituted thiophens; various conditions 8: 90 percent / H₂SO₄ / H₂O / 1 h / 100 °C
	Multi-step reaction with 9 steps 1: SOCl₂ 3: 94 percent / bromine / CCl₄ / 5 h / Heating; Irradiation 4: 90 percent / H₂SO₄ / 4 h 5: Na₂S / ethanol / 1 h 6: acetone / 2 h / Ambient temperature 7: 68 percent / NH₂OH*HCl, NaOAc / ethanol / 1 h / 0 °C 8: 66 percent / bis-(2-hydroxy-ethyl) ether / 0.5 h / 200 °C 9: 90 percent / H₂SO₄ / H₂O / 1 h / 100 °C

Reference： [1]Clarke, Kenneth; Fox, William Richard; Scrowston, Richard M. [Journal of the Chemical Society. Perkin transactions I, 1980, p. 1029 - 1037]
[2]Clarke, Kenneth; Fox, William Richard; Scrowston, Richard M. [Journal of the Chemical Society. Perkin transactions I, 1980, p. 1029 - 1037]

6
[ 74598-03-1 ]
[ 74598-18-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: SOCl₂ 3: 94 percent / bromine / CCl₄ / 5 h / Heating; Irradiation 4: 90 percent / H₂SO₄ / 4 h 5: 92 percent / NH₂OH / ethanol / 2 h / 0 °C 6: 93 percent / acetic anhydride / 4 h / Heating 7: NaHS, DMSO / acetone / 2 h / Ambient temperature

Reference： [1]Clarke, Kenneth; Fox, William Richard; Scrowston, Richard M. [Journal of the Chemical Society. Perkin transactions I, 1980, p. 1029 - 1037]

7
[ 74598-03-1 ]
[ 74598-06-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: SOCl₂ 3: 94 percent / bromine / CCl₄ / 5 h / Heating; Irradiation 4: 90 percent / H₂SO₄ / 4 h

Reference： [1]Clarke, Kenneth; Fox, William Richard; Scrowston, Richard M. [Journal of the Chemical Society. Perkin transactions I, 1980, p. 1029 - 1037]

8
[ 74598-03-1 ]
[ 74598-14-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: SOCl₂ 3: 94 percent / bromine / CCl₄ / 5 h / Heating; Irradiation 4: 90 percent / H₂SO₄ / 4 h 5: 92 percent / NH₂OH / ethanol / 2 h / 0 °C 6: 93 percent / acetic anhydride / 4 h / Heating

Reference： [1]Clarke, Kenneth; Fox, William Richard; Scrowston, Richard M. [Journal of the Chemical Society. Perkin transactions I, 1980, p. 1029 - 1037]

9
[ 74598-03-1 ]
[ 74598-11-1 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1980,p. 1029 - 1037
[2]Journal of the Chemical Society. Perkin transactions I,1980,p. 1029 - 1037

10
[ 74598-03-1 ]
[ 74598-08-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: SOCl₂ 3: 94 percent / bromine / CCl₄ / 5 h / Heating; Irradiation 4: 90 percent / H₂SO₄ / 4 h 5: 92 percent / NH₂OH / ethanol / 2 h / 0 °C 6: 79 percent / NaHS, DMSO / acetone / 2 h / Heating

Reference： [1]Clarke, Kenneth; Fox, William Richard; Scrowston, Richard M. [Journal of the Chemical Society. Perkin transactions I, 1980, p. 1029 - 1037]

11
[ 74598-03-1 ]
[ 74598-15-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: SOCl₂ 3: 94 percent / bromine / CCl₄ / 5 h / Heating; Irradiation 4: 90 percent / H₂SO₄ / 4 h 5: 92 percent / NH₂OH / ethanol / 2 h / 0 °C

Reference： [1]Clarke, Kenneth; Fox, William Richard; Scrowston, Richard M. [Journal of the Chemical Society. Perkin transactions I, 1980, p. 1029 - 1037]

12
[ 74598-03-1 ]
[ 74598-16-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: SOCl₂ 3: 94 percent / bromine / CCl₄ / 5 h / Heating; Irradiation 4: 90 percent / H₂SO₄ / 4 h 5: 92 percent / NH₂OH / ethanol / 2 h / 0 °C 6: 93 percent / acetic anhydride / 4 h / Heating 7: 84 percent / H₂O₂, NaOH / ethanol; H₂O / 2 h / Heating

Reference： [1]Clarke, Kenneth; Fox, William Richard; Scrowston, Richard M. [Journal of the Chemical Society. Perkin transactions I, 1980, p. 1029 - 1037]

13
[ 74598-03-1 ]
[ 74598-20-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1: SOCl₂ 3: 94 percent / bromine / CCl₄ / 5 h / Heating; Irradiation 4: 90 percent / H₂SO₄ / 4 h 5: 92 percent / NH₂OH / ethanol / 2 h / 0 °C 6: 93 percent / acetic anhydride / 4 h / Heating 7: 84 percent / H₂O₂, NaOH / ethanol; H₂O / 2 h / Heating 8: 93 percent / NaHS, DMSO / acetone / Ambient temperature

Reference： [1]Clarke, Kenneth; Fox, William Richard; Scrowston, Richard M. [Journal of the Chemical Society. Perkin transactions I, 1980, p. 1029 - 1037]

14
[ 74598-03-1 ]
[ 74598-05-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: SOCl₂ 3: 94 percent / bromine / CCl₄ / 5 h / Heating; Irradiation

Reference： [1]Clarke, Kenneth; Fox, William Richard; Scrowston, Richard M. [Journal of the Chemical Society. Perkin transactions I, 1980, p. 1029 - 1037]

15
[ 74598-03-1 ]
[ 74598-09-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: SOCl₂ 3: 94 percent / bromine / CCl₄ / 5 h / Heating; Irradiation 4: 90 percent / H₂SO₄ / 4 h 5: Na₂S / ethanol / 1 h 6: acetone / 2 h / Ambient temperature

Reference： [1]Clarke, Kenneth; Fox, William Richard; Scrowston, Richard M. [Journal of the Chemical Society. Perkin transactions I, 1980, p. 1029 - 1037]

16
[ 74598-03-1 ]
[ 74625-80-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: SOCl₂ 3: 94 percent / bromine / CCl₄ / 5 h / Heating; Irradiation 4: 90 percent / H₂SO₄ / 4 h 5: Na₂S / ethanol / 1 h 6: acetone / 2 h / Ambient temperature 7: 68 percent / NH₂OH*HCl, NaOAc / ethanol / 1 h / 0 °C

Reference： [1]Clarke, Kenneth; Fox, William Richard; Scrowston, Richard M. [Journal of the Chemical Society. Perkin transactions I, 1980, p. 1029 - 1037]

17
[ 74598-03-1 ]
[ 74598-17-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1: SOCl₂ 3: 94 percent / bromine / CCl₄ / 5 h / Heating; Irradiation 4: 90 percent / H₂SO₄ / 4 h 5: 92 percent / NH₂OH / ethanol / 2 h / 0 °C 6: 93 percent / acetic anhydride / 4 h / Heating 7: NaHS, DMSO / acetone / 2 h / Ambient temperature 8: 77 percent / iodine / ethanol

Reference： [1]Clarke, Kenneth; Fox, William Richard; Scrowston, Richard M. [Journal of the Chemical Society. Perkin transactions I, 1980, p. 1029 - 1037]

18
[ 74598-03-1 ]
[ 74598-19-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1: SOCl₂ 3: 94 percent / bromine / CCl₄ / 5 h / Heating; Irradiation 4: 90 percent / H₂SO₄ / 4 h 5: 92 percent / NH₂OH / ethanol / 2 h / 0 °C 6: 93 percent / acetic anhydride / 4 h / Heating 7: 84 percent / H₂O₂, NaOH / ethanol; H₂O / 2 h / Heating 8: 93 percent / NaHS, DMSO / acetone / Ambient temperature 9: 89 percent / iodine, KI, NaOH / H₂O

Reference： [1]Clarke, Kenneth; Fox, William Richard; Scrowston, Richard M. [Journal of the Chemical Society. Perkin transactions I, 1980, p. 1029 - 1037]

19
[ 74598-03-1 ]
[ 74598-10-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: SOCl₂ 3: 94 percent / bromine / CCl₄ / 5 h / Heating; Irradiation 4: 90 percent / H₂SO₄ / 4 h 5: Na₂S / ethanol / 1 h

Reference： [1]Clarke, Kenneth; Fox, William Richard; Scrowston, Richard M. [Journal of the Chemical Society. Perkin transactions I, 1980, p. 1029 - 1037]

20
[ 74598-03-1 ]
[ 3773-71-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1: SOCl₂ 3: 94 percent / bromine / CCl₄ / 5 h / Heating; Irradiation 4: 90 percent / H₂SO₄ / 4 h 5: 92 percent / NH₂OH / ethanol / 2 h / 0 °C 6: 79 percent / NaHS, DMSO / acetone / 2 h / Heating 7: 74 percent / dimethylsulfoxide / 0.08 h / 170 °C / other 2,3-disubstituted thiophens; various conditions 8: 90 percent / H₂SO₄ / H₂O / 1 h / 100 °C 9: 85 percent / copper bronze / quinoline / 190 - 200 °C
	Multi-step reaction with 10 steps 1: SOCl₂ 3: 94 percent / bromine / CCl₄ / 5 h / Heating; Irradiation 4: 90 percent / H₂SO₄ / 4 h 5: Na₂S / ethanol / 1 h 6: acetone / 2 h / Ambient temperature 7: 68 percent / NH₂OH*HCl, NaOAc / ethanol / 1 h / 0 °C 8: 66 percent / bis-(2-hydroxy-ethyl) ether / 0.5 h / 200 °C 9: 90 percent / H₂SO₄ / H₂O / 1 h / 100 °C 10: 85 percent / copper bronze / quinoline / 190 - 200 °C

21
[ 14282-78-1 ]
ethyl 4-methylthiophene-2-carboxylate [ No CAS ]
sodium thiosulfate [ No CAS ]
[ 74598-04-2 ]
[ 74598-03-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; sulfuryl dichloride; In tetrahydrofuran; ethanol; acetonitrile;	Reference Example 145 5-Chloro-4-methyl-2-thiophenecarboxylic Acid 4-Methyl-2-thiophenecarboxylic acid ethyl ester (3.4 g) synthesised in accordance with the method of Reference Example 140 was dissolved in acetonitrile (30 ml), and sulfuryl chloride (2.4 ml) in acetonitrile (20 ml) was added dropwise. The mixture was stirred at room-temperature for 30 minutes, and 10% aqueous sodium thiosulfate (100 ml) was added. The mixture was stirred at room temperature for 2 hours and extracted with diethyl ether. The extract was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography, and the desired fractions were concentrated under reduced pressure to give 5-chloro-<strong>[14282-78-1]4-methyl-2-thiophenecarboxylic acid</strong> ethyl ester (4.09 g). 5-Chloro-<strong>[14282-78-1]4-methyl-2-thiophenecarboxylic acid</strong> ethyl ester (4.09 g) was dissolved in a mixture of ethanol (20 ml) and tetrahydrofuran (20 ml), and 1N aqueous sodium hydroxide (40 ml) was added. The mixture was stirred at 60 C for 2 hours and washed with diethyl ether. The aqueous layer was acidified with 1N hydrochloric acid and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 5-chloro-<strong>[14282-78-1]4-methyl-2-thiophenecarboxylic acid</strong> (2.37 g) as crystals. mp 144-145 C.

Reference： [1]Patent: US5840917,1998,A

22
NaOCl-solution [ No CAS ]
(5-chloro-4-methyl-thien-2-yl)-methylketone [ No CAS ]
[ 74598-03-1 ]

Yield	Reaction Conditions	Operation in experiment
11,45 g (76%)	With sodium hydroxide; sodium hydrogen sulfate; chlorine In water	1 5-Chloro-4-methyl-thiophene-2-carboxylic acid 5-Chloro-4-methyl-thiophene-2-carboxylic acid 160 g of ice were added to a solution of 43,21 g (1,08 mol) of NaOH in 80 ml of water and 28,5 g (0,40 mol) of Cl2 were introduced such that the temperature did not exceed 5° C. Then this NaOCl-solution was heated to 55° C. and 14,9 g (85,3 mmol) of (5-chloro-4-methyl-2-thienyl)-methylketone were added at once under stirring. The reaction mixture was heated to 60° C. for 1 hour under stirring, cooled to room temperature, 15 g of NaHSO3 were added, extracted by shaking with CH2 Cl2 and acidified with conc. HCl. The colorless crystals were sucked off, washed with water and dried in vacuo at 80° C. Yield 11,45 g (76%), melting point (CH3 /H2 O) 175°-178° C.

Reference： [1]Current Patent Assignee: FRESENIUS SE & CO. KGAA - US4590203, 1986, A

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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. 74598-03-1 ] {[proInfo.proName]}

Quality Control of [ 74598-03-1 ]

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Product Details of [ 74598-03-1 ]

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[ 74598-03-1 ] Synthesis Path-Downstream 1~22

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