Product Name

  • Name

    3-(Benzoylthio)-2-methylpropionic acid

  • EINECS 277-867-9
  • CAS No. 74431-50-8
  • Article Data4
  • CAS DataBase
  • Density 1.249 g/cm3
  • Solubility
  • Melting Point
  • Formula C11H12O3S
  • Boiling Point 367.5 °C at 760 mmHg
  • Molecular Weight 224.28
  • Flash Point 176 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 74431-50-8 (3-(Benzoylthio)-2-methylpropionic acid)
  • Hazard Symbols
  • Synonyms Propanoic acid,3-(benzoylthio)-2-methyl-, (?à)-;3-(Benzoylthio)-2-methylpropionic acid;3-(Benzoylthio)isobutyric acid;
  • PSA 79.67000
  • LogP 2.28070

Synthetic route

thiobenzoic acid
98-91-9

thiobenzoic acid

poly(methacrylic acid)
79-41-4

poly(methacrylic acid)

(D)-3-(Benzoylthio)-2-methylpropanoic acid
74431-50-8

(D)-3-(Benzoylthio)-2-methylpropanoic acid

toluene-ethyl acetate

toluene-ethyl acetate

(D)-3-(Benzoylthio)-2-methylpropanoic acid
74431-50-8

(D)-3-(Benzoylthio)-2-methylpropanoic acid

(S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid, methyl ester, hydrochloride
78183-55-8

(S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid, methyl ester, hydrochloride

methyl (3S)-2-(3-benzoylthio-2-methylpropionyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate

methyl (3S)-2-(3-benzoylthio-2-methylpropionyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate

Conditions
ConditionsYield
With thionyl chloride; triethylamine In tetrahydrofuran; chloroform80.5%
...Expand
methyldopa
555-30-6

methyldopa

(D)-3-(Benzoylthio)-2-methylpropanoic acid
74431-50-8

(D)-3-(Benzoylthio)-2-methylpropanoic acid

N-(S-benzoyl-3-mercapto-2-methylpropanoyl)-L-α-methyldopa
79559-48-1, 79559-49-2

N-(S-benzoyl-3-mercapto-2-methylpropanoyl)-L-α-methyldopa

Conditions
ConditionsYield
With sodium borate; triethylamine; isobutyl chloroformate 1.) THF, -10 deg C, 10 min, 2.) THF, water, room temperature, 1h; Yield given. Multistep reaction;
(D)-3-(Benzoylthio)-2-methylpropanoic acid
74431-50-8

(D)-3-(Benzoylthio)-2-methylpropanoic acid

(D)-3-(benzoylthio)-2-methylpropanoic acid chloride
76740-20-0

(D)-3-(benzoylthio)-2-methylpropanoic acid chloride

Conditions
ConditionsYield
With thionyl chloride at 30 - 40℃; for 2h;
With thionyl chloride at 50℃; for 3h; Heating;
With thionyl chloride In toluene
(D)-3-(Benzoylthio)-2-methylpropanoic acid
74431-50-8

(D)-3-(Benzoylthio)-2-methylpropanoic acid

(R)-3-Benzoylsulfanyl-2-methyl-propionic acid
74407-70-8

(R)-3-Benzoylsulfanyl-2-methyl-propionic acid

(D)-3-(Benzoylthio)-2-methylpropanoic acid
74431-50-8

(D)-3-(Benzoylthio)-2-methylpropanoic acid

(2S)-3-(benzoylthio)-2-methylpropionic acid
72679-02-8

(2S)-3-(benzoylthio)-2-methylpropionic acid

(D)-3-(Benzoylthio)-2-methylpropanoic acid
74431-50-8

(D)-3-(Benzoylthio)-2-methylpropanoic acid

L-thioproline
34592-47-7

L-thioproline

(4R)-3-<(2S)-S-benzoyl-3-mercapto-2-methylpropanoyl>-4-thiazolidinecarboxylic acid
67714-38-9

(4R)-3-<(2S)-S-benzoyl-3-mercapto-2-methylpropanoyl>-4-thiazolidinecarboxylic acid

Conditions
ConditionsYield
With triethylamine; isobutyl chloroformate 1) tetrahydrofuran, RT, 10 min, 2) water, RT, 30 min; Yield given. Multistep reaction;
(D)-3-(Benzoylthio)-2-methylpropanoic acid
74431-50-8

(D)-3-(Benzoylthio)-2-methylpropanoic acid

L-Tryptophan
73-22-3

L-Tryptophan

(S)-2-(3-Benzoylsulfanyl-2-methyl-propionylamino)-3-(1H-indol-3-yl)-propionic acid
78818-51-6, 78818-53-8

(S)-2-(3-Benzoylsulfanyl-2-methyl-propionylamino)-3-(1H-indol-3-yl)-propionic acid

Conditions
ConditionsYield
With 2.) aq. alkali Yield given. Multistep reaction;
methanol
67-56-1

methanol

(D)-3-(Benzoylthio)-2-methylpropanoic acid
74431-50-8

(D)-3-(Benzoylthio)-2-methylpropanoic acid

(R)-(+)-3-benzoylthio-2-methylpropanoic acid methyl ester

(R)-(+)-3-benzoylthio-2-methylpropanoic acid methyl ester

Conditions
ConditionsYield
In toluene at 40℃; lipase PS-30;
(D)-3-(Benzoylthio)-2-methylpropanoic acid
74431-50-8

(D)-3-(Benzoylthio)-2-methylpropanoic acid

tert-butyl (3S)-2-(3-benzoylthio-2-methylpropionyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate
77832-24-7, 77832-28-1, 84641-55-4

tert-butyl (3S)-2-(3-benzoylthio-2-methylpropionyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: thionyl chloride / 3 h / 50 °C / Heating
2: 81.6 percent / triethyl amine / tetrahydrofuran / 4 h / Ambient temperature
View Scheme
(D)-3-(Benzoylthio)-2-methylpropanoic acid
74431-50-8

(D)-3-(Benzoylthio)-2-methylpropanoic acid

(2S)-3-benzoylthio-2-methylpropionyl chloride
72679-01-7

(2S)-3-benzoylthio-2-methylpropionyl chloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: thionyl chloride
View Scheme
(D)-3-(Benzoylthio)-2-methylpropanoic acid
74431-50-8

(D)-3-(Benzoylthio)-2-methylpropanoic acid

(S)-3-(benzoylthio)-2-methylpropanoylchloride
74654-91-4

(S)-3-(benzoylthio)-2-methylpropanoylchloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: thionyl chloride
View Scheme
(D)-3-(Benzoylthio)-2-methylpropanoic acid
74431-50-8

(D)-3-(Benzoylthio)-2-methylpropanoic acid

(3S)-2-(3-benzoylthio-2-methylpropionyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid
77832-25-8, 77832-29-2, 77972-27-1

(3S)-2-(3-benzoylthio-2-methylpropionyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: thionyl chloride / 3 h / 50 °C / Heating
2: 81.6 percent / triethyl amine / tetrahydrofuran / 4 h / Ambient temperature
3: trifluoroacetic acid / 1 h / Ambient temperature
View Scheme
(D)-3-(Benzoylthio)-2-methylpropanoic acid
74431-50-8

(D)-3-(Benzoylthio)-2-methylpropanoic acid

benzyl (3S)-2-(3-benzoylthio-2-methylpropionyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate
87022-29-5, 87022-30-8

benzyl (3S)-2-(3-benzoylthio-2-methylpropionyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: thionyl chloride / 3 h / 50 °C / Heating
2: 96.2 percent / triethyl amine / tetrahydrofuran / 4 h / 5 - 10 °C
View Scheme
(D)-3-(Benzoylthio)-2-methylpropanoic acid
74431-50-8

(D)-3-(Benzoylthio)-2-methylpropanoic acid

(R)-2-((S)-3-Benzoylsulfanyl-2-methyl-propionyl)-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid benzyl ester
87022-29-5, 87022-30-8

(R)-2-((S)-3-Benzoylsulfanyl-2-methyl-propionyl)-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid benzyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
2: thionyl chloride
3: triethyl amine / tetrahydrofuran / 4 h / 5 - 10 °C
View Scheme
(D)-3-(Benzoylthio)-2-methylpropanoic acid
74431-50-8

(D)-3-(Benzoylthio)-2-methylpropanoic acid

(R)-2-((R)-3-Benzoylsulfanyl-2-methyl-propionyl)-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid benzyl ester
87022-29-5, 87022-30-8

(R)-2-((R)-3-Benzoylsulfanyl-2-methyl-propionyl)-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid benzyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
2: thionyl chloride
3: triethyl amine / tetrahydrofuran / 4 h / 5 - 10 °C
View Scheme
(D)-3-(Benzoylthio)-2-methylpropanoic acid
74431-50-8

(D)-3-(Benzoylthio)-2-methylpropanoic acid

(S)-2-((R)-3-Benzoylsulfanyl-2-methyl-propionyl)-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid benzyl ester
87022-29-5

(S)-2-((R)-3-Benzoylsulfanyl-2-methyl-propionyl)-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid benzyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
2: thionyl chloride
3: 90 percent / triethyl amine / tetrahydrofuran / 4 h / 5 - 10 °C
View Scheme
(D)-3-(Benzoylthio)-2-methylpropanoic acid
74431-50-8

(D)-3-(Benzoylthio)-2-methylpropanoic acid

(S)-2-(3-Benzoylsulfanyl-2-methyl-propionylamino)-4-methylsulfanyl-butyric acid
110949-46-7

(S)-2-(3-Benzoylsulfanyl-2-methyl-propionylamino)-4-methylsulfanyl-butyric acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: SOCl2 / 2 h / 30 - 40 °C
2: 1N NaOH / acetone / Ambient temperature
View Scheme
(D)-3-(Benzoylthio)-2-methylpropanoic acid
74431-50-8

(D)-3-(Benzoylthio)-2-methylpropanoic acid

(R)-2-[(3-Benzoylsulfanyl-2-methyl-propionyl)-methyl-amino]-3-benzylsulfanyl-propionic acid
110949-48-9

(R)-2-[(3-Benzoylsulfanyl-2-methyl-propionyl)-methyl-amino]-3-benzylsulfanyl-propionic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: SOCl2 / 2 h / 30 - 40 °C
2: 1N NaOH / acetone / Ambient temperature
View Scheme
(D)-3-(Benzoylthio)-2-methylpropanoic acid
74431-50-8

(D)-3-(Benzoylthio)-2-methylpropanoic acid

(R)-2-(3-Benzoylsulfanyl-2-methyl-propionylamino)-3-benzylsulfanyl-propionic acid
110949-47-8

(R)-2-(3-Benzoylsulfanyl-2-methyl-propionylamino)-3-benzylsulfanyl-propionic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: SOCl2 / 2 h / 30 - 40 °C
2: 1N NaOH / acetone / Ambient temperature
View Scheme
(trans)-4-methoxy-L-proline
910878-12-5

(trans)-4-methoxy-L-proline

3-benzoylthio-2-methylpropionyl acid chloride

3-benzoylthio-2-methylpropionyl acid chloride

(D)-3-(Benzoylthio)-2-methylpropanoic acid
74431-50-8

(D)-3-(Benzoylthio)-2-methylpropanoic acid

(cis)-4-methoxy-1-[3-(benzoylthio)-2-methyl-1-oxopropyl]-L-proline

(cis)-4-methoxy-1-[3-(benzoylthio)-2-methyl-1-oxopropyl]-L-proline

Conditions
ConditionsYield
With thionyl chloride
...Expand
4-hydroxyproline
51-35-4, 913000-57-4

4-hydroxyproline

(D)-3-(benzoylthio)-2-methylpropanoic acid chloride
76740-20-0

(D)-3-(benzoylthio)-2-methylpropanoic acid chloride

(D)-3-(Benzoylthio)-2-methylpropanoic acid
74431-50-8

(D)-3-(Benzoylthio)-2-methylpropanoic acid

(trans)-1-[D-3-(benzoylthio)-2-methyl-1-oxopropyl]-4-hydroxy-L-proline

(trans)-1-[D-3-(benzoylthio)-2-methyl-1-oxopropyl]-4-hydroxy-L-proline

Conditions
ConditionsYield
With thionyl chloride; sodium carbonate In N-methyl-acetamide; water; toluene
...Expand

3-(Benzoylthio)-2-methylpropionic acid Specification

The IUPAC name of 3-(Benzoylthio)-2-methylpropionic acid is 3-benzoylsulfanyl-2-methylpropanoic acid. With the CAS registry number 74431-50-8, it is also named as (1)-3-(Benzoylthio)-2-methylpropionic acid. The product's category is API intermediates and its EINECS is 277-867-9. In addition, its molecular formula is C11H12O3S and molecular weight is 224.28. Besides, it can be used as pharmaceutical intermediate.

The other characteristics of 3-(Benzoylthio)-2-methylpropionic acid can be summarized as: (1)ACD/LogP: 2.39; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.07; (4)ACD/LogD (pH 7.4): -0.7; (5)ACD/BCF (pH 5.5): 1.86; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 22.91; (8)ACD/KOC (pH 7.4): 1; (9)H bond acceptors: 3; (10)H bond donors: 1; (11)Freely Rotating Bonds: 5; (12)Polar Surface Area: 68.67 Å2; (13)Index of Refraction: 1.579; (14)Molar Refractivity: 59.69 cm3; (15)Molar Volume: 179.4 cm3; (16)Polarizability: 23.66×10-24cm3; (17)Surface Tension: 51.8 dyne/cm; (18)Density: 1.249 g/cm3; (19)Flash Point: 176 °C; (20)Enthalpy of Vaporization: 64.78 kJ/mol; (21)Boiling Point: 367.5 °C at 760 mmHg; (22)Vapour Pressure: 4.77E-06 mmHg at 25 °C.

People can use the following data to convert to the molecule structure.
1. SMILES:O=C(O)C(CSC(=O)c1ccccc1)C
2. InChI:InChI=1/C11H12O3S/c1-8(10(12)13)7-15-11(14)9-5-3-2-4-6-9/h2-6,8H,7H2,1H3,(H,12,13)
3. InChIKey:BCAYPPFBOJCRPN-UHFFFAOYAC
4. Std. InChI:InChI=1S/C11H12O3S/c1-8(10(12)13)7-15-11(14)9-5-3-2-4-6-9/h2-6,8H,7H2,1H3,(H,12,13)
5. Std. InChIKey:BCAYPPFBOJCRPN-UHFFFAOYSA-N

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